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Steroids and related studies, part 66: Crystal and molecular structure of 17a-(2-acetoxyethyl)-17a-aza-d-homo-5-androsten-3β-yl-acetate methiodide (HS465), a monoquaternary azasteroid incorporating an acetylcholine-like moiety

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Abstract

The crystal stucture of a synthetic monoquaternary azasteroid containig an acetylcholine-like moiety, 17a-(2-acetoxyethyl)-17a-aza-d-homo-5 androsten-3β-yl-acetate methiodide (HS465) (C26H42NO4)+I−, has been determined by the heavy-atom method and refined by full-matrix least squares toR=0.0410 for 2462 reflections, using MoKα radiation (λ=0.7114 Å). The crystals are monoclinic:P21,a=15.244(4),b=9.009(6),c=9.886(3) Å,β=104.26°(3),Z=2. RingsA andC have distorted-chair conformations, ring d-homo is a symmetrical chair, and ringB is a half-chair. The acetoxyethyl side-group appended to N(17a) simulates an acetylcholine-like moiety, and exhibits a conformation similar to that frequently adopted by acetylcholine itself in the presence of heavy anions.

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Authors and Affiliations

  1. Department of Crystallography, Birkbeck College, Malet Street, WC1E 7HX, London, England

    Tapan K. Chattopadhyay & Rex A. Palmer

  2. Department of Pharmaceutical Sciences, Panjab University, 160014, Chandigarh, India

    Harkishan Singh & Dharam Paul

Authors
  1. Tapan K. Chattopadhyay
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  2. Rex A. Palmer
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  3. Harkishan Singh
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  4. Dharam Paul
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Chattopadhyay, T.K., Palmer, R.A., Singh, H. et al. Steroids and related studies, part 66: Crystal and molecular structure of 17a-(2-acetoxyethyl)-17a-aza-d-homo-5-androsten-3β-yl-acetate methiodide (HS465), a monoquaternary azasteroid incorporating an acetylcholine-like moiety. Journal of Crystallographic and Spectroscopic Research 16, 233–254 (1986). https://doi.org/10.1007/BF01161111

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