ABSTRACT
N,N'-Diarylethylene-bis-thiourea derivatives 1 and 8 were synthesized and their reactions with hydrazonoyl chlorides yielded the corresponding bis-(2-(N-arylimino)-1,3-thiazolidine derivatives 5a-d and 11a-c. The reaction of compound 1 with several α-haloketones afforded the bis-(5-methyl-2-(N-phenylimino)-1,3-thiazolidine derivatives 15a-c and 19a, b. The newly synthesized compounds were tested for their antimicrobial activity against four fungi, two Gram-positive and two Gram-negative bacteria and showed high antibacterial and antifungal activities against all the test microorganisms except Pseudomonas aeruginosa and Candida albicans. Compounds 5b, 15b and 19a exhibited the highest activities against the test microorganisms. The MIC evaluation showed that compound 15b has higher activity than Amphotericin B and Ampicillin against all tested fungi and Gram-positive bacteria (Staphylococcus pneumonia) and showed similar activity like Ampicillin against Gram-negative bacteria (Escherichia coli).
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Thiazoles/chemical synthesis , Thiazoles/pharmacology , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Bacteria/drug effects , Dose-Response Relationship, Drug , Fungi/drug effects , Microbial Sensitivity Tests , Molecular Structure , Structure-Activity Relationship , Thiazoles/chemistryABSTRACT
New 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine and 1,3-thiazole derivatives incorporating indole nucleus were prepared using 3-acetylindole as precursor and evaluated for their antiviral activity against herpes simplex type 1 (HSV-1).
Subject(s)
Antiviral Agents/chemical synthesis , Antiviral Agents/pharmacology , Herpes Simplex/drug therapy , Herpesvirus 1, Human/drug effects , Indoles/chemical synthesis , Indoles/pharmacology , Thiazoles/chemical synthesis , Thiazoles/pharmacology , Animals , Antiviral Agents/chemistry , Cell Survival/drug effects , Chlorocebus aethiops , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/pharmacology , Humans , Indoles/chemistry , Thiazoles/chemistry , Vero CellsABSTRACT
Benzo[d]imidazole 3 and 1,2,4-triazin-5(2H)-one 6 were prepared by the reaction of starting ethyl (3-hydroxy-1H-inden-2-yl)(oxo)-acetate 2 with o-phenylenediamine and thiosemicarbazide respectively. Reaction of 1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carbohydrazide 8 with phenylisothiocyanate gave thiosemicarbazide 9, and its reaction with chloroacetic acid or phenacylbromides led to the formation of thiazolidinone-4-one 10 or 1,3-thiazoles 12a, b. The reactivity of hydrazide 8 towards fluorinated aldehyde, phthalic anhydride, and hydrazonoyl chlorides 15a, b was studied to give fluorinated hydrazones, imide bis-hydrazones 13-16. The newly synthesized compounds were screened for their cytotoxic activities and compounds 6, 8, 9 and 10 were found the most potentially cytotoxic. The detailed synthesis, spectroscopic and biological data are reported.
