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
收藏
页码：3854 / 3864
页数：11
相关论文
共 50 条
  • [41] Synthesis, characterization, molecular docking and molecular dynamics simulations of novel 2,5-disubstituted-1,3,4-thiadiazole derivatives as potential cholinesterase/monoamine oxidase dual inhibitors for Alzheimer's disease
    AL-Sharabi, Amal A.
    Evren, Asaf Evrim
    Saglik, Beguem Nurpelin
    Yurttas, Leyla
    JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2024, 42 (23): : 13023 - 13041
  • [42] Synthesis of Novel 2,5-Disubstituted-1,3,4-thiadiazoles Clubbed 1,2,4-Triazole, 1,3,4-Thiadiazole, 1,3,4-Oxadiazole and/or Schiff Base as Potential Antimicrobial and Antiproliferative Agents
    Rezki, Nadjet
    Al-Yahyawi, Amjad M.
    Bardaweel, Sanaa K.
    Al-Blewi, Fawzia F.
    Aouad, Mohamed R.
    MOLECULES, 2015, 20 (09): : 16048 - 16067
  • [43] Regioselective Synthesis of 2,5-Disubstituted-1,3,4-thiadiazoles and 1,3,4-Oxadiazoles via Alkyl 2-(Methylthio)-2-thioxoacetates and Alkyl 2-Amino-2-thioxoacetates
    Santhosh, Chikkappaiahnayaka
    Singh, Krishna Ravi
    Sheela, Kalleshappa
    Swaroop, Toreshettahally R.
    Sadashiva, Maralinganadoddi P.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11486 - 11496
  • [44] Studies on biologically active heterocycles .1. Synthesis and antibacterial activity of some 2,5-disubstituted-1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 4-thiazolidinone
    Shafi, SS
    Radhakrishnan, TR
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 5 (02) : 135 - 138
  • [45] Aroylpropionic acid based 2,5-disubstituted-1,3,4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities
    Akhter, Mymoona
    Husain, Asif
    Azad, Bismillah
    Ajmal, Mohd.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (06) : 2372 - 2378
  • [46] November 2017 Convenient Synthesis and Biological Activity of Mono and Diacyl 2,5-Dimercapto-1,3,4-thiadiazole Derivatives
    Jasiak, Karolina
    Kudelko, Agnieszka
    Wroblowska, Monika
    Biernasiuk, Anna
    Malm, Anna
    Krawczyk, Maria
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3241 - 3249
  • [47] Design, Synthesis, and Anti-Alzheimer Activity of 2,5-Disubstituted 1,3,4-Thiadiazole: Kinetic Studies, Molecular Docking, and MD Simulations
    M. L. Sujatha
    Prabhu Jalihal
    Manjunatha S. Katagi
    Durgesh Paresh Bidye
    Sheshagiri R. Dixit
    B. P. Nandeshwarappa
    Russian Journal of Bioorganic Chemistry, 2025, 51 (2) : 912 - 931
  • [48] Synthesis, crystal structures, and biological activity of zinc(II) complexes derived from 2-amino-1,3,4-thiadiazole derivatives
    Zhu, Hui-Long
    Liu, Yu-Wei
    Tang, Zong-Ming
    Yin, Fu-Jun
    Liu, Wei-Wei
    Cao, Zhi-Ling
    Bao, Juan
    Li, Meng
    Qin, Ling-Yan
    Shi, Da-Hua
    INORGANIC AND NANO-METAL CHEMISTRY, 2017, 47 (01) : 78 - 81
  • [49] Asymmetric synthesis of non-natural amino acid derivatives: (2R/3S) and (2S/3R) 2-(tert-butoxycarbonylamino)-3-cyclohexyl-3-phenyl propanoic acids
    Yang, Rui
    Guo, Ya-Fei
    Gao, Zhan-Yong
    Zhao, Qian
    Zhang, Qian-Yang
    Lin, Jun
    JOURNAL OF CHEMICAL RESEARCH, 2015, (02) : 86 - 89
  • [50] Synthesis, anti-HIV, and antifungal activity of new benzensulfonamides bearing the 2,5-disubstituted-1,3,4-oxadiazole moiety
    Zareef, Muhammad
    Iqbal, Rashid
    Al-Masoudi, Najim A.
    Zaidi, Javid H.
    Arfan, Muhammad
    Shahzad, Sohail A.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (02) : 281 - 298
12345