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Aryl acetylene inhibitors for cytochrome P450-based monooxygenase isozymes

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Abstract

The structures of 1-propynylpyrene (1), 4-ethynylbiphenyl (2), 3-ethynylphenanthrene (3), 9-propynylphenanthrene (4) and 9-ethynylphenenthrene (5) have been determined using MoKα radiation.1 crystallizes in the monoclinic space groupP21/n witha=8.972(2)b=10.136(2),c=14.060(2)Å, β=99.77(1)°,V=1260.0(7) Å3,Z=4. Refinement of 1261 reflections gaveR=0.042 andR w =0.054.2 crystallizes in the orthorhombic space groupPbcn witha=17.7159(9),b=6.250(2),c=18.544(2) Å,V=2053(1) Å3,Z=8. Refinement of 1710 observed reflections gaveR=0.046 andR w =0.053.3 crystallizes in the orthorhombic space group Pbca witha=7.891(1),b=16.459(1),c=16.879(2) Å,V=2192.2(7) Å3,Z=8. Refinement of 1520 observed reflections gaveR=0.032 andR w =0.047.4 crystallizes in the orthorhombic space groupP212121 witha=5.8867(6),b=13.476(1).c=14.838(2) Å,V=1177.1(4) Å3,Z=4. Refinement of 1217 observed reflections gaveR=0.041 andR w =0.055.5 crystallizes in the monoclinic space groupP21/c witha=27.755(7),b=5.1447(9),c=15.500(2) Å, β-105.53(2)°,Z=2133(2) Å3,Z=8. There are two independent molecules in the unit cell. Refinement of 1276 observed reflections gaveR=0.061 andR w =0.065. In2–5 there are no significant intermolecular interactions while in1 the molecules are associated in pairs via π-π stacking intarctions. Bond distances within the pyrene and phenanthrene portions of the molecules compare favorably with those found in other derivatives.

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Authors and Affiliations

  1. Department of Chemistry, Tulane University, 70118, New Orleans, Louisiana

    Joel T. Mague

  2. Tulane/Xavier Centre for Bioenvironmental Research and Department of Chemistry Xavier University of Louisiana, 70118, New Orleans, Louisiana

    Maryam Foroozesh & Nancy E. Hopkins

  3. Stine-Haskel Research Center, DuPont Merck Pharmaceutical Company, 1090 Elkton Road, 19714, Newark, Delaware

    Lawrence L. S. Gan

  4. Tulane/Xavier Centre for Bioenvironmental Research and Department of Chemistry, Tulane University, 70118, New Orleans, Louisiana

    William L. Alworth

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  1. Joel T. Mague
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  2. Maryam Foroozesh
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  4. Lawrence L. S. Gan
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  5. William L. Alworth
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Mague, J.T., Foroozesh, M., Hopkins, N.E. et al. Aryl acetylene inhibitors for cytochrome P450-based monooxygenase isozymes. J Chem Crystallogr 27, 183–189 (1997). https://doi.org/10.1007/BF02575987

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  • DOI: https://doi.org/10.1007/BF02575987

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