Synthesis and antibacterial activity of certain quinoline and quinazoline derivatives containing sulfide and sulfone moieties.

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 and/or sodium hydroxide in absolute ethanol to give corresponding 8-quinolyl-alpha-mercaptoacetate (V), 8-quinolinoxythioacetate (VI) and 3-(2'-arylmercaptoethyl)-2-methyl-4-(3H)quinazolin-4-ones or 3-(2'-heterocyclicmercaptoethyl)-2-methyl-4(3H)-quinazolin-4 -ones (XIa-h). The mercaptans V and XI were subjected to oxidation with hydrogen peroxide/acetic acid mixture (1:2) to afford the corresponding sulfones VII and XII. The structures of the synthesized compounds were elucidated by spectroscopic (IR and 1H-NMR) and elemental analyses. Some of these compounds were tested for their antimicrobial activities in comparison with tetracycline as a reference compound.

[1]  T. Molinski,et al.  An antibacterial pigment from the sponge dendrilla membranosa. , 1988 .

[2]  A. Moharram,et al.  Some transition metal chelates of 8-hydroxyquinoline-5-sulfonamides as possible drugs. , 1986, Journal of inorganic biochemistry.

[3]  F. Vögtle,et al.  Ligandstruktur und Komplexierung, XL. Nichtcyclische Kronenether‐artige Ester und ihre Metallion‐Komplexe , 1979 .

[4]  N. Shimidzu,et al.  Studies on Benzothiazole Derivatives as Chelating Agents. IV. Coordination to Divalent Metal Ions , 1978 .

[5]  D. Williams.  Metals, ligands, and cancer. , 1972, Chemical reviews.

[6]  H. Snyder,et al.  Nitrofuryl heterocytes. IX. Some derivatives and analogs of 6,7-dihydro-3-(5-nitro-2-furyl)-5H-imidazo[2,1-b]thiazolium chloride. , 1970, Journal of medicinal chemistry.

[7]  W. Peters,et al.  The chemotherapy of rodent malaria. VI. The action of some sulphonamides alone or with folic reductase inhibitors against malaria vectors and parasites. I. Introduction and anti-vector studies. , 1968, Annals of tropical medicine and parasitology.

[8]  D. Clayson,et al.  4-ethylsulphonylnaphthalene-1-sulphonamide: a new chemical for the study of bladder cancer in the mouse. , 1967, Biochemical pharmacology.

[9]  H. J. Creech,et al.  Heterocyclic derivatives of 2-chloroethyl sulfide with antitumor activity. , 1966, Journal of medicinal chemistry.

[10]  R. A. Kulp,et al.  New sedative and hypotensive 3-substituted 2,4(1H,3H)-quinazolinediones. , 1965, Journal of medicinal chemistry.

[11]  H. J. Creech,et al.  FURTHER INVESTIGATIONS OF HETEROCYCLIC ALKYLATING AGENTS. , 1964, Journal of medicinal chemistry.

[12]  D. A. Jarman,et al.  Bronchodilating Action of Vasicinone and Related Compounds , 1962, Nature.

[13]  W. Siefken,et al.  Synthesen in der Reihe des 3‐Aminochinazol‐4‐ons und des 3‐Aminobenzotriazin‐4‐ons , 1962 .

[14]  C. Bianchi,et al.  THE ANTICONVULSANT PROPERTIES OF 2‐METHYL‐3‐p‐BROMOPHENYL‐3H‐4‐QUINAZOLONE HYDROCHLORIDE (B.D.H. 1880) AND SOME RELATED COMPOUNDS , 1960, The Journal of pharmacy and pharmacology.

[15]  A. Ravina.  [Clinical study of a new synthetic non-barbituric hypnotic: 2-methyl-3-o-tolyl-4-quinazolone]. , 1959, La Presse medicale.

[16]  B. R. Baker,et al.  AN ANTIMALARIAL ALKALOID FROM HYDRANGEA. XII. SYNTHESIS OF 3-[β-KETO-γ-(3-HYDROXY-2-PIPERIDYL) PROPYL]-4-QUINAZOLONE, THE ALKALOID , 1952 .

[17]  S. Gordon,et al.  AN ANTIMALARIAL ALKALOID FROM HYDRANGEA. III. DEGRADATION , 1952 .

[18]  S. Gordon,et al.  AN ANTIMALARIAL ALKALOID FROM HYDRANGEA. II. ISOLATION , 1952 .

[19]  O. Nagel.  Über o-Chinolyloxylessigsäure , 1897 .