[Synthesis of hydrazino alcohols with anti-inflammatory activity].

Abstract

Two-step transformations (N-nitrosation and subsequent LiAlH4 reduction) of alicyclic or acyclic amines and 1,2-amino alcohols containing a secondary amino group were applied to prepare novel N1-substituted hydrazines and hydrazino alcohols with wide structural diversity. Methods for the synthesis of certain enantiopure hydrazino alcohols were also developed. The prepared compounds specifically inhibited Vascular Adhesion Protein-1 (VAP-1), a human endothelial cell adhesion molecule with a well-documented role in inflammation. VAP-1 is a semicarbazide-sensitive amine oxidase, activity of which has been demonstrated to play a role in VAP-1 induced inflammation. Some of the hydrazino alcohols obtained reduced the clinical symptoms of inflammation in experimental arthritis in rodents and appear to be potential novel anti-inflammatory drugs.

• Authors: Laszló Lázár, Zsolt Szakonyi, Eniko Forró, Márta Palkó, Zita Zalán, István Szatmári, Ferenc Fülöp
• Journal: Acta pharmaceutica Hungarica (Acta Pharm Hung) Vol. 74 Issue 1 Pg. 11-8 ( 2004) ISSN: 0001-6659 [Print] Hungary
• Vernacular Title: Gyulladásgátló hatású hidrazinoalkoholok szintézise.
• PMID: 15524044 (Publication Type: English Abstract, Journal Article)

Chemical References

• Alcohols
• Anti-Inflammatory Agents, Non-Steroidal
• Cell Adhesion Molecules
• Hydrazines
• AOC3 protein, human
• Amine Oxidase (Copper-Containing)

Topics

• Alcohols (chemical synthesis)
• Amine Oxidase (Copper-Containing) (analysis, physiology)
• Anti-Inflammatory Agents, Non-Steroidal (chemical synthesis)
• Cell Adhesion Molecules (analysis, physiology)
• Drug Design
• Humans
• Hydrazines (chemical synthesis)
• Inflammation