The new Schiff bases of 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles and their antimicrobial activity

被引：2

作者：

Ismailova, D. S. ^{[1
]}

Ziyaev, A. A. ^{[1
]}

Bobakulov, Kh. M. ^{[1
]}

Sasmakov, S. A. ^{[1
]}

Makhmudov, U. S. ^{[1
]}

Yusupova, E. G. ^{[1
]}

Azimova, Sh. S. ^{[1
]}

机构：

[1] Acad Sci Uzbek, Acad S Yu Yunusov Inst Chem Plant Subst, 77 M Ulugbek Str, Tashkent 100170, Uzbekistan

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2019年 / 16卷 / 03期

关键词：

5-(4-Aminophenyl)-1,3,4-oxadiazol-2-thione; Aromatic aldehyde; Amino group; NMR spectra; X-ray analysis; Antimicrobial activity; DERIVATIVES;

D O I：

10.1007/s13738-018-1530-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By the reaction of 5-(4-aminophenyl)-1,3,4-oxadiazolin-2-thione with alkyl halides 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles, 2-4 were obtained. By the reaction of compounds 2-4 with aromatic aldehydes, new Schiff bases 5a-d and 6a-d were synthesized. The structures of synthesized compounds are confirmed by the IR, UV, H-1 NMR for all compounds, C-13 NMR for compounds 3, 4, 5a-5d, 6a, 6d and X-ray for compound 3. All substances were tested in vitro for their antibacterial and antifungal activity. The results showed that Compound 2 exhibited remarkable activity against Candida albicans. Compounds 5a-d were found to exhibit a weak selective activity against Gram-positive bacteria of Bacillus subtilis and compounds 6a-d against Gram-negative bacteria of Escherichia coli.

引用

页码：545 / 551

页数：7

共 50 条

[1] The new Schiff bases of 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles and their antimicrobial activity
D. S. Ismailova
A. A. Ziyaev
Kh. M. Bobakulov
S. A. Sasmakov
U. S. Makhmudov
E. G. Yusupova
Sh. S. Azimova
Journal of the Iranian Chemical Society, 2019, 16 : 545 - 551
[2] Design, Synthesis, and Fungicidal Activity of 2-Alkylthio-5-(1,2,4-triazol-1-ylmethyl)-1,3,4-oxadiazoles
Tsaplin, G. V.
Kazakov, S. A.
Semchukova, M. I.
Alekseeva, E. A.
Alekseenko, A. L.
Chernega, I. M.
Popkov, S. V.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2023, 96 (12) : 1076 - 1085
[3] Synthesis and fungicidal activities of 2-alkylthio-5-(3, 4, 5-tribenzyloxyphenyl)-1, 3, 4-oxadiazoles
Long, De Qing
Li, De Jiang
Cai, Wei Quan
Chen, Sheng Sheng
CHINESE CHEMICAL LETTERS, 2006, 17 (11) : 1427 - 1430
[4] Synthesis of Schiff bases of 2-amino-5-aryl-1,3,4-oxadiazoles and their evaluation for antimicrobial activities
Mishra, P
Rajak, H
Mehta, A
JOURNAL OF GENERAL AND APPLIED MICROBIOLOGY, 2005, 51 (02): : 133 - 141
[5] 1,3,4-oxadiazoles .16. Synthesis and antimicrobial activity of substituted 1,3,4-oxadiazoles
Joshi, N
Korgaokar, S
Parekh, H
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 5 (03) : 241 - 242
[6] Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4-aminophenyl)-1,3,4-thiadiazoles and their Schiff bases
Solak, Nilufer
Rollas, Sevim
ARKIVOC, 2006, : 173 - 181
[7] STUDIES ON 2,5-DISUBSTITUTED-1,3,4-OXADIAZOLES .1. PREPARATION AND ANTIMICROBIAL ACTIVITY OF 2-ARYL-5-(4'-BENZENESULPHONAMIDOPHENYL)-(4'-PYRIDYL)-1,3,4-OXADIAZOLES
PACHHAMIA, VL
PARIKH, AR
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1989, 66 (04) : 250 - 251
[8] STUDIES ON 1,3,4-OXADIAZOLES .10. PREPARATION AND ANTIMICROBIAL ACTIVITY OF 2-ARYL-5-PARA-PHENYLSULPHOPHENYL-1,3,4-OXADIAZOLES
VANSDADIA, RN
RODA, KP
PAREKH, H
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1988, 65 (11) : 809 - 811
[9] STUDIES ON 1,3,4-OXADIAZOLES - PREPARATION AND ANTIMICROBIAL ACTIVITY OF 2-ARYL-5-(5',7'-DIIODO-8'-QUINOLINOXY)-1,3,4-OXADIAZOLES
JOSHI, HS
PARIKH, AR
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1990, 67 (10) : 858 - 859
[10] Synthesis and Fungicidal Activities of 2-Alkylthio-5-(3,4,5-tribenzyloxyphenyl)-l, 3,4-oxadiazoles
De Qing LONG
ChineseChemicalLetters, 2006, (11) : 1427 - 1430

← 1 2 3 4 5 →