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

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

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.

Original languageEnglish (US)
Article number152336
JournalTetrahedron Letters
Volume61
Issue number40
DOIs
StatePublished - Oct 1 2020
Externally publishedYes

Bibliographical note

Funding Information:
The authors thank the management of Dr. Reddy's Institute of Life Sciences, Hyderabad, India, for continuous support and encouragement.

Publisher Copyright:
© 2020 Elsevier Ltd

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Keywords

  • Alkyne
  • Chloroquinoxaline
  • COVID-19
  • In silico study
  • Ultrasound

PubMed: MeSH publication types

  • Journal Article

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