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Phase behavior and crystal structure of 3-(1-naphthyloxy)- and 3-(4-indolyloxy)-propane-1,2-diol, synthetic precursors of chiral drugs propranolol and pindolol
- Source :
- Journal of Molecular Structure. 1045:104-111
- Publication Year :
- 2013
- Publisher :
- Elsevier BV, 2013.
-
Abstract
- Valuable precursors of popular chiral drugs propranolol and pindolol, 3-(1-naphthyloxy)-propane-1,2-diol 3 and 3-(4-indolyloxy)-propane-1,2-diol 4 were investigated by IR spectroscopy, DSC, and X-ray diffraction methods. Both compounds, crystallizing from enantiopure feed material, form “guaifenesin-like” crystal packing in which the classic H-bonded bilayers, framed in both sides by hydrophobic fragments of the molecules, acts as the basic crystal-forming motif. Diol 4 prone to spontaneous resolution and conserves its packing pattern crystallizing from racemate. Under the same conditions, diol 3 forms weakly stable solid racemic compound. Some reasons for such a behavior are identified and discussed.
- Subjects :
- integumentary system
organic chemicals
Organic Chemistry
Diol
Infrared spectroscopy
Crystal structure
Analytical Chemistry
Inorganic Chemistry
Crystal
chemistry.chemical_compound
Enantiopure drug
chemistry
Phase (matter)
polycyclic compounds
medicine
Molecule
Organic chemistry
Pindolol
Spectroscopy
medicine.drug
Subjects
Details
- ISSN :
- 00222860
- Volume :
- 1045
- Database :
- OpenAIRE
- Journal :
- Journal of Molecular Structure
- Accession number :
- edsair.doi...........efda683b46024670f35d53cba31121e7