920113-03-7

Basic information

• Product Name: P276
• Synonyms: P276;4H-1-Benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methyl-3-pyrrolidinyl]-, hydrochloride (1:1);P276-00 4H-1-Benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-((2R,3S)-2-(hydroxymethyl)-1-methyl-3-pyrrolidinyl)-, hydrochloride (1:1);2-(2-chlorophenyl)-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one:hydrochloride;2-(2-chlorophenyl)-5,7-dihydroxy-8-((2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)-4H-chromen-4-one hydrochloride
• CAS NO: 920113-03-7
• Molecular Formula: C₂₁H₂₀ClNO₅*ClH
• Product Categories: Inhibitors
• Mol File: 920113-03-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: P276(CAS DataBase Reference)
• NIST Chemistry Reference: P276(920113-03-7)
• EPA Substance Registry System: P276(920113-03-7)

Safety Data

• Hazardous Substances Data: 920113-03-7(Hazardous Substances Data)

Usage

Uses

P276-00 is a cyclin-dependent kinase (CDK) inhibitor. P276-00 has shown to be highly selective for cancer cells and has shown to produce potent inhibition of Cdk4-D1 activity. P276-00 also induces apoptosis in human promyelocytic leukemia (HL-60) cells.

Enzyme inhibitor

This cell cycle-inhibiting flavone and anticancer agent (FW = 438.30 g/mol; CAS 920113-03-7), also named 2-(2-chlorophenyl)-5,7-dihydroxy-8- [(2R,3S)-2-(hydroxymethyl)-1-methyl-3-pyrrolidinyl]-4H-1-benzopyran-4- one, targets the Cyclin-Dependent Kinases CDK1 (IC50 = 79 nM), CDK4 (IC50 = 63 nM) and CDK9 (IC50 = 20 nM). p276-00 showed potent antiproliferative effects against various human cancer cell lines (IC50 values ranging from 300 to 800 nmol/L), but has little effect on cultured fibroblasts. A significant down-regulation of cyclin D1 and Cdk4 and a decrease in Cdk4-specific pRb Ser(780) phosphorylation is observed. P276-00 produces potent inhibition of Cdk4-D1 activity that is competitive with ATP, and not with retinoblastoma protein. The compound also induced apoptosis in human promyelocytic leukemia (HL-60) cells, as evidenced by the induction of caspase-3 and DNA ladder studies. In 22 human cancer xenografts, P276-00 is approximately 26x more potent than cisplatin, and is also active against cisplatin-resistant tumors of central nervous system, melanoma, prostate, and renal cancers. Synchronized human non-small cell lung carcinoma (H-460) and human normal lung fibroblast (WI-38) cells are arrested in G1

Upstream product

• 113225-08-4 (±)-trans-1-methyl-4-(2,4,6-trimethoxyphenyl)piperidin-3-ol 
• 621-23-8 1,2,3-trimethoxybenzene 
• 113225-07-3 1-methyl-4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine 
• 920113-01-5 (+)-trans-2-(2-chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one 
• 1622998-49-5 (-)-trans-2-(2-(acetoxymethyl)-1-methylpyrrolidin-3-yl)-6-acetyl-3,5-dimethoxyphenyl-2-chlorobenzoate 
• 920112-99-8 ((-)-trans-acetic acid-3-(3-acetyl-2-hydroxy-4,6-dimethoxyphenyl)-1-methylpyrrolidin-2-yl)methyl ester 
• 118-91-2 ortho-chlorobenzoic acid 
• 609-65-4 o-chlorobenzoyl chloride 
• 1254504-57-8 C₁₅H₂₃NO₄*C₁₈H₁₄O₈ 
• 920112-97-6 (-)-trans-[1-methyl-3-(2,4,6-trimethoxyphenyl)pyrrolidin-2-yl]methanol 
• 117955-09-6 (±)-trans-[1-methyl-3-(2,4,6-trimethoxyphenyl)pyrrolidin-2-yl]methanol 
• 920113-02-6 (+)-trans-2-(2-chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one 

Relevant articles and documents

AN IMPROVED PROCESS FOR PREPARATION OF AN INTERMEDIATE OF THE PYRROLIDINE SUBSTITUTED FLAVONES

The present invention relates to a process for the preparation of a key intermediate (as described herein) used in the synthesis of (+)-trans enantiomer of pyrrolidine substituted flavones, represented by the compounds of formula (1) or pharmaceutically a

AN ENANTIOSELECTIVE SYNTHESIS OF PYRROLIDINE-SUBSTITUTED FLAVONES

The present invention relates to an enantioselective synthesis of (+)-trans enantiomer of pyrrolidines substituted with flavones, represented by Formula 1 or salts thereof, which are inhibitors of cyclin dependant kinases and can be used for treatment of