Journal of the Chemical Society. Perkin transactions I p. 2217 - 2228 (1987)
Update date:2022-09-26
Topics:
Bliss, Edward A.
Griffin, Roger J.
Stevens, Malcolm F. G.
A series of 2,4-diamino-5-(azidoaryl)-6-alkylpyrimidines has been prepared.The azide (36) (MZP) can be reduced by thiol reagents to the corresponding amine (28) but reductive deazidation occured when the series of azidophenyl derivatives was heated with hydrazine hydrate.Degradation of azide (36) in a trifluoroacetic acid-trifluoromethanesulphonic acid mixture at 0 deg C affords a means of introducing the bulky trifluoromethylsulphonyloxy substituent into the hindered ortho-position of the 5-aryl substituent.The products formed from thermolysis and photolysis of the azide (36) and the planar analogue 2,4-diamino-6-azidoquinazoline (70) derive from the triplet nitrene reactive intermediates. The azido compounds are potent inhibitors of rat liver dihydrofolate reductase although not as active as metoprin.The azide (36), as its ethanesulphonic acid salt, was selected for clinical trial on the basis of its ease of synthesis and suitable biological and pharmaceutical properties, and has a shorter biological half-life than compounds of comparable hydrophobicity.
View MoreZhuhai Rundu Pharmaceutical co.,Ltd
Contact:+86-756-7630755
Address:No.6,North Airport Road,Sanzao Town,Jinwan District
Jinan Decheng Hemu Medical Technology Co.,Ltd.
Contact:+86-531-68650525
Address:NO.554 Zhengfeng Road High-new Technology Development Zone
Changsha Goomoo Chemical Technology Co.Ltd
Contact:+86-731-82197655
Address:No.649,Chezhan Rd.(N),Changsha,Hunan,China
Contact:86-574-83851061 86-574-87083208
Address:Room 905, No.3 Building,East Business Center, 456 Xingning Road, Ningbo City,China
Contact:732.938.2777
Address:5012 Industrial Road Farmingdale, NJ 07727
Doi:10.1021/jm00403a002
(1988)Doi:10.1021/ja00220a037
(1988)Doi:10.1134/S1070428008070026
(2008)Doi:10.1016/j.tetlet.2008.12.115
(2009)Doi:10.1021/jo00244a040
(1988)Doi:10.1016/S0040-4039(00)96534-1
(1987)