Azab Mohamed E, Rizk Sameh A, Amr Abd El-Galil E
Department of Chemistry, Faculty of Science, University of Ain Shams, Cairo 11566, Egypt.
Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.
Molecules. 2015 Oct 7;20(10):18201-18. doi: 10.3390/molecules201018201.
Treatment of 2,3-diaryloxirane-2,3-dicarbonitriles 1a-c with different nitrogen nucleophiles, e.g., hydrazine, methyl hydrazine, phenyl hydrazine, hydroxylamine, thiosemicarbazide, and/or 2-amino-5-phenyl-1,3,4-thiadiazole, afforded pyrazole, isoxazole, pyrrolotriazine, imidazolothiadiazole derivatives 2-5, respectively. Reacting pyrazoles 2a-c with aromatic aldehydes and/or methyl glycinate produced Schiff's bases 7a-d and pyrazolo[3,4-b]-pyrazinone derivative 8, respectively. Treating 7 with ammonium acetate and/or hydrazine hydrate, furnished the imidazolopyrazole and pyrazolotriazine derivatives 9 and 10, respectively. Reaction of 8 with chloroacetic acid and/or diethyl malonate gave tricyclic compound 11 and triketone 12, respectively. On the other hand, compound 1 was reacted with active methylene precursors, e.g., acetylacetone and/or cyclopentanone producing adducts 14a,b which upon fusion with ammonium acetate furnished the 3-pyridone derivatives 15a,b, respectively. Some of newly synthesized compounds were screened for activity against bacterial and fungal strains and most of the newly synthesized compounds showed high antimicrobial activities. The structures of the new compounds were elucidated using IR, ¹H-NMR, (13)C-NMR and mass spectroscopy.
用不同的氮亲核试剂，如肼、甲基肼、苯肼、羟胺、硫代氨基脲和/或2-氨基-5-苯基-1,3,4-噻二唑处理2,3-二芳基环氧乙烷-2,3-二甲腈1a - c，分别得到吡唑、异恶唑、吡咯并三嗪、咪唑并噻二唑衍生物2 - 5。吡唑2a - c与芳香醛和/或甘氨酸甲酯反应，分别生成席夫碱7a - d和吡唑并[3,4 - b]吡嗪酮衍生物8。用醋酸铵和/或水合肼处理7，分别得到咪唑并吡唑和吡咯并三嗪衍生物9和10。8与氯乙酸和/或丙二酸二乙酯反应，分别得到三环化合物11和三酮12。另一方面，化合物1与活性亚甲基前体，如乙酰丙酮和/或环戊酮反应，生成加合物14a,b，它们与醋酸铵熔融后，分别得到3 - 吡啶酮衍生物15a,b。对一些新合成的化合物进行了抗细菌和真菌菌株活性筛选，大多数新合成的化合物显示出高抗菌活性。使用红外光谱、¹H - NMR、(13)C - NMR和质谱对新化合物的结构进行了阐明。
