Synthesis, X-ray crystallographic analysis, and antitumor activity of N-(benzothiazole-2-yl)-1-(fluorophenyl)-O,O-dialkyl-α-aminophosphonates

• Published in: Bioorganic & medicinal chemistry letters Vol. 16; no. 6; pp. 1537 - 1543
• Main Authors: Jin, Linhong, Song, Baoan, Zhang, Guoping, Xu, Ruiqing, Zhang, Sumei, Gao, Xingwen, Hu, Deyu, Yang, Song
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15.03.2006; Elsevier
• Subjects: Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antitumor activity; Benzothiazole moiety; Benzothiazoles; Biological and medical sciences; Cell Proliferation - drug effects; Crystallography, X-Ray; Drug Screening Assays, Antitumor; General aspects; Humans; Inhibitory Concentration 50; Ionic liquids; Lung Neoplasms - drug therapy; Magnetic Resonance Spectroscopy; Male; Medical sciences; Melanoma - drug therapy; Organophosphonates - chemical synthesis; Organophosphonates - chemistry; Organophosphonates - pharmacology; Pharmacology. Drug treatments; Prostatic Neoplasms - drug therapy; Skin Neoplasms - drug therapy; Structure-Activity Relationship; Synthesis; Thiazoles - chemical synthesis; Thiazoles - chemistry; Thiazoles - pharmacology; Tumor Cells, Cultured; α-Aminophosphonate; Ionic liquids; Antitumor activity; Synthesis; α-Aminophosphonate; Benzothiazole moiety; Antineoplastic agent; Molecular structure; Cytotoxicity; Phosphorus Organic compounds; Structure activity relation; Malignant melanoma; Bicyclic compound; Aromatic compound; Chemical synthesis; Tumor cell; Human; Sulfur nitrogen heterocycle; Squamous cell carcinoma; Benzene derivatives; Organic phosphonate; Benzothiazole derivatives; X ray diffraction; In vitro; Cell line; Prostate; Crystalline structure
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2005.12.041

The Mannich-type addition of 2-aminobenzothiazole and O,O-dialkylphosphite to 2-fluorobenzoaldehyde or 4-trifluorobenzoaldehyde in ionic liquids is used to synthesize the corresponding product α-aminophosphonate with benzothiazole and fluorine moiety. And their inhibitory activities against cancer cells are preformed. α-Aminophosphonates containing benzothiazole and fluorine moiety, 4a–4m, were synthesized by Mannich-type addition in ionic liquid media with high yield and short reaction time. Their structures were established by IR, 1H NMR, 13C NMR, and elemental analysis. The X-ray crystallographic data of compounds 4j and 4m were provided. The newly synthesized compounds were evaluated for their anticancer activities against PC3, A431, A375, and Bcap37 cells in vitro by the MTT method. Compound 4c is highly effective against PC3 cells and moderate to A431 cells. Hence, further study is necessary to find out the potential antitumor activities.