7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

Base Information

• Chemical Name: 7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
• CAS No.: 58880-19-6
• Molecular Formula: C₁₇H₂₂N₂O₃
• Molecular Weight: 302.373
• Hs Code.: 29280000
• NSC Number: 709238,311042
• Metabolomics Workbench ID: 113891
• ChEMBL ID: CHEMBL26159
• Mol file: 58880-19-6.mol

Synonyms:7-(4-(dimethylamino)phenyl)-N-hydroxy- 4,6-dimethyl-7-oxo-2,4-heptadienamide;503610-77-3;2, 7-[4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-;2, 7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-;7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide;NSC-311042;Trichostatin A (racemate);CHEMBL26159;SCHEMBL446806;CHEBI:91570;NSC311042;NSC709238;AKOS030213149;NSC-709238;PD128664;CS-0021924;BRD-A19037878-001-01-5;Hepta-2, 7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl- 7-oxo-, (2E,4E,6R)-;1208356-08-4

Chemical Property of 7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

Chemical Property:

• Appearance/Colour: Off-white powder
• Melting Point: 141°C -143°C
• Refractive Index: 136 ° (C=0.3, MeOH)
• PKA: 8.93±0.23(Predicted)
• PSA: 69.64000
• Density: 1.139 g/cm³
• LogP: 2.97020
• Storage Temp.: −20°C
• Solubility.: ethanol: 1 mg/mL
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 302.16304257
• Heavy Atom Count: 22
• Complexity: 447

Purity/Quality:

98%,99%, ^*data from raw suppliers

Trichostatin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-43
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C
• Isomeric SMILES: CC(/C=C(\C)/C=C/C(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C
• Description: Trichostatin A (58880-19-6) is a potent and selective histone deacetylase (HDAC) inhibitor (Ki = 3.4 nM). Induces reversion of ras transformed cells to normal morphology. Trichostatin A induces dedifferentiation of primordial germ cells into embryonic germ cells. Cell permeable and active in vivo.
• Uses: Trichostatin A is a known inhibitor of fibrosis in vitro and in vivo, and is used as an anticancer agent. Potent differentiation inducer of friend leukemic cells. Trichostatin A is a histone deacetylase inhibitor that enhances the cytotoxic efficacy of anticancer drugs that target DNA. Trichostatin A displays antifungal, antiprotozoan and antitumour activity Trichostatin A, ready-made solution has been used:as a histone deacetylase inhibitor to study its effect on transcriptome changes by stem cell testingto inhibit histone deacetylase (HDAC) class I, II, or III in primary pituitary cell cultures and to investigate insulin control of endogenous human growth hormone gene (hGH)to treat cells for the HDAC inhibition experiments

Technology Process of 7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

There total 41 articles about 7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

O-(2-methoxypropyl)-(R)-trichostatin A (122222-87-1) → trichostatin A (58880-19-6,122292-85-7) + (S)-(-)-trichostatin A (122292-85-7)

Guidance literature:

With Amberlyst 15; In methanol; at 45 ℃; for 1h; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)89789-1

Reference yield:

C23H36N2O3Si (1334686-47-3) → trichostatin A (58880-19-6,122292-85-7)

Guidance literature:

With methanol; cesium fluoride; at 20 ℃; for 3h;

Reference yield:

(+)-(R)-trichostatin acid (114127-18-3) → trichostatin A (58880-19-6,122292-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / Et₃N, ClCOOEt / tetrahydrofuran / 0.08 h / 0 °C

2: 81 percent / Amberlyst 15 / methanol / 1 h / 45 °C

With Amberlyst 15; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)89789-1

upstream raw materials:

O-(2-methoxypropyl)-(S)-trichostatin A

O-(2-methoxypropyl)-(R)-trichostatin A

ethyl (2E,4E)-(6R,7R)-7-[4-(dimethylamino)phenyl]-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

(S)-3-(4-Dimethylamino-phenyl)-3-(1-methoxy-1-methyl-ethoxy)-2-methyl-propionaldehyde

Downstream raw materials:

trichostatin C

2,3-dihydrotrichostatin A

Refernces

• 1、 -. "SYNTHESIS OF HDAC INHIBITORS: TRICHOSTATIN A AND ANALOGUES". . . Retrieved 2011/10/12.
• 2、 -. "Processes and compounds for preparing histone deacetylase inhibitors and intermediates thereof". Page/Page column title page; 12. . Retrieved 2010/11/25.