CP 91149

Base Information

• Chemical Name: CP 91149
• CAS No.: 186392-40-5
• Molecular Formula: C21H21ClN3O3
• Molecular Weight: 399.870697
• European Community (EC) Number: 687-420-3
• UNII: O8EV00W45A
• DSSTox Substance ID: DTXSID70171897
• Nikkaji Number: J945.850F
• Wikidata: Q27285479
• Pharos Ligand ID: 3FM112X7GLHB
• ChEMBL ID: CHEMBL319136
• Mol file: 186392-40-5.mol

Synonyms:UNII-O8EV00W45A;HMS3261K03;

Chemical Property of CP 91149

Chemical Property:

• Melting Point: 190-192°C
• PSA: 88.92000
• LogP: 3.18630
• Storage Temp.: Refrigerator
• Solubility.: DMSO: >20mg/mL
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 399.1349693
• Heavy Atom Count: 28
• Complexity: 553

Purity/Quality:

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

CP-91149 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)C(=O)C(C(CC1=CC=CC=C1)NC(=O)C2=CC3=C(N2)C=CC(=C3)Cl)O
• Isomeric SMILES: CN(C)C(=O)[C@@H]([C@H](CC1=CC=CC=C1)NC(=O)C2=CC3=C(N2)C=CC(=C3)Cl)O
• Description: CP 91,149 is an inhibitor of human liver glycogen phosphorylase a (LGPa), muscle glycogen phosphorylase a (MGPa), and MGPb (IC50s = 0.13, 0.2, and 0.3 μM, respectively, in the presence of glucose). CP 91,149 is 5- to 10-fold less potent in the absence of glucose. In vitro, it inhibits glucagon-stimulated glycogenolysis in primary human hepatocytes (IC50 = 2.1 μM) and increases glycogen synthesis in rat hepatocytes at a concentration of 2.5 μM in the presence of 5 mM glucose. CP 91,149 inhibits brain GP (IC50 = 0.5 μM) and, at a concentration of 30 μM, inhibits glycogen accumulation and proliferation of A549 non-small cell lung carcinoma (NSCLC) cells that express endogenous brain GP. In vivo, CP 91,149 (25 mg/kg, p.o.) lowers the plasma glucose level in diabetic ob/ob mice within 3 hours of administration without producing hypoglycemia, but has no effect on normoglycemic, non-diabetic mice.
• Uses: Inhibition of glycogen phosphorylase (GP) by CP-91,149 induces growth inhibition correlating with brain GP expression. Antitumor agent.

Technology Process of CP 91149

There total 20 articles about CP 91149 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,N-dimethylammonium chloride (506-59-2) + (2R,3R)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid (186392-36-9) → 5-Chloro-1H-indole-2-carboxylic acid ((1R,2R)-1-benzyl-2-dimethylcarbamoyl-2-hydroxy-ethyl)-amide (186392-40-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 23 ℃; for 18h;

DOI:10.1021/jm980264k

Reference yield:

N,N-dimethylammonium chloride (506-59-2) + (2S,3S)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid (186393-16-8) → 5-Chloro-1H-indole-2-carboxylic acid ((1S,2S)-1-benzyl-2-dimethylcarbamoyl-2-hydroxy-ethyl)-amide (186392-40-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 23 ℃; for 18h;

DOI:10.1021/jm980264k

Reference yield:

N,N-dimethylammonium chloride (506-59-2) + (2R,3S)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid (186392-32-5) → [R-(R*,S*)]-5-chloro-N-[3-(dimethylamino)-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-1H-indole-2-carboxamide (186392-40-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 23 ℃; for 18h;

DOI:10.1021/jm980264k

upstream raw materials:

N,N-dimethylammonium chloride

5-chloro-1H-Indole-2-carboxylic acid

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

(2R,3R)-3-[(5-Chloro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid

Refernces

• 1、 -. "Tetrazole compounds as thyroid receptor ligands". . . Retrieved 2008/06/13.
• 2、 -. "Methods of treating diabetic cardiomyopathy using glycogen phosphorylase inhibitors". . . Retrieved 2008/06/13.