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The synthesis of a series of isoelectronic analogues of (S)-2-[3-(tert-butylamino)-2-hydroxypropoxy]-3-cyanopyridine (1) are described; included in this group are examples of thiazole, isothiazole, thiadiazole, pyrazine, and the structurally related naphthyridines. All of the compounds are similar to 1 in that they contain a cyano group ortho to the aminohydroxypropoxy side chain and meta to the nitrogen heteroatom. In addition, several related examples, having additional nuclear substituents and/or groups other than CN in the position adjacent to the aminohydroxypropoxy group, were prepared, and beta-adrenoceptor antagonist activity and vasodilating potency were determined. Three compounds, thiazole 2 and isothiazoles 3 and 27, effectively lowered mean arterial pressure in the SH rat at 5 mg/kg. Compounds 2, 3, and 27 increased iliac blood flow and exhibited beta-adrenergic blocking properties in the dog.
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
May 1983,
Journal of medicinal chemistry,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
October 1979,
The Journal of pharmacology and experimental therapeutics,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
December 1979,
Journal of pharmaceutical sciences,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
January 1980,
Drug metabolism and disposition: the biological fate of chemicals,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
September 1976,
Journal of medicinal chemistry,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
June 1971,
Journal of medicinal chemistry,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
May 1976,
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
March 1976,
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
January 1981,
Journal of cardiovascular pharmacology,
J J Baldwin, and
E L Engelhardt, and
R Hirschmann, and
G S Ponticello, and
J G Atkinson, and
B K Wasson, and
C S Sweet, and
A Scriabine
October 1979,
Nihon yakurigaku zasshi. Folia pharmacologica Japonica,
