X-ray structures of two methoxybenzo[b]thiophenes

Mullica, D. F.; Pinney, Kevin G.; Dingeman, Koren M.; Bounds, A. Dawn; Sappenfield, E. L.

doi:10.1007/bf01670312

Cited by 4 publications

(2 citation statements)

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“…In addition, relatively simple adjustments to these protocols should allow for the preparation of the corresponding benzo[b]thiophen and indole analogues. Thus, further investigation of these biologically significant 19,20,25,26,33 classes of compound should be facilitated by the chemistry described herein, especially as it is likely to be capable of adaptation to the solid phase 24,34 and, thereby, permitting the production of combinatorial libraries.…”

Section: Resultsmentioning

confidence: 99%

“…12−18 In connection with such endeavours, the benzo[b]thiophens (2) and (3) were recently prepared and structurally characterized by Pinney and coworkers. 19 This same group has subsequently reported 20 that compound (2) inhibits tubulin polymerization (IC 50 c. 1·5-2 · 5 µM) and has significant cell growth inhibitory activity (GI 50 < 10 µg/ml) against a selection of human cancer cell lines. It is especially active against colon cancer (GI 50 0 · 049 µg/ml).…”

Section: Introductionmentioning

confidence: 98%

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Synthesis, X-Ray Crystal Structure and Tubulin- Binding Properties of a Benzofuran Analogue of the Potent Cytotoxic Agent Combretastatin A4

et al. 1999

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Synthesis, X-Ray Crystal Structure and Tubulin- Binding Properties of a Benzofuran Analogue of the Potent Cytotoxic Agent Combretastatin A4

et al. 1999

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Application of the McMurry coupling reaction in the synthesis of tri- and tetra-arylethylene analogues as potential cancer chemotherapeutic agents

Tanpure¹,

Harkrider²,

Strecker³

et al. 2009

Bioorganic & Medicinal Chemistry

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Structural redesign of selected non-steroidal estrogen receptor binding compounds has previously been successful in the discovery of new inhibitors of tubulin assembly. Accordingly, tetra-substituted alkene analogues (21-30) were designed based in part on combinations of the structural and electronic components of tamoxifen and combretastatin A-4 (CA4). The McMurry coupling reaction was used as the key synthetic step in the preparation of these tri-and tetra-arylethylene analogues. The structural assignment of E, Z isomers was determined on the basis of 2D-NOESY experiments. The ability of these compounds to inhibit tubulin polymerization and cell growth in selected human cancer cell lines was evaluated. Although the compounds were found to be less potent than CA4, these analogues significantly advance the known structure activity relationship associated with the colchicine binding site on β-tubulin.

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