Synthesis, structure, and bioactivity of N′-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 19, 2006, Pages 5036-5040

  Jin, Linhong ^a   Chen, Jiang ^a   Song, Baoan ^a   Chen, Zhuo ^a   Yang, Song ^a   Li, Qianzhu ^a   Hu, Deyu ^a   Xu, Ruiqing ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

1,3,4 Oxadiazole derivatives; 3,4,5 Trimethoxybenzohydrazide; Antitumor activity; Synthesis

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; BENZYLIDEN 3,4,5 TRIMETHOXYBENZOHYDRAZIDE; OXADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CANCER INHIBITION; CELL PROLIFERATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INFRARED RADIATION; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; BENZYLIDENE COMPOUNDS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NEOPLASMS; OXADIAZOLES; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33747499171     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.07.048     Document Type: Article

References (18)

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13. General experimental procedure for the synthesis of N′-substituted benzylidene-3,4,5-trimethoxybenzohydrazide 2. To the mixture of 3,4,5-trimethoxybenzohydrazide 1 (2 mmol) in ethanol (10 mL) was added appropriate aldehyde (2 mmol). Then the mixture was refluxed for 30 min. After cooling, the crude product was obtained by filtration and recrystallized from ethanol-DMF to afford 2a-2o as white solids. Their physico-chemical properties and the spectra data can be found in supporting information.
14. Synthesis of 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazoles (3). Compound 2 (1 mmol) was refluxed in acetic anhydride (5 mL) for 2 h. The mixture was cooled, poured into crush ice, and allowed to stand at room temperature over night. The separated solid was washed by water, dried, and recrystallized from acetone-water to give title compound 3a-3o. Their physico-chemical properties and the spectra data can be found in supporting information.
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