Synthesis of novel ring-substituted histidines and histamines

被引:22
作者
Jain, R
Cohen, LA
King, MM
机构
[1] NIDDK,NIH,BIOORGAN CHEM LAB,BETHESDA,MD 20892
[2] GEORGE WASHINGTON UNIV,DEPT CHEM,WASHINGTON,DC 20052
关键词
D O I
10.1016/S0040-4020(97)00177-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of novel 2-cycloalkyl-L-histidines and 2-cycloalkylhistamines via radical alkylation with cycloalkylcarboxylic acids and silver nitrate in the presence of 10% H2SO4 by ammonium persulfate is described The method is also extended to the synthesis of 1,2-dialkyl-L-histidines and 1,2-dialkylhistamines. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4539 / 4548
页数:10
相关论文
共 21 条
[1]  
*AM CHEM SOC, 1995, 210 NAT M AM CHEM SO
[2]   PHENACYL-DIRECTED ALKYLATION OF IMIDAZOLES - A NEW REGIOSPECIFIC SYNTHESIS OF 3-SUBSTITUTED L-HISTIDINES [J].
CHIVIKAS, CJ ;
HODGES, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3591-3594
[3]   2-alkyl-substituted histamines and hydroxyethylimidazoles with G-protein-stimulatory activity [J].
Detert, H ;
Leschke, C ;
Togel, W ;
Seifert, R ;
Schunack, W .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (05) :397-405
[4]   NEW SYNTHESIS OF IMIDAZOLE DERIVATIVES .1. PREPARATION OF 2-SUBSTITUTED IMIDAZOLE-4-ALCOHOLS [J].
DZIURON, P ;
SCHUNACK, W .
ARCHIV DER PHARMAZIE, 1973, 306 (05) :347-350
[5]   A GENERAL, SELECTIVE, AND CONVENIENT PROCEDURE OF HOMOLYTIC FORMYLATION OF HETEROAROMATIC BASES [J].
GIORDANO, C ;
MINISCI, F ;
VISMARA, E ;
LEVI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :536-537
[6]  
GONZALEZ FB, 1991, B CHEM SOC JPN, V64, P674
[7]   INHIBITORY EFFECTS OF HISTIDINE ANALOGS ON GROWTH AND PROTEIN-SYNTHESIS BY PLASMODIUM-FALCIPARUM INVITRO [J].
HOWARD, RJ ;
ANDRUTIS, AT ;
LEECH, JH ;
ELLIS, WY ;
COHEN, LA ;
KIRK, KL .
BIOCHEMICAL PHARMACOLOGY, 1986, 35 (09) :1589-1596
[8]   Regiospecific alkylation of histidine and histamine at N-1 (tau) [J].
Jain, R ;
Cohen, LA .
TETRAHEDRON, 1996, 52 (15) :5363-5370
[9]  
JAIN R, 1996, IN PRESS TETRAHEDRON
[10]  
JAIN RK, UNPUB