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