title: Efficient approaches to S-alkyl-N-alkylisothioureas: syntheses of histamine H3 antagonist clobenpropit and its analogues.
abstract: 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).
authors.affiliation: Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Yoneyama
authors.forename: Ayako
authors.initials: A
authors.lastname: Shimoda
authors.forename: Lisa
authors.initials: L
authors.lastname: Araki
authors.forename: Kouta
authors.initials: K
authors.lastname: Hatano
authors.forename: Yasuhiko
authors.initials: Y
authors.lastname: Sakamoto
authors.forename: Takushi
authors.initials: T
authors.lastname: Kurihara
authors.forename: Atsushi
authors.initials: A
authors.lastname: Yamatodani
authors.forename: Shinya
authors.initials: S
authors.lastname: Harusawa
mesh_terms: D000478:Alkylation; D054828:Histamine H3 Antagonists / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis*; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D054828:Histamine H3 Antagonists; D007093:Imidazoles; D013890:Thiourea; C086108:clobenpropit