One-pot synthesis of new benzo[4,5]imidazo[2,1-b]pyrimido[4,5-d][1,3] thiazine-2,4(3H)-dione and benzo[4,5]imidazo[2,1-b][1,3]thiazin-4-one derivatives as new anti-cancer components

被引:5
作者
Batooie, Nasim [1 ,2 ]
Khodaei, Mohammad Mehdi [1 ]
Bahrami, Kiumars [1 ]
Miraghaee, Seyyed Shahram [2 ]
Hosseinzadeh, Nouraddin [3 ]
Sajadimajd, Soraya [4 ]
机构
[1] Razi Univ, Fac Chem, Dept Organ Chem, Kermanshah 6714967346, Iran
[2] Kermanshah Univ Med Sci, Hlth Technol Inst, Med Biol Res Ctr, POB 67155-1616, Kermanshah, Iran
[3] Sharif Univ Technol, Dept Chem, Lab Organ Synth & Nat Prod, POB 11155-9516, Tehran, Iran,
[4] Razi Univ, Fac Sci, Dept Biol, Kermanshah 6714967346, Iran
关键词
Multicomponent reaction; Phosphorus ionic liquid; 2-mercaptobenzimidazole; Anti -cancer activity; HIGHLY FUNCTIONALIZED CYCLOHEXENONES; MULTICOMPONENT REACTIONS; BENZIMIDAZOLE; CATALYST; LIQUID;
D O I
10.1016/j.molstruc.2022.134037
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient and one-pot process has been developed for the synthesis of novel benzo[4,5]imidazo[2,1-b]pyrimido[4,5-d][1,3]thiazine-2,4(3H)-diones and benzo[4,5]imidazo[2,1-b][1,3]thiazin-4-ones from CH acids, aldehydes and 2-mercaptobenzimidazole using hexyltriphenylphosphonium bromide ionic liquid (HTPB) as a green promoter and solvent at ambient temperature. The reaction afforded product s in high yields and short reaction times, bypassing the conventional harsh reaction conditions and without the need for using volatile solvents. In addition, we evaluated the anti-cancer activity of these compounds on different cancer cells, including A431, PC3, and Panc1 and HDF (human dermal fibroblast) normal cells. Notably, we found that these synthesized compounds have prominent anti-cancer effects on skin, prostate, and pancreatic cancers. (c) 2022 Elsevier B.V. All rights reserved.
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页数:8
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