ABSTRACT
BACKGROUND: Several chromene derivatives have a wide variety of biological and pharmacological activity. They had anticancer activity, antimicrobial activity, antituberculosis activity, anticonvulsant activity, antidiabetic activity, antichlolinesterase activity, and inhibitor of monoamine oxidase activity. The above-mentioned activities directed us to synthesize novel chromene derivatives, chromeno[2,3-d][1,3]oxazines, and chromeno[2,3-d]pyrimidines. The starting material was 2- amino-8-(2-chlorobenzylidene)-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile. METHODS: Several novel chromene derivatives had been synthesized. Compound 1 reacted with carbon disulfide, and ethyl chloroformate to afford chromene derivatives 2, 3. Chromene derivative 3 reacted with hydrazine dydrate to give compound 4. Chromene derivative 1 reacted with acetic acid and sulphuric acid to produce compounds 5, and 6. Amino derivative 5 reacted with chloroacyl derivative to afford compounds 7a-c which cycalized in dry xylene to afford compounds 8a-c. Chromene derivative 8a reacted with hydroxyl amine to afford compound 9. RESULTS: The structures of novel synthesized chromene derivatives had been confirmed using mass spectroscopy, infrared spectroscopy, nuclear magnetic resonance spectroscopy, and elemental analysis. Most of the prepared compounds were screened against liver cancer cell lines (HepG-2), human colon cancer cell lines (HT-29), and breast adenocarcinoma cell lines (MCF-7). Chromene derivative 2 had anticancer activity against human colon cancer cell lines (HT-29) higher than the reference drug doxorubicin. The rest of the tested compounds had anticancer activity against human colon cancer cell lines (HT-29) lower than that of the reference drug doxorubicin. Chromene derivative 5 had anticancer activity against liver cancer cell lines (HepG-2) higher than the reference drug doxorubicin. CONCLUSION: Several chromene derivatives had been synthesized and their structures had been confirmed using different spectroscopic techniques. Some of the chromene derivatives that were screened against different cancer cell lines showed promising anticancer activity higher than the reference standard drug. For example, chromene derivative 2 had anticancer activity against human colon cancer cell lines (HT-29) higher than the reference drug doxorubicin. Chromene derivative 5 had anticancer activity against liver cancer cell lines (HepG-2) higher than the reference drug doxorubicin. Chromene derivative 6 had anticancer activity against breast adenocarcinoma cell lines (MCF-7) higher than the standard drug.
Subject(s)
Adenocarcinoma , Antineoplastic Agents , Liver Neoplasms , Humans , Structure-Activity Relationship , Benzopyrans/chemistry , Pyrimidines/chemistry , Antineoplastic Agents/chemistry , Cell Proliferation , Oxazines/pharmacology , Drug Screening Assays, Antitumor , Cell Line, Tumor , Doxorubicin/pharmacology , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
A series of novel substituted pyrimidinones and fused pyrimidinones (compounds 3-18) were synthesized starting with oxiranylmethanone 2. The in vitro cytotoxicity against a human breast adenocarcinoma (MCF-7) cell line was investigated and most of the tested compounds showed potent cytotoxic activity against the MCF-7 cell line comparable to the activity of the commonly used anticancer drug cisplatin. Treatment of MCF-7 cells with increasing doses (2, 5, 10, and 20 µg/mL) of the tested compounds revealed that the activity of superoxide dismutase and the level of hydrogen peroxide were significantly increased, while the activities of catalase and glutathione peroxidase and the levels of reduced glutathione were significantly lowered compared with control MCF-7 cells. In general, derivatives 11 and 16 revealed the highest anticancer activity among the tested compounds.
Subject(s)
Antineoplastic Agents/chemical synthesis , Drug Design , Pyrimidinones/chemical synthesis , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Catalase/metabolism , Cell Culture Techniques , Cell Survival/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Glutathione Peroxidase/metabolism , Humans , Hydrogen Peroxide/pharmacology , MCF-7 Cells , Molecular Structure , Neoplasm Proteins/metabolism , Nitric Oxide/metabolism , Nucleic Acids/metabolism , Pyrimidinones/chemistry , Pyrimidinones/pharmacology , Superoxide Dismutase/metabolismABSTRACT
A number of new disubstituted 2,5-thiazolidinone derivatives were synthesized and tested for their antimicrobial activity against Bacillus subtilis (Gram-positive), Pseudomonas aeruginosa (Gram-negative), and Streptomyces species (Actinomycetes). They displayed different degrees of antimicrobial activities or inhibitory actions.
Subject(s)
Anti-Infective Agents/pharmacology , Thiazolidinediones/pharmacology , Anti-Bacterial Agents/pharmacology , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/chemistry , Bacillus subtilis/drug effects , Microbial Sensitivity Tests , Pseudomonas aeruginosa/drug effects , Streptomyces/drug effects , Structure-Activity Relationship , Thiazolidinediones/chemical synthesis , Thiazolidinediones/chemistryABSTRACT
3-arylazo-5-phenyl-2(3H)-furanones 3 were prepared and converted into a variety of heterocyclic systems of synthetic and biological importance. Hydrazine hydrate reacted with furanones as nucleophiles and gave the corresponding acid hydrazides 4. The latter products were used as starting materials for the synthesis of 1,3,4-oxadiazoles 6, 9, and the 1,2,4-triazoles 8. Evaluation of the antiviral activity of selected compounds obtained was performed using two viruses: HAV and HSV-1. Some of the tested compounds showed promising activities.