دورية أكاديمية

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

التفاصيل البيبلوغرافية
العنوان: Ultrasound assisted synthesis of 3-alkynyl substituted 2-chloroquinoxaline derivatives: Their in silico assessment as potential ligands for N-protein of SARS-CoV-2.
المؤلفون: Shahinshavali S; Department of Chemistry, Krishna University, Machilipatnam 521001, Andhra Pradesh, India., Hossain KA; Department of Physical Chemistry, Gdansk University of Technology, Gdańsk, Poland., Kumar AVDN; Department of Chemistry, GIS, GITAM Deemed to be University, Visakhapatnam, Andhra Pradesh, INDIA, 530045., Reddy AG; Department of Pharmacy, Sana College of Pharmacy, Kodad 508 206, Telangana, India., Kolli D; Department of Chemistry, Koneru Lakshmaiah Education Foundation, Green Fields, Vaddeswaram 522502, Andhra Pradesh, India., Nakhi A; Dr. Reddy's Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500046, India., Rao MVB; Department of Chemistry, Krishna University, Machilipatnam 521001, Andhra Pradesh, India., Pal M; Dr. Reddy's Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500046, India.
المصدر: Tetrahedron letters [Tetrahedron Lett] 2020 Oct 01; Vol. 61 (40), pp. 152336. Date of Electronic Publication: 2020 Aug 27.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Elsevier Country of Publication: England NLM ID: 2984819R Publication Model: Print-Electronic Cited Medium: Print ISSN: 0040-4039 (Print) Linking ISSN: 00404039 NLM ISO Abbreviation: Tetrahedron Lett Subsets: PubMed not MEDLINE
أسماء مطبوعة: Publication: Oxford : Elsevier
Original Publication: Oxford, New York, Pergamon Press.
مستخلص: 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, PPh 3 and K 2 CO 3 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.
Competing Interests: The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(© 2020 Elsevier Ltd. All rights reserved.)
References: Nature. 2020 Mar;579(7798):270-273. (PMID: 32015507)
Bioinformatics. 2011 Apr 1;27(7):1021-2. (PMID: 21335612)
J Comput Chem. 2004 Oct;25(13):1605-12. (PMID: 15264254)
Acta Pharm Sin B. 2020 Jul;10(7):1228-1238. (PMID: 32363136)
Bioorg Med Chem Lett. 2012 Oct 15;22(20):6433-41. (PMID: 22981335)
J Med Chem. 1986 Jan;29(1):79-84. (PMID: 3001308)
Org Biomol Chem. 2013 Aug 14;11(30):4930-4. (PMID: 23824158)
J Comput Chem. 2010 Jan 30;31(2):455-61. (PMID: 19499576)
Antiviral Res. 2013 Nov;100(2):446-54. (PMID: 24084488)
Int J Antimicrob Agents. 2020 Mar;55(3):105923. (PMID: 32070753)
Nat Biotechnol. 2020 Apr;38(4):379-381. (PMID: 32205870)
Lancet Infect Dis. 2003 Nov;3(11):722-7. (PMID: 14592603)
Antimicrob Agents Chemother. 1991 Apr;35(4):679-84. (PMID: 2069373)
Nucleic Acids Res. 2005 Jul 1;33(Web Server issue):W289-94. (PMID: 15980472)
J Comput Chem. 2009 Dec;30(16):2785-91. (PMID: 19399780)
J Crit Care. 2020 Jun;57:279-283. (PMID: 32173110)
Mol Biosyst. 2016 Jan;12(1):59-66. (PMID: 26542199)
فهرسة مساهمة: Keywords: Alkyne; COVID-19; Chloroquinoxaline; In silico study; Ultrasound
تواريخ الأحداث: Date Created: 20200902 Latest Revision: 20200919
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC7449981
DOI: 10.1016/j.tetlet.2020.152336
PMID: 32868957
قاعدة البيانات: MEDLINE
الوصف
تدمد:0040-4039
DOI:10.1016/j.tetlet.2020.152336