Premium
Synthesis of Novel Pyrimido[4,5‐ b ]quinolin‐4‐ones with Potential Antitumor Activity
Author(s) -
Insuasty Braulio,
Becerra Diana,
Quiroga Jairo,
Abonia Rodrigo,
Nogueras Manuel,
Cobo Justo
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1510
Subject(s) - chemistry , oxidizing agent , in vitro , catalysis , stereochemistry , cancer cell lines , chloranil , combinatorial chemistry , medicinal chemistry , cancer cell , cancer , organic chemistry , biochemistry , medicine
The 5,6,7,8,9,10‐hexahydro‐2‐methylthiopyrimido[4,5‐ b ]quinolines 4a , 4b , 4c , 4d , 5a , 5b , 5c , 5d and their oxidized forms 6a , 6b , 6c , 6d , 7a , 7b , 7c , 7d were obtained from the reaction of 6‐amino‐2‐(methylthio)pyrimidin‐4(3 H )‐one 2 or 6‐amino‐3‐methyl‐2‐(methylthio)pyrimidin‐4(3 H )‐one 3 and α , β ‐unsaturated ketones 1a , 1b , 1c , 1d using BF 3 .OEt 2 as catalyst and p ‐chloranil as oxidizing agent. Some of the new compounds were evaluated in the US National Cancer Institute (NCI), where compound 5a presented remarkable activity against 46 cancer cell lines, with the most important GI 50 values ranging from 0.72 to 18.4 μM from in vitro assays.