Synthesis and antibacterial activity of certain quinoline and quinazoline derivatives containing sulfide and sulfone moieties.
作者： Maher F. El-Zohry , Abd El-Hamed N. Ahmed , Farghaly A. Omar , Mohamed A. Abd-Alla
关键词:
摘要: Some aryl and/or heterocyclic mercaptans were allowed to react with 8-quinolyl chloroacetate (II), 8-quinolinoxyacetyl chloride (IV) and 3-(2′-chloroethyl)-2-methyl-3,4-dihydroquinazolin-4-one (X) in dry benzene sodium hydroxide absolute ethanol give corresponding 8-quinolyl-α-mercaptoacetate (V), 8-quinolinoxythioacetate (VI) 3-(2′-arylmercaptoethyl)-2-methyl-4-(3H)quinazolin-4-ones or 3-(2′-heterocyclicmercaptoethyl)-2-methyl-4(3H)-quinazolin-4-ones (XIa-h). The V XI subjected oxidation hydrogen peroxide/acetic acid mixture (1:2) afford the sulfones VII XII. structures of synthesized compounds elucidated by spectroscopic (IR 1H-NMR) elemental analyses. Some these tested for their antimicrobial activities comparison tetracycline as a reference compound.
sci-hub.se 参考文章(21)
NAOKI SHIMIDZU, TOYOZO UNO, Studies on Benzothiazole Derivatives as Chelating Agents. IV. Coordination to Divalent Metal Ions Chemical & Pharmaceutical Bulletin. ,vol. 26, pp. 127- 134 ,(1978) , 10.1248/CPB.26.127
David R. Williams, Metals, ligands, and cancer Chemical Reviews. ,vol. 72, pp. 203- 213 ,(1972) , 10.1021/CR60277A001
G. W. CAMBRIDGE, A. B. A. JANSEN, D. A. JARMAN, Bronchodilating action of vasicinone and related compounds. Nature. ,vol. 196, pp. 1217- 1217 ,(1962) , 10.1038/1961217A0
S. Petersen, H. Herlinger, E. Tietze, W. Siefken, Synthesen in der Reihe des 3-Aminochinazol-4-ons und des 3-Aminobenzotriazin-4-ons Angewandte Chemie. ,vol. 74, pp. 855- 861 ,(1962) , 10.1002/ANGE.19620742112
Harry R. Snyder, Louis E. Benjamin, Nitrofuryl heterocytes. IX. Some derivatives and analogs of 6,7-dihydro-3-(5-nitro-2-furyl)-5H-imidazo[2,1-b]thiazolium chloride. Journal of Medicinal Chemistry. ,vol. 13, pp. 164- 165 ,(1970) , 10.1021/JM00295A056
Abd El-Hamid N. Ahmed, Mohamed A. Abd-Alla, Maher F. El-Zohry, Synthesis and antibacterial activity of some quinazolin containing oxadiazolin‐5‐thione moieties Journal of Chemical Technology & Biotechnology. ,vol. 43, pp. 63- 70 ,(2007) , 10.1002/JCTB.280430107
Richard M. Peck, Anna P. O'Connell, Hugh J. Creech, Heterocyclic derivatives of 2-chloroethyl sulfide with antitumor activity. Journal of Medicinal Chemistry. ,vol. 9, pp. 217- 221 ,(1966) , 10.1021/JM00320A015
S.A. Ibrahim, M.Th. Makhlouf, A.A. Abdel-Hafez, A.M. Moharram, Some transition metal chelates of 8-hydroxyquinoline-5-sulfonamides as possible drugs. Journal of Inorganic Biochemistry. ,vol. 28, pp. 57- 65 ,(1986) , 10.1016/0162-0134(86)80023-X
Tadeusz F. Molinski, D. John Faulkner, An antibacterial pigment from the sponge dendrilla membranosa. Tetrahedron Letters. ,vol. 29, pp. 2137- 2138 ,(1988) , 10.1016/S0040-4039(00)86692-7
D.B. Clayson, J.A.S. Pringle, G.M. Bonser, 4-ethylsulphonylnaphthalene-1-sulphonamide: a new chemical for the study of bladder cancer in the mouse. Biochemical Pharmacology. ,vol. 16, pp. 619- 626 ,(1967) , 10.1016/0006-2952(67)90072-X