Anti-tuberculosis activity and its structure-activity relationship (SAR) studies of oxadiazole derivatives: A key review

被引:66
作者
Verma, Santosh Kumar [1 ,2 ]
Verma, Rameshwari [1 ,2 ]
Verma, Shekhar [3 ]
Vaishnav, Yogesh [4 ]
Tiwari, S. P. [5 ]
Rakesh, K. P. [6 ]
机构
[1] Yulin Univ, Sch Chem & Chem Engn, Yulin 719000, Shaanxi, Peoples R China
[2] Yulin Univ, Shaanxi Key Lab Low Metamorph Coal Clean Utilizat, Yulin 719000, Shaanxi, Peoples R China
[3] Pt Deendayal Upadhyay Mem Hlth Sci & Aayush Univ, Univ Coll Pharm Raipur, Raipur 492010, Chhattisgarh, India
[4] Shri Shankaracharya Grp Inst, Shri Shankaracharya Tech Campus, Bhilai 491001, Chhattisgarh, India
[5] Xi An Jiao Tong Univ, Sch Life Sci & Technol, Xian 710049, Shaanxi, Peoples R China
[6] Wuhan Inst Technol, Sch Mat Sci & Engn, Wuhan 430073, Peoples R China
关键词
Oxadiazole; Anti-Tuberculosis; SAR; Drug discovery; MYCOBACTERIUM-TUBERCULOSIS; BIOLOGICAL EVALUATION; 1,3,4-OXADIAZOLE DERIVATIVES; ANTIMYCOBACTERIAL ACTIVITY; MOLECULAR DOCKING; DRUG DISCOVERY; INHIBITORS; ANALOGS; TETRAZOLE; HYBRIDS;
D O I
10.1016/j.ejmech.2020.112886
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
With the increasing number of cases of inactive and drug-resistance tuberculosis, there is an urgent need to develop new potent molecules set for fighting this brutal disease. Medicinal chemistry concerns the discovery, the development, the identification, and the interpretation of the mode of action of biologically active compounds at the molecular level. Molecules bearing oxadiazoles are one such class that could be considered to satisfy this need. Oxadiazole regioisomers have been investigated in drug discovery programs for their capacity to go about as powerful linkers and as pharmacophoric highlights. Oxadiazoles can go about as bioisosteric substitutions for the hydrazide moiety which can be found in first-line anti-TB drugs, and some have been likewise answered to cooperate with more current anti-TB targets. This present review summarizes the current innovations of oxadiazole-based derivatives with potential antituberculosis activity and bacteria discussing various aspects of structure-activity relationship (SAR). (c) 2020 Elsevier Masson SAS. All rights reserved.
引用
收藏
页数:13
相关论文
共 93 条
[1]   Discovery of novel antitubercular 1,5-dimethyl-2-phenyl-4-([5-(arylamino)-1, 3,4-oxadiazol-2-yl]methylamino)-1,2-dihydro-3H-pyrazol-3-one analogues [J].
Ahsan, Mohamed Jawed ;
Samy, Jeyabalan Govinda ;
Jain, Chandra Bhushan ;
Dutt, Kunduri Rajeswar ;
Khalilullah, Habibullah ;
Nomani, Md. Shivli .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) :969-972
[2]   Molecular properties prediction and synthesis of novel 1,3,4-oxadiazole analogues as potent antimicrobial and antitubercular agents [J].
Ahsan, Mohamed Jawed ;
Samy, Jeyabalan Govinda ;
Khalilullah, Habibullah ;
Nomani, Md Shivli ;
Saraswat, Pankaj ;
Gaur, Ramakant ;
Singh, Abhimanyu .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (24) :7246-7250
[3]   Oxadiazole mannich bases: Synthesis and antimycobacterial activity [J].
Ali, Mohamed Ashraf ;
Shaharyar, Mohammad .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (12) :3314-3316
[4]   A solvent free, four-component synthesis and 1,3-dipolar cycloaddition of 4(H)-pyrans with nitrile oxides: Synthesis and discovery of antimycobacterial activity of enantiomerically pure 1,2,4-oxadiazoles [J].
Almansour, Abdulrahman I. ;
Kumar, Raju Suresh ;
Arumugam, Natarajan ;
Sriram, Dharmarajan .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 53 :416-423
[5]   Ribosome Rescue Inhibitors Kill Actively Growing and Nonreplicating Persister Mycobacterium tuberculosis Cells [J].
Alumasa, John N. ;
Manzanillo, Paolo S. ;
Peterson, Nicholas D. ;
Lundrigan, Tricia ;
Baughn, Anthony D. ;
Cox, Jeffery S. ;
Keiler, Kenneth C. .
ACS INFECTIOUS DISEASES, 2017, 3 (09) :634-644
[6]   Design, synthesis and in silico study of pyridine based 1,3,4-oxadiazole embedded hydrazinecarbothioamide derivatives as potent anti-tubercular agent [J].
Ambhore, Ajay N. ;
Kamble, Sonali S. ;
Kadam, Shuddhodan N. ;
Kamble, Rahul D. ;
Hebade, Madhav J. ;
Hese, Shrikant V. ;
Gaikwad, Milind V. ;
Meshram, Rohan J. ;
Gacche, Rajesh N. ;
Dawane, Bhaskar S. .
COMPUTATIONAL BIOLOGY AND CHEMISTRY, 2019, 80 :54-65
[7]   Synthesis and antitubercular activity of imidazo[2,1-b] thiazoles [J].
Andreani, A ;
Granaiola, M ;
Leoni, A ;
Locatelli, A ;
Morigi, R ;
Rambaldi, M .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (09) :743-746
[8]  
[Anonymous], 2017, WHO | Global tuberculosis report
[9]   New Classes of Alanine Racemase Inhibitors Identified by High-Throughput Screening Show Antimicrobial Activity against Mycobacterium tuberculosis [J].
Anthony, Karen G. ;
Strych, Ulrich ;
Yeung, Kacheong R. ;
Shoen, Carolyn S. ;
Perez, Oriana ;
Krause, Kurt L. ;
Cynamon, Michael H. ;
Aristoff, Paul A. ;
Koski, Raymond A. .
PLOS ONE, 2011, 6 (05)
[10]   Aromaticity as a cornerstone of heterocyclic chemistry [J].
Balaban, AT ;
Oniciu, DC ;
Katritzky, AR .
CHEMICAL REVIEWS, 2004, 104 (05) :2777-2812