کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1408711 1501769 2013 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
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
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
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
چکیده انگلیسی


• Crystallization features of chiral drugs propranolol and pindolol precursors are investigated.
• 3-(4-Indolyloxy)-propane-1,2-diol is a conglomerate formative compound.
• Hydrogen N–H⋯N bonds are responsible for conglomerate stabilization.
• 3-(1-Naphthyloxy)-propane-1,2-diol forms weakly stable solid racemic compound.
• The predominant formation of the racemic compound may be due to kinetic effects.

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.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 1045, 6 August 2013, Pages 104–111
نویسندگان
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