Ultrasound assisted synthesis of 3-alkynyl substituted 2-chloroquinoxaline derivatives: Their in silico assessment as potential ligands for N-protein of SARS-CoV-2

Shaik Shahinshavali; Kazi Amirul Hossain; Abbaraju Venkata Durga Nagendra Kumar; Alugubelli Gopi Reddy; Deepti Kolli; Ali Nakhi; Mandava Venkata Basaveswara Rao; Manojit Pal

doi:10.1016/j.tetlet.2020.152336

Ultrasound assisted synthesis of 3-alkynyl substituted 2-chloroquinoxaline derivatives: Their in silico assessment as potential ligands for N-protein of SARS-CoV-2

Abstract

In view of recent global pandemic the 3-alkynyl substituted 2-chloroquinoxaline framework has been explored as a potential template for the design of molecules targeting COVID-19. Initial in silico studies of representative compounds to assess their binding affinities via docking into the N-terminal RNA-binding domain (NTD) of N-protein of SARS-CoV-2 prompted further study of these molecules. Thus building of a small library of molecules based on the said template became essential for this purpose. Accordingly, a convenient and environmentally safer method has been developed for the rapid synthesis of 3-alkynyl substituted 2-chloroquinoxaline derivatives under Cu-catalysis assisted by ultrasound. This simple and straightforward method involved the coupling of 2,3-dichloroquinoxaline with commercially available terminal alkynes in the presence of CuI, PPh3 and K2CO3 in PEG-400. Further in silico studies revealed some remarkable observations and established a virtual SAR (Structure Activity Relationship) within the series. Three compounds appeared as potential agents for further studies.

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Authors (8)

Shaik Shahinshavali
Kazi Amirul Hossain (formerly: Kazi Hossain)
Abbaraju Venkata Durga Nagendra Kumar
Alugubelli Gopi Reddy
Deepti Kolli
Ali Nakhi
Mandava Venkata Basaveswara Rao
Manojit Pal

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Category:: Articles
Type:: artykuły w czasopismach
Published in:: TETRAHEDRON LETTERS no. 61,
ISSN: 0040-4039
Language:: English
Publication year:: 2020
Bibliographic description:: Shahinshavali S., Hossain K., Kumar A. V. D. N., Reddy A. G., Kolli D., Nakhi A., Rao M. V. B., Pal M.: Ultrasound assisted synthesis of 3-alkynyl substituted 2-chloroquinoxaline derivatives: Their in silico assessment as potential ligands for N-protein of SARS-CoV-2// TETRAHEDRON LETTERS -Vol. 61,iss. 40 (2020), s.152336-
DOI:: Digital Object Identifier (open in new tab) 10.1016/j.tetlet.2020.152336
Verified by:: Gdańsk University of Technology