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dc.creatorKrstić, Natalija
dc.creatorPavlovic, Vladimir D.
dc.creatorNovaković, Irena
dc.creatorMatić, Ivana Z.
dc.creatorSladić, Dušan
dc.date.accessioned2019-01-30T17:34:38Z
dc.date.available2019-01-30T17:34:38Z
dc.date.issued2013
dc.identifier.issn1381-1991
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1200
dc.description.abstractThe reactions of 21-hydroxyprogesterone with Lawesson's reagent in toluene or gave four P-heterocyclic androst-4-ene derivatives (two tautomeric pairs): 4-(3-thioxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2- sulfide (2), 4-(3-thioxoandrost-4-en-17-ylidene)-1,3,2-oxathiaphospholane-2-sulfide (3), 4-(3-oxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2-sulfide (4), and 4-(3-oxoandrost-4-en-17-ylidene)-1,3,2- oxathiaphospholane-2-sulfide (5). The structures of all novel 17-substituted steroids were elucidated from their analytic and spectral data (HRMS, IR, 1D NMR and 2D NMR-HSQC, HMBC, NOESY, COSY). The detailed NMR analysis for all compounds revealed the presence of two pairs of signals in approx. 8:2 ratio indicating the existence of two diastereoisomers (a and b) with different configurations at the phosphorus atom. A parallel analysis of heteronuclear 2D - spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY and COSY) enabled complete and assignments of each isomer and provided evidence for the preferred configuration on phosphorus atom. Cytotoxic activity in vitro was tested against four tumor cell lines (human cervix carcinoma HeLa cells, chronic myelogenous leukemia K-562 and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compounds 3a,b and 4a,b showed a poor activity against HeLa and MDA-MB-453 cell lines, while against MDA-MB-361 cell line, all tested compounds exerted very weak cytotoxic effect. All compounds exerted moderate activity against K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina were evaluated. All tested compounds showed strong antifungal activity.en
dc.publisherSpringer, Dordrecht
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172055/RS//
dc.rightsrestrictedAccess
dc.sourceMolecular Diversity
dc.subject21-Hydroxyprogesteroneen
dc.subjectLawesson's reagenten
dc.subject17-Substituted androstene derivativesen
dc.subjectPhosphorus heterocycleen
dc.subjectcytotoxic activityen
dc.subjectAntimicrobial activityen
dc.titleSynthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivativesen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractНоваковић, Ирена; Крстић, Наталија; Сладиц, Дусан М.; Матиц, Ивана З.; Павловиц, Владимир Д.;
dc.citation.volume17
dc.citation.issue3
dc.citation.spage547
dc.citation.epage561
dc.citation.other17(3): 547-561
dc.citation.rankM21
dc.identifier.pmid23748368
dc.identifier.doi10.1007/s11030-013-9455-9
dc.identifier.rcubConv_3000
dc.identifier.scopus2-s2.0-84880794449
dc.identifier.wos000321912600013
dc.type.versionpublishedVersion


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