Cridanimod

Base Information

• Chemical Name: Cridanimod
• CAS No.: 38609-97-1
• Molecular Formula: C15H11NO3
• Molecular Weight: 253.257
• Hs Code.: 2933990090
• European Community (EC) Number: 634-833-1
• UNII: X91E9EME19
• DSSTox Substance ID: DTXSID6046557
• Nikkaji Number: J66.887G
• Wikidata: Q27293702
• NCI Thesaurus Code: C77948
• Metabolomics Workbench ID: 154462
• ChEMBL ID: CHEMBL1569545
• Mol file: 38609-97-1.mol

Synonyms:10(9H)-acridineacetic acid, 9-oxo-;10-carboxymethyl-9-acridanone;10-carboxymethyl-9-acridanone, sodium salt;9-oxo-10-acridineacetic acid;acridone N-methyl-N-(alpha,D-glucopyranosyl)ammonium 10-methylenecarboxylate;cridanimod;cridanimod sodium;cycloferon;meglumine acridone acetate

Chemical Property of Cridanimod

Chemical Property:

• Vapor Pressure: 2.79E-10mmHg at 25°C
• Melting Point: ~289 °C (dec.)
• Refractive Index: 1.657
• Boiling Point: 486.6 °C at 760 mmHg
• PKA: 3.69±0.10(Predicted)
• Flash Point: 248.1 °C
• PSA: 59.30000
• Density: 1.362 g/cm³
• LogP: 2.23930
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 253.07389321
• Heavy Atom Count: 19
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

9-Oxo-10(9H)-acridineacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3N2CC(=O)O
• Recent EU Clinical Trials: A Phase II Study of Sodium Cridanimod in Conjunction with Progestin Therapy in Patients with Progesterone Receptor Negative Recurrent or Persistent Endometrial Carcinoma.
• Uses: 9-Oxo-10(9H)-acridineacetic acid is a reagent for pre-column derivatization of amino acids for fluorescent determination in HPLC and it is also a building block in pharmaceutics.

Technology Process of Cridanimod

There total 17 articles about Cridanimod 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: 95.7%

chloroacetic acid (79-11-8) + 10H-acridin-9-one (578-95-0,790240-54-9) → cridanimod (38609-97-1)

Guidance literature:

With [Pmim]OH; at 20 - 25 ℃; for 12h; Ionic liquid;

Reference yield: 90.0%

ethyl bromoacetate (105-36-2) + 10H-acridin-9-one (578-95-0,790240-54-9) → cridanimod (38609-97-1)

Guidance literature:

ethyl bromoacetate; 10H-acridin-9-one; With sodium hydride;

With sodium hydroxide;

DOI:10.1021/acs.orglett.6b03356

Reference yield: 86.0%

9-oxoacridan-10-acetamide (77778-90-6) → cridanimod (38609-97-1)

Guidance literature:

With potassium hydroxide; In butan-1-ol; for 5h; Heating;

DOI:10.1135/cccc19803593

upstream raw materials:

2-<(carboxymethyl)phenylamino>benzoic acid

9-oxoacridan-10-acetamide

ethyl bromoacetate

10H-acridin-9-one

Downstream raw materials:

10-methyl-9, 10-dihydro-9-acridinone

10-carboxymethylacridanone sodium salt

Refernces

• 1、 Chang, Jia-jia,Hou, Shi,Lan, Xiu-juan,Li, Song,Li, Wei,Sun, Wei,Xiao, Jun-hai,Yan, Xin-lin,Yang, Xiao-hong. "Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists". . . Retrieved 2020/01/09.
• 2、 Wen, Jiangwei,Tang, Shan,Zhang, Fan,Shi, Renyi,Lei, Aiwen. "Palladium/copper Co-catalyzed oxidative C-H/C-H carbonylation of diphenylamines: A way to access acridones". . p. 94 - 97. Retrieved 2017/11/27.