Syntheses and antitumor activities of the derivatives of P-methyl goniotriol in vitro / 药学学报
Acta Pharmaceutica Sinica
;
(12): 775-780, 2002.
Article
in Chinese
| WPRIM
| ID: wpr-312051
ABSTRACT
<p><b>AIM</b>To find derivatives of p-methyl-goniotriol with more potent antitumor activities and lacking undesirable effects.</p><p><b>METHODS</b>Eighty derivatives of p-methyl-goniotriol have been synthesized in nine steps from alpha-D-glucoheptonic-delta-lactone (2). Compound 2 reacted with acetone in the catalyzer, H2SO4 and anhydrous MgSO4, and then reacted with 60% aqua HOAc, finally was oxidized by NaIO4 at room temperature into aldehyde 3 in a yield of 71.3%. The aldehyde 3 reacted immediately with P-CH3-PhMgBr giving mixture 4. The mixture 4 was oxidized by NaIO4, reacted with Ph3P = CHCO2Et and then induced by catalyzer. 1,8-Diazabicylclo[5, 4, 0]undec-7-ene in THF providing the compounds 6 and 7. The esterfication of 6 with cinnamyl chloride et al in 4-dimethylaminopyridine, Et3N gave the esters 8a-h. Acid hydrolysis of the acetone protecting group of 8a-h in 75% aqua HOAc gave compounds 9a-h. Their chemical structures were confirmed by IR, 1HNMR, MS and element analysis. The antitumor activities of the compounds were screened by MTT methods.</p><p><b>RESULTS</b>Fifteen derivatives of p-methyl-goniotriol (7, 8b-h, 9b-h) are new compounds.</p><p><b>CONCLUSION</b>Pharmacological tests indicate that these compounds showed antitumor activities toward tumor cells (A2780, HCT-8, Bel742, KB) in vitro. The antitumor activities of 8b, 8d, 8g and 9h were more potent than howiinol A.</p>
Full text:
Available
Index:
WPRIM (Western Pacific)
Main subject:
Pathology
/
Pharmacology
/
Pyrones
/
Tumor Cells, Cultured
/
KB Cells
/
Molecular Structure
/
Chemistry
/
Colonic Neoplasms
/
Antineoplastic Agents
Limits:
Humans
Language:
Chinese
Journal:
Acta Pharmaceutica Sinica
Year:
2002
Type:
Article
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