ABSTRACT
New (tetrazol-5-yl)methylindole derivatives were synthesized from 2-phenylindole. Furthermore, the sugar acetyl hydrazones of the tetrazole derivatives as well as their derived acyclic C-nucleoside analogs were prepared. The synthesized compounds were studied for their anticancer activity against human liver carcinoma cell line (HepG2) and the results showed that arylidine substituted tetrazole derivatives 7c and 7d were the most active.
Subject(s)
Antineoplastic Agents/pharmacology , Indoles/pharmacology , Nucleosides/pharmacology , Tetrazoles/pharmacology , Antineoplastic Agents/chemical synthesis , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , Hep G2 Cells , Humans , Indoles/chemical synthesis , Inhibitory Concentration 50 , Molecular Structure , Nucleosides/chemical synthesis , Structure-Activity Relationship , Tetrazoles/chemical synthesisABSTRACT
The pyrimidine thione derivatives 2a-d were prepared by the reaction of thiourea, ethyl cyanoacetate and several aromatic aldehydes. The acyclic thioglycosides 4a-7d were prepared by the reaction of the synthesized pyrimidine thiones 2a-d with different alkyl halides, whereas the reaction of 2a-d with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide afforded the cyclic thioglycosides 8a-d whose deprotection afforded 9a-d. The obtained compounds were tested for their antischistosomal and antiviral activity against hepatitis B virus (HBV). Compounds 5a, 5d, 7a showed high activity against HBV using the MTT assay; moreover compounds 5c, 6d, 7a, 9a, 9c exhibited high activity as antischistosomal agents.
Subject(s)
Antiviral Agents/chemical synthesis , Schistosomicides/chemical synthesis , Thioglycosides/chemical synthesis , Animals , Antiviral Agents/pharmacology , Carcinoma, Hepatocellular , Cell Line, Tumor/drug effects , Enzyme-Linked Immunosorbent Assay , Humans , Lamivudine/pharmacology , Liver Neoplasms , Pyrimidines/chemical synthesis , Pyrimidines/pharmacology , Schistosoma mansoni/drug effects , Schistosomicides/pharmacology , Spectrophotometry, Infrared , Thioglycosides/pharmacology , Thiones/chemical synthesis , Thiones/pharmacologyABSTRACT
A number of new N-arylaminomethyl-1,3,4-oxadiazole derivatives 2, 3a,b, and 9-12a,b were prepared. Sugar (5-N-arylaminomethyl-1,3,4-oxadiazol-2-yl) hydrazones 4-6a,b were synthesized by the reaction of the hydrazino derivatives 3a,b with the corresponding monosaccharides. The novel acyclo-C-nucleosides 7, 8a,b were prepared by heterocyclization of the sugar hydrazones 4, 5a,b with acetic anhydride. A number of the synthesized compounds were tested for their antiviral activity against herpes simplex virus type-1 (HSV-1) and hepatitis-A virus (HAV, MBBcell culture-adapted strain). The results revealed that the sugar hydrazones 6a,b showed higher antiviral activity compared to the other hydrazones and their acetylated derivatives.
