新型2-甲硫基-3-取代-5,6,7,8-四氢苯并(b)噻吩并[2,3-d]嘧啶-4(3H)-酮的合成、镇痛、抗炎、致溃疡指数及抗菌活性
Synthesis, analgesic, anti-inflammatory, ulcerogenic index and antibacterial activities of novel 2-methylthio-3-substituted-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-4(3H)-ones.
作者信息
Alagarsamy V, Meena S, Ramseshu K V, Solomon V R, Thirumurugan K, Dhanabal K, Murugan M
机构信息
Medicinal Chemistry R&D Laboratory, Arulmigu Kalasalingam College of Pharmacy, Anand Nagar, Krishnankovil, India.
出版信息
Eur J Med Chem. 2006 Nov;41(11):1293-300. doi: 10.1016/j.ejmech.2006.06.005. Epub 2006 Aug 22.
A variety of novel 2-methylthio-3-substituted-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-4(3H)-ones have been synthesized by reacting (2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)dithiocarbamic acid methyl ester (5) with a variety of amines. The starting material dithiocarbamate (5) was synthesized from 2-amino-3-carbethoxy-4,5,6,7-tetrahydrobenzo (b) thiophene (1) by a novel innovative route. The title compounds were investigated for analgesic, anti-inflammatory, ulcerogenicity index and antibacterial activities. While the test compounds exhibited significant activity, the compounds 1-methyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A1), 1-dimethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A2), 1-diethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A3) and 1-pyrrolidinyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A4) showed more potent analgesic activity and the compounds 1-dimethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A2), 1-diethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno-[2,3-d]pyrimidin-3-yl)thiourea (A3) and 1-pyrrolidinyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d] pyrimidin-3-yl)thiourea (A4) showed more potent anti-inflammatory activity than the reference standard diclofenac sodium.
通过使（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）二硫代氨基甲酸甲酯（5）与多种胺反应，合成了多种新型的2-甲硫基-3-取代-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-4（3H）-酮。起始原料二硫代氨基甲酸盐（5）是通过一条新颖的创新路线由2-氨基-3-乙氧羰基-4,5,6,7-四氢苯并（b）噻吩（1）合成的。对标题化合物进行了镇痛、抗炎、致溃疡指数和抗菌活性研究。虽然测试化合物表现出显著活性，但化合物1-甲基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A1）、1-二甲基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A2）、1-二乙基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A3）和1-吡咯烷基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A4）显示出更强的镇痛活性，并且化合物1-二甲基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A2）、1-二乙基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A3）和1-吡咯烷基-3-（2-甲硫基-4-氧代-3H-5,6,7,8-四氢苯并（b）噻吩并[2,3-d]嘧啶-3-基）硫脲（A4）显示出比参比标准双氯芬酸钠更强的抗炎活性。
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