Synthesis of progesterone heterocyclic derivatives of potential antimicrobial activity

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dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorMohareb R.M.
dc.contributor.authorHana H.Y.
dc.contributor.otherDepartment of Organic Chemistry
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherUniversity of Modern Sciences and Arts (MSA)
dc.contributor.otherOctober City
dc.contributor.otherGiza
dc.contributor.otherEgypt; Hormone Department
dc.contributor.otherNational Research Centre
dc.contributor.otherDokki
dc.contributor.otherGiza
dc.contributor.otherEgypt
dc.date.accessioned2020-01-25T19:58:34Z
dc.date.available2020-01-25T19:58:34Z
dc.date.issued2008
dc.descriptionScopus
dc.description.abstractThe 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.en_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=19398&tip=sid&clean=0
dc.identifier.doihttps://doi.org/10.2478/v10007-007-0043-3
dc.identifier.doiPubMed ID 18337206
dc.identifier.issn13300075
dc.identifier.otherhttps://doi.org/10.2478/v10007-007-0043-3
dc.identifier.otherPubMed ID 18337206
dc.identifier.urihttps://t.ly/EXDPK
dc.language.isoEnglishen_US
dc.relation.ispartofseriesActa Pharmaceutica
dc.relation.ispartofseries58
dc.subjectAntimicrobialen_US
dc.subjectEnamineen_US
dc.subjectProgesteroneen_US
dc.subjectPyraneen_US
dc.subjectPyrazoleen_US
dc.subject17 (1 phenylpyrazol 3 yl)androst 4 en 3 oneen_US
dc.subject17 (2 amino 3 cyanopyran 6 yl)androst 4 en 3 oneen_US
dc.subject17 (2 hydroxy 3 acetylpyran 6 yl)androst 4 en 3 oneen_US
dc.subject17 (2 hydroxy 3 cyanopyran 6 yl)androst 4 en 3 oneen_US
dc.subject17 (3 cyanomethylpyridazin 6 yl)androst 4 en 3 oneen_US
dc.subject17 (isoxazol 6 yl)androst 4 en 3 oneen_US
dc.subject17 (pyrazol 3 yl)androst 4 en 3 oneen_US
dc.subject17 (pyrol 3 yl)androst 4 en 3 oneen_US
dc.subject20 (1 phenyl 2 cyanopropenoylhydrazono)pregn 4 en 3 oneen_US
dc.subject20 (4 oxothiazol 2 acetylhydrazonyl 2 yl)pregn 4 en 3 oneen_US
dc.subject20 (coumarin 3 carbohydrazonyl)pregn 4 en 3 oneen_US
dc.subject20 (cyanoacetylhydrazono)pregn 4 en 3 oneen_US
dc.subject20 hydrazono n (4 amino 3 cyano 2,6 dioxopyridin 1 yl)pregn 4 en 3 oneen_US
dc.subject20 hydrazono n (4,6 dimethyl 2 oxopyridin 1 yl)pregn 4 en 3 oneen_US
dc.subject21 (dimethylaminoacryloyl 20 (ethylacetoacetato)pregn 4 en 3 oneen_US
dc.subjectampicillinen_US
dc.subjectbenzo[a]pyreneen_US
dc.subjectcycloheximideen_US
dc.subjectenamineen_US
dc.subjectisoxazoleen_US
dc.subjectprogesteroneen_US
dc.subjectpyran derivativeen_US
dc.subjectpyrazoleen_US
dc.subjectpyridazineen_US
dc.subjectthiazoleen_US
dc.subjectunclassified drugen_US
dc.subjectantimicrobial activityen_US
dc.subjectarticleen_US
dc.subjectBacillus cereusen_US
dc.subjectBacillus subtilisen_US
dc.subjectCandida albicansen_US
dc.subjectcontrolled studyen_US
dc.subjectcyclizationen_US
dc.subjectdrug structureen_US
dc.subjectdrug synthesisen_US
dc.subjectEscherichia colien_US
dc.subjectin vitro studyen_US
dc.subjectnonhumanen_US
dc.subjectnuclear magnetic resonance spectroscopyen_US
dc.subjectphysical chemistryen_US
dc.subjectPseudomonas aeruginosaen_US
dc.subjectAnti-Infective Agentsen_US
dc.subjectDrug Designen_US
dc.subjectDrug Evaluation, Preclinicalen_US
dc.subjectFungien_US
dc.subjectGram-Negative Bacteriaen_US
dc.subjectGram-Positive Bacteriaen_US
dc.subjectMicrobial Sensitivity Testsen_US
dc.subjectMolecular Structureen_US
dc.subjectProgesteroneen_US
dc.subjectSteroids, Heterocyclicen_US
dc.subjectStructure-Activity Relationshipen_US
dc.titleSynthesis of progesterone heterocyclic derivatives of potential antimicrobial activityen_US
dc.typeArticleen_US
dcterms.isReferencedByDesarnaud, F., Dothi, A.N., Brown, A.M., Lemke, G., Suter, U., Baulieu, E.E., Schumacher, M., Progesterone stimulates the activity of the promoters of peripheral myelin protein-22 and protein zero genes in Schwann cells (1998) J. Neurochem, 71, pp. 1765-1768; Melcangi, R.C., Magnaghi, V., Cavarretta, I., Zucchi, I., Bovolin, P., D'Urso, D., Martini, L., Progesterone derivatives are able to influence peripheral myelin protein-22 and P0 gene expression: Possible mechanisms of action (1999) J. Neurosci. Res, 56, pp. 349-357. , DOI: 10.1002/(SICI)1097- 454719990515; Mohareb, R.M., Ho, J.Z., Elfarouk, F.E., Synthesis of thiophenes, azoles and azines with potential biological activity by employing the versatile heterocyclic precursor N-benzoylcyanoacetylhydrazine (2007) J. Chin. Chem. Soc, 54, pp. 1053-1066; Shams, H.Z., Mohareb, R.M., Helal, M.H., Mahmoud, A.E., Synthesis, structure elucidation, and biological evaluation of some fused and/or pendant thiophene, pyrazole, imidazole, thiazole, triazole, triazine and coumarin systems based on cyanoacetic 2-[(benzoylamino)thioxomethyl]hydrazide (2007) Phosphorus Sulfur, 182, pp. 237-263. , DOI: 10.1080/ 1042500600892776; Mohareb, R.M., Ho, J.Z., Mohamed, A.A., Uses of 1-cyanoacetyl-4- phenyl-3-thiosemicarbazide in heterocyclic synthesis: Synthesis of thiazole, coumarin and pyridine derivatives with antimicrobial and antifungal activities (2007) Phosophus Sulfur, 182, pp. 1661-1681. , DOI: 10.1080/ 10426500701289914; Nomenclature of Steroids (1989) Pure Appl. Chem, 61, pp. 1783-1822. , IUPAC, Joint Commission on Biochemical Nomenclature JCBN; The Nomenclature of Steroids, Recommendations (1989), Eur (1989) J. Biochem, 186, pp. 429-458. , IUPAC, Joint Commission on Biochemical Nomenclature JCBN; Abdelhamid, O., Abdelhalim, M.M., Elmegeed, G.A., New routes to steroidal heterocyclic derivatives: Synthesis of biologically active pyrazol- and isoxazolylpregnene derivatives (2007) J. Heterocyclic Chem, 44, pp. 7-11; Hawkey, P.M., Lewis, A.A., (1994) Medical Bacteriology - A Practical Approach, pp. 181-194. , Oxford University Press, Oxford; Rameshkumar, N., Ashokkumar, M., Subramanian, E.H., Ilavarasan, E.R., Sridhar, S.K., Synthesis of 6-flouro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives as potential antimicrobial agents (2003) Eur. J. Med. Chem, 38, pp. 1001-1004. , DOI: 10.1016/S0223-5234(03)00151; Mohareb, R.M., Ibrahim, R.A., Ho, J.Z., The reaction of cyanoacetylhydrazine with -?-bromoacetophenone: Novel synthesis of 1,3,4-oxadiazine, pyridazine and coumarin derivatives (2007) J. Chil. Chem. Soc, 52, pp. 1076-1081; Archana, V., Srivastava, K., Kumar, A., Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents (2002) Eur. J. Med. Chem, 37, pp. 873-882. , DOI: 10.1016/S0223-5234(02) 01389-2; D. I. Brahmbhatt, S. Shashibala and K. C. Patel, Characterization and biological activity of some polycoumarin ethylenes, Eur. Polymer J. 35 (1999) 317-324; DOI: 101016/Chodankar and S. Seshadri, Absorption-emission spectra studies of 3-hetarylcoumarin, Dyes S0014-3057(98)00127; Chodankar, N.K., Seshadri, S., Absorption-emission spectra studies of 3-hetarylcoumarin (1984) Dyes Pigments, 6, pp. 331-340
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