Display options
Cite
Asselin AA, Humber LG, Crosilla D, et al. Indole-phenol bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analogue of labetalol. J Med Chem. 1986;29(6):1009-15doi: 10.1021/jm00156a019.
Asselin, A. A., Humber, L. G., Crosilla, D., Oshiro, G., Wojdan, A., Grimes, D., Heaslip, R. J., Rimele, T. J., & Shaw, C. C. (1986). Indole-phenol bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analogue of labetalol. Journal of medicinal chemistry, 29(6), 1009-15. https://doi.org/10.1021/jm00156a019
Asselin, A A, et al. "Indole-phenol bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analogue of labetalol." Journal of medicinal chemistry vol. 29,6 (1986): 1009-15. doi: https://doi.org/10.1021/jm00156a019
Asselin AA, Humber LG, Crosilla D, Oshiro G, Wojdan A, Grimes D, Heaslip RJ, Rimele TJ, Shaw CC. Indole-phenol bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analogue of labetalol. J Med Chem. 1986 Jun;29(6):1009-15. doi: 10.1021/jm00156a019. PMID: 3012084.
Copy Download .nbib Format: NLM
Share it on

J Med Chem. 1986 Jun;29(6):1009-15. doi: 10.1021/jm00156a019.

Indole-phenol bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analogue of labetalol.

Journal of medicinal chemistry

A A Asselin, L G Humber, D Crosilla, G Oshiro, A Wojdan, D Grimes, R J Heaslip, T J Rimele, C C Shaw

PMID: 3012084 DOI: 10.1021/jm00156a019

Abstract

The synthesis of 5-[hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-7- carboxamide, 5, a pyrrolo analogue of labetalol, is described. Compound 5 was found to reduce blood pressure in spontaneously hypertensive rats with an ED50 of 5 mg/kg po, without causing any decrease in heart rate. Isolated tissue studies with 5 shows that it is a nonselective beta-adrenoceptor antagonist and that it is a weaker alpha-adrenoceptor antagonist with a relative selectivity for alpha 1-receptors. Additionally, the compound displayed significant beta-adrenoceptor intrinsic sympathomimetic activity. Evidence is presented that the beta-adrenoceptor antagonist and agonist properties of 5 are mediated via hydrogen-bond formation with the receptor.

Similar articles

Cited by

Substances

MeSH terms

Publication Types

LinkOut - more resources