New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities

Steroids
Natalija M KrstićDušan M Sladić

Abstract

The reactions of 17α-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH(2)Cl(2) and/or CCl(4) gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D (1)H-(13)C spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY) enabled complete (1)H and (13)C assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia salina, were eval...Continue Reading

References

Mar 1, 1976·Steroids·E L Foster, R T Blickenstaff
Nov 1, 1996·Chemical & Pharmaceutical Bulletin·N KoizumiK Shibata
May 1, 1982·Planta medica·B N MeyerJ L McLaughlin
Apr 17, 2007·Steroids·Natalija M KrstićVladimir D Pavlović
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Natalija M KrstićVladimir D Pavlović

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Citations

Jun 15, 2014·Steroids·Anabel Romero-LópezJosé Luis Vega-Baez
May 3, 2013·Daru : Journal of Faculty of Pharmacy, Tehran University of Medical Sciences·Mohsen VosooghiAlireza Foroumadi
Jun 14, 2014·The Journal of Steroid Biochemistry and Molecular Biology·Natalija M KrstićDušan M Sladić
Jun 4, 2013·The Journal of Steroid Biochemistry and Molecular Biology·Atul GuptaArvind S Negi
May 30, 2014·Chemical Reviews·Ranju Bansal, Pratap Chandra Acharya

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