2-Cyano-3-(1-phenylindol-3-yl)acrylate

Base Information

• Chemical Name: 2-Cyano-3-(1-phenylindol-3-yl)acrylate
• CAS No.: 56396-35-1
• Molecular Formula: C₁₈H₁₂N₂O₂
• Molecular Weight: 288.305
• European Community (EC) Number: 693-266-8
• Nikkaji Number: J479.075H
• Wikidata: Q76386662
• ChEMBL ID: CHEMBL4303684
• Mol file: 56396-35-1.mol

Synonyms:2-CPIYA;2-cyano-3-(1-phenylindol-3-yl)acrylate;alpha-cyano-beta-(1-phenylindol-3-yl)acrylate;UK 5099;UK-5099

Chemical Property of 2-Cyano-3-(1-phenylindol-3-yl)acrylate

Chemical Property:

• Vapor Pressure: 7.79E-09mmHg at 25°C
• Boiling Point: 448.6°C at 760 mmHg
• PKA: 1.49±0.19(Predicted)
• Flash Point: 225.1°C
• PSA: 68.85000
• Density: 1.20
• LogP: 2.28738
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 288.089877630
• Heavy Atom Count: 22
• Complexity: 499

Purity/Quality:

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

UK-5099 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C=C(C3=CC=CC=C32)C=C(C#N)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)N2C=C(C3=CC=CC=C32)/C=C(\C#N)/C(=O)O
• Description: UK-5099 (56396-35-1) is a potent inhibitor of the mitochondrial pyruvate carrier (MPC).1?Rapidly increases glucose uptake in human monocytes.2?Attenuates mitochondrial oxidative phosphorylation and increases glycolysis creating greater stem-like properties in LnCap prostate cancer cells.3?Blocks the neuroprotective action of L-lactate or pyruvate during glutamate-induced excitotoxicity.4?Inhibits pyruvate transport across the plasma membrane of trypanosomes (Ki=49 μM).5
• Uses: Pyruvate transport into mitochondria is facilitated by mitochondrial pyruvate carrier (MPC) 1 and 2, two small transmembrane proteins that are part of a larger 150 kDa protein transport complex in the inner mitochondrial membrane. UK 5099 is a specific and potent inhibitor of MPC carrier activity. It potently inhibits pyruvate-dependent oxygen consumption by rat heart mitochondria with an IC50 value of 50 nM. UK-5099 has been used:as a mitochondrial pyruvate blocker to reduce pyruvate transportation into mitochondria in Roswell park memorial institute (RPMI) 1640 medium for prostatic cancer cell line culturein dimethyl sulfoxide (DMSO) stock, to study the effect of inhibiting pyruvate transport into mitochondria on pro-inflammatory responses in lipopolysaccharide activated macrophagesin topical treatment in order to study its effect on hair cycle induction in experimental mice Inhibitor of plasma membrane monocarboxylate transporters (MCTs) and the mitochondrial pyruvate carrier (MPC).

Technology Process of 2-Cyano-3-(1-phenylindol-3-yl)acrylate

There total 4 articles about 2-Cyano-3-(1-phenylindol-3-yl)acrylate 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: 65.0%

ethyl (E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)acrylate → (E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid (56396-35-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 21 ℃; for 1h;

Reference yield:

iodobenzene (591-50-4) → (E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid (56396-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; copper(I) oxide / N,N-dimethyl-formamide / 24 h / Reflux

2: L-proline / ethanol; water / 12 h / 21 °C

3: lithium hydroxide / tetrahydrofuran / 1 h / 21 °C

With copper(I) oxide; potassium carbonate; L-proline; lithium hydroxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

Reference yield:

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) → (E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid (56396-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; copper(I) oxide / N,N-dimethyl-formamide / 24 h / Reflux

2: L-proline / ethanol; water / 12 h / 21 °C

3: lithium hydroxide / tetrahydrofuran / 1 h / 21 °C

With copper(I) oxide; potassium carbonate; L-proline; lithium hydroxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

upstream raw materials:

iodobenzene

Indole-3-carboxaldehyde

1-phenyl-1H-indol-3-carboxaldehyde

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR MODULATING HAIR GROWTH". . . Retrieved 2020/07/21.