Palmer, RA;
Lisgarten, DR;
Cockcroft, JK;
Lisgarten, JN;
Talbert, R;
Dines, T;
Bansal, R;
... Suryan, A; + view all
(2019)
Crystal and Molecular Structure and DFT Calculations of the Steroidal Oxime 6E-Hydroximino-androst-4-ene-3,17-dione (C_{19}H_{25}NO_{3}) a Molecule with Antiproliferative Activity.
Journal of Chemical Crystallography
, 49
(1)
pp. 29-36.
10.1007/s10870-018-0747-x.
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Abstract
The single crystal X-ray structure of the novel steroid derivative, 6E-hydroximino-androst-4-ene-3,17-dione (C_{19}H_{25}NO_{3}) (code name RB-499), possessing antiproliferative activity against various cell lines is presented. The analysis produced the following results: chemical formula C_{19}H_{25}NO_{3}; Mr = 315.40; crystals are orthorhombic space group P2_{1}2_{1}2_{1} with Z = 4 molecules per unit cell with a = 6.2609(2), b = 12.5711(4), c = 20.0517(4) Å,Vc = 1578.18(7) Å3, crystal density Dc = 1.327 g/cm^{3}. Structure determination was performed by direct methods, Fourier and full-matrix least-squares refinement. Hydrogens were located in the electron density and refined in position with isotropic thermal parameters. The final R-index was 0.0324 for 3140 reflections with I > 2σ and 308 parameters. The Absolute Structure Parameter − 0.07(5) confirms the correct allocation of the absolute configuration. The presence of the double bond C=O at position 3 in Ring A has caused a distortion from the usual chair conformation and created an unusual distorted sofa conformation folded across an approximate m-plane through C(1)–C(4). Ring B is a distorted chair, its conformation being influenced by the presence of the C(6)=N(6)–O(6)H group in position 6. Ring C is a symmetrical chair. Ring D exhibits both a distorted mirror symmetry conformation [influenced by the C(17)=O(17) group] and a distorted twofold conformation. DFT calculations indicated some degree of flexibility in rings A, C and D with ring A showing the greatest variation in torsion angles. The crystal packing is governed by H-bonds involving O(3), O(6) and O(17). DFT calculations of bond distances and angles, optimized at the B3LYP/6–31++G(d,p) level, were in good agreement with the X-ray structure.
| Type: | Article |
|---|---|
| Title: | Crystal and Molecular Structure and DFT Calculations of the Steroidal Oxime 6E-Hydroximino-androst-4-ene-3,17-dione (C_{19}H_{25}NO_{3}) a Molecule with Antiproliferative Activity |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1007/s10870-018-0747-x |
| Publisher version: | https://doi.org/10.1007/s10870-018-0747-x |
| Language: | English |
| Additional information: | © The Author(s) 2018. This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/). |
| Keywords: | Steroidal oximes, Cytotoxic steroids, Antiproliferates, Crystal structure, X-ray crystallography, DFT calculations |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10063257 |
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