Hdac-IN-1

Base Information

• Chemical Name: Hdac-IN-1
• CAS No.: 852475-26-4
• Molecular Formula: C₁₇H₁₅FN₂O₃
• Molecular Weight: 314.316
• European Community (EC) Number: 685-051-2
• ChEMBL ID: CHEMBL191089
• DSSTox Substance ID: DTXSID40464187
• Nikkaji Number: J3.588.633H
• Wikidata: Q72488284
• Mol file: 852475-26-4.mol

Synonyms:852475-26-4;HDAC-IN-1;MC 1568;1239610-44-6;MC-1568;(E)-3-[4-[(E)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methylpyrrol-2-yl]-N-hydroxyprop-2-enamide;CHEMBL191089;(E)-3-(4-((E)-3-(3-fluorophenyl)-3-oxoprop-1-enyl)-1-methyl-1H-pyrrol-2-yl)-N-hydroxyacrylamide;(E)-3-(4-((E)-3-(3-fluorophenyl)-3-oxoprop-1-en-1-yl)-1-methyl-1H-pyrrol-2-yl)-N-hydroxyacrylamide;C17H15FN2O3;3-[5-(3-(3-Fluorophenyl)-3-oxoprope n-1-yl)-1-methyl-1H-pyrrol-2-yl]-N-hydroxy-2-prope namide;MLS006011094;SCHEMBL14974121;SCHEMBL14974122;CHEBI:95072;GTPL11121;DTXSID40464187;BCPP000170;BDBM50166164;HB1390;MFCD16875423;s1484;AKOS024457966;BCP9000898;CCG-267627;CS-1259;MC1568?;compound 2f [PMID: 15857140];NCGC00346534-07;3-[5-(3-(3-Fluorophenyl)-3-oxopropen-1-yl)-1-methyl-1h-pyrrol-2-yl]-n-hydroxy-2-propenamide;HY-15140;SMR004702882;SW219738-1;A12891;A906937;J-510633;3-(4-(3-(3-fluorophenyl)-3-oxoprop-1-enyl)-1-methyl-1H-pyrrol-2-yl)-N-hydroxyacrylamide;(2E)-3-[4-[(1E)-3-(3-Fluorophenyl)-3-oxo-1-propen-1-yl]-1-methyl-1H-pyrrol-2-yl]-N-hydroxy-2-propenamide;(E)-3-(4-((E)-3-(3-fluorophenyl)-3-oxoprop-1-enyl)-1-methyl-1Hpyrrol-2-yl)-N-hydroxyacrylamide;(E)-3-{4-[3-(3-Fluoro-phenyl)-3-oxo-propenyl]-1-methyl-1H-pyrrol-2-yl}-N-hydroxy-acrylamide

Chemical Property of Hdac-IN-1

Chemical Property:

• PSA: 74.82000
• LogP: 3.41920
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 314.10667051
• Heavy Atom Count: 23
• Complexity: 492

Purity/Quality:

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

MC 1568 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C=C1C=CC(=O)NO)C=CC(=O)C2=CC(=CC=C2)F
• Isomeric SMILES: CN1C=C(C=C1/C=C/C(=O)NO)/C=C/C(=O)C2=CC(=CC=C2)F
• Description: While class I HDACs are localized predominantly within the nucleus, class II HDACs shuttle into and out of the nucleus in response to intracellular signaling. Class IIa HDACs, which includes HDAC4, 5, 7, and 9, commonly act as corepressors and play diverse roles in cell biology. MC 1568 is a selective inhibitor of class IIa HDACs, with greater than 170-fold selectivity over class I HDACs, including HDAC1. It has been used in cells (1-10 μM) and in mice to elucidate the roles of class IIa HDACs in cell proliferation and differentiation, apoptosis, myogenesis, adipogenesis, and fibrosis.
• Uses: A selective class II (IIa) histone deacetylase (HDAC II) inhibitor. It exhibits tissue-selective inhibition between members of class II acetylases in vivo, particularly in skeletal muscle and the heart. It arrests myogenesis through the stabilization of myocyte enhancer factor 2D (MEF2D)-HDAC3/4 complex. While class I HDACs are localized predominantly within the nucleus, class II HDACs shuttle into and out of the nucleus in response to intracellular signaling. Class IIa HDACs, which includes HDAC4, 5, 7, and 9, commonly act as corepressors and play diverse roles in cell biology. MC 1568 is a selective inhibitor of class IIa HDACs, with greater than 170-fold selectivity over class I HDACs, including HDAC1. It has been used in cells (1-10 μM) and in mice to elucidate the roles of class IIa HDACs in cell proliferation and differentiation, apoptosis, myogenesis, adipogenesis, and fibrosis.[Cayman Chemical]

Technology Process of Hdac-IN-1

There total 8 articles about Hdac-IN-1 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: 70.0%

C22H23FN2O4 → 3-(5-(3-(3-fluorophenyl)-3-oxo-1-propen-1-yl)-1-methyl-1H-pyrrol-2-yl)-N-hydroxy-2-propenamide (1262776-28-2,852475-26-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 21 ℃; for 1h;

DOI:10.1021/jm401945k

Reference yield: 54.0%

(E)-3-{5-[(E)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methyl-1H-pyrrol-2-yl}-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide → (2E)-3-[5-[(1E)-3-(3-fluorophenyl)-3-oxo-1-propen-1-yl]-1-methyl-1H-pyrrol-2-yl]-N-hydroxy-2-propenamide (852475-26-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; water;

Reference yield:

ethyl (2E)-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate (2769-90-6) → (2E)-3-[5-[(1E)-3-(3-fluorophenyl)-3-oxo-1-propen-1-yl]-1-methyl-1H-pyrrol-2-yl]-N-hydroxy-2-propenamide (852475-26-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride / 1,2-dichloro-ethane / 0.5 h / 0 °C

1.2: 1 h / 0 °C

2.1: potassium hydroxide / ethanol; water / 0.25 h / 22 °C

2.2: 22 - 60 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 16 h / 22 °C

4.1: toluene-4-sulfonic acid / water; methanol

With oxalyl dichloride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium hydroxide; In methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane;

upstream raw materials:

ethyl 3-(1-methyl-1H-pyrrol-2-yl)-2-propenoate

N-methylpyrrole aldehyde

ethyl (2E)-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR TREATING EPIGENETIC DISEASE". Page/Page column 33-34. . Retrieved 2020/02/16.