9-Benzylidene-naphtho[2,3-b]thiophen-4-ones as Novel Antimicrotubule AgentsSynthesis, Antiproliferative Activity, and Inhibition of Tubulin Polymerization

• Published in: Journal of medicinal chemistry Vol. 49; no. 26; pp. 7816 - 7825
• Main Authors: Zuse, Anne, Schmidt, Peter, Baasner, Silke, Böhm, Konrad J, Müller, Klaus, Gerlach, Matthias, Günther, Eckhard G, Unger, Eberhard, Prinz, Helge
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.12.2006; Amer Chemical Soc
• Subjects: Animals; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological and medical sciences; Cell Cycle - drug effects; Cell Proliferation - drug effects; Cell Survival - drug effects; Chemistry, Medicinal; Colchicine - pharmacology; Drug Resistance, Neoplasm; Drug Screening Assays, Antitumor; Female; Flow Cytometry; General aspects; Humans; Inhibitory Concentration 50; K562 Cells - drug effects; Leukemia P388 - drug therapy; Life Sciences & Biomedicine; Medical sciences; Mice; Molecular Structure; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Structure-Activity Relationship; Thiophenes - chemical synthesis; Thiophenes - chemistry; Thiophenes - pharmacology; Tubulin - chemistry; Tubulin Modulators - chemical synthesis; Tubulin Modulators - chemistry; Tubulin Modulators - pharmacology; Tumor Cells, Cultured; KETO-ENOL TAUTOMERISM; ANTITUBULIN AGENTS; ANTIMITOTIC AGENTS; ACTIVITY IN-VIVO; CELL-GROWTH; MICROTUBULE DYNAMICS; THIOPHENE ANALOGS; DERIVATIVES; BINDING; CANCER; Antineoplastic agent; Human; Lung; Gut; Central nervous system; Antitubulin; Uterine cervix; In vitro; Hela cell line; Biological activity; Ovary; Cell line; Glioma; Cell cycle; G2 Phase; Phenols; Colon; Chemical synthesis; Antimitotic; Tumor cell

A novel series of 9-benzylidene-naphtho[2,3-b]thiophen-4-ones and structurally related compounds were synthesized and evaluated for their ability to inhibit tubulin polymerization. The 4-hydroxy-3,5-dimethoxy-benzylidene analogue 15d was identified as a potent cytotoxic agent in an assay based on K5...