Synthesis of 1-(3′,4′,5′-trimethoxy) phenyl naphtho[2,1b]furan as a novel anticancer agent

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 4, 2006, Pages 911-914

  Srivastava, Vandana ^a   Negi, Arvind S ^a   Kumar, J K ^a   Faridi, Uzma ^a   Sisodia, Brijesh S ^a   Darokar, M P ^a   Luqman, Suaib ^a   Khanuja, S P S ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

Author keywords

Anticancer; Aryl naphthofurans; Gallic acid; HMQC; Intramolecular condensation; MTT assay

Indexed keywords

1 (3',4',5' TRIMETHOXY)PHENYL NAPHTHO[2,2 B]FURAN; 3',4',5' TRIMETHOXY BENZOYLNEPHTHALENE 2 O ACETIC ACID; ACETIC ACID DERIVATIVE; ANTINEOPLASTIC AGENT; FURAN DERIVATIVE; PACLITAXEL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CATALYSIS; CELL STRAIN CACO 2; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER CANCER; POLYMERIZATION; SPECTROSCOPY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 30344457020     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.10.105     Document Type: Article

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19. General experimental procedure for the synthesis of aryl naphtho[2,1b] furans: Synthesis of 1-(3′,4′,5′-trimethoxy) phenyl naphtho[2,1b]furan (8). In a 25 ml round-bottomed flask 3′,4′, 5′-trimethoxy benzoyl naphthalene 2-O-acetic acid (5, 100 mg, 0.25 mmol) was taken in dry dichloromethane (10 ml). To this 1-hydroxy benzotriazole (80 mg, 0.63 mmol), EDC-HCl (120 mg, 0.63 mmol) and triethyl amine (0.5 ml) were added. The reaction mixture was stirred at room temperature for 20 min. Now to this mixture 3,4,5-trimethoxy aniline (60 mg, 0.32 mmol) was added and the reaction mixture was refluxed for 2 h. After completion of the reaction, 20 ml water was added to this and stirred for 10 min. It was extracted with dichloromethane (30 ml x 3) and washed with water. The organic layer was dried over anhydrous sodium sulfate and distilled off to get a residue. The residue was passed through a small column of silica gel (60-120 mesh) and eluted with hexane-ethyl acetate. The compound 8 was obtained in 8-10% ethyl acetate-hexane as an oil (89%).
20. 90 is the concentration μg/mL required for 90% inhibition of cell growth as compared to that of untreated control.