Literature DB >> 29353728

Synthesis of pyrazole acrylic acid based oxadiazole and amide derivatives as antimalarial and anticancer agents.

Garima Verma1, Gousia Chashoo2, Asif Ali3, Mohemmed Faraz Khan1, Wasim Akhtar1, Israr Ali4, Mymoona Akhtar1, Mohammad Mumtaz Alam1, Mohammad Shaquiquzzaman5.   

Abstract

Depravity of malaria in terms of morbidity and mortality in human beings makes it a major health issue in tropical and subtropical areas of the globe. Drug counterfeiting and non-adherence to the treatment regimen have significantly contributed to development and spread of multidrug resistance that has highlighted the need for development of novel and more efficient antimalarial drugs. Complexity associated with cancer disease and prevalence of diversified cell populations vindicates highly specific treatment options for treatment of cancer. Resistance to these anticancer agents has posed a great hindrance in successful treatment of cancer. Pondering this ongoing situation, it was speculated to develop novel compounds targeting malaria and cancer. Moving on the same aisle, we synthesized pyrazole acrylic acid based oxadiazole and amide derivatives using multi-step reaction pathways (6a-x; 6a'-h'). Schizont maturation inhibition assay was employed to determine antimalarial potential. Compound 6v emerged as the most potent antimalarial agent targeting falcipain-2 enzyme. Anticancer activity was done using sulforhodamine B assay. Compounds 6b' and 6g' demonstrated promising results against all the tested cell lines. Further, Microscopic view clearly indicated formation of apoptotic bodies, chromatin condensation, shrinkage of cells and bleb formation. Validation of the results was achieved using molecular docking studies. From the obtained results, it was observed that cyclization (oxadiazole) favored antimalarial activity while non-cyclized compounds (amides) emerged as better anticancer agents.
Copyright © 2018 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  1,3,4-Oxadiazole; Amide; Cancer; Malaria; Pyrazole acrylic acids

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Substances:

Year:  2018        PMID: 29353728     DOI: 10.1016/j.bioorg.2018.01.007

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN: 0045-2068            Impact factor:   5.275


  6 in total

Review 1.  Comparative Study of the Synthetic Approaches and Biological Activities of the Bioisosteres of 1,3,4-Oxadiazoles and 1,3,4-Thiadiazoles over the Past Decade.

Authors:  Rana M El-Masry; Hanan H Kadry; Azza T Taher; Sahar M Abou-Seri
Journal:  Molecules       Date:  2022-04-22       Impact factor: 4.927

2.  Development of 1,3,4-Oxadiazole Derived Antifungal Agents and Their Application in Maize Diseases Control.

Authors:  Lin Yao; Guanghua Zhang; Lili Yu; Shaojing Liu; Xiaoku Wang; Tao Fan; Hui Kang; Wenzhi Feng
Journal:  Front Plant Sci       Date:  2022-05-04       Impact factor: 5.753

3.  Synthesis of α-indolylacrylates as potential anticancer agents using a Brønsted acid ionic liquid catalyst and the butyl acetate solvent.

Authors:  Ahmed El-Harairy; Mennatallah Shaheen; Jun Li; Yuzhou Wu; Minghao Li; Yanlong Gu
Journal:  RSC Adv       Date:  2020-04-02       Impact factor: 4.036

4.  Copper-Catalyzed One-Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from Arylacetic Acids and Hydrazides via Dual Oxidation.

Authors:  Chinnari Lekkala; Varaprasad Bodala; Kumari Yettula; Bharat Kumar Karasala; Rajitha Lakshmi Podugu; Siddaiah Vidavalur
Journal:  ACS Omega       Date:  2022-07-27

5.  Novel heterocyclic 1,3,4-oxadiazole derivatives of fluoroquinolones as a potent antibacterial agent: Synthesis and computational molecular modeling.

Authors:  Tejeswara Rao Allaka; Bhaskar Kummari; Naveen Polkam; Naveen Kuntala; Kalyani Chepuri; Jaya Shree Anireddy
Journal:  Mol Divers       Date:  2021-08-02       Impact factor: 2.943

Review 6.  Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives.

Authors:  Teresa Glomb; Piotr Świątek
Journal:  Int J Mol Sci       Date:  2021-06-29       Impact factor: 5.923

  6 in total

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