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A series of novel compounds having a benzothiazoline skeleton was studied for their structure-activity relationship (SAR) with respect to Ca2+ antagonistic activity. As test compounds, analogues of 3-acyl-2-arylbenzothiazolines (3) were synthesized. Benzothiazoline derivatives (3) exerted higher Ca2+ antagonistic activity than the corresponding thiazolidine derivatives (2). Effects of substituents R1-R4, the substitution position of the aminoalkoxy group and R2, and the length of the methylene chain on biological activities were examined. Compound 4 [3-acetyl-2-[5-methoxy-2-[4-[N-methyl-N-(3,4,5-trimethoxyphenethyl ) amino]butoxy]phenyl]benzothiazoline hydrochloride] showed a potent Ca2+ antagonistic activity in vitro and dual inhibition on the fast Na+ inward channel and the slow Ca2+ inward channel in Langendorff perfused rabbit hearts. Compound 4 also showed a long-acting hypotensive effect in spontaneously hypertensive rats and prevented acute pulmonary thrombotic death in mice.
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
December 2010,
Bioorganic & medicinal chemistry,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
February 1999,
Journal of medicinal chemistry,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
March 2009,
Bioorganic & medicinal chemistry letters,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
November 2008,
Bioorganic & medicinal chemistry letters,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
February 2016,
Bioorganic & medicinal chemistry,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
June 2011,
Pest management science,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
January 1988,
Journal de pharmacie de Belgique,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
January 2015,
European journal of medicinal chemistry,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
December 2008,
Bioorganic & medicinal chemistry letters,
K Yamamoto, and
M Fujita, and
K Tabashi, and
Y Kawashima, and
E Kato, and
M Oya, and
T Iso, and
J Iwao
August 2012,
European journal of medicinal chemistry,
