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Solvent‐Free Synthesis and In Vitro Antitumor Activity of a New Class of ( Z )‐3‐Arylidene‐1 H ‐pyrano[3,4‐ b ]quinolin‐4(3 H )‐ones
Author(s) -
Li Yang,
Tang Bingyue,
Dong Shiyu,
Gao Wentao,
Jiang Wenting,
Chen Yu
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904434
Subject(s) - moiety , chemistry , quinoline , solvent , base (topology) , in vitro , grinding , stereochemistry , combinatorial chemistry , organic chemistry , materials science , mathematics , biochemistry , mathematical analysis , composite material
Abstract In the present investigation, an efficient and green synthesis of an intriguing array of structurally novel quinoline‐based α‐arylidene cycloketones i. e., ( Z )‐3‐arylidene/ferrocenylmethylene‐5‐methyl/phenyl‐1 H ‐pyrano[3,4‐ b ]quinolin‐4(3 H )‐ones ( 6 a‐z , 6 aa and 6 ab ) has been successfully accomplished involving solvent‐free reaction between pyrano[3,4‐ b ]quinolin‐4(3 H )‐ones ( 7 a‐b ) and various aromatic aldehydes by simple hand‐grinding in a mortar and pestle using KOH as base at room temperature. The synthetic strategy has the attractive features such as experimental simplicity, mild and environmentally benign reaction conditions, easy work‐up procedure and good yields. A primary screening for their in vitro inhibitory activities against cancer cell lines A549, HT29 and T‐24 revealed that compounds 6 g and 6 t containing 3,4,5‐trimethoxyphenyl moiety showed promising antitumor activity against A549 (IC 50 = 3.68 ± 0.69 and 4.82 ± 0.19 μmol•mL −1 ) and HT29 (IC 50 = 6.69 ± 1.16 and 7.69 ± 0.64 μmol•mL −1 .