Synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl) amino] propanoic acid and evaluation of anti-microbial activity

被引：9

作者：

Pund, Amit A. ^{[1
]}

Saboo, Shweta S. ^{[2
]}

Sonawane, Gajanan M. ^{[3
]}

Dukale, Amol C. ^{[4
]}

Magare, Baban K. ^{[1
]}

机构：

[1] Shivaji Arts Commerce & Sci Coll, Dept Chem, UG PG & Res Ctr, Aurangabad, Maharashtra, India

[2] Govt Coll Pharm, Aurangabad, Maharashtra, India

[3] Rajarshi Shahu Coll Pharm, Buldhana, Maharashtra, India

[4] Swami Muktanand Coll Sci Yeola, Yeola, Maharashtra, India

来源：

SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 24期

关键词：

Anti-microbial; carbonyldiimidazole; evaluation; pyridine-2-carboxylic acid hydrazide; 1; 3; 4-thiadiazole; SCHIFF-BASE; SPECTRAL CHARACTERIZATION; ANTIOXIDANT ACTIVITIES; CYTOTOXIC ACTIVITIES; 1,3,4-THIADIAZOLE; ANTIBACTERIAL; 1,3,4-OXADIAZOLE; 1,2,4-TRIAZOLE; ANTIFUNGAL; DESIGN;

D O I：

10.1080/00397911.2020.1817488

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The new compoundsAP-1toAP-10were synthesized from starting material (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl) amino]propanoic acid (1). The intermediate 2,5-disubstituted-1,3,4-thiadiazole amine (5) was prepared by coupling of (2S)-3-(Benzyloxy)-2-[(tert-butoxycarbonyl) amino]propanoic acid (1) with pyridine-2-carboxylic acid hydrazide (2) in the presence of carbonyldiimidazole (CDI) followed by 1,3,4-thiadiazole ring formation via diacylhydrazines derivative (3) and deprotection with shorter reaction time and excellent yield. The structures of new compounds were confirmed by spectral analysis. The series of new synthesized compoundsAP-1toAP-10were evaluated for their anti-microbial activitiesin vitroand compoundsAP-1,AP-3,AP-4, andAP-10showed strong activities against all tested microorganisms.

引用

页码：3854 / 3864

页数：11

共 43 条

[1] Synthesis, antitubercular activity and pharmacokinetic studies of some Schiff bases derived from 1-alkylisatin and isonicotinic acid hydrazide (INH)
Aboul-Fadl, T
Mohammed, FAH
Hassan, EAS
[J]. ARCHIVES OF PHARMACAL RESEARCH, 2003, 26 (10) : 778 - 784
[2] Non-carboxylic analogues of naproxen: Design, synthesis, and pharmacological evaluation of some 1,3,4-oxadiazole/thiadiazole and 1,2,4-triazole derivatives
Amir, Mohammad
Kumar, Harish
Javed, Sadique A.
[J]. ARCHIV DER PHARMAZIE, 2007, 340 (11) : 577 - 585
[3] Asati KC, 2006, INDIAN J CHEM B, V45, P526
[4] Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bis hydrazone
Avaji, Prakash Gouda
Kumar, C. H. Vinod
Patil, Sangamesh A.
Shivananda, K. N.
Nagaraju, C.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (09) : 3552 - 3559
[5] Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases
Bagihalli, Gangadhar B.
Avaji, Prakash Gouda
Patil, Sangamesh A.
Badami, Prema S.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (12) : 2639 - 2649
[6] CHAUBEY AK, 2012, INT J PHARM TECH RES, V4, P590
[7] Synthesis, characterization, and analgesic activity of novel schiff base of isatin derivatives
Chinnasamy, Rajaram Prakash
Sundararajan, Raja
Govindaraj, Saravanan
[J]. JOURNAL OF ADVANCED PHARMACEUTICAL TECHNOLOGY & RESEARCH, 2010, 1 (03) : 342 - 347
[8] Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4-thiadiazole derivatives containing 5-phenyl-2-furan
Cui, Zi-Ning
Li, Ya-Sheng
Hu, De-Kun
Tian, Hao
Jiang, Jia-Zhen
Wang, Yuan
Yan, Xiao-Jing
[J]. SCIENTIFIC REPORTS, 2016, 6
[9] Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain
Foroumadi, Alireza
Rineh, Ardeshir
Emami, Saeed
Siavoshi, Farideh
Massarrat, Sadegh
Safari, Fatemeh
Rajabalian, Saeed
Falahati, Mehraban
Lotfali, Ensieh
Shafiee, Abbas
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (11) : 3315 - 3320
[10] Gharu C., 2014, RES J CHEM SCI, V4

← 1 2 3 4 5 →