| Identification | Back Directory | [Name]
2-[[(2E)-3-(2-NAPHTHALENYL)-1-OXO-2-BUTEN-1-YL]AMINO]BENZOIC ACID | [CAS]
321674-73-1 | [Synonyms]
CS-1061
BIBR 1532
BIBR 1532, >=98%
BIBR 1532;BIBR-1532
(E)-2-(3-phenylbut-2-enamido)benzoic acid
(E)-2-(3-(naphthalen-2-yl)but-2-enamido)benzoic acid
2-[[(2E)-3-(2-Naphthalenyl)-1-oxo-2-butenyl]amino]benzoic acid
2-[[(2E)-3-(2-Naphthalenyl)-1-oxo-2-butenyl1-yl]amino]benzoicacid
2-[[(2E)-3-(2-NAPHTHALENYL)-1-OXO-2-BUTEN-1-YL]AMINO]BENZOIC ACID
Benzoic acid, 2-[[(2E)-3-(2-naphthalenyl)-1-oxo-2-buten-1-yl]amino]-
2-[[(2E)-3-(2-NAPHTHALENYL)-1-OXO-2-BUTEN-1-YL]AMINO]BENZOIC ACID USP/EP/BP | [Molecular Formula]
C21H17NO3 | [MDL Number]
MFCD11112195 | [MOL File]
321674-73-1.mol | [Molecular Weight]
331.37 |
| Chemical Properties | Back Directory | [Melting point ]
>173oC (dec.) | [Boiling point ]
600.6±48.0 °C(Predicted) | [density ]
1.284 | [storage temp. ]
Store at RT | [solubility ]
DMSO (Slightly), Methanol (Slightly, Sonicated) | [form ]
Solid | [pka]
3.46±0.36(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C21H17NO3/c1-14(16-11-10-15-6-2-3-7-17(15)13-16)12-20(23)22-19-9-5-4-8-18(19)21(24)25/h2-13H,1H3,(H,22,23)(H,24,25)/b14-12+ | [InChIKey]
PGFQXGLPJUCTOI-WYMLVPIESA-N | [SMILES]
C(O)(=O)C1=CC=CC=C1NC(=O)/C=C(/C1=CC=C2C(=C1)C=CC=C2)\C |
| Hazard Information | Back Directory | [Description]
BIBR 1532 is a mixed-type non-competitive inhibitor of telomerase (IC50 = 93 nM) that has little effect on several mammalian DNA and RNA polymerases, bacterial DNA helicase, or HIV-1 reverse transcriptase.1,2,3 It specifically targets the telomerase reverse transcriptase catalytic subunit, TERT.2,4 Through its effects on telomerase, BIBR 1532 induces senescence or apoptosis in cancer cells.1,5 Apoptosis in triple negative breast cancer cells induced by BIBR 1532 is potentiated by glucose restriction.5 | [Uses]
BIBR 1532 is a mixed-type non-competitive inhibitor of telomerase. It specifically targets the telomerase reverse transcriptase catalytic subunit, TERT. | [Definition]
ChEBI: 2-[[3-(2-naphthalenyl)-1-oxobut-2-enyl]amino]benzoic acid is an amidobenzoic acid. | [Biological Activity]
Selective telomerase inhibitor (IC 50 values are 93, > 100000 and > 100000 nM for human telomerase, human RNA polymerase I and human RNA polymerase II + III respectively). Causes telomere shortening in exponentially growing NCI-H460 lung carcinoma cells and eventual growth arrest. | [storage]
Store at RT | [References]
[1]. damm, k.; hemmann, u.; garin-chesa, p.; hauel, n.; kauffman, i.; priepke, h.; niestroj, c.; daiber, c.; enenkel, b.; guilliard, b.; lauritsch, i.; muller, e.; pascolo, e.; sauter, g.; pantic, m.; martens, u. m.; wenz, c.; linger, j.; kraut, n.; rettig, w. j.;schnapp, a. a highly selective telomerase inhibitor limiting human cancer cell proliferation. embo j. 2001, 20, 6958?6968.
[2]. bashash d1, ghaffari sh, mirzaee r, alimoghaddam k, ghavamzadeh a. telomerase inhibition by non-nucleosidic compound bibr1532 causes rapid cell death in pre-b acute lymphoblastic leukemia cells. leuk lymphoma. 2013 mar;54
[4]:561-8. doi: 10.3109/10428194.2012.704034. epub 2012 sep 28.
[3]. bashash d1, ghaffari sh, zaker f, kazerani m, hezave k, hassani s, rostami m, alimoghaddam k, ghavamzadeh a. anticancer agents med chem. 2013 sep;13(7):1115-25. bibr 1532 increases arsenic trioxide-mediated apoptosis in acute promyelocytic leukemia cells: therapeutic potential for apl. |
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