Faculty Collaboration Database

Synthesis of 6-alkoxy and 6-hydroxy-alkyl amine derivatives of braylin as vasorelaxing agents. Bioorg Med Chem Lett 2023 Jun 01;89:129311

Date

05/07/2023

Pubmed ID

37149230

DOI

10.1016/j.bmcl.2023.129311

Scopus ID

2-s2.0-85159203421 (requires institutional sign-in at Scopus site)   1 Citation

Abstract

Braylin (10b) is a 8,8-dimethyl chromenocoumarin present in the plants of the family Rutaceae and Meliaceae and possesses vasorelaxing and anti-inflammatory activities. In this study, six 6-alkoxy (10b, 15-19), and twelve 6-hydroxy-alkyl amine (20a-20l) derivatives of braylin (11 and 12) were synthesized to delineate its structural requirement for vasorelaxing activity. The synthesized compounds were evaluated for vasorelaxation response in preconstricted intact rat Main Mesenteric Artery (MMA). The compounds showed l-type VDCC channel blockade depended and endothelium-independent vasorelaxation within the range of Emax < 50.00-96.70 % at 30 µM. Amongst all, 6-alkoxy derivatives were more active than 6-hydroxy-alkyl amine derivatives. The structural refinements about braylin showed that deletion of its methoxy group or homologation beyond ethoxy group presented deleterious effect on vasorelaxation response of braylin. Interestingly, substituting the ethoxy group in 10b presented the best activity and selectivity towards l-type VDCC channel blockade, a specific target cardiovascular function.

Author List

Nainawat KS, Singh S, Agarwal K, Iqbal H, Rani P, Bhatt D, Khan S, Chanda D, Bawankule DU, Tandon S, Khan F, Kumar Gupta A, Gupta A

Author

Hina Iqbal PhD Postdoctoral Researcher 2 in the Physiology department at Medical College of Wisconsin

MESH terms used to index this publication - Major topics in bold

Alcohols
Amines
Animals
Calcium Channels, L-Type
Rats
Vasodilation