ABSTRACT
Synthesis of 2-thioxopyrimido[4,5-b]quinoline 3a-c by microwave oven was used as a base to synthesis acyclic nucleosides analogue of types, 3-(penta-O-acetyl-glycosyl)-6-(4-chlorophenyl)-10-(4-chlorophenylmethylene)-7,8,9,10-tetrahydro[1,2,4]triazolo[4',3':1,2]-pyrimido[4,5-b]quinolin-4-ones (7a-c), 2-tetra-O-acetyl-glycosylhydrazon-N3-acetyl-5-(4-chlorophenyl)-9-(4-chlorophenylmethylene)-6,7,8,9-pentahydro-1H-pyrimido[4,5-b]-quinolin-4-ones (10a-c) and 3-(glycosyl)-6-(4-chlorophenyl)-10-(4-chlorophenylmethylene)-7,8,9,10-tetrahydro[1,2,4]triazolo[4',3':1,2]pyrimido[4,5-b]quinolin-4-ones (8a-c), (12a-c). The title compounds were investigated for analgesic, anti-inflammatory, anti-oxidant and anti-microbial activities. Compounds 8a,b and 12a,b exhibited highly significant activity towards gram-negative and gram-positive bacteria, showed more potent anti-inflammatory and analgesic activities than the acetylated glycoside derivatives 7a,b and 10a,b and exhibited high anti-oxidant activity when compared to the ascorbic acid.
Subject(s)
Analgesics/pharmacology , Anti-Infective Agents/pharmacology , Anti-Inflammatory Agents/pharmacology , Antioxidants/pharmacology , Nucleosides/pharmacology , Quinolines/chemistry , Analgesics/chemical synthesis , Analgesics/chemistry , Analgesics/therapeutic use , Animals , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/chemistry , Anti-Infective Agents/therapeutic use , Anti-Inflammatory Agents/chemical synthesis , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/therapeutic use , Antioxidants/chemical synthesis , Antioxidants/chemistry , Antioxidants/therapeutic use , Bacteria/drug effects , Carrageenan/adverse effects , Drug Discovery , Edema/chemically induced , Edema/drug therapy , Female , Lipid Peroxidation/drug effects , Male , Mice , Microwaves , Nucleosides/chemical synthesis , Nucleosides/chemistry , Nucleosides/therapeutic use , RatsABSTRACT
Two series of 5-ethyl-2-amino-3-pyrazolyl-4-methylthiophenecarboxylate and 2-thioxo-N(3)-aminothieno[2,3-d]pyrimidines were prepared from 3,5-diethyl-2-amino-4-methylthio-phenecaboxylate and evaluated as anti-inflammatory, analgesic and ulcerogenic activities. Among the compounds studied, compounds which containing the substituted hydrazide at C-3 position 7, 16, and 17a showed more potent anti-inflammatory and analgesic activities than the standard drug (Indomethacin and Aspirin), along without ulcerogenity. While compounds 2, 5, 9, 10, and 11c showed moderate activities. Some of the newly synthesized compounds have good to excellent antimicrobial activity.
Subject(s)
Analgesics/chemical synthesis , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Pyrimidines/chemical synthesis , Thiophenes/chemical synthesis , Alternaria/drug effects , Analgesics/chemistry , Analgesics/pharmacology , Aspirin/pharmacology , Bacillus cereus/drug effects , Fusarium/drug effects , Indomethacin/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Pyrimidines/chemistry , Pyrimidines/pharmacology , Salmonella typhi/drug effects , Structure-Activity Relationship , Thiophenes/chemistry , Thiophenes/pharmacologyABSTRACT
The 1,3-dipolar cycloaddition of nitrile imines to 9H-thioxanthone-9-thione and 9H-xanthone-9-thione afforded novel spiro-thioxanthene-9',2-[1,3,4]thiadiazoles 6a-g and spiro-xanthene-9',2-[1,3,4]thiadiazoles 7a-g in good yields. Some of the newly synthesized compounds were tested for anti-inflammatory and analgesic activities comparable to ibuprofen. Compounds 6a,d,e and 7a,d,e showed significant activity compared to standard drug. The toxicity studies revealed that neither death nor other behavioral or toxicological changes were observed on rats up to a dose as high as 200 mg/kg.
