Molecular and absolute crystal structure of pindolol-1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol: A specific beta-adrenoreceptor antagonist with partial agonist activity

Tapan K. Chattopadhyay, Rex A. Palmer, Daruka Mahadevan

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

The crystal and molecular structure of pindolol, 1-(1H indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol, has been determined by direct methods. Crystals are tetragonal, {Mathematical expression}, a=b=15.809(4), c=11.246(2) Å, Z=8, Dc=1.174 mg m-3. The final R-factor for 2271 reflections with I>2σ(I) is 0.038. Refinement by full-matrix least-squares on F2 also enabled the absolute configuration of the structure to be established. The molecule is essentially planar, including much of the side-chain which is stabilized by the existence of two intramolecular H-bonds, between the ethyl oxygen and OH group, and between the OH and side-chain amide groups, respectively. The crystal structure is formed by three intermolecular hydrogen bonds including two side-chain-side-chain interactions, between ethyl oxygen to amide and OH to amide, and an interaction between the side-chain OH to indole NH.

Original languageEnglish (US)
Pages (from-to)195-199
Number of pages5
JournalJournal of Chemical Crystallography
Volume25
Issue number4
DOIs
StatePublished - Apr 1 1995
Externally publishedYes

Keywords

  • amide
  • beta blockers
  • Pindolol

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

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