404951-53-7

Basic information

• Product Name: 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-
• Synonyms: 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-;(E)-N-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1H-indol-3-yl)ethyl]amino]meth yl]phenyl]prop-2-enamide;dacinostat;3-[4-[N-(2-Hydroxyethyl)-N-[2-(1H-indol-3-yl)ethyl]aminomethyl]phenyl]-2(E)-propenohydroxamic acid;LAQ824(NVP-LAQ824,Dacinostat);LAQ824 (NVP-LAQ824);NVP-LAQ824;Dacinostat(NVP-LAQ 824)
• CAS NO: 404951-53-7
• Molecular Formula: C22H25N3O3
• Molecular Weight: 379.4522
• Product Categories: Inhibitor;Inhibitors
• Mol File: 404951-53-7.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Density: 1.29 g/cm³
• Refractive Index: 1.692
• Solubility: insoluble in H2O; insoluble in EtOH; ≥17.45 mg/mL in DMSO
• PKA: 8.81±0.23(Predicted)
• CAS DataBase Reference: 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-(404951-53-7)
• EPA Substance Registry System: 2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-(404951-53-7)

Safety Data

• Hazardous Substances Data: 404951-53-7(Hazardous Substances Data)

Usage

Description

2-Propenamide, N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-, also known as Dacinostat, is a chemical compound with a complex structure derived from 2-propenamide. It possesses unique properties that make it a valuable compound in various applications, particularly in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
Dacinostat is used as an inhibitor of aberrant chromatin accessibility, playing a crucial role in the regulation of gene expression. Its ability to target and modulate chromatin structure makes it a promising candidate for the development of novel therapeutic strategies against various diseases, including cancer.
Used in Synthesis of Anticancer Agents:
In the field of medicinal chemistry, Dacinostat is utilized in the synthesis of triazole-linked indole and oxindole glycoconjugates. These compounds have shown potential as anticancer agents, as they effectively inhibit the proliferation of various cancer cell lines. The development of such agents contributes to the ongoing efforts to discover new and more effective treatments for cancer.
Used in Cancer Research:
Dacinostat is also employed in cancer research to study the mechanisms underlying the regulation of chromatin structure and its impact on cancer development and progression. Understanding these mechanisms can lead to the identification of new therapeutic targets and the development of innovative treatments for cancer patients.

Biological Activity

laq824 (also known as nvp-laq824 or dacinostat), a derivative of 4-aminomethylcinnamic hydroxamic acid, is a novel and potent inhibitor of histone deacetylase (hdac) that inhibits the activity of hdac with 50% inhibition concentration ic50 value of 0.03 μm. laq824 has been found to inhibit the growth of a variety of cancer cell lines, including colon cancer h1299 and hct116 cells, breast cancer mda435 cells, prostate cancer du145 and pc3 cells and non-small cell lung cancer a549 cells, with ic50 value < 1 μm and induce apoptosis in human breast cancer skbr-3, bt-474 and mb-468 cells. laq824 also dose- and time-dependently inhibits the growth of multiple myeloma cells.catley l, weisberg e, tai yt, atadja p, remiszewski s, hideshima t, mitsiades n, shringarpure r, leblanc r, chauhan d, munshi nc, schlossman r, richardson p, griffin j, anderson kc. nvp-laq824 is a potent novel histone deacetylase inhibitor with significant activity against multiple myeloma. blood. 2003 oct 1;102(7):2615-22. epub 2003 jun 19.

InChI:InChI=1/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+