Synthesis and Evaluation of Stilbene and Dihydrostilbene Derivatives as Potential Anticancer Agents That Inhibit Tubulin Polymerization (Record no. 47117)

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control field MX-MdCICY
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control field 20250625153912.0
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Transcribing agency CICY
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Classification number (OCLC) (R) ; Classification number, CALL (RLIN) (NR) B-12915
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Title Synthesis and Evaluation of Stilbene and Dihydrostilbene Derivatives as Potential Anticancer Agents That Inhibit Tubulin Polymerization
490 0# - SERIES STATEMENT
Volume/sequential designation J. Med. Chem., 34(8), p.2579-2588, 1991
520 3# - SUMMARY, ETC.
Summary, etc. An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in t.he five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Several cis-stilbenes, structurally similar to combretastatins, were highly cytotoxic in all five cell lines and these were also found to be active as inhibitora of tubulin polymerization. The most active compounds also inhibited the binding of colchicine to tubulin. The most potent of the new compounds, both as a tubulin polymerization inhibitor and as a cytotoxic agent, was (Z)-l-(4-methoxyphenyl)- 2-(3,4,5-trimethoxyphenyl)ethen(eS a). This substance was almost as potent as combretastatin A-4 (la), the most active of the combretastatins, as a tubulin polymerization inhibitor. Compound 5a was found to be approximately 140 times more cytotoxic against HT-29 colon adenocarcinoma cells and about 10 times more cytotoxic against MCF-7 breast carcinoma cells than combretastatin A-4. However, 5a was found to be about 20 times less cytotoxic against A-549 lung carcinoma cells, 30 times less cytotoxic against SKMEL-5 melanoma cells, and 7 times less cytotoxic against MLM melanoma cells than combretastatin A-4. The relative potencies 5a > 8a > 6a for the cis, dihydro, and trans compounds, respectively, as inhibitors of tubulin polymerization are in agreement with the relative potencies previously observed for combretastatin A-4 (la), dihydrocombretastatin A-4 (IC), and transcombretastatin A-4 (lb). The relative potencies 5a > 8a > 6a were also reflected in the results of the cytotoxicity assays. Structure-activity relationships of this group of compounds are also discussed.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Cushman, M.
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Personal name Nagarathnam; D.
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Personal name Gopal, D.
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Personal name Chakraborti, A.K.
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Personal name Lin, C.M.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Hamel, E.
856 40 - ELECTRONIC LOCATION AND ACCESS
Uniform Resource Identifier <a href="https://drive.google.com/file/d/1bl7wiupwoxsccp19H32MiGNBD0N4azZm/view?usp=drivesdk">https://drive.google.com/file/d/1bl7wiupwoxsccp19H32MiGNBD0N4azZm/view?usp=drivesdk</a>
Public note Para ver el documento ingresa a Google con tu cuenta: @cicy.edu.mx
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  Clasificación local     Ref1 CICY CICY Documento préstamo interbibliotecario 25.06.2025   B-12915 25.06.2025 25.06.2025 Documentos solicitados