Synthesis and biological evaluation of some nitrogen containing steroidal heterocycles |
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| Authors: | Mervat M. Abdelhalim Eman M. Kamel Samira T. Rabie Nadia R. Mohamed |
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| Affiliation: | 1. Hormones Department, National Research Centre, Dokki, Giza, Egypt;2. Photochemistry Department, National Research Centre, Dokki, Giza, Egypt;3. Chemistry Department, El-Aflaj Girls College, El-Kharj University Kingdom of Saudi Arabia, Saudi Arabia;1. College of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, China;2. Key Laboratory of Development and Application of Forest Chemicals of Guangxi, Nanning 530006, China;3. Xingyi Normal University for Nationalities Xingyi, Guizhou 562400, China;4. Department of Development and Planning, Guangxi University, Nanning, China;5. School of Medicine, Guangxi University, Nanning, Guangxi 530004, China;1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;2. Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eöttvös u. 6, H-6720 Szeged, Hungary;1. Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovi?a 3, 21000 Novi Sad, Serbia;2. Oncology Institute of Vojvodina, Put Dr. Goldmana 4, 21204 Novi Sad, Serbia;3. Department of Physics, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovi?a 4, 21000 Novi Sad, Serbia;1. Department of Chemistry and Physics, Halmos College of Natural Sciences and Oceanography, Nova Southeastern University, Fort Lauderdale, FL 33314, USA;2. Department of Chemistry and Biochemistry, Florida International University, 11200 SW 8th Street, Miami, FL 33199, USA;1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov st. 8, Kazan, Tatarstan 420088 Russia;2. Department of Industrial Chemistry “Toso Montanari”, Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy;3. The Research Institute of Biology, Southern Federal University (SFedU), 194/1 Stachki Ave., 344090 Rostov-on-Don, Russia |
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| Abstract: | epi-Androsterone 1 was converted into its hydrazone derivative through the reaction with hydrazine hydrate 80%. Hydrazonoandrostane derivative 2b reacted with hydrazonoyl halides in the presence of K2CO3 forming the corresponding hydrazopyridazinoandrostane derivatives 6a–d. The 3β-acetyl-17-hydrazonoandrostane derivative 2b reacted with a halogen reagent, benzoyl chloride, to form the non-cyclic 16-benzoylated hydrazone 9.On the other hand, compound 2b produced the corresponding pyridazinoandrostane derivatives 11 and 12 via its reaction with phenacyl bromide and chloroacetone respectively. Reaction of the hydrazono derivative 2b with benzaldehyde in the presence of acetic acid drops led to the formation of the benzylidenehydrazonoandrostane derivative 13. The product 14, phosphinom-ethylenehydrazonoandrostane was obtained by the reaction of the derivative 13 with trisdimethylaminophosphine in the presence of dry benzene. The reaction of compound 2b with phenyl isothiocyanate followed by boiling in chloroacetic acid or thioglycolic acid produced the pyrazoloandrostane derivatives 17 and 18 respectively. The biological activity of compounds 6a, 6d, 11, 12, and 15 was evaluated as inhibitor of growth in a human liver carcinoma cell line and doxorubicine was used for comparison. Compounds 15 and 12 showed a higher potency than the other tested compounds. |
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