Home Aminos 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-

2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-

CAS No.:
404951-53-7
Catalog Number:
AG00BXVU
Molecular Formula:
C22H25N3O3
Molecular Weight:
379.4522
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$111
- +
5mg
≥95%
1 week
United States
$301
- +
10mg
98%
1 week
United States
$357
- +
50mg
98%
1 week
United States
$857
- +
Product Description
Catalog Number:
AG00BXVU
Chemical Name:
2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-
CAS Number:
404951-53-7
Molecular Formula:
C22H25N3O3
Molecular Weight:
379.4522
MDL Number:
MFCD09970778
IUPAC Name:
(E)-N-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide
InChI:
InChI=1S/C22H25N3O3/c26-14-13-25(12-11-19-15-23-21-4-2-1-3-20(19)21)16-18-7-5-17(6-8-18)9-10-22(27)24-28/h1-10,15,23,26,28H,11-14,16H2,(H,24,27)/b10-9+
InChI Key:
BWDQBBCUWLSASG-MDZDMXLPSA-N
SMILES:
OCCN(Cc1ccc(cc1)/C=C/C(=O)NO)CCc1c[nH]c2c1cccc2
UNII:
V10P524501
Properties
Complexity:
505  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
379.19g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
379.46g/mol
Monoisotopic Mass:
379.19g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
88.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.6  
Literature
Title Journal
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Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors. Journal of medicinal chemistry 20110714
Restoring the functional immunogenicity of chronic lymphocytic leukemia using epigenetic modifiers. Leukemia research 20110301
Conformational refinement of hydroxamate-based histone deacetylase inhibitors and exploration of 3-piperidin-3-ylindole analogues of dacinostat (LAQ824). Journal of medicinal chemistry 20100408
Chemical phylogenetics of histone deacetylases. Nature chemical biology 20100301
Diphenylmethylene hydroxamic acids as selective class IIa histone deacetylase inhibitors. Bioorganic & medicinal chemistry letters 20091001
Phase I pharmacokinetic and pharmacodynamic study of LAQ824, a hydroxamate histone deacetylase inhibitor with a heat shock protein-90 inhibitory profile, in patients with advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research 20081015
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Role of histone deacetylase inhibitor-induced reactive oxygen species and DNA damage in LAQ-824/fludarabine antileukemic interactions. Molecular cancer therapeutics 20081001
Experimental treatment of pancreatic cancer with two novel histone deacetylase inhibitors. World journal of gastroenterology 20080621
Mitochondrial Bax translocation partially mediates synergistic cytotoxicity between histone deacetylase inhibitors and proteasome inhibitors in glioma cells. Neuro-oncology 20080601
Histone deacetylase inhibition and blockade of the glycolytic pathway synergistically induce glioblastoma cell death. Clinical cancer research : an official journal of the American Association for Cancer Research 20080515
Noninvasive magnetic resonance spectroscopic pharmacodynamic markers of a novel histone deacetylase inhibitor, LAQ824, in human colon carcinoma cells and xenografts. Neoplasia (New York, N.Y.) 20080401
Probing the elusive catalytic activity of vertebrate class IIa histone deacetylases. Bioorganic & medicinal chemistry letters 20080315
Inhibitors of histone deacetylases induce tumor-selective cytotoxicity through modulating Aurora-A kinase. Journal of molecular medicine (Berlin, Germany) 20080101
Novel aminophenyl benzamide-type histone deacetylase inhibitors with enhanced potency and selectivity. Journal of medicinal chemistry 20071115
The multikinase inhibitor sorafenib potentiates TRAIL lethality in human leukemia cells in association with Mcl-1 and cFLIPL down-regulation. Cancer research 20071001
Inhibition of histone deacetylase for the treatment of biliary tract cancer: a new effective pharmacological approach. World journal of gastroenterology 20070921
HDAC inhibitors and cardiac safety. Clinical cancer research : an official journal of the American Association for Cancer Research 20070201
Antitumor effect of the histone deacetylase inhibitor LAQ824 in combination with 13-cis-retinoic acid in human malignant melanoma. Molecular cancer therapeutics 20070101
Effect of histone deacetylase inhibitor LAQ824 on antineoplastic action of 5-Aza-2'-deoxycytidine (decitabine) on human breast carcinoma cells. Cancer chemotherapy and pharmacology 20061101
Class II histone deacetylases are associated with VHL-independent regulation of hypoxia-inducible factor 1 alpha. Cancer research 20060901
In vivo biological activity of the histone deacetylase inhibitor LAQ824 is detectable with 3'-deoxy-3'-[18F]fluorothymidine positron emission tomography. Cancer research 20060801
The histone deacetylase inhibitor LAQ824 induces human leukemia cell death through a process involving XIAP down-regulation, oxidative injury, and the acid sphingomyelinase-dependent generation of ceramide. Molecular pharmacology 20060101
Potentiation of the lethality of the histone deacetylase inhibitor LAQ824 by the cyclin-dependent kinase inhibitor roscovitine in human leukemia cells. Molecular cancer therapeutics 20051101
Chemical ablation of androgen receptor in prostate cancer cells by the histone deacetylase inhibitor LAQ824. Molecular cancer therapeutics 20050901
Histone deacetylase inhibitor NVP-LAQ824 has significant activity against myeloid leukemia cells in vitro and in vivo. Leukemia 20041201
The histone deacetylase inhibitor NVP-LAQ824 inhibits angiogenesis and has a greater antitumor effect in combination with the vascular endothelial growth factor receptor tyrosine kinase inhibitor PTK787/ZK222584. Cancer research 20040915
Superior activity of the combination of histone deacetylase inhibitor LAQ824 and the FLT-3 kinase inhibitor PKC412 against human acute myelogenous leukemia cells with mutant FLT-3. Clinical cancer research : an official journal of the American Association for Cancer Research 20040801
In bcr-abl-positive myeloid cells resistant to conventional chemotherapeutic agents, expression of Par-4 increases sensitivity to imatinib (STI571) and histone deacetylase-inhibitors. Biochemical pharmacology 20040701
Use of a novel histone deacetylase inhibitor to induce apoptosis in cell lines of acute lymphoblastic leukemia. Haematologica 20040401
Selective growth inhibition of tumor cells by a novel histone deacetylase inhibitor, NVP-LAQ824. Cancer research 20040115
The discovery of NVP-LAQ824: from concept to clinic. Current medicinal chemistry 20031101
N-hydroxy-3-phenyl-2-propenamides as novel inhibitors of human histone deacetylase with in vivo antitumor activity: discovery of (2E)-N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2-propenamide (NVP-LAQ824). Journal of medicinal chemistry 20031009
NVP-LAQ824 is a potent novel histone deacetylase inhibitor with significant activity against multiple myeloma. Blood 20031001
Histone deacetylase inhibitor LAQ824 down-regulates Her-2 and sensitizes human breast cancer cells to trastuzumab, taxotere, gemcitabine, and epothilone B. Molecular cancer therapeutics 20031001
Histone deacetylase inhibitor LAQ824 both lowers expression and promotes proteasomal degradation of Bcr-Abl and induces apoptosis of imatinib mesylate-sensitive or -refractory chronic myelogenous leukemia-blast crisis cells. Cancer research 20030815
Properties