ABSTRACT
Pyrazolo[1,5-a]pyrimidines were synthesized via the reaction of ketene dithioacetals and 5-aminopyrazoles. The antibacterial and antifungal activities of some selected compounds are also reported.
Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Pyrazoles/chemical synthesis , Pyrazoles/pharmacology , Pyrimidines/chemical synthesis , Pyrimidines/pharmacology , Acetals/chemistry , Anti-Bacterial Agents , Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Bacteria/drug effects , Fungi/drug effects , Indicators and Reagents , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Spectrophotometry, InfraredABSTRACT
Some novel 1,2-bis(s-triazolo[3,4b][1,3,4]thiadiazino-3-yl)ethane (4-7); 1,2-bis(s-triazolo[3,4b][1,3,4]thiadiazol-3-yl)ethane (16a,b) and 1,2-bis(s-triazolo[3,4b][1,3,4]thiadiazepino-3-yl)ethane (17) were synthesized via reaction of 1,2-bis(4-amino-5-mercapto-s-triazol-3-yl)ethane (3) with different reagents. Identification of the new compounds was established by elemental analyses, IR, 1H NMR and mass spectral data. Compounds 12, 13, 16b and 17 were promising antifungal activity. The biologically active compounds 13, 16b and 17 were radioresistant retaining their structures unchanged up to 40 k Gy. Radiosterilization of these compounds in the dry state may prove to be applicable.
Subject(s)
Gamma Rays , Triazoles/chemical synthesis , Antifungal Agents/chemical synthesis , Antifungal Agents/radiation effects , Drug Stability , Microbial Sensitivity Tests , Spectrum Analysis , Sterilization , Triazoles/radiation effectsABSTRACT
1,3-Diphenyl-4-thione-2,5-imidazolidinedione (3) was reacted with amino compounds and o-diamines to give 1,3-diphenyl-4-substituted imino-2,5-imidazolinediones (4a-m) and 1,3-diphenyl-1H-imidazo[4,5-b]quinoxaline-2(3H)-ones (5a-c), respectively. Condensation of 3 with hydrazines afforded the corresponding hydrazone derivatives (6a-c). Reaction of 6a with acetyl chloride, aromatic aldehydes, arylsulphonyl chlorides, phthalic acid anhydrides and isocyanates or thiocyanates furnished 6d, furnished the acetyl-amido derivative 6b, the benzylidenimino derivatives 7a-d, the arylsulphonamido derivatives 8a-b, the phthalimido derivatives 9a-b and the ureido and thioureido derivatives 10a-b, respectively. Again compound 3 was reacted with n-butylmagnesium bromide or diazomethane to give the dibutyl derivative 12 or 13.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Imidazoles/chemical synthesis , Bacteria/drug effects , Chemical Phenomena , Chemistry , Imidazoles/pharmacology , Microbial Sensitivity TestsABSTRACT
The reaction of bergapten and ammajin with chlorosulfonic acid i shown to give the sulfonyl chlorides 1 and 11 which react with aliphatic, aromatic, and heterocyclic amines to give the corresponding sulfonamides. Phenols also react with 1 and 11 to give the sulfonate esters 5 and 15. Interaction of bergapten with phosphorous(V)sulfide gave the thione 7 which on reaction with amines gave 9. The antibacterial activity of the products is reported.
