Rajasekaran A, Thampi P P
Department of Medicinal Chemistry, Arulmigu Kalasalingam College of Pharmacy, Anand Nagar, Krishnankoil 626 190, TamilNadu, India.
Eur J Med Chem. 2004 Mar;39(3):273-9. doi: 10.1016/j.ejmech.2003.11.016.
A series of novel 5[beta-(phenothiazinyl-10-yl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles (3-14) have been synthesized via condensation of 5-[beta-(phenothiazinyl-10-yl)ethyl]-1-2,3,4-tetrazole (2) with various acylating/sulphonating reagents. 5-[beta-(phenothiazinyl-10-yl)ethyl]-1-2,3,4-tetrazole was synthesized by cyanoethylation of phenothiazine with acrylonitrile and Triton B, followed by the cycloaddition of 3-(phenothiazin-10-yl)-propionitrile (1) with sodium azide and ammonium chloride. The compounds were screened for analgesic activity, anti-inflammatory activity and ulcerogenicity index. Out of the 12 compounds synthesized, compound (5) 5[beta-(phenothiazinyl-10-yl)ethyl]-1-(benzoyl)-1,2,3,4-tetrazole, compound (11) 5[beta-(phenothiazinyl-10-yl)ethyl]-1-(p-tolyl)-1,2,3,4-tetrazole showed promising analgesic activity and compound (6) 5[beta-(phenothiazinyl-10-yl)ethyl]-1-(p-chlorobenzoyl)-1,2,3,4-tetrazole and compound (8) 5[beta-(phenothiazinyl-10-yl)ethyl]-1-(p-nitrobenzoyl)-1,2,3,4-tetrazole showed promising anti-inflammatory activity.
通过5-[β-(吩噻嗪-10-基)乙基]-1,2,3,4-四唑(2)与各种酰化/磺化试剂缩合，合成了一系列新型的5-[β-(吩噻嗪-10-基)乙基]-1-(酰基)-1,2,3,4-四唑(3-14)。5-[β-(吩噻嗪-10-基)乙基]-1,2,3,4-四唑是通过吩噻嗪与丙烯腈和Triton B进行氰乙基化反应，然后3-(吩噻嗪-10-基)丙腈(1)与叠氮化钠和氯化铵进行环加成反应合成的。对这些化合物进行了镇痛活性、抗炎活性和致溃疡指数筛选。在合成的12种化合物中，化合物(5)5-[β-(吩噻嗪-10-基)乙基]-1-(苯甲酰基)-1,2,3,4-四唑、化合物(11)5-[β-(吩噻嗪-10-基)乙基]-1-(对甲苯基)-1,2,3,4-四唑显示出有前景的镇痛活性，化合物(6)5-[β-(吩噻嗪-10-基)乙基]-1-(对氯苯甲酰基)-1,2,3,4-四唑和化合物(8)5-[β-(吩噻嗪-10-基)乙基]-1-(对硝基苯甲酰基)-1,2,3,4-四唑显示出有前景的抗炎活性。
