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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/20194
Title: Synthesis and cytotoxicity of novel 14α-O-(1,4-disubstituted-1,2,3-triazolyl) ester derivatives of andrographolide
Authors: Mokenapelli S.
Gutam M.
Vadiyaala N.
Yerrabelli J.R.
Banerjee S.
Roy, Partha
Kancha R.K.
Kunduru B.R.
Sagurthi S.R.
Chitneni P.R.
Published in: Natural Product Research
Abstract: A series of novel 14α-O-(1,4-disubstituted-1,2,3-triazolyl) ester derivatives of andrographolide (5a-n) were synthesized from andrographolide (1). For this endeavour, selective esterification at C-14 hydroxyl group of andrographolide (1) with propiolic acid via protection, deprotection strategy followed by 1,4-regioselective [1,3]dipolar cycloaddition of alkyne, azide using Cu(I) catalyzed Click chemistry. All the synthesized derivatives were screened for their cytotoxicity on HCT-15, HeLa and K562 cell lines. Compounds 5c and 5j showed highest activity against HCT-15 and K562 cell lines whereas compound 5a displayed activity in all the three cell lines. Loss of cell viability was not observed with the non-transformed cell line MRC-5 with compounds 5j, 5k, 5h and 2 indicating cytotoxic activity of these compounds towards cancer cell lines. Further, molecular docking analysis and SAR studies of highly active compounds 5c and 5j revealed enhanced binding affinity to the target NF-κB protein. © 2019 Informa UK Limited, trading as Taylor & Francis Group.
Citation: Natural Product Research, 35(2): 289-297
URI: https://doi.org/10.1080/14786419.2019.1628746
http://repository.iitr.ac.in/handle/123456789/20194
Issue Date: 2021
Publisher: Taylor and Francis Ltd.
Keywords: 1,2,3-triazolyl andrographolide esters
Andrographolide
click reaction
cytotoxic activity
SAR studies
ISSN: 14786419
Author Scopus IDs: 57208399637
57208392278
57209475740
57209466768
57192818131
35509207200
11439424000
57190050986
23005879300
56568248700
Author Affiliations: Mokenapelli, S., Natural Products Laboratory, Department of Chemistry, Osmania University, Hyderabad, Telangana, India
Gutam, M., Natural Products Laboratory, Department of Chemistry, Osmania University, Hyderabad, Telangana, India
Vadiyaala, N., Natural Products Laboratory, Department of Chemistry, Osmania University, Hyderabad, Telangana, India
Yerrabelli, J.R., Natural Products Laboratory, Department of Chemistry, Osmania University, Hyderabad, Telangana, India
Banerjee, S., Department of Biotechnology, Indian Institute of Technology, Roorkee, Uttarakhand, India
Roy, P., Department of Biotechnology, Indian Institute of Technology, Roorkee, Uttarakhand, India
Kancha, R.K., Molecular Medicine and Therapeutics Laboratory, Centre for Plant Molecular Biology, Osmania University, Hyderabad, Telangana, India
Kunduru, B.R., Department of Genetics and Biotechnology, Osmania University, Hyderabad, Telangana, India
Sagurthi, S.R., Department of Genetics and Biotechnology, Osmania University, Hyderabad, Telangana, India
Chitneni, P.R., Natural Products Laboratory, Department of Chemistry, Osmania University, Hyderabad, Telangana, India
Funding Details: The authors are thankful to Department of Chemistry, CFRD of Osmania University, Hyderabad, Telangana, India for providing facilities. We wish to thank UGC, New Delhi for the award of Senior Research Fellowship to Sudhakar M. University Grants Committee, UGC; Osmania University, OU
Corresponding Author: Chitneni, P.R.; Natural Products Laboratory, India; email: prasadraoou@yahoo.com
Appears in Collections:Journal Publications [BT]

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