cis-Tranilast

Base Information

• Chemical Name: cis-Tranilast
• CAS No.: 91920-58-0
• Molecular Formula: C₁₈H₁₇NO₅
• Molecular Weight: 327.337
• DSSTox Substance ID: DTXSID30424972
• Nikkaji Number: J511.890E
• Wikidata: Q82237724
• ChEMBL ID: CHEMBL1474479
• Mol file: 91920-58-0.mol

Synonyms:cis-Tranilast;91920-58-0;2-[[(Z)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid;Tocris-1098;Lopac-T-0318;CHEMBL1474479;SCHEMBL10978582;DTXSID30424972;(Z)-2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid;2-[[(2Z)-3-(3,4-Dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic Acid;NCGC00015995-01;NCGC00018185-01;NCGC00018185-02;NCGC00018185-03;NCGC00021458-02

Chemical Property of cis-Tranilast

Chemical Property:

• Melting Point: 138-141°C
• Boiling Point: 585.6±50.0 °C(Predicted)
• PKA: 3.45±0.36(Predicted)
• PSA: 88.35000
• Density: 1.299±0.06 g/cm3(Predicted)
• LogP: 3.70340
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 327.11067264
• Heavy Atom Count: 24
• Complexity: 464

Purity/Quality:

97% ^*data from raw suppliers

cis-Tranilast ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC(=O)NC2=CC=CC=C2C(=O)O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C\C(=O)NC2=CC=CC=C2C(=O)O)OC
• Uses: cis-Tranilast is an antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.

Technology Process of cis-Tranilast

There total 9 articles about cis-Tranilast 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: 62.0%

2-[(2-carboxyacetyl)amino]benzoic acid (53947-84-5) + 3,4-dimethoxy-benzaldehyde (120-14-9) → N-(3,4-dimethoxycinnamoyl)anthranilic acid (53902-12-8,70806-55-2,91920-58-0)

Guidance literature:

2-[(2-carboxyacetyl)amino]benzoic acid; 3,4-dimethoxy-benzaldehyde; With piperidine; In toluene; for 3h; Reflux; Dean-Stark;

With methanol; In water; at 40 ℃;

With hydrogenchloride; In water;

DOI:10.1016/j.ejmech.2019.02.074

Reference yield: 48.0%

→ N-(3,4-dimethoxycinnamoyl)anthranilic acid (53902-12-8,70806-55-2,91920-58-0)

Guidance literature:

Reference yield:

3,4-dimethoxy-trans-cinnamic acid (14737-89-4) + 2-carbomethoxyaniline (134-20-3) → N-(3,4-dimethoxycinnamoyl)anthranilic acid (53902-12-8,70806-55-2,91920-58-0)

Guidance literature:

With pyridine; trichlorophosphate; In 1,4-dioxane; ethanol;

upstream raw materials:

3,4-dimethoxy-trans-cinnamic acid

2-carbomethoxyaniline

anthranilic acid

2-[(2-carboxyacetyl)amino]benzoic acid

Downstream raw materials:

Tranilast

C₃₆H₃₄N₂O₁₀

Refernces

• 1、 Chandrabalan, Arundhasa,McPhillie, Martin J.,Morice, Alyn H.,Boa, Andrew N.,Sadofsky, Laura R.. "N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites". . p. 141 - 156. Retrieved 2019/03/17.
• 2、 Kakegawa,Mitsuo,Matsumoto,Satoh,Akagi,Tasaka. "Hyaluronidase-inhibitory and anti-allergic activities of the photo-irradiated products of tranilast". . p. 3738 - 3744. Retrieved 2007/10/02.