Journal of the Chemical Society. Perkin transactions I p. 2145 - 2150 (1985)
Update date:2022-08-04
Topics:
Al-Hassan, Saiba S.
Cameron, Robert
Nicholson, Sydney H.
Robinson, David H.
Suckling, Colin J.
Wood, Hamish C. S.
Reactions of 7,7-dialkyl-7,8-dihydropteridines which are of potential use in modifying substituents on the pyrazine ring to yield compounds with inhibitory activity against 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase and dihydrofolate reductase are described.These enzymes lie along the pathway leading to the coenzyme tetrahydrofolate. 6-Methyl substituents showed typical reactivity of alkyl groups α- to a pyrazine nitrogen atom and underwent exchange of protium for deuterium under acidic and basic conditions: however, they failed to undergo clean bromination or aldol condensation.Autoxidation of alkyl groups at this position provided ready access to pteridines substituted with carbonyl groups at C-6. 6-Formyl derivatives underwent Wittig-type reactions to yield 6-aralkylidene compounds that are potential inhibitors of dihydrofolate reductase.Alkylation of the anion of 2,4-diamino-7,8-dihydro-6,7,7-trimethylpteridine occured at N-8 in low yield.The reduction of the blocked dihydropteridine system was readily accomplished using catalytic hydrogenation in a manner analogous to that used for normal pteridines.
View MoreShanghai Kefu Chemical Co.,Ltd.
Contact:+86-21-34616196
Address:Room601-602, Xuhui Business Building, No.168, Yude Road, Shanghai
Beijing Merson Pharmaceutical Co., Ltd
Contact:0086-10-80484934 0086-10-80484574/
Address:2nd Floor , No. 2 Building , No. 14 Houshayu Duan, Jingmi Road ,Shunyi District , Beijing 101318, P.R.China
HANGZHOU FOREWIN PHARMA CO., LTD
Contact:+86-571-89053961
Address:hangzhou
Hangzhou Mole's Science & Technology Co.,Ltd.(expird)
Contact:+86-571-56880228
Address:15F Guodu development Building, NO.182 Zhaohui Road
CHANGYI CITY FENGRUN FINE CHEMICAL CO.,LTD
website:http://www.fengrunhuagong.com
Contact:+86-536-7869976
Address:Changyi Coastal Economic Development Zone
Doi:10.1039/j39660001775
(1966)Doi:10.1016/S0040-4020(01)91406-1
(1985)Doi:10.1021/jm00135a005
(1981)Doi:10.1021/ja509893s
(2014)Doi:10.1021/jo01114a007
(1956)Doi:10.1055/s-1997-1207
(1997)
