ABSTRACT
The triethylammonium chloride complexes of N-substituted N'-cyano-O-(triphenylstannyl)isoureas were generally found to be better antifungal and antibacterial agents than the uncomplexed compounds.
Subject(s)
Anti-Infective Agents/chemical synthesis , Trialkyltin Compounds/chemical synthesis , Triethyltin Compounds/chemical synthesis , Anti-Bacterial Agents , Antifungal Agents/chemical synthesis , Bacteria/drug effects , Fungi/drug effects , Microbial Sensitivity Tests , Organotin Compounds/pharmacology , Triethyltin Compounds/pharmacologyABSTRACT
Five triorganotin 5-nitro-2-furoates were synthesized by reacting 5-nitro-2-furoic acid with either the corresponding bis(triorganotin) oxide or the corresponding triorganotin hydroxide. The IR spectrum of each compound was obtained over the 4000--200-cm-1 range, and some of the bands were assigned. One compound, tri-n-butyltin 5-nitro-2-furoate, was an excellent antifungal agent, completely inhibiting the growth of six of ten test fungi at a concentration of 1 microgram/ml. The new compounds were also investigated for antibacterial activity and were especially inhibitory toward Gram-positive species. Two of the compounds completely inhibited the Gram-negative bacterium Escherichia coli at a concentration of 100 microgram/ml.
Subject(s)
Bacteria/drug effects , Fungicides, Industrial/chemical synthesis , Organotin Compounds/chemical synthesis , Chemical Phenomena , Chemistry , Fungi/drug effects , Nitrofurans/chemical synthesis , Nitrofurans/pharmacology , Organotin Compounds/pharmacology , Pesticides/chemical synthesisABSTRACT
N-Substituted N-(triphenylstannyl)cyanamides were studied and found to be better antifungal agents than the previously tested N-substituted N'-cyano-S-(triphenylstannyl)isothioureas and N-substituted N'-cyano-O-(triphenylstannyl)isoureas. They were similar in activity to the previously tested ethyl N-aryl-S-(triphenylstannyl)-isothiocarbamates. The antifungal activity of triethylammonium (organocyanoamino)chlorotriphenylstannates, which are the triethylammonium chloride complexes of N-substituted N-(triphenylstannyl)-cyanamides, was similar to or better than that of the N-substituted N-(triphenylstannyl)cyanamides. Triethylammonium (acetylcyanoamino)chlorotriphenylstannate and triethylammonium dichlorotriphenylstannate were highly inhibitory toward Gram-positive bacteria.
Subject(s)
Anti-Bacterial Agents , Organotin Compounds/pharmacology , Antifungal Agents , Bacteria/drug effectsABSTRACT
Five ethyl N-aryl-S-(triphenylstannyl)isothiocarbamates were synthesized by the reaction of triphenyltin iodide with the appropriate ethyl N-arylthiocarbamate in the presence of triethylamine. The IR spectrum of each compound was obtained over the 4000--200-cm--1 range, and some bands were assigned. These new compounds were found to be generally better antifungal agents than the previously tested N-substituted N'-cyano-S-(triphenylstannyl)isothioureas. The new compounds were also investigated for antibacterial activity and were especially inhibitory toward Gram-positive species. Except for their lower activity toward Bacillus subtilis, their antibacterial activity was identical to the previously tested N-phenyl-N'-cyano-S-(triphenylstannyl)isothiourea.
Subject(s)
Anti-Infective Agents/chemical synthesis , Organotin Compounds/chemical synthesis , Anti-Bacterial Agents , Bacteria/drug effects , Fungi/drug effects , Organotin Compounds/pharmacology , Thiocarbamates/chemical synthesis , Thiocarbamates/pharmacologyABSTRACT
Six N-substituted N'-cyano-S-(trimethylstannyl)isothioureas were synthesized by the reaction of (trimethylstannyl)cyanamide with various organic isothiocyanates. The IR spectrum of each compound was obtained over the 4000-30-cm(-1) range, and some bands were assigned. The six new compounds and five previously synthesized N-substituted N'-cyano-S-(triphenylstannyl)isothioureas were tested for and were found to exhibit antifungal activity. N-Phenyl-N'-cyano-S-(triphenylstannyl)isothiourea was also investigated for antibacterial activity and was observed to be especially inhibitory toward Gram-positive species. The antimicrobial activity of two compounds was compared to that of the oxygen analogs of these compounds.
