title: Design and synthesis of D-ring steroidal isoxazolines and oxazolines as potential antiproliferative agents against LNCaP, PC-3 and DU-145 cells.
abstract: Two series of novel steroidal isoxazolines and oxazolines were synthesized through different routes from dehydroepiandrosterone acetate and pregnenolone acetate, respectively. The synthesis of the analogs of both series is multistep and proceeds in good overall yields. While the key step in the synthesis of former is the cycloaddition of aromatic nitrile oxides across α,β-unsaturated olefins, it is the condensation of α,β-azidoalcohols with aromatic aldehydes in the later. Compounds of both the series were tested for their cytotoxic activities against LNCaP, PC-3 and DU-145 prostate cancer cell lines. Amongst all the compounds of both the series screened for their prostate cancer activity, compound 6a, 6e and 12a are the most active especially against LNCaP and DU-145 cancer cell lines.
authors.affiliation: Department of Chemistry, Islamia College of Science and Commerce, Srinagar 190009, India; Department of Chemistry and Biochemistry, University of Arizona, Tucson 85721, USA. Electronic address: abidrrl@gmail.com.
authors.forename: Abid H
authors.initials: AH
authors.lastname: Banday
authors.affiliation: Department of Chemistry and Biochemistry, University of Arizona, Tucson 85721, USA.
authors.forename: Aswini K
authors.initials: AK
authors.lastname: Giri
authors.affiliation: Department of Chemistry, Islamia College of Science and Commerce, Srinagar 190009, India.
authors.forename: Rifat
authors.initials: R
authors.lastname: Parveen
authors.affiliation: Department of Chemistry, Islamia College of Science and Commerce, Srinagar 190009, India.
authors.forename: Nusrat
authors.initials: N
authors.lastname: Bashir
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D006801:Humans; D008297:Male; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013256:Steroids / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D010080:Oxazoles; D013256:Steroids
keywords: Azidoalcohols; Cytotoxicity; Dehydroepiandrosterone; Isoxazolines; Oxazolines; Pregnenolone