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1: J Org Chem. 2008 Mar 21;73(6):2096-104. Epub 2008 Feb 16.Click here to read Links

Efficient approaches to S-alkyl-N-alkylisothioureas: syntheses of histamine H3 antagonist clobenpropit and its analogues.

Yoneyama H, Shimoda A, Araki L, Hatano K, Sakamoto Y, Kurihara T, Yamatodani A, Harusawa S.

Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan.

S-Alkyl-N-alkylisothioureas were efficiently synthesized via synthetic approach (A) using 3-phenylpropionyl isothiocyanate (PPI). The utility of the approach was proved by the syntheses of clobenpropit, a potent histamine H(3) antagonist, and its analogues. Alternatively, clobenpropit could be prepared via intramolecular amide cleavage (B) with use of 2-nitrophenylacetyl isothiocyanate (NPAI).

PMID: 18278935 [PubMed - indexed for MEDLINE]