Mohareb R.M.Hana H.Y.Department of Organic ChemistryFaculty of PharmacyUniversity of Modern Sciences and Arts (MSA)October CityGizaEgypt; Hormone DepartmentNational Research CentreDokkiGizaEgypt2020-01-252020-01-25200813300075https://doi.org/10.2478/v10007-007-0043-3PubMed ID 18337206https://t.ly/EXDPKScopusThe aim of this work was to synthesize steroidal heterocycles and to elucidate the potential role of these compounds as antimicrobial agents. The synthesis of steroidal heterocycles containing the pyrazole, isoxazole, thiazole, pyrane, pyridine, pyridazine, or benzopyrane ring attached to the pregnene nucleus is reported. Progesterone (1) reacts with dimethyl formamide dimethyl acetal to form enamine 2. Heterocyclization of 2 with hydrazines, hydroxylamine, glycine, ethyl acetoacetate or cyanomethylene afforded novel steroidal heterocyclic derivatives. The in vitro antimicrobial evaluation showed that all synthesized compounds show activity against the used strains of Gram positive bacteria and fungi.EnglishAntimicrobialEnamineProgesteronePyranePyrazole17 (1 phenylpyrazol 3 yl)androst 4 en 3 one17 (2 amino 3 cyanopyran 6 yl)androst 4 en 3 one17 (2 hydroxy 3 acetylpyran 6 yl)androst 4 en 3 one17 (2 hydroxy 3 cyanopyran 6 yl)androst 4 en 3 one17 (3 cyanomethylpyridazin 6 yl)androst 4 en 3 one17 (isoxazol 6 yl)androst 4 en 3 one17 (pyrazol 3 yl)androst 4 en 3 one17 (pyrol 3 yl)androst 4 en 3 one20 (1 phenyl 2 cyanopropenoylhydrazono)pregn 4 en 3 one20 (4 oxothiazol 2 acetylhydrazonyl 2 yl)pregn 4 en 3 one20 (coumarin 3 carbohydrazonyl)pregn 4 en 3 one20 (cyanoacetylhydrazono)pregn 4 en 3 one20 hydrazono n (4 amino 3 cyano 2,6 dioxopyridin 1 yl)pregn 4 en 3 one20 hydrazono n (4,6 dimethyl 2 oxopyridin 1 yl)pregn 4 en 3 one21 (dimethylaminoacryloyl 20 (ethylacetoacetato)pregn 4 en 3 oneampicillinbenzo[a]pyrenecycloheximideenamineisoxazoleprogesteronepyran derivativepyrazolepyridazinethiazoleunclassified drugantimicrobial activityarticleBacillus cereusBacillus subtilisCandida albicanscontrolled studycyclizationdrug structuredrug synthesisEscherichia coliin vitro studynonhumannuclear magnetic resonance spectroscopyphysical chemistryPseudomonas aeruginosaAnti-Infective AgentsDrug DesignDrug Evaluation, PreclinicalFungiGram-Negative BacteriaGram-Positive BacteriaMicrobial Sensitivity TestsMolecular StructureProgesteroneSteroids, HeterocyclicStructure-Activity RelationshipArticlehttps://doi.org/10.2478/v10007-007-0043-3PubMed ID 18337206