Nα-Urocanylhistamine A Natural Histamine Derivative 英文参考文献.docVIP

Molecules 2002, 7, 813-816 molecules ISSN 1420-3049 Nα-Urocanylhistamine: A Natural Histamine Derivative Paul W. Baures, Karupaiyan Kaliyan, and John Desper ?,* Department of Chemistry, 111 Willard Hall, Kansas State University, Manhattan, Kansas, 66506, USA. ? Current Address: Signature BioScience, Inc., 1240 S. 47th Street, Richmond, CA 94804, USA. Tel. (+1) 510 323-1051, Fax: (+1) 510 323-1002. * Author to whom correspondence should be addressed; e-mail: pbaures@ Received: 22 October 2002; in revised form: 2 December 2002 / Accepted: 2 December 2002 / Published: 2 December 2002 Abstract: Nα-Urocanylhistamine and two related compounds were synthesized by using PyBOP coupling protocols. These compounds represent naturally occurring histamine derivatives. Keywords: Amide coupling, histamine, urocanic acid, imidazole. Introduction Nα-Urocanylhistamine (1) was reported in 1973 as being naturally occurring in neogastropod mollusks [1]. It is one of several natural histamine derivatives known [2], although little information exists about the possible role of this compound in the living systems where it is found. Moreover, there are no literature reports describing the synthesis of this compound or of closely related analogs. Herein we report the synthesis of 1-3, work that was initially undertaken as part of a project to discover new classes of histamine H2 receptor agonists. These compounds are structurally related to compounds that have proven to be useful in metal complexation [3] and non-enzymatic catalysis [4].  Molecules 2002, 7 814 Results and Discussion The coupling reactions were straightforward with benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) [5], although the reactions were unsuccessful when attempted with either dicyclohexylcarbodiimide (DCC) or 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl). In the case of DCC, a reagent that