Regiospecific synthesis of 2,3-disubstituted-L-histidines and histamines

被引:33
作者
Narayanan, S [1 ]
Vangapandu, S [1 ]
Jain, R [1 ]
机构
[1] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, SAS Nagar 160062, Punjab, India
关键词
D O I
10.1016/S0960-894X(01)00154-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Regiospecific synthesis of 2,3-disubstituted-L-histidines and 2,3-disubstituted histamines starting from L-histidine methyl ester and histamine is reported, The key step involves homolytic free radical alkylation via silver catalyzed oxidative decarboxylation of alkylcarboxylic acids with ammonium persulfate. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1133 / 1136
页数:4
相关论文
共 23 条
[1]   SILVER(I)-CATALYZED OXIDATIVE DECARBOXYLATION OF ACIDS BY PEROXYDISULFATE - ROLE OF SILVER(II) [J].
ANDERSON, JM ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) :1651-&
[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]   Histaprodifens:: Synthesis, pharmacological in vitro evaluation, and molecular modeling of a new class of highly active and selective histamine H1-receptor agonists [J].
Elz, S ;
Kramer, K ;
Pertz, HH ;
Detert, H ;
ter Laak, AM ;
Kühne, R ;
Schunack, W .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (06) :1071-1084
[4]   Ring-substituted histaprodifen analogues as partial agonists for histamine H1 receptors:: synthesis and structure-activity relationships [J].
Elz, S ;
Kramer, K ;
Leschke, C ;
Schunack, W .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (01) :41-52
[5]   IMIDAZOLE-SUBSTITUTED ANALOGS OF TRH LIMIT BEHAVIORAL DEFICITS AFTER EXPERIMENTAL BRAIN TRAUMA [J].
FADEN, AI ;
LABROO, VM ;
COHEN, LA .
JOURNAL OF NEUROTRAUMA, 1993, 10 (02) :101-108
[6]   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
[7]  
GONZALEZ FB, 1991, B CHEM SOC JPN, V64, P674
[8]  
GOOT H, 2000, EUR J MED CHEM, V35, P5
[9]   Potent antagonists of somatostatin: Synthesis and biology [J].
Hocart, SJ ;
Jain, R ;
Murphy, WA ;
Taylor, JE ;
Morgan, B ;
Coy, DH .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (07) :1146-1154
[10]   Highly potent cyclic disulfide antagonists of somatostatin [J].
Hocart, SJ ;
Jain, R ;
Murphy, WA ;
Taylor, JE ;
Coy, DH .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (11) :1863-1871