Antimicrobial and insect antifeedant activities of some Tröger’s bases

G. Thirunarayanan

doi:10.1016/j.arabjc.2012.10.025

View/Download PDF

Buy Reprints

PDF

Translate this page into:

Original article

10 (

1_suppl

); S636-S643

doi:

10.1016/j.arabjc.2012.10.025

Antimicrobial and insect antifeedant activities of some Tröger’s bases

G. Thirunarayanan^⁎

Department of Chemistry, Annamalai University, Annamalainagar 608002, India

⁎Tel.: +91 4144 220015. drgtnarayanan@gmail.com (G. Thirunarayanan)

Received: 2011-7-11, Accepted: 2012-10-22, Published: 2012-02-01

Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

A series of substituted Tröger’s bases (2,8-dimethyl-6H, 12H- 5,11-methanodibenzo[b, f][1,5] diazocines) have been synthesized and resolved. These bases are characterized by their physical constants, micro analyses, IR, NMR and mass spectral data. The antimicrobial and insect antifeedant activities of these Tröger’s bases have been screened.

Keywords

Substituted Tröger’s bases

Enantioselectivity

IR, NMR and mass spectra

Antimicrobial and insect antifeedant activity

Show Related Articles from PubMed

1 Introduction

Configurationally stable chiral nitrogen in the dibenzodiazocine nucleus has been described as fascinating or concave molecule or Tröger’s base and was first synthesized by Tröger (1887). In the past decades, the synthesis of symmetrical or unsymmetrical Tröger’s bases and the rigidity of the dibenzodiazocine nucleus were made. These molecules are attractive systems for exploitation in a variety of guest–host molecules, forming the scaffold blocks for the synthesis of various rigid molecules including synthetic receptors. Tröger’s base analogs provide relatively rigid chiral armatures for the construction of chelating and biomimetic systems (Galaso et al., 2003). The structures of Tröger’s bases were elucidated later by Spielman (1935). Prelog and his co-workers assessed and recognized that Tröger’s base is an asymmetric molecule due to the pyramidal nitrogens (Prelog and Wieland, 1944). Many Tröger’s bases such as substituted or condensed aromatic ring types have been reported as 8H,16H-7,15-methanodi-naphtho[2,1-b][2′,1′-f][1,5]-diazocine, and synthesized by Farrar et al. (Farrar, 1964; Tálas et al., 1998). Organic chemists synthesized various kinds of Tröger’s base derivatives from C-amino heterocycle (Carree et al., 2003; Cudero et al., 1997; Brigita et al., 2001 ), naphthalimide flurophore (Deprez et al., 2005), rigid C₂-symmetric crown ether (Hansson et al., 1998), Chiral primary bis-ammonium salts (Kim and Choe, 2006), rearrangement of pyrazolines (Wu et al., 2009), mercaptans (Bag and Kiedrowski, 1999), halogenation (Faroughi et al., 2009) and N-methyl pyrrole units (Aabonia et al., 2002; Valík et al., 2003, 2005 ). Chiral recognition phenomena (Sathishkumar and Periasamy, 2006, 2009) are important for various fields like racemic mixture resolution, determination of enantiomeric purity of chiral compounds and selectivity of catalysts. Many natural products and drug molecules possess chiral carboxylic acid structural units. Periasamy and Sathishkumar investigated the chiral recognition of carboxylic acids in Tröger’s base derivatives (Sathishkumar and Periasamy, 2006, 2009). Several catalysts were employed for the synthesis of enantioselective rigid Tröger’s base derivatives such as TiCl₄, AlCl₃, SnCl₄, ZnCl₂, ZrCl₄ (Sathishkumar and Periasamy, 2006), TFFA (Mahon et al., 2008), Na₂CO₃ (Vardelle et al., 2009). The absolute configuration of Tröger’s base derivatives was studied by Lenev et al. using XRD and CD data. Didier and Sergeyev synthesized a few symmetrical amino and aminoethyl Tröger’s base derivatives via Pd catalyzed C–C and C–N bond formation (Didier and Sergeyev, 2007). Tröger’s base derivatives are also used as catalysts for organic synthesis–construction of new supramolecular hosts (Try et al., 1998; Adbo et al., 1999), complexation (Bresson et al., 2004), diastereoselective self-assembly of double standard helicates (Kiehne et al., 2007; Hansson et al., 2005), molecular tweezers (Pardo et al., 2001; Mas et al., 2004), scaffolds (Goswami et al., 2000; Valík et al., 2006) and HPLC chromophoric solid phase supporters (Sergeyev et al., 2009; Michlbachler et al., 2002; Putnam and Guiochon, 2009 ). Wu et al. have studied the stereo selective Mannich reaction catalyzed by Tröger’s base derivatives in aqueous media (Wu et al., 2009). The synthesis of pure optically active Ru(II) complexes with chiral Tröger’s base ligands and their interaction toward DNA were investigated by Classens et al. (2007). The mechanism of the formation of Tröger’s base derivatives was investigated by Abella et al. (2007) through EI mass spectral data. DFT phenomena and NMR spectroscopy data were used for an investigation of various properties of Tröger’s base derivatives (Pardo et al., 2006). Generally compounds which are having hetero atom like O, S, N and notified functional group such as carbonyl, alkene, alkynes, halogens possess biological activities. Herein, the author wishes to report the synthesis of a series of enantioselective Tröger’s base derivatives by the reaction of substituted anilines and para-formaldehyde in the presence of Lewis acid catalyst. The author has also evaluated the antibacterial and antifungal activities of the above Tröger’s base derivatives by in vitro method.

2 Experimental

All chemicals used were purchased from Sigma–Aldrich and E-Merck chemical company. Melting points of all Tröger’s bases were determined in open glass capillaries on Mettler FP51 melting point apparatus and are uncorrected. Infrared spectra (KBr, 4000–400 cm⁻¹) were recorded on AVATAR-300 Fourier transform spectrophotometer. The NMR spectra are recorded in INSTRUM AV500 NMR spectrometer, operating at 500 MHz for ¹H spectra and 125.46 MHz for ¹³C spectra in CDCl₃ solvent using TMS as internal standard. Electron impact (EI) (70 eV) and FAB⁺ mass spectra were recorded using VARIAN 500 mass spectrometer.

2.1

2.1 General procedure for the synthesis of substituted Tröger’s bases

To substituted anilines (10 mmol) and para-formaldehyde (20 mmol) in CH₂Cl₂ (30 mL), anhydrous AlCl₃ (1.36 g, 10 mmol) was added under N₂ atmosphere. The reaction mixture was stirred for 12 h at 25 °C (Scheme 1) and quenched with cold water (10 mL). The reaction mixture was extracted with CH₂Cl₂ (20 mL) and the combined organic extracts were successively washed with water, brine and dried over anhydrous Na₂SO₄. After removal of the solvent, the residue was subjected to chromatography on an alumina (basic) column using 10% ethyl acetate in hexane to elute the desired Tröger’s base analogs, the obtained yields were more than 30%. These Tröger’s bases were resolved according to the literature procedure (Sathishkumar and Periasamy, 2006, 2009) and the enantioselectivities of all the bases are more than 95% ee for (R, R) isomer and 25–35% ee for (S, S) isomer. The analytical and mass spectral data are presented in Table 1. The infrared and NMR spectral data of selected compounds are given in Table 2.

Table 1 Physical constants, microanalysis and mass spectral data of Tröger’s bases.

Entry	Molecular formula	Molecular weight	M.p.(°C)	Yield	%ee		Found (Calcd.)			Mass (m/z)
Entry	Molecular formula	Molecular weight	M.p.(°C)	(%) (±)	(R, R)	(S, S)	C	H	N	Mass (m/z)
1	C₁₅H₁₄N₂	222	131–132	75	–	–	–	–	–	222[M⁺]
1	C₁₅H₁₄N₂	222	130–131^a	75	–	–	–	–	–	222[M⁺]
2	C₁₅H₁₂N₂Br₂	378	163–164	73	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
2	C₁₅H₁₂N₂Br₂	378	164–165^b	73	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
3	C₁₅H₁₂N₂Cl₂	290	144–145	70	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
3	C₁₅H₁₂N₂Cl₂	290	143–144^b	70	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
4	C₁₅H₁₂N₂F₂	246	117–118	76	–	–	–	–	–	246[M⁺], 248[M²⁺], 250[M⁴⁺]
4	C₁₅H₁₂N₂F₂	246	116–117^a	76	–	–	–	–	–	246[M⁺], 248[M²⁺], 250[M⁴⁺]
5	C₁₉H₁₉N₂O₂	310	137–138	74	–	–	–	–	–	310[M⁺]
5	C₁₉H₁₉N₂O₂	310	136–137^a	74	–	–	–	–	–	310[M⁺]
6	C₁₇H₁₅N₂O₂	282	170–171	75	–	–	–	–	–	282[M⁺]
6	C₁₇H₁₅N₂O₂	282	171–172^c	75	–	–	–	–	–	282[M⁺]
7	C₁₇H₁₈N₂	250	136–137	72	–	–	–	–	–	250[M⁺]
7	C₁₇H₁₈N₂	250	135–137^d	72	–	–	–	–	–	250[M⁺]
8	C₁₇H₁₂N₂	282	249–250	68	–	–	–	–	–	282[M⁺]
8	C₁₇H₁₂N₂	282	248–249^e	68	–	–	–	–	–	282[M⁺]
9	C₁₇H₁₂N₂F₆	316	129–130	70	–	–	–	–	–	316[M⁺], 318[M²⁺], 320[M⁴⁺]
9	C₁₇H₁₂N₂F₆	316	130–131^e	70	–	–	–	–	–	316[M⁺], 318[M²⁺], 320[M⁴⁺]
10	C₁₅H₁₂N₄O₄	274	256–257	66	–	–	–	–	–	274[M⁺]
10	C₁₅H₁₂N₄O₄	274	258–259^e	66	–	–	–	–	–	274[M⁺]
11	C₂₁H₂₂N₂O₄	366	125–126	67	–	–	–	–	–	366[M⁺]
11	C₂₁H₂₂N₂O₄	366	126–127^e	67	–	–	–	–	–	366[M⁺]
12	C₂₃H₂₄N₂O₄	392	116–117	40	78	–	70.00	6.02	7.24	392[M⁺]
12	C₂₃H₂₄N₂O₄	392	116–117	40	78	–	(70.42	6.12	7.13)	392[M⁺]
13	C₁₅H₁₆N₄	252	267–268	56	–	–	–	–	–	252[M⁺]
13	C₁₅H₁₆N₄	252	266^f	56	–	–	–	–	–	252[M⁺]
14	C₁₉H₁₈N₂O₂	306	122–123	36	75	–	74.43	5.80	9.09	306[M⁺]
14	C₁₉H₁₈N₂O₂	306	122–123	36	75	–	(74.50	5.88	9.15)	306[M⁺]
15	C₁₅H₁₂N₂Br₂	378	162–163	44	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
15	C₁₅H₁₂N₂Br₂	378	161.7–163.7^g	44	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
16	C₁₅H₁₂N₂Cl₂	290	144–145	65	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
16	C₁₅H₁₂N₂Cl₂	290	144.8–147.0^g	65	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
17	C₁₅H₁₂N₂F₂	246	123–124	69	–	–	–	–	–	246[M⁺], 248[M²⁺], 250[M⁴⁺]
17	C₁₅H₁₂N₂F₂	246	124.1–125.8^g	69	–	–	–	–	–	246[M⁺], 248[M²⁺], 250[M⁴⁺]
18	C₁₅H₁₂N₂Br₂	378	203–204	72	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
18	C₁₅H₁₂N₂Br₂	378	201.6–203.9^b	72	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
19	C₁₅H₁₂N₂Cl₂	290	192–193	71	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
19	C₁₅H₁₂N₂Cl₂	290	191.4–192.9^g	71	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
20	C₁₅H₁₂N₂F₂	246	140–141	38	–	–	–	–	–	246[M⁺], 248[M²⁺], 250[M⁴⁺]
20	C₁₅H₁₂N₂F₂	246	141.3–143.7^g	38	–	–	–	–	–	246[M⁺], 248[M²⁺], 250[M⁴⁺]
21	C₁₅H₁₂N₂Br₂	378	230–231	55	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
21	C₁₅H₁₂N₂Br₂	378	231–231.7^g	55	–	–	–	–	–	378[M⁺], 380[M²⁺], 382[M⁴⁺]
22	C₁₅H₁₂N₂Cl₂	290	222–223	67	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
22	C₁₅H₁₂N₂Cl₂	290	222.6–224.1^g	67	–	–	–	–	–	290[M⁺], 292[M²⁺], 294[M⁴⁺]
23	C₁₇H₂₀N₄	274	204–205	67	–	–	–	–	–	274[M⁺]
23	C₁₇H₂₀N₄	274	206^f	67	–	–	–	–	–	274[M⁺]
24	C₁₇H₁₆N₂Br₂	406	194–195^h	71	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
24	C₁₇H₁₆N₂Br₂	406	194–195	71	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
25	C₁₇H₁₆N₂Cl₂	318	155–156	63	–	–	–	–	–	318[M⁺], 320[M²⁺], 322[M⁴⁺]
25	C₁₇H₁₆N₂Cl₂	318	156–157^b	63	–	–	–	–	–	318[M⁺], 320[M²⁺], 322[M⁴⁺]
26	C₁₉H₁₆N₄	300	257–258	64	–	–	–	–	–	300[M⁺]
26	C₁₉H₁₆N₄	300	258–261^f	64	–	–	–	–	–	300[M⁺]
27	C₁₅H₁₀N₂F₄	284	136–137	49	–	–	–	–	–	284[M⁺], 286[M²⁺], 288[M⁴⁺], 288[M⁶⁺],
27	C₁₅H₁₀N₂F₄	284	135–136ⁱ	49	–	–	–	–	–	284[M⁺], 286[M²⁺], 288[M⁴⁺], 288[M⁶⁺],
28	C₁₇H₁₆N₂F₂	284	214–215	67	–	–	–	–	–	284[M⁺], 286[M²⁺], 288[M⁴⁺]
28	C₁₇H₁₆N₂F₂	284	215–217.5^j	67	–	–	–	–	–	284[M⁺], 286[M²⁺], 288[M⁴⁺]
29	C₁₇H₁₆N₂Br₂O₂	410	245–246	68	–	–	–	–	–	410[M⁺], 412[M²⁺], 414[M⁴⁺]
29	C₁₇H₁₆N₂Br₂O₂	410	246–247^b	68	–	–	–	–	–	410[M⁺], 412[M²⁺], 414[M⁴⁺]
30	C₁₇H₁₆N₂Cl₂O₂	326	224–225	73	–	–	–	–	–	326[M⁺], 324[M²⁺], 324[M⁴⁺]
30	C₁₇H₁₆N₂Cl₂O₂	326	225–227^b	73	–	–	–	–	–	326[M⁺], 324[M²⁺], 324[M⁴⁺]
31	C₁₇H₁₆N₂Br₂	406	260–261	71	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
31	C₁₇H₁₆N₂Br₂	406	262.6–264.7^g	71	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
32	C₁₇H₁₆N₂Cl₂	318	197–198	70	–	–	–	–	–	318[M⁺], 320[M²⁺], 322[M⁴⁺]
32	C₁₇H₁₆N₂Cl₂	318	198.3–199.7^g	70	–	–	–	–	–	318[M⁺], 320[M²⁺], 322[M⁴⁺]
33	C₁₇H₁₆I₂N₂	518	309–310	65	–	–	–	–	–	518[M⁺], 520[M²⁺], 522[M⁴⁺]
33	C₁₇H₁₆I₂N₂	518	308–310.4^f	65	–	–	–	–	–	518[M⁺], 520[M²⁺], 522[M⁴⁺]
34	C₁₇H₁₈N₂O₂	282	275–276	56	–	–	–	–	–	282[M⁺]
34	C₁₇H₁₈N₂O₂	282	273–275ⁱ	56	–	–	–	–	–	282[M⁺]
35	C₁₅H₁₀N₂Cl₂	278	102–103	42	82	–	71.99	5.29	6.41	278[M⁺], 280[M²⁺], 3284[M⁴⁺]
35	C₁₅H₁₀N₂Cl₂	278	102–103	42	82	–	(72.05	5.31	6.46)	278[M⁺], 280[M²⁺], 3284[M⁴⁺]
36	C₁₇H₁₆N₂Br₂	406	241–242	63	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
36	C₁₇H₁₆N₂Br₂	406	239.9–242.1^b	63	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
37	C₁₅H₁₀N₂Cl₂F₂	324	119–120	55	68	–	55.48	3.03	8.59	324[M⁺], 326[M²⁺], 328[M⁴⁺], 330[M⁶⁺]
37	C₁₅H₁₀N₂Cl₂F₂	324	119–120	55	68	–	(55.55	3.08	8.64)	324[M⁺], 326[M²⁺], 328[M⁴⁺], 330[M⁶⁺]
38	C₁₇H₁₄N₂Cl₂O₂	348	189–191	64	–	–	–	–	–	348[M⁺], 350[M²⁺], 352[M⁴⁺]
38	C₁₇H₁₄N₂Cl₂O₂	348	190–191^g	64	–	–	–	–	–	348[M⁺], 350[M²⁺], 352[M⁴⁺]
39	C₁₇H₁₆N₂Cl₂	318	229–210	67	–	–	–	–	–	318[M⁺], 320[M²⁺], 324[M⁴⁺]
39	C₁₇H₁₆N₂Cl₂	318	227.6–229.6^g	67	–	–	–	–	–	318[M⁺], 320[M²⁺], 324[M⁴⁺]
40	C₁₇H₁₆N₂ F₂	284	241–242	59	–	–	–	–	–	284[M⁺], 286[M²⁺], 288[M⁴⁺]
40	C₁₇H₁₆N₂ F₂	284	238.7–241.8^g	59	–	–	–	–	–	284[M⁺], 286[M²⁺], 288[M⁴⁺]
41	C₁₇H₁₆I₂N₂	518	259–260	66	–	–	–	–	–	518[M⁺], 520[M²⁺], 522[M⁴⁺]
41	C₁₇H₁₆I₂N₂	518	258.3–259.6^g	66	–	–	–	–	–	518[M⁺], 520[M²⁺], 522[M⁴⁺]
42	C₁₇H₁₆I₂N₂	518	229–230	64	–	–	–	–	–	518[M⁺], 520[M²⁺], 522[M⁴⁺]
42	C₁₇H₁₆I₂N₂	518	228.2–229.8^g	64	–	–	–	–	–	518[M⁺], 520[M²⁺], 522[M⁴⁺]
43	C₁₇H₂₀N₄	274	227–228	71	–	–	–	–	–	274[M⁺]
43	C₁₇H₂₀N₄	274	224–228^g	71	–	–	–	–	–	274[M⁺]
44	C₁₇H₁₆N₂Br₂	406	195–196	65	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
44	C₁₇H₁₆N₂Br₂	406	195–196^g	65	–	–	–	–	–	406[M⁺], 408[M²⁺], 410[M⁴⁺]
45	C₁₇H₁₄N₂Cl₂	216	182–183	66	–	–	–	–	–	216[M⁺], 218[M²⁺], 220[M⁴⁺]
45	C₁₇H₁₄N₂Cl₂	216	180–182^b	66	–	–	–	–	–	216[M⁺], 218[M²⁺], 220[M⁴⁺]
46	C₁₉H₂₂N₂	278	110–111	69	–	–	–	–	–	278[M⁺]
46	C₁₉H₂₂N₂	278	111–112^h	69	–	–	–	–	–	278[M⁺]
47	C₁₇H₁₆N₄O₄	340	327–328	68	–	–	–	–	–	340[M⁺]
47	C₁₇H₁₆N₄O₄	340	>300^h	68	–	–	–	–	–	340[M⁺]
48	C₁₇H₁₆N₂	248	98–98	70	–	–	–	–	–	248[M⁺]
48	C₁₇H₁₆N₂	248	96–97^h	70	–	–	–	–	–	248[M⁺]
49	C₁₉H₂₀N₂O₂	308	132–133	63	–	–	–	–	–	308[M⁺]
49	C₁₉H₂₀N₂O₂	308	133–134^h	63	–	–	–	–	–	308[M⁺]
50	C₁₉H₂₀N₂	276	157–159	66	–	–	–	–	–	276[M⁺]

Table 2 The infrared and NMR spectral data of Troger’s bases 12, 14, 35 and 37.

Entry	IR data ν (cm⁻¹)	¹H NMR data δ (ppm)	¹³C NMR data δ (ppm)
12	3035Ar–CH, 2967(CH), 1713(CO), 1488(CNC), 1526(CN), 1279(COC)	7.638(H_1,7, 2H, s), 7.833(H_3,9, 2H, d), 6.655(H_4,10, 2H,d) 4.327(H_6,12, 4H, s), 4.601(H₁₃, 1H, d), 4.760(H_13′, 1H, d), 4.217 (CH₂, 2H, t), 1.752(CH₂, 2H, m), 1.008((CH₃, 3H, t)	131.192(C₁,₇), 117.382(C₂,₈), 128.781(C₃,₉), 115.80(C₄,₁₀), 58.70(C₆, ₁₂), 152.834(C_4a, _10a), 124.863(C_6a, _12a), 66.382(C₁₃), 166.146(CO), 66.632(CH₂), 22.241(CH₂), 10.563(CH₃)

14	3063Ar–CH, 2923(CH), 1683(CO), 1526(CN), 1422(CNC)	7.284(H_1,7, 2H, d), 6.679(H_2,8, 2H, t), 7.899(H_3,9, 2H,d) 3.835(H_6,12, 4H, s), 5.362(H₁₃, 1H, d), 5.260(H_13′, 1H, d), 2.528(CH₃, 6H, s)	130.521(C₁,₇), 118.612(C₂,₈), 130.483(C₃,₉), 110.618(C₄,₁₀), 56.030(C₆, ₁₂), 153.421(C_4a, _10a), 125.38(C_6a, _12a), 66.738(C₁₃), 196.401(CO), 29.8(CH₃)

35	3053Ar–CH, 2929(CH), 1687(CO), 1531(CN), 1443(CNC), 786(CCl)	7.891(H_1,7, 2H, d), 7.284(H_3,9, 2H, t), 4.981(H_6,12, 4H, s), 6.661(H₁₃, 1H, d), 6.672(H_13′, 1H, d), 7.151(Ar–H, 5H, s)	110.217(C₁,₇), 130.524(C₂,₈), 118.793(C₃,₉), 130.571(C₄,₁₀), 128.5621–129.961(Ar–C), (C₆, ₁₂), 150.126(C_4a, _10a), 125.251(C_6a, _12a), 69.752(C₁₃), 196.405(CO)

37	3053Ar–CH, 2929(CH), 1531(CN), 1443(CNC), 825(CBr), 768(CCl)	6.724(H_1,7, 2H, s), 6.737(H_3,9, 2H, s), 4.724(H_6,12, 4H, s), 4.664(H₁₃, 1H, d), 4.672(H_13′, 1H, d)	116.972(C₁,₇), 152.441(C₂,₈), 120.531(C₃,₉), 118.194(C₄,₁₀), 58.236 (C₆, ₁₂), 144.524(C_4a, _10a), 121.362(C_6a, _12a), 66.574(C₁₃),

3 Results and discussion

3.1

3.1 Antimicrobial activities

Organic compounds which are having a hetero atom such as O, S and N with one functional group such as alkene, alkyne, carbonyl, azo and halogens possess biological activities. All heterocycles both five and six membered, aryl chalcones, esters, organo mercapto and phenolic derivatives possess antibacterial, antifungal, anti fertile, antitumor, anti viral, antioxidant, anticancer, anti-HIV and anticonvulsant activities. Based on this trend the author has examined the antimicrobial activities such as antibacterial and antifungal activities of all the synthesized Tröger’s bases by in vitro method.

3.1.1

3.1.1 Evaluation of antibacterial activities

The antibacterial activities of all prepared Tröger’s bases were evaluated against two gram positive pathogenic strains Staphylococcus aureus, Entrococcus faecalis while Escherichia coli, Klebsiella pneumoniae, Psuedomonas species and Proteus vulgaris were the gram negative strains. The disc diffusion technique was followed using the Kirby–Bauer (Bauer et al., 1996) method, at a concentration of 250 μg/mL with Ampicillin and Streptomycin taken as standard drugs. The measured antibacterial activities of all title compounds are presented in Table 3. Against Escherichia coli, eight compounds 5, 6, 10, 11, 29, 30, 38 and 49 showed a maximum zone of inhibition greater than 20 mm. The Troger bases 2, 5, 11, 12, 29, 30, 38 and 49 were active against Staphylococcus, showing maximum inhibition. The other compounds were less effective against S. aureus. Troger base derivatives 5, 6, 11, 12, 29, 30, 38 and 49 were more active against Pseudomonas with a greater than 20 mm zone of inhibition and the other derivatives inhibit the growth of bacteria between 12 and 19 mm zones of inhibition. Compounds 2, 12, 29, 30, 38 and 49 are effective against Klebsiella in 20–24 mm zone of inhibition while the other bases show a moderate activity. The bases 29, 30 and 38 are active when they were screened against P. vulgaris and the other compounds are less effective. Compound 50 is inactive. Compounds 2, 6, 10–12 showed to be active against E. faecalis in the 20 mm zone of inhibition and less active in the 13–19 mm zone of inhibition. Compounds 1, 3, 5, 7–9, 13–15, 17, 18, 20, 23–28, 35, 37 and 41 were inactive.

Table 3 Antibacterial activity of Troger’s bases.

Entry	E. coli	Staphylococcus aures	Pseudomonas	Klebsiella	Proteus vulgaris	Entrococcus faecalis
1	±	+	±	±	±	–
2	++	++	+	++	+	++
3	+	+	+	+	+	–
4	+	+	±	+	+	–
5	++	++	++	+	+	–
6	++	++	++	+	+	++
7	±	+	±	±	±	–
8	+	+	+	+	+	–
9	+	+	+	+	+	–
10	++	+	+	+	+	++
11	++	++	++	+	+	++
12	+	++	++	++	+	++
13	+	+	+	+	+	–
14	±	+	±	±	±	–
15	+	±	±	±	±	–
16	±	+	±	±	±	+
17	+	±	±	±	±	–
18	±	+	±	±	±	–
19	+	+	+	+	+	+
20	+	+	±	+	+	–
21	±	±	+	+	±	+
22	±	+	±	±	±	+
23	+	+	+	+	+	–
24	+	+	+	+	+	–
25	+	+	±	+	+	–
26	+	±	±	±	±	–
27	+	±	±	±	±	–
28	+	+	±	+	+	–
29	++	++	++	++	++	+
30	++	++	++	++	++	+
31	+	+	+	+	+	±
32	+	+	+	+	+	±
33	±	±	+	+	±	+
34	±	+	±	±	±	+
35	+	+	+	+	+	–
36	±	+	±	±	±	+
37	+	+	+	+	+	–
38	++	++	++	++	++	±
39	±	±	+	+	±	+
40	+	+	+	+	+	±
41	±	+	±	±	±	–
42	+	+	±	+	+	±
43	+	+	+	+	+	±
44	±	±	+	+	±	+
45	±	±	+	+	±	+
46	+	+	±	+	+	±
47	+	+	+	+	+	±
48	±	±	+	+	±	+
49	++	++	++	++	±	+
50	+	±	±	+	–	±

Disc size: 6.35 mm; Duration: 24–45 h; Standard: Ampicillin (30–33 mm) and Streptomycin (20–25 mm); Control: Methanol; –: No activities; ±: Active (8–12 mm); +: Moderately active (13–19 mm); ++: Active (20–24 mm).

3.1.2

3.1.2 Antifungal activity

Antifungal activities of all Tröger’s bases were evaluated by Bauer-Kirby (Bauer et al., 1996) disc diffusion technique using Candida albicans Penicillium species and Aspergillus niger fungal strains. The drug dilution was 50 μg/mL. Griseofulvin is taken as the standard drug. The observed antifungal activities of all bases are presented in Table 4. The antifungal activities of all bases against C. albicans, the compounds 2, 6, 14, 30, 35, 38 and 49 are effective with 20 mm as the zone of inhibition at 250 μg/disc while compounds 7, 8, 12, 13, 23, 26, 29, 32–34, 36, 37, 39–43, 46–48 were active with 13–19 mm zone of inhibition and the bases 4, 5, 16–22, 24, 28, 31, 44, 45 and 50 were less active with 8–12 mm zone of inhibitions. Compounds 2, 5, 6, 12, 23, 29, 30, 37, 38, 45, 49 and 50 showed high activity against Penicililum species. Compounds 2, 5, 12, 29 and 35 are active against Aspergillus and the compounds 1, 4, 7, 9, 10, 13, 15, 24, 25, 27, 28, 32–24, 36, 39–41 and 46 were inactive. The presence of amino, methoxy, methyl, dimethyl, ester and bromo substituents is responsible for high antimicrobial activities of Tröger’s bases.

Table 4 Antifungal activities of Troger’s bases.

Entry	Disc diffusion technique (250 μg/mL)	Drug dilution method (50 μg/mL)
Entry	Candida albicans	Penicillium	Aspergillus niger
1	–	–	–
2	++	++	++
3	–	±	+
4	±	–	–
5	±	++	++
6	++	++	+
7	+	+	–
8	+	–	+
9	–	–	–
10	–	+	–
11	–	–	–
12	+	++	++
13	+	±	–
14	++	+	++
15	–	–	–
16	±	±	±
17	±	±	±
18	±	±	±
19	±	±	±
20	±	±	±
21	±	±	±
22	±	±	±
23	+	++	+
24	±	–	–
25	–	±	–
26	+	+	+
27	–	–	–
28	±	–	–
29	+	++	++
30	++	++	±
31	±	–	±
32	+	–	–
33	+	–	–
34	+	–	–
35	++	+	++
36	+	–	–
37	+	++	+
38	++	++	+
39	+	–	–
40	+	+	–
41	+	–	–
42	+	+	+
43	+	+	+
44	±	±	±
45	±	++	+
46	+	–	–
47	+	+	+
48	+	+	+
49	++	++	+
50	±	++	+

Standard: Griseofulvin and gentamycin; Duration: 72 h; Control: Methanol; Medium: Potato dextrose agar; ++: No fungal colony; +: One fungal colony; ±: Two–three fungal colony; –: Heavy fungal colony.

3.2

3.2 Insect antifeedant activities

The multipronged activities present in different Tröger’s bases are intended to examine their insect antifeedant activities against castor semilooper. The larvae of Achoea Janata L were reared as described on the leaves of castor Riclmus communls in the laboratory at a temperature range of 26 ± 1 °C and a relative humidity of 75–85%. The leaf – disc bioassay method (Thirunarayanan, 2008; Thirunarayanan et al., 2010) was used against the 4th instar larvae to measure the antifeedant activity. The 4th instar larvae were selected for testing because the larvae at this stage feed very voraciously.

3.2.1

3.2.1 Measurement of insect antifeedant activity of Trogers’ bases

Leaf discs of a diameter of 1.85 cm were punched from castor leaves with the petioles intact. All Tröger’s bases were dissolved in acetone at a concentration of 200 ppm dipped for 5 min. The leaf discs were air-dried and placed in 1 L beaker containing little water in order to facilitate translocation of water. Therefore the leaf discs remain fresh throughout the duration of rest, 4th instar larvae of the test insect, which had been preserved on the leaf discs of all bases and allowed to feed on them for 24 h. The area of the leaf disc consumed was measured by Dethlers (Dethler, 1947; Thirunarayanan et al., 2010) method. The observed antifeedant activity of Tröger’s bases has been presented in Table 5.

Table 5 Insect antifeedant activities of Troger’s bases.

Entry	4–6 pm	6–8 pm	8–10 pm	10–12 pm	12–6 am	6–8 am	8am–12Nn	12Nn–2 pm	2–4 pm	Total leaf disc consumed in 24 h
1	1	1	0.5	0.5	1	1	1	1	1	8
2	0.5	0.25	0.25	0.5	0.5	0.5	1	1	0.5	1
3	0.5	0.25	0.25	0.5	0.5	0.5	1	1	0.5	0.5
4	0.5	0.5	0.25	1	0.5	0.5	0.25	0.25	0.25	0.5
5	5	2	2	1	3	6	2	2	3	10
6	0.5	3	2	1	2	0.5	1	1	1	9
7	1	2	2	1	2	3	1	1	1	9
8	1	1	0.5	0.5	1	1	1	1	1	8
9	1	0.5	0.5	0	0.25	0	1	0.5	1	0.4
10	0.5	0.5	0.5	2	2	1	1	1	1	9
11	2	3	3	1	1	1	0.5	1	0	12
12	2	3	3	1	1	1	0.5	1	0	12
13	1	2	2	2	1	0.5	0.5	1	0	10
14	1	1	0.5	0.5	0.5	1	1	1	1	8
15	1	0.25	0.25	0.5	0.5	0.5	1	1	0.5	1
16	0.5	0.25	0.25	0.5	0.5	0.5	1	1	0.5	0.5
17	0.5	1	0.25	1	0.25	0.5	1	1	1	1.5
18	1	0.25	0.5	1	1	0.5	0.5	0.5	0.25	1
19	0.5	0.5	0.25	1	1	0.5	1	1	0.5	1
20	1	2	2	1	0	0.5	1	0.25	1	1.5
21	0.25	0.5	0.5	0.5	0.5	1	1	1	0.25	1
22	0.25	0.5	0.5	1	1	0.5	0.5	0.5	0.5	1
23	0.5	0.5	0.5	2	2	1	1	1	1	9
24	0.25	1	1	1	0.5	1	0.5	1	0	1
25	0.5	1	0.5	1	0	0	0.5	1	0	1
26	1	2	2	2	1	0.5	0.5	1	0	10
27	0.25	0	0	0	0.5	0.5	1	1	0.5	0.4
28	0.5	1	1	1	0	0	1	1	0.5	1.5
29	0.5	1	0.25	0.5	1	0.5	1	1	0.5	1.5
30	0.5	0.5	0.	1	0.5	0.5	0.25	0.25	0.25	0.5
31	0.5	0	0.25	1	0.5	0.5	0.25	0.25	0.25	0.5
32	0.5	0.5	0.25	1	0.5	0.5	0.25	0.25	0.25	0.5
33	0.5	0	1	1	0	0	1	1	1	1
34	1	1	0.5	0.5	0.5	1	1	1	1	8
35	0.5	0.5	0.5	0	1	0	1	1	1	1.5
36	0.5	0.5	0.5	0	0.5	0	1	1	1	1
37	0.25	0	0.25	0	0	1	0.5	1	0	0.4
38	0	0	0.5	0	0.5	1	0.5	1	0	1
39	1	1	0	2	0	0.5	0.5	1	0	1
40	0.5	0	0.5	0.5	0.5	1	1	1	1	1
41	0	0.5	0	0	0.5	0.5	1	1	1	1
42	0.5	1	1	0.5	0	0.5	1	1	0.5	1
43	0.5	2	0	1.5	5	0.5	0.25	0.25	0.25	1.5
44	0.5	0	1	1	0.5	0.5	0.25	0.	1	1.5
45	0.5	0.5	0.25	1	0.5	0.5	0.25	0.25	0.25	1
46	1	2	2	1	0	0	1	1	1	9
47	1	1	0.5	0.5	0.5	1	1	1	1	8
48	1	0.5	0.5	1	1	0	1	1	1	9
49	0.5	0.5	0.5	2	2	1	1	1	1	9
50	2	3	3	1	1	1	0.5	1	0	12

Number of leaf discs consumed by the insect (values are mean + SE of five).

The results of the antifeedant activity of Tröger’s bases presented in Table 5 reveal that the halogen substituted compounds 2–4, 9, 15–22, 25, 27–33, 35, 37–42, 44 and 45 are found to reflect remarkable antifeedant activity among all other Tröger’s bases. This test is performed in the insects which ate only two-leaf disc soaked under the solution of this compound. Compounds 9, 27 and 37 also show enough antifeedant activity. Further these three compounds were subjected to measure the antifeedant activity at different 50, 100 and 150 ppm concentrations and the observation reveals that as the concentrations decreased, the activity also decreased. It is observed from the results in Table 6 that Troger bases 9, 27 and 37 show an appreciable antifeedant activity at 150 ppm concentration.

Table 6 Antifeedant activity of Tröger bases 9, 27 and 37 at three different concentrations.

ppm	4–6 pm	6–8 pm	8–10 pm	10–12 pm	12 am–6 am	6–8 am	8 am–12 Nn	12 Nn–2 pm	2–4 pm	Total leafdisc consumed in 24 h
	4–6 pm	6–8 pm	8–10 pm	10–12 pm	12 am–6 am	6–8 am	8 am–12 Nn	12 Nn–2 pm	2–4 pm	Total leafdisc consumed in 24 h
50	0.5	0.5	0	0	0	0	0	0	0	0.1
100	0	0.25	0.25	0	0	0	0	0	0	0.05
150	0	0.5	0.25	0	0.25	0	0	0	0	0.1

Number of leaf discs consumed by the insect (values are mean + SE of five).

Acknowledgements

The author (Dr. G. T.) thanks 1. The UGC-Network Resource Centre, School of Chemistry, Central University, Hyderabad-500 040, for providing Summer Visiting Fellowship-June 2008, under the guidance of Prof. Dr. Mariappan Periasamy for initiating this Tröger’s bases synthesizing work. 2. Mr. M. Suresh, Department of Chemistry, Annamalai University, for synthesizing some other Tröger’s bases. 3. Mr. K. Ravi, Proventus Life Lab for synthesizing some other Tröger’s bases, and enabling partial completion of antimicrobial evaluation and insect antifeedant work. 4. Prof. G. Vanangamudi, Associate Professor and Head, Govt. Arts College for completion of antimicrobial evaluation and insect antifeedant work. 5. The Head, RSIC, IIT Chennai for recording NMR spectra of selective compounds.

References

Abella C.A.M., Benassi M., Santos L.S., Eberlin M., Coelho F., . J. Org. Chem.. 2007;2:4048.
Abonia R., Rengifo E., Quiroga J., Insuasty B., Sanchez A., Cobo J., Low J., Nogueras M., . Tetrahedron Lett.. 2002;43:5617.
Adbo K., Andersson H.S., Ankarloo J., Karlsson J.G., Norell M.C., Olofsson L., Svenson J., Ortegren U., Nicholls I.A., . Bioorg. Chem.. 1999;27:363.
Bag G.G., Kiedrowski G., . Tetrahdron Lett.. 1999;40:289.
Bauer A.W., Kirby W.M.M., Sherris J.C., Truck M., . Am. J. Clin. Pathol.. 1996;45:492.
Bresson C., Luhmer M., Demeunynck M., Mesmaeker A.K.-D., Pierard F., . Tetrahedron Lett.. 2004;45:2863.
Brigita C., Liepinsh E., Vigante B., Sobolevs A., Ozols J., Duburs G., . Tetrahedron Lett.. 2001;42:4239.
Carree F., Pardo C., Galy J.-P., Boyer G., Robin M., Elguero G., . Arkivoc. 2003;1:1.
Classens N., Perard F., Bresson C., Moucheron C., Mesmaeker A.K.-D., . J. Inorg. Biochem.. 2007;101:987.
Cudero J., Padro C., Ramos M., . Tetrahedron. 1997;53(6):2233.
Didier D., Sergeyev S., . Tetrahedron. 2007;63:3864.
Didier D., Tylleman B., Lambert N., Velde C.M.L.V., Blockhuys F., Collas A., Sergeyev S., . Tetrahedron. 2008;64:6252.
Depres N.R., McNitt K.A., Petersen M.E., Brown R.G., Lewis D.E., . Tetrahedron Lett.. 2005;46:2149.
Dethler V.G., . Chemical Insect Attractants and Repellents. Philadeciphia: Blackistan; 1947.
Faroughi M., Jenssen P., Try A.C., . Arkivoc. 2009;2:269.
Farrar W.V., . J. Appl. Chem. 1964:389.
Galaso V., Jones D., Modelli A., . Chem. Phys.. 2003;33–42:288.
Goswami S., Ghosh K., Dasgupta S., . J. Org. Chem.. 2000;65:1907.
Hansson A., Norrby P.-O., Warnmark K., . Tetrahedron Lett.. 1998;39:4565.
Hansson A., Jensen J., Wendt O.F., Warnmark K., . Eur. J. Org. Chem. 2003:3179.
Hansson A., Wixe T., Bergquist K.-E., Warnmark K., . Org. Lett.. 2005;7(10):2019.
Kiehne U., Weilandt T.Y., Lutzen A., . Org. Lett.. 2007;9(7):1283.
Kim K., Choe J.-I., . Bull. Korean Chem. Soc.. 2006;27(11):1737.
Li Z., Xu X., Peng Y., Jiang Z., Ding C., Qian X., . Synthesis. 2005;8:1228.
Mahon A.B., Craig D.C., Try A.C., . Arkivoc. 2008;12:148.
Mas T., Pardo C., Elguero J., . Mendeleev Commun.. 2004;14(6):235.
Mihlbachler K., Kaczmarski K., Morgenstern A.S., Guiochon G., . J. Chromatogr.. 2002;955A:35.
Pardo C., Alkorta I., Elguero J., . Tetrahedron: Asymmetr.. 2006;17:191.
Pardo C., Sesmilo E., Gutierrez-Puebla E., Angeles M., . J. Org. Chem.. 2001;66:1607.
Prelog V., Wieland P., . Helv. Chim. Acta.. 1944;27:1127.
Putnam J., Guiochon G., . J. Chromatogr.. 2009;1216A:8488.
Sathishkumar S., Periasamy M., . Tetrahedron: Asymmetr.. 2006;17:1116.
Sathishkumar S., Periasamy M., . Tetrahedron: Asymmetr.. 2009;20:2257.
Segeyev S., Stas S., Remacle A., Velde C.M.L.V., Dolensky B., Havlik M., Kral V., Cejka J., . Tetrahedron: Asymmetr.. 2009;20:1918.
Spielman M.A., . J. Am. Chem. Soc.. 1935;57:583.
Tálas E., Margitfalvi J., Machytka D., Czugler M., . Tetrahedron: Asymmetr.. 1998;9:4151.
Thirunarayanan G., . J. Indian Chem. Soc.. 2008;85:447.
Thirunarayanan G., Surya S., Srinivasan S., Vanangamudi G., Sathiyendiran V., . Spectrochim. Acta.. 2010;75A:152.
Tröger J., . J. Prakt. Chem.. 1887;36:225.
Try A.C., Painter L., Harding M.M., . Tetrahedron Lett.. 1998;39:9809.
Valík M., Dolensky B., Petříčková H., Vašek P., Král V., . Tetrahedron Lett.. 2003;44:2083.
Valík M., Dolensky B., Herdtweck E., Král V., . Tetrahedron: Asymmetr.. 2005;16:1969.
Valík M., Malina J., Palivec L., Foltýnová J., Tkadlecová M., Urbanová M., Brabec V., Král V., . Tetrahedron. 2006;62:8591.
Vardelle E., Agnes M.-M., Jouannetaud M.-P., Jacquesy J.-C., Marrot J., . Tetrahedron Lett.. 2009;50:1093.
Wu H., Chen X.-C., Wan Y., Ye L., Xin H., Xu H., Yue C., Pang L., Ma R., Shi D., . Tetrahedron Lett.. 2009;50:1062.

Introduction

Experimental

General procedure for the synthesis of substituted Tröger’s bases

Results and discussion

Antimicrobial activities
Insect antifeedant activities

Fulltext Views
885

PDF downloads
461

View/Download PDF
Download Citations

BibTeX
RIS

Show Sections

[1] Abella C.A.M., Benassi M., Santos L.S., Eberlin M., Coelho F., . J. Org. Chem.. 2007;2:4048.

[2] Abonia R., Rengifo E., Quiroga J., Insuasty B., Sanchez A., Cobo J., Low J., Nogueras M., . Tetrahedron Lett.. 2002;43:5617.

[3] Adbo K., Andersson H.S., Ankarloo J., Karlsson J.G., Norell M.C., Olofsson L., Svenson J., Ortegren U., Nicholls I.A., . Bioorg. Chem.. 1999;27:363.

[4] Bag G.G., Kiedrowski G., . Tetrahdron Lett.. 1999;40:289.

[5] Bauer A.W., Kirby W.M.M., Sherris J.C., Truck M., . Am. J. Clin. Pathol.. 1996;45:492.

[6] Bresson C., Luhmer M., Demeunynck M., Mesmaeker A.K.-D., Pierard F., . Tetrahedron Lett.. 2004;45:2863.

[7] Brigita C., Liepinsh E., Vigante B., Sobolevs A., Ozols J., Duburs G., . Tetrahedron Lett.. 2001;42:4239.

[8] Carree F., Pardo C., Galy J.-P., Boyer G., Robin M., Elguero G., . Arkivoc. 2003;1:1.

[9] Classens N., Perard F., Bresson C., Moucheron C., Mesmaeker A.K.-D., . J. Inorg. Biochem.. 2007;101:987.

[10] Cudero J., Padro C., Ramos M., . Tetrahedron. 1997;53(6):2233.

[11] Didier D., Sergeyev S., . Tetrahedron. 2007;63:3864.

[12] Didier D., Tylleman B., Lambert N., Velde C.M.L.V., Blockhuys F., Collas A., Sergeyev S., . Tetrahedron. 2008;64:6252.

[13] Depres N.R., McNitt K.A., Petersen M.E., Brown R.G., Lewis D.E., . Tetrahedron Lett.. 2005;46:2149.

[14] Dethler V.G., . Chemical Insect Attractants and Repellents. Philadeciphia: Blackistan; 1947.

[15] Faroughi M., Jenssen P., Try A.C., . Arkivoc. 2009;2:269.

[16] Farrar W.V., . J. Appl. Chem. 1964:389.

[17] Galaso V., Jones D., Modelli A., . Chem. Phys.. 2003;33–42:288.

[18] Goswami S., Ghosh K., Dasgupta S., . J. Org. Chem.. 2000;65:1907.

[19] Hansson A., Norrby P.-O., Warnmark K., . Tetrahedron Lett.. 1998;39:4565.

[20] Hansson A., Jensen J., Wendt O.F., Warnmark K., . Eur. J. Org. Chem. 2003:3179.

[21] Hansson A., Wixe T., Bergquist K.-E., Warnmark K., . Org. Lett.. 2005;7(10):2019.

[22] Kiehne U., Weilandt T.Y., Lutzen A., . Org. Lett.. 2007;9(7):1283.

[23] Kim K., Choe J.-I., . Bull. Korean Chem. Soc.. 2006;27(11):1737.

[24] Li Z., Xu X., Peng Y., Jiang Z., Ding C., Qian X., . Synthesis. 2005;8:1228.

[25] Mahon A.B., Craig D.C., Try A.C., . Arkivoc. 2008;12:148.

[26] Mas T., Pardo C., Elguero J., . Mendeleev Commun.. 2004;14(6):235.

[27] Mihlbachler K., Kaczmarski K., Morgenstern A.S., Guiochon G., . J. Chromatogr.. 2002;955A:35.

[28] Pardo C., Alkorta I., Elguero J., . Tetrahedron: Asymmetr.. 2006;17:191.

[29] Pardo C., Sesmilo E., Gutierrez-Puebla E., Angeles M., . J. Org. Chem.. 2001;66:1607.

[30] Prelog V., Wieland P., . Helv. Chim. Acta.. 1944;27:1127.

[31] Putnam J., Guiochon G., . J. Chromatogr.. 2009;1216A:8488.

[32] Sathishkumar S., Periasamy M., . Tetrahedron: Asymmetr.. 2006;17:1116.

[33] Sathishkumar S., Periasamy M., . Tetrahedron: Asymmetr.. 2009;20:2257.

[34] Segeyev S., Stas S., Remacle A., Velde C.M.L.V., Dolensky B., Havlik M., Kral V., Cejka J., . Tetrahedron: Asymmetr.. 2009;20:1918.

[35] Spielman M.A., . J. Am. Chem. Soc.. 1935;57:583.

[36] Tálas E., Margitfalvi J., Machytka D., Czugler M., . Tetrahedron: Asymmetr.. 1998;9:4151.

[37] Thirunarayanan G., . J. Indian Chem. Soc.. 2008;85:447.

[38] Thirunarayanan G., Surya S., Srinivasan S., Vanangamudi G., Sathiyendiran V., . Spectrochim. Acta.. 2010;75A:152.

[39] Tröger J., . J. Prakt. Chem.. 1887;36:225.

[40] Try A.C., Painter L., Harding M.M., . Tetrahedron Lett.. 1998;39:9809.

[41] Valík M., Dolensky B., Petříčková H., Vašek P., Král V., . Tetrahedron Lett.. 2003;44:2083.

[42] Valík M., Dolensky B., Herdtweck E., Král V., . Tetrahedron: Asymmetr.. 2005;16:1969.

[43] Valík M., Malina J., Palivec L., Foltýnová J., Tkadlecová M., Urbanová M., Brabec V., Král V., . Tetrahedron. 2006;62:8591.

[44] Vardelle E., Agnes M.-M., Jouannetaud M.-P., Jacquesy J.-C., Marrot J., . Tetrahedron Lett.. 2009;50:1093.

[45] Wu H., Chen X.-C., Wan Y., Ye L., Xin H., Xu H., Yue C., Pang L., Ma R., Shi D., . Tetrahedron Lett.. 2009;50:1062.

Antimicrobial and insect antifeedant activities of some Tröger’s bases

Abstract

Keywords

Substituted Tröger’s bases

Enantioselectivity

IR, NMR and mass spectra

Antimicrobial and insect antifeedant activity

1 Introduction

2 Experimental

2.1 General procedure for the synthesis of substituted Tröger’s bases

3 Results and discussion

3.1 Antimicrobial activities

3.1.1 Evaluation of antibacterial activities

3.1.2 Antifungal activity

3.2 Insect antifeedant activities

3.2.1 Measurement of insect antifeedant activity of Trogers’ bases

Acknowledgements

References

Suggested read for related articles:

We value your privacy