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Synthesis and biological evaluation of substituted amide derivatives of C4-ageratochromene dimer analog.

Authors :
Agarwal, Karishma
Gupta, Kratika
Sharma, Kriti
Khanka, Sonu
Singh, Shilpi
Singh, Jyoti
Trivedi, Laxmikant
Vasdev, Prema G.
Luqman, Suaib
Khan, Feroz
Singh, Divya
Gupta, Atul
Source :
Bioorganic & Medicinal Chemistry Letters. Oct2021, Vol. 50, pN.PAG-N.PAG. 1p.
Publication Year :
2021

Abstract

[Display omitted] Substituted amide derivatives of C4-ageratochromene dimer analog (19) were synthesized through structural modification of precocene-I (4a), isolated from the essential oil of Ageratum conyzoides L. The target compounds (18 – 20 , 23I-VI , 24I-VI, and 25I-VI) were evaluated for their bone-forming effect using osteoblast differentiation assay. Seven compounds (23I, 23II, 23IV, 23VI, 24III, 24VI, and 25VI) presented good activity within 1 pM–1 nM concentration. At 1 pM concentration, the most active compound i.e. 23II showed effective mineralization of osteoblast cells along with expression of osteogenic marker genes viz RUNX 2, BMP-2, and type 1 collagen (Type-1 col) without any toxicity towards osteoblast cells. Single crystal X-ray analysis of 18 and 20 revealed that the core nucleus of these molecules bear phenyl rings in a Trans -stilbenoid system and had a good structural correlation with 17β-estradiol (1) and diethylstilbestrol (DES, 3). In-silico study about 23II showed its structural complementarities with the LBD of estrogen receptor (ER) which indicated possible ER-mediated activity of compounds. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
0960894X
Volume :
50
Database :
Academic Search Index
Journal :
Bioorganic & Medicinal Chemistry Letters
Publication Type :
Academic Journal
Accession number :
152631143
Full Text :
https://doi.org/10.1016/j.bmcl.2021.128340