Crystal and molecular structure and DFT calculations of the steroidal oxime 6E-hydroximino-androst-4-ene-3,17-dione ( C19H25NO3) a Molecule with Antiproliferative Activity

Journal article


Palmer, R., Lisgarten, D., Cockcroft, J., Lisgarten, J., Talbert, R., Dines, T., Bansal, R., Chandra Archarya, P. and Amruta, S. 2018. Crystal and molecular structure and DFT calculations of the steroidal oxime 6E-hydroximino-androst-4-ene-3,17-dione ( C19H25NO3) a Molecule with Antiproliferative Activity. Journal of Chemical Crystallography. 49, pp. 1-8. https://doi.org/10.1007/s10870-018-0747-x
AuthorsPalmer, R., Lisgarten, D., Cockcroft, J., Lisgarten, J., Talbert, R., Dines, T., Bansal, R., Chandra Archarya, P. and Amruta, S.
Abstract

The single crystal X-ray structure of the novel steroid derivative, 6E-hydroximino-androst-4-ene-3,17-dione ( C19H25NO3) (code name RB-499), possessing antiproliferative activity against various cell lines is presented.

The analysis produced the following results: chemical formula C19H25NO3; Mr = 315.40; crystals are orthorhombic space group P212121 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/cm³. 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 0.0324for 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.

Year2018
JournalJournal of Chemical Crystallography
Journal citation49, pp. 1-8
PublisherSpringer Link
ISSN1572-8854 1074-1542
Digital Object Identifier (DOI)https://doi.org/10.1007/s10870-018-0747-x
FunderESPRC (Grant Reference EP/K0390X/1)..
Publication dates
Online09 Nov 2018
Publication process dates
Deposited14 Dec 2018
Accepted26 Oct 2018
Accepted author manuscript
Output statusPublished
Additional information

Open Access http://creativecommons.org/licenses/by/4.0/

ContributorsPalmer, R., Lisgarten, D., Cockcroft, J., Lisgarten, J., Talbert, R., Dines, T., Bansal, R., Chandra, P. and Suryan, A.
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