TY - JOUR
T1 - Studies on 1,2,4-benzothiadiazine 1,1-dioxides VII and quinazolinones IV
T2 - Synthesis of novel built-in hydroxyguanidine tricycles as potential anticancer agents
AU - Chern, Ji Wang
AU - Liaw, Yen Chywan
AU - Chen, Chien Shu
AU - Rong, Jiann Gwo
AU - Huang, Chien Lin
AU - Chan, Chao Han
AU - Wang, Andrew H.J.
PY - 1993/5/1
Y1 - 1993/5/1
N2 - Two representative built-in hydroxyguanidine tricycles containing 1,2,4-benzothiadiazine 1,1-dioxides (3) and quinazolinones (4) were prepared by reductive cyclization of 1-(2-nitrophenyl-sulfonyl)-2-benzylthio-2-imidazoline (9a), 1-(2-nitrophenylsulfonyl)-2-benzylthio-1,4,5,6-tetrahydropyrimidine (9b), 1-(2-nitrobenzoyl)-2-benzylthio-2-imidazolidine (10a) and 1-(2-nitrobenzoyl)-2-benzyl-thio-1,4,5,6-tetrahydropyrimidine hydrobromide respectively (10b) with zinc dust in acetic acid under ice-cooling. 2,10-Dihydro-10-hydroxy-3H-imidazo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide (3a) and 2,3,4,11-tetrahydro-11-hydroxypyrimido[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide (3b) were found to be active against solid tumor cell lines such as KB, Colo 205, HeLa, and Hepa-2.
AB - Two representative built-in hydroxyguanidine tricycles containing 1,2,4-benzothiadiazine 1,1-dioxides (3) and quinazolinones (4) were prepared by reductive cyclization of 1-(2-nitrophenyl-sulfonyl)-2-benzylthio-2-imidazoline (9a), 1-(2-nitrophenylsulfonyl)-2-benzylthio-1,4,5,6-tetrahydropyrimidine (9b), 1-(2-nitrobenzoyl)-2-benzylthio-2-imidazolidine (10a) and 1-(2-nitrobenzoyl)-2-benzyl-thio-1,4,5,6-tetrahydropyrimidine hydrobromide respectively (10b) with zinc dust in acetic acid under ice-cooling. 2,10-Dihydro-10-hydroxy-3H-imidazo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide (3a) and 2,3,4,11-tetrahydro-11-hydroxypyrimido[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide (3b) were found to be active against solid tumor cell lines such as KB, Colo 205, HeLa, and Hepa-2.
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U2 - 10.3987/COM-92-6285
DO - 10.3987/COM-92-6285
M3 - Article
AN - SCOPUS:0000692265
SN - 0385-5414
VL - 36
SP - 1091
EP - 1103
JO - Heterocycles
JF - Heterocycles
IS - 5
ER -