Synthesis, Cytotoxic Evaluation, and In Silico Studies of 4‐Substituted Coumarins

Abstract

in Wiley Online Library (wileyonlinelibrary.com).Two series of coumarins possessing the aniline-and heterocyclic ring at 4 th position have been synthesized and evaluated for their in vitro cytotoxic activity against MCF-7 cancer cell line in MTT assay. Structure activity relationship (SAR) studies reveal that the electron donor group at position-8 of coumarin played an important role in cytotoxic activity. Compound VIId showed the potent cytotoxic activity followed by compound Xa with IC 50 = 6.25 and 6.50 μM, respectively. A docking study has also been carried out for the most potent compound to get an insight into molecular interactions with p50 subunit of NF-κB protein.

PhI(OAc)2/I2‐Mediated Decarboxylative C4‐Amination of Coumarin‐3‐Carboxylic Acids via Csp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions

“…All the synthesized products 3 aa – 3 ge were purified by dint of column chromatographic technique ( see experimental) . Except 3 aa , [10c] all are new compounds and were fully characterized based on their detailed spectral studies, including 1 H NMR, 13 C NMR, 19 F NMR (for 3 fa , 3 fc and 3 fd ), DEPT‐135, 2D NMR (for 3 da ), and HRMS. Further confirmation of the structural framework was verified from the single‐crystal X‐ray analysis for a representative entry, 6‐( tert ‐butyl)‐4‐morpholino‐2 H ‐chromen‐2‐one ( 3 ca ; CCDC 2202645; Figure 1); unit cell parameters: a =9.2276(10) Å, b =12.6825(14) Å, c =13.8446(13) Å, α=73.670(9)°, β=89.381(8)°, γ=79.422(9)°, P‐1) (see Supporting Information ).…”

“…Physical and Spectral Data of Synthesized compounds 3 (3 aa–3 ge) and isolated intermediate 1′i are given below : 4.4.1. 4‐Morpholino‐2H‐chromen‐2‐one ( 3 aa ): [10c] White solid, yield: 74 % (34 mg; 0.2 mmol scale), mp=132–133 °C. 1 H NMR (400 MHz, CDCl 3 ): δ=7.60 (dd, 1H, J= 8.0 and 1.6 Hz, Ar−H), 7.53–7.49 (m, 1H, Ar−H), 7.35 (d, 1H, J= 8.0 Hz, Ar−H), 7.27–7.23 (m, 1H, Ar−H), 5.74 (s, 1H, C 3 − H ), 3.95–3.92 (m, 4H, 2 ⋅ C H 2 ), 3.26–3.24 (m, 4H, 2 ⋅ C H 2 ) ppm.…”

Design, Synthesis, and Anticancer Activity of 3H–benzo[f]chromen‐3‐one Derivatives

“…) with inhibition for two ER+ human breast cancer cell lines with 20‐fold more potency compared with Tamoxifen . Bariwal et al reported 4‐substituted coumarin derivatives as cytotoxic agents against MCF7 cell line . 8‐Methyl‐4‐substituted coumarin derivatives 2a and 2b (Fig.…”