Synthesis of 3,5-dihydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)benzopyran-4-one derivatives as anticancer agents.
Different alkyl amide (15a-l) and alkyl amine (16a-e) derivatives of 7,8-dimethoxy-3-hydroxy-2-(4-methoxyphenyl)benzopyran-4-one were synthesized and evaluated for their anticancer activity against five different cancer cell lines using SRB assay. Compounds 15e, 15i, 15j and 16a-e showed significant anticancer activity within the range of IC502.58-34.86μM. The most promising molecule, 16c, was further analyzed for its effect on cell cycle and apoptosis of estrogen receptor positive cancer cells (MCF-7 cells) which showed that 16c triggered apoptosis in MCF-7 cells and arrested cells population at sub-G0(apoptotic) and G2M phase. In tubulin polymerization assay, 16c interfered with kinetics of tubulin polymerization.
Medicinal Chemistry Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Sarita
S
Singh
Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Ateeque
A
Ahmad
Medicinal Chemistry Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Dushyant Singh
DS
Raghuvanshi
Division of Biochemistry, CSIR-Central Drug Research Institute, Sector-10, Jankipuram Extension, Lucknow 226 031, India.
Mohammad
M
Hasanain
Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Karishma
K
Agarwal
Molecular Bioprospection Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Vijaya
V
Dubey
Molecular Bioprospection Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Kaniz
K
Fatima
Metabolic Structural Biology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Sarfaraz
S
Alam
Division of Biochemistry, CSIR-Central Drug Research Institute, Sector-10, Jankipuram Extension, Lucknow 226 031, India.
Jayanta
J
Sarkar
Molecular Bioprospection Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Suaib
S
Luqman
Metabolic Structural Biology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Feroz
F
Khan
Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Sudeep
S
Tandon
Medicinal Chemistry Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India. Electronic address: atisky2001@yahoo.co.in.
Atul
A
Gupta
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D001578:Benzopyrans; C575677:benzopyran-4-one
Anticancer; Benzopyran; Chromanone; Flavone; Flavonoids