Oxadiazole a nucleus with versatile biological behaviour

Authors

  • Deepak Sitaram Musmade Assistant Professor, Department of Pharmaceutical chemistry, SRES
  • Shashikant R. Pattan Department of Pharmaceutical Chemistry, Adv. Abasaheb kakade
  • Manjunath S. Yalgatti Head, Department of Pharmaceutical chemistry, Srikripa institute of Pharmaceutical sciences, Medak, Siddipeth, Telangana, 502277

DOI:

https://doi.org/10.7439/ijpc.v5i1.1417

Keywords:

Youth, smoking, Prevalence, Enjoyment

Abstract

The discovery of Oxadiazoles leads to the development of some medicinally important compounds with wide range of biological activities. Oxadiazoles can be synthesized by several methods using carboxylic acid as a starting material. Since Oxadiazoles had been widely investigated, this review is focused on defining the place of oxadiazoles derivatives in biomedical research, highlighting their versatile biological properties, the mode of action and Structure Activity Relationship (SAR) studies for a variety of antimicrobial, anti-tubercular, anti-cancer activity along with some enzyme inhibitory activities.

Downloads

References

Navin B. Patel, Jaymin C. Patel, Synthesis and Antimicrobial Activity of 3-(1,3,4-Oxadiazol-2-yl) quinazolin-4(3H)-ones, Scientia Pharmaceuica, 78, 171

Jnyanaranjan Panda, V. Jagannath Patro, Chandra Sekhar Panda and Jitendriya Mishra, Synthesis, characterization, antibacterial and analgesic evaluation of some 1,3,4- oxadiazole derivatives, Der PharmaChemica, 3(2), 485- 490 (2011)

Rakesh R. Somani, Anuj G. Agrawal, Pushkar P. Kalantri, Pratibha S. Gavarkar and Erik De Clerq, Investigation of 1,3,4-OxadiazoleScaffold as Potentially Active Compounds, International Journal of Drug Design and Discovery, 2(1), 353-360 (2011)

Jignesh P. Raval , Tarunkumar N. Akhaja, Dhaval M. Jaspara, Kruti N. Myangar, Nilesh H. Patel, Synthesis and in vitro antibacterial activity of new oxoethylthio-1,3,4-oxadiazole derivatives, Journal of Saudi Chemical Society (2014) 18, 101

Adil A. Othman , Mebrouk Kihel, Sarah Amara, 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents, Arabian Journal of Chemistry (2014) 32-714-725.

A.H. Shridhar , J. Keshavayya , S.K. Peethambar , H. Joy Hoskeri, Synthesis and biological activities of Bis alkyl 1,3,4-oxadiazole incorporated azo dye derivatives, Arabian Journal of Chemistry (2012) 014-741-758.

Fliur Macaev , Zinaida Ribkovskaia , Serghei Pogrebnoi , Veaceslav Boldescu , Ghenadie Rusu, Nathaly Shvets , Anatholy Dimoglo, Athina Geronikakic, Robert Reynolds, The structure

Jos

Rajesh A. Rane , Pavankumar Bangalore , Sheetal D. Borhade, Preeti K. Khandare, Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4- oxadiazole derivatives as antimicrobial and anti-tubercular agents, European Journal of Medicinal Chemistry 70 (2013) 49-58.

Aziz-ur-Rehman , Asia Siddiqa , Muhammad A. Abbasi , Shahid Rasool ,Sabahat Z. Siddiqui, Irshad Ahmad , Saira Afzal, Synthesis of some new 5-substituted-2-((6-chloro-3,4-methylenedioxyphenyl)methylthio)-1,3,4-Oxadiazole derivatives as suitable antibacterial inhibitors, Bulletin of Faculty of Pharmacy, Cairo University (2014) xxx, xxx

B. Chandrakantha a, Prakash Shetty b, Vijesh Nambiyar c, Nishitha Isloor d, Arun M. Isloor, Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxy phenyl moiety, European Journal of Medicinal Chemistry 45 (2010) 1206

K. Manjunatha , Boja Poojary , Prajwal L. Lobo , Jennifer Fernandes , N. Suchetha Kumari, Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives, European Journal of Medicinal Chemistry 45 (2010) 5225-5233.

Harish Kumar, Sadique A. Javed, Suroor A. Khan, Mohammad Amir, 1,3,4-Oxadiazole/thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: Synthesis and preliminary evaluation of biological properties, European Journal of Medicinal Chemistry 43 (2008) 2688-2698.

Maria Ispikoudi , Michalis Amvrazis , Christos Kontogiorgis, Alexandros E. Koumbis , Konstantinos E. Litinas , Dimitra Hadjipavlou-Litina , Konstantina C. Fylaktakidou, Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives, European Journal of Medicinal Chemistry 45 (2010) 5635-5645.

Mymoona Akhter, Asif Husain, Bismillah Azad, Mohd. Ajmal, Aroylpropionic acid based 2,5-disubstituted-1,3,4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities, European Journal of Medicinal Chemistry 44 (2009) 2372

N.C. Desai , Amit M. Dodiya, Synthesis, characterization and in vitro antimicrobial screening of quinoline nucleus containing 1,3,4-oxadiazole and 2- zetidinone derivatives, Journal of Saudi Chemical Society (2014) 18, 425

Habibullah Khalilullah , Shamshir Khan , Md. Shivli Nomani, Bahar Ahmed, Synthesis, characterization and antimicrobial activity of benzodioxane ring containing 1,3,4-oxadiazole derivatives, Arabian Journal of Chemistry (2011) 012, 567-581.

Antonio Palumbo Piccionello a, Rosario Musumeci b,**, Clementina Cocuzza b, Cosimo Gianluca Fortuna , Annalisa Guarcello a,d, Paola Pierro a,d, Andrea Pace Synthesis and preliminary antibacterial evaluation of Linezolid-like 1,2,4-oxadiazole derivatives, European Journal of Medicinal Chemistry 50 (2012) 441-448.

N.C. Desai , Amit M. Dodiya, Kiran M. Rajpara, Yogesh M. Rupala, Synthesis and antimicrobial screening of 1,3,4-oxadiazole and clubbed thiophene derivatives, Journal of Saudi Chemical Society (2014) 18, 255

Hira Khalid a, Aziz-ur-Rehman , M. Athar Abbasi ,Abdul Malik b, Shahid Rasool a, Khadija Nafeesa a, Irshad Ahmad c, Saira Afzal, Synthesis, spectral analysis and anti-bacterial study of N-substituted derivatives of 2-(5-(1-(phenylsulfonyl)piperidin-4-yl)-1,3,4-oxadiazol- 2-ylthio)acetamide, Journal of Saudi Chemical Society (2013) 014,701-715.

Salahuddin , Mohammad Shaharyar , Avijit Mazumder ,Mohamed Jawed Ahsan, Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole, Arabian Journal of Chemistry (2014) 7, 418

Dalip Kumar , Gautam Patel , Angela K. Chavers , Kuei-Hua Chang , Kavita Shah, Synthesis of novel 1,2,4-oxadiazoles and analogues as potential anticancer agents, European Journal of Medicinal Chemistry 46 (2011) 3085-3092.

Azza T. Taher , Hanan H. Georgey , Hussein I. El-Subbagh, Novel 1,3,4-heterodiazole analogues: Synthesis and in-vitro antitumor activity, European Journal of Medicinal Chemistry 47 (2012) 445-451.

Cai-Jun Chen, Bao-An Song, Song Yang, Guang-Fang Xu, Pinaki S. Bhadury, Lin-Hong Jin, De-Yu Hu, Qian-Zhu Li, Fang Liu, Wei Xue, Ping Lu and Zhuo Chen, Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5- (3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives, Bioorganic & Medicinal Chemistry 15 (2007) 3981

Jumat Salimon , Nadia Salih , Emad Yousif , Ayad Hameed , Ayad Kreem, Synthesis and pharmacological evaluation of 9(10H)-acridone bearing 1,3,4-oxadiazole derivatives as antimicrobial agents, Arabian Journal of Chemistry (2010) 3, 205

Ivan H.R. Tomi , Alaa H.J. Al-Qaisi , Zyad H.J. Al-Qaisi, Synthesis, characterization and effect of bis-1,3,4-oxadiazole rings containing glycine moiety onthe activity of some transferase enzymes, Journal of King Saud University (Science) (2011) 23, 23

Jie Ren, Lin Wu, Wen Qun Xin, Xin Chen , Kun Hu, Synthesis and biological evaluation of novel 4b-(1,3,4-oxadiazole-2-amino)- podophyllotoxin derivatives, Bioorganic & Medicinal Chemistry Letters 22 (2012) 4778

Kai Zhang, Peng Wang, Li-Na Xuan, Xiao-Yun Fu, Fen Jing, Sha Li, Yu-Ming Liu, Bao-Quan Chen, Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety, Bioorganic & Medicinal Chemistry Letters 24 (2014) 5154

Ali Ramazani a,Mehdi Khoobi b, Azar Torkaman a, Fatemeh Zeinali Nasrabadi c, Hamid Forootanfar d, Mojtaba Shakibaie d, Mandana Jafari d, Alieh Ameri d, Saeed Emami e, Mohammad Ali Faramarzi f, Alireza Foroumadi b, Abbas Shafiee, One-pot, four-component synthesis of novel cytotoxic agents 1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines, European Journal of Medicinal Chemistry 78 (2014) 151-156.

Pushpan Puthiyapurayil a,b, Boja Poojary a,*, Chandrashekhar Chikkanna c, Sunil Kumar BuridipadDesign, synthesis and biological evaluation of a novel series of 1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety as cytotoxic agents, European Journal of Medicinal Chemistry 53 (2012) 203-210.

Samreen Gul , Aziz-ur-Rehman , M. Athar Abbasi , Khalid Mohammed Khan , Khadija Nafeesa , Asia Siddiqa , M. Nadeem Akhtar , Muhammad Shahid ,Zinayyera Subhani, Synthesis, antimicrobial evaluation and haemolytic activity of 2-[[5-alkyl/aralkyl substituted-1,3,4- oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl) phenyl]acetamide derivatives, Journal of Saudi Chemical Society (2014015,156-174.

V. Padmavathi, G. Dinneswara Reddy, S. Nagi Reddy, K. Mahesh, Synthesis and biological activity of 2-(bis((1,3,4-oxadiazolyl/1,3,4-thiadiazolyl) methylthio)methylene)malononitriles, European Journal of Medicinal Chemistry 46 (2011) 1367-1373.

Angela G. Koryakova, Yan A. Ivanenkov, Elena A. Ryzhova, Elena A. Bulanova, Ruben N. Karapetian, Olga V. Mikitas, Eugeny A. Katrukha, Vasily I. Kazey, Ilya Okun, Dmitry V. Kravchenko,Yan V. Lavrovsky, Oleg M. Korzinov and Alexandre V. Ivachtchenko, Novel aryl and heteroaryl substituted N-[3-(4-phenylpiperazin- 1-yl)propyl]-1,2,4-oxadiazole-5-carboxamides as selective GSK-3 inhibitors, Bioorganic & Medicinal Chemistry Letters 18 (2008) 3661

Fabio Lo Monte , Thomas Kramer , Jiamin Gu , Martin Brodrecht , Johannes Pilakowski , Ana Fuertes , Juan Manuel Dominguez , Batya Plotkin , Hagit Eldar-Finkelman c, Boris Schmidt, Structure-based optimization of oxadiazole-based GSK-3 inhibitors, European Journal of Medicinal Chemistry 61 (2013) 26-40.

Shaoyong Ke, Zhong Li, Xuhong Qian, 1,3,4-Oxadiazole-3(2H)-carboxamide derivatives as potential novel class of monoamine oxidase (MAO) inhibitors: Synthesis, evaluation, and role of urea moiety, Bioorganic & Medicinal Chemistry 16 (2008) 7565

Terry V. Hughes *, Guozhang Xu, Steven K. Wetter, Peter J. Connolly, Stuart L. Emanuel, Prabha Karnachi,Scott R. Pollack, Niranjan Pandey, Mary Adams, Sandra Moreno-Mazza, Steven A. Middleton, Lee M. Greenberger, A novel 5-[1,3,4-oxadiazol-2-yl]-N-aryl-4,6-pyrimidine diamine having dual EGFR/HER2 kinase activity: Design, synthesis, and biological activity, Bioorganic & Medicinal Chemistry Letters 18 (2008) 4896

Dinneswara Reddy Guda a, Sae-Jin Park b, Min-Woo Lee b, Tack-Joong Kim b, Myong Euy Lee, Syntheses and anti-allergic activity of 2-((bis(trimethylsilyl) methylthio/methylsulfonyl)methyl)-5-aryl-1,3,4-oxadiazoles, European Journal of Medicinal Chemistry 62 (2013) 84-88.

Kaitlin J. Basham , Vasudev R. Bhonde , Collin Kieffer , James B. C. Mack , Matthew Hess , Bryan E. Welma,, Ryan E. Looper, Bis-aryloxadiazoles as effective activators of the aryl hydrocarbon receptor, Bioorganic & Medicinal Chemistry Letters 24 (2014) 2473

Ravindra D. Jadhav , Kishorkumar S. Kadam , Shivaji Kandre , Tandra Guha , M. Mahesh Kumar Reddy , Manoj K. Brahma , Nitin J. Deshmukh , Amol Dixit , Lalit Doshi , Nisha Potdar , Arno A. Enose , Ram A. Vishwakarma , H. Sivaramakrishnan , Shaila Srinivasan , Kumar V.S. Nemmani , Amol Gupte Ashok K. Gangopadhyay , Rajiv Sharma, Synthesis and biological evaluation of isoxazole, oxazole, and Oxadiazole containing heteroaryl analogs of biaryl ureas as DGAT1 inhibitors, European Journal of Medicinal Chemistry 54 (2012) 324-342.

Fliur Macaev, Ghenadie Rusu, Serghei Pogrebnoi, Alexandru Gudima, Eugenia Stingaci, Ludmila Vlad, Nathaly Shvets, Fatma Kandemirli, Anatholy Dimogloa,b,and Robert Reynolds, Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure

Mohamed Jawed Ahsan , Jeyabalan Govinda Samy , Habibullah Khalilullah , Md. Shivli Nomani ,Pankaj Saraswat , Ramakant Gaur , Abhimanyu Singh, Molecular properties prediction and synthesis of novel 1,3,4-oxadiazole analogues as potent antimicrobial and antitubercular agents, Bioorganic & Medicinal Chemistry Letters 21 (2011) 7246

Andrei A. Gakh , Andrey V. Sosnov , Mikhail Krasavin , Tam Luong Nguyen , Ernest Hamel, Identification of diaryl 5-amino-1,2,4-oxadiazoles as tubulin inhibitors: The special case of 3-(2-fluorophenyl)-5- (4-methoxyphenyl)amino-1,2,4-oxadiazole, Bioorganic & Medicinal Chemistry Letters 23 (2013) 1262

Aziz-ur-Rehman , Ambreen Fatima , Muhammad Athar Abbasi , Shahid Rasool , Abdul Malik , Muhammad Ashraf , Irshad Ahmad , Syeda Abida Ejaz, Synthesis of new N-(5-chloro-2-methoxyphenyl)-4- (5-substituted-1,3,4-oxadiazol-2-ylthio)butanamide derivatives as suitable lipoxygenase inhibitors, Journal of Saudi Chemical Society (2013) 016,156-174.

Downloads

Published

2015-01-31

Issue

Section

Review Article

How to Cite

1.
Oxadiazole a nucleus with versatile biological behaviour. Int J of Pharm Chem [Internet]. 2015 Jan. 31 [cited 2025 Jun. 15];5(1):11-20. Available from: https://ssjournals.co.in/index.php/ijpc/article/view/1417