D-64131 - CAS 74588-78-6
Catalog number: 74588-78-6
Category: Inhibitor
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Molecular Formula:
C16H13NO2
Molecular Weight:
251.28
COA:
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Targets:
Microtubule/Tubulin
Description:
D-64131, under the IUPAC name (5-methoxy-1H-indol-2-yl)-phenylmethanone, is a 2-aroylindole derivatives that inhibits tubulin polymerization. In vitro: Inhibits tumor cell proliferation (IC50= 74 nM); In vivo: After oral administration, prevents tumor models growing in mice
Brife Description:
Inhibits tubulin polymerization
Appearance:
Yellow crystalline solid
Synonyms:
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol; 1-(3,4,5-trimethoxyphenyl)-2-(3'-hydroxy-4'-methoxyphenyl)ethene; D-64131; 74588-78-6; (5-METHOXY-1H-INDOL-2-YL)PHENYLMETHANONE; CHEMBL140220; C16H13NO2; (5-methoxy-1H-indol-2-yl)-phenylmethanone; (5-Methoxy-1H-indol-2-yl)(phenyl)methanone; (5-Methoxy-1H-indol-2-yl)-phenyl-methanone; NCGC00025243-01; Tocris-1643; AC1N0QCR; 2-Benzoyl-5-methoxyindole; SCHEMBL5828518; CTK8F8930; DTXSID30397970; ICMIJSRDISNKOC-UHFFFAOYSA-N; HMS3268K07; ZINC2526466; 3570AH; BDBM50107658; AKOS022507157; CS-1008; 2-BENZOYL-5-METHOXY-1H-INDOLE; NCGC00025243-02; AN-25376; HE053371; HE187776; HY-15482; LS-83224; QC-11710; AB0165802; KB-208742; D64131; W-5310; BRD-K26997899-001-01-4; D-64131|(5-Methoxy-1H-indol-2-yl)phenylmethanone
Solubility:
Soluble to 20 mg/ml in DMSO, to 0.25 mg/ml in water at 25ºC, to 0.25 mg/ml in PBS pH7.2, and to 10 mg/ml in DMF.
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -54℃ for long term (months to years).
MSDS:
Inquire
Boiling Point:
455.2ºC at 760 mmHg
Melting Point:
167-169ºC
Density:
1.231 g/cm3
InChIKey:
ICMIJSRDISNKOC-UHFFFAOYSA-N
InChI:
1S/C16H13NO2/c1-19-13-7-8-14-12(9-13)10-15(17-14)16(18)11-5-3-2-4-6-11/h2-10,17H,1H3
Canonical SMILES:
COC1=CC2=C(C=C1)NC(=C2)C(=O)C3=CC=CC=C3
1.2-aroylindoles, a novel class of potent, orally active small molecule tubulin inhibitors.
Beckers T1, Reissmann T, Schmidt M, Burger AM, Fiebig HH, Vanhoefer U, Pongratz H, Hufsky H, Hockemeyer J, Frieser M, Mahboobi S. Cancer Res. 2002 Jun 1;62(11):3113-9.
2-Aroylindoles with 5-methoxy-1H-2-indolyl-phenylmethanone (D-64131) as the lead structure were discovered as a new class of synthetic, small molecule tubulin inhibitors. By competitively binding with [(3)H]colchicine to alphabeta-tubulin and inhibiting microtubule formation, cycling cells were arrested in the G(2)-M phase of the cell division cycle. The proliferation of tumor cells from 12 of 14 different organs and tissues was inhibited with mean IC(50)s of 62 nM and 24 nM by D-64131 and D-68144, respectively, comparable with the potency of paclitaxel with mean IC(50) of 10 nM. By measuring the cytotoxicity in a human colon carcinoma cell model with ectopic ecdysone-inducible expression of the cyclin-dependent kinase inhibitor p21(WAF1), specificity toward cycling cells was demonstrated. In contrast to microtubule inhibitors from natural sources, 2-aroylindoles did not alter the polymerization-dependent GTPase activity of beta-tubulin and are not substrates of the multidrug resistance/multidrug resistance protein efflux pump.
2.Indolobenzazepin-7-ones and 6-, 8-, and 9-membered ring derivatives as tubulin polymerization inhibitors: synthesis and structure--activity relationship studies.
Putey A1, Popowycz F, Do QT, Bernard P, Talapatra SK, Kozielski F, Galmarini CM, Joseph B. J Med Chem. 2009 Oct 8;52(19):5916-25. doi: 10.1021/jm900476c.
Several small weight indole derivatives (D-64131, D-24851, BPR0L075, BLF 61-3, and ATI derivatives) are potent tubulin polymerization inhibitors and show nanomolar antiproliferative activity. Among them, indolobenzazepin-7-ones were recently disclosed as potent antimitotic agents. In an effort to improve this structure, we prepared new derivatives in order to evaluate their antiproliferative activity. 5,6,7,9-Tetrahydro-8H-indolo[2,3-e][3]benzazocin-8-one (1m) was found to be the most potent derivative inhibiting the cell growth of several cancer cell lines in the lower nanomolar range.
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CAS 74588-78-6 D-64131

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