(E)-2-(3-(naphthalen-2-yl)but-2-enamido)benzoic acid

Base Information

• Chemical Name: (E)-2-(3-(naphthalen-2-yl)but-2-enamido)benzoic acid
• CAS No.: 321674-73-1
• Molecular Formula: C21H17NO3
• Molecular Weight: 331.36
• DSSTox Substance ID: DTXSID70432975
• Nikkaji Number: J1.715.069C
• Wikidata: Q27455481
• Pharos Ligand ID: 34AKFGQJX49W
• ChEMBL ID: CHEMBL27323
• Mol file: 321674-73-1.mol

Synonyms:BIBR 1532;BIBR-1532;BIBR1532

Chemical Property of (E)-2-(3-(naphthalen-2-yl)but-2-enamido)benzoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.698
• Boiling Point: 600.607 °C at 760 mmHg
• PKA: 3.46±0.36(Predicted)
• Flash Point: 317.036 °C
• PSA: 66.40000
• Density: 1.285 g/cm³
• LogP: 4.65300
• Storage Temp.: Store at RT
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 331.12084340
• Heavy Atom Count: 25
• Complexity: 527

Purity/Quality:

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

BIBR 1532 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)NC1=CC=CC=C1C(=O)O)C2=CC3=CC=CC=C3C=C2
• Isomeric SMILES: C/C(=C\C(=O)NC1=CC=CC=C1C(=O)O)/C2=CC3=CC=CC=C3C=C2
• Description: BIBR 1532 is a mixed-type non-competitive inhibitor of telomerase (IC50 = 93 nM) that has little effect on several mammalian DNA and RNA polymerases, bacterial DNA helicase, or HIV-1 reverse transcriptase. It specifically targets the telomerase reverse transcriptase catalytic subunit, TERT. Through its effects on telomerase, BIBR 1532 induces senescence or apoptosis in cancer cells. Apoptosis in triple negative breast cancer cells induced by BIBR 1532 is potentiated by glucose restriction.
• Uses: BIBR 1532 is a mixed-type non-competitive inhibitor of telomerase. It specifically targets the telomerase reverse transcriptase catalytic subunit, TERT.

Technology Process of (E)-2-(3-(naphthalen-2-yl)but-2-enamido)benzoic acid

There total 13 articles about (E)-2-(3-(naphthalen-2-yl)but-2-enamido)benzoic acid 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:

N-(2-carbomethoxyphenyl)-3-(naphthalen-2-yl)-but-2(Z)-enamide (565190-73-0) → trans-3-(naphth-2-yl)-but-2-enoic acid-N-(2-carboxy-phenyl)-amide (321674-73-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0960-894X(03)00101-X

Reference yield:

N-(2-carbomethoxyphenyl)-3-(naphthalen-2-yl)-but-2(E)-enamide (321674-72-0) → 2-[[(2E)-3-(2-naphthalenyl)-1-oxo-2-butenyl-1-yl]amino]benzoic acid (321674-73-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0960-894X(03)00101-X

Reference yield:

(E)-3-Naphthalen-2-yl-but-2-enoyl chloride (321675-01-8) → 2-[[(2E)-3-(2-naphthalenyl)-1-oxo-2-butenyl-1-yl]amino]benzoic acid (321674-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / diethyl ether / 5 h / 20 °C

2: aq. LiOH / tetrahydrofuran / 12 h / 20 °C

With pyridine; lithium hydroxide; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0960-894X(03)00101-X

upstream raw materials:

N-(2-carbomethoxyphenyl)-3-(naphthalen-2-yl)-but-2(Z)-enamide

methyl (Z)-3-(naphthalen-2-yl)-but-2-enoate

methyl 2-naphthyl ketone

N-(2-carbomethoxyphenyl)-3-(naphthalen-2-yl)-but-2(E)-enamide

Refernces

• 1、 -. "N-substituted acrylamide derivatives as DHODH inhibitors and preparation and use of N-substituted acrylamide derivatives". Paragraph 0178-0179; 0183; 0320-0322. . Retrieved 2019/11/04.
• 2、 -. "Carboxylic acid amides, pharmaceutical compositions containing these compounds and their use". . . Retrieved 2008/06/13.