Carboxyamidotriazole

Base Information

• Chemical Name: Carboxyamidotriazole
• CAS No.: 99519-84-3
• Molecular Formula: C17H12Cl3N5O2
• Molecular Weight: 424.674
• European Community (EC) Number: 804-580-3
• NSC Number: 609974
• UNII: 6ST3ZF52WB
• DSSTox Substance ID: DTXSID40244108
• Nikkaji Number: J385.691G
• Wikipedia: Carboxyamidotriazole
• Wikidata: Q5038072
• NCI Thesaurus Code: C1141
• Metabolomics Workbench ID: 153032
• ChEMBL ID: CHEMBL95431
• Mol file: 99519-84-3.mol

Synonyms:4-CAI;carboxyamido-triazole;carboxyamidotriazole;L 651582;L-651582;L651582

Chemical Property of Carboxyamidotriazole

Chemical Property:

• Vapor Pressure: 1.22E-18mmHg at 25°C
• Melting Point: 200-202 °C
• Refractive Index: 1.73
• Boiling Point: 685.5 °C at 760 mmHg
• PKA: 14.16±0.50(Predicted)
• Flash Point: 368.3 °C
• PSA: 116.89000
• Density: 1.65g/cm³
• LogP: 4.48020
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: soluble10mg/mL (clear solution)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 423.005658
• Heavy Atom Count: 27
• Complexity: 549

Purity/Quality:

99% ^*data from raw suppliers

L-651,582 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)C2=C(C=C(C=C2Cl)CN3C(=C(N=N3)C(=O)N)N)Cl)Cl
• Recent ClinicalTrials: Carboxyamidotriazole + RT in Treating Patients Newly Diagnosed Supratentorial GBM
• Uses: Carboxyamidotriazole is an orally active calcium channel blocker. Carboxyamidotriazole also exhibits inhibition of pro-inflammatory cytokines in tumor associated macrophages as potential anti-cancer m echanism.

Technology Process of Carboxyamidotriazole

There total 13 articles about Carboxyamidotriazole 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: 90.0%

(4-(azidomethyl)-2,6-dichlorophenyl)(4-chlorophenyl)methanone (99508-26-6) + cyanoacetic acid amide (107-91-5) → carboxyamidotriazole (99519-84-3)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; for 2h; Ambient temperature;

Reference yield:

propargylformamide + (4-(azidomethyl)-2,6-dichlorophenyl)(4-chlorophenyl)methanone (99508-26-6) → carboxyamidotriazole (99519-84-3)

Guidance literature:

With potassium carbonate; In acetonitrile; Heating;

Reference yield:

(4-chlorophenyl)(2,6-dichloro-4-(hydroxymethyl)phenyl)methanone (99508-25-5) → carboxyamidotriazole (99519-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / Cooling

2: potassium carbonate / acetonitrile / Heating

With diphenyl phosphoryl azide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; acetonitrile;

upstream raw materials:

(4-(azidomethyl)-2,6-dichlorophenyl)(4-chlorophenyl)methanone

cyanoacetic acid amide

3,5-dichlorotoluene

4-chloro-benzoyl chloride

Downstream raw materials:

5-benzamido-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1H-1,2,3-triazole-4-carboxamide

Refernces

• 1、 Allen, Timothy E. H.,Chung, Injae,Fischer, Peter,Hardy, Rachel,Harvey, Robert F.,Hirst, Judy,Kellam, Barrie,Macfarlane, Marion,Mistry, Sarah,Pryde, Kenneth R.,Serreli, Riccardo,Stephenson, Zo? A.,Stoneley, Mark,Willis, Anne E.. "Identification of a novel toxicophore in anti-cancer chemotherapeutics that targets mitochondrial respiratory complex i". . . Retrieved 2020/06/10.
• 2、 -. "Novel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazoles orotate formulations". Paragraph 0051; 0083. . Retrieved 2014/07/23.