Flavopiridol hydrochloride

Base Information

• Chemical Name: Flavopiridol hydrochloride
• CAS No.: 131740-09-5
• Molecular Formula: C21H20ClNO5^.HCl
• Molecular Weight: 438.30
• European Community (EC) Number: 634-346-4
• UNII: D48MS3A6N9
• DSSTox Substance ID: DTXSID6048961
• Wikidata: Q27163006
• NCI Thesaurus Code: C1571
• ChEMBL ID: CHEMBL2105698
• Mol file: 131740-09-5.mol

Synonyms:(-)cis-5,7-dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4H-1-benzopyran-4-one;alvocidib;flavopiridol;HMR 1275;L 868275;L-868275;L86-8275

Chemical Property of Flavopiridol hydrochloride

Chemical Property:

• Vapor Pressure: 2.03E-15mmHg at 25°C
• Melting Point: 169.5-170℃
• Boiling Point: 603.6oC at 760 mmHg
• PKA: 5.68 ± 0.06(at 25℃)
• Flash Point: 318.8oC
• PSA: 94.14000
• LogP: 4.04450
• Storage Temp.: 2-8°C
• Solubility.: H2O: ~2mg/mL
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 437.0796782
• Heavy Atom Count: 29
• Complexity: 628

Purity/Quality:

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

Flavopiridol hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(C(C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O.Cl
• Isomeric SMILES: CN1CC[C@@H]([C@@H](C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O.Cl
• Recent ClinicalTrials: Alvocidib in Combination With Decitabine and Venetoclax in Patients With Relapsed or Refractory AML or as Frontline Therapy in Unfit Patients With AML
• Recent EU Clinical Trials: A Phase 2, Randomized, Biomarker-driven, Clinical Study in Patients with Relapsed or Refractory Acute Myeloid Leukemia (AML) with an Exploratory Arm in Patients with Newly Diagnosed High-Risk AML and Exploratory
• Description: Flavopiridol is an orally bioavailable inhibitor of cyclin dependent kinases (IC50s = ~100, ~100, ~100, and 300 nM for Cdk1, Cdk2, Cdk4, and Cdk7, respectively). It also inhibits TEFb, a complex composed of Cdk9 and cyclin T1, with a Ki value of 3 nM. Flavopiridol inhibits transcription of a CMV promoter in HeLa nuclear extract (IC50 = 34 nM), Tat-stimulated transcription of an HIV-1 promotor (IC50 = 7 nM), and HIV-1 replication in HEK239T cells (IC50 = <10 nM). In vivo, flavopiridol (5 mg/kg, i.p.) induces apoptosis and cyclin D1 depletion and delays tumor growth in an HN-12 head and neck carcinoma mouse xenograft model. It also suppresses synovial hyperplasia and joint destruction in a mouse model of collagen-induced arthritis.
• Uses: An inhibitor of cyclin-dependent kinases; the (-)-cis form induces apoptosis in certain tumor cells An inhibitor of cyclin-dependent kinases; the (-)-cis form induces apoptosis in certain tumor cells. Flavopiridol hydrochloride hydrate has been used:as a cyclin-dependent kinase 9 (CDK9) inhibitor to study its effects on histone H3 methylation at lysine 36 (H3K36) and deactivation of transcription in porcine fetal fibroblastsas an RNA polymerase inhibitor to study its effects on hepatic cellsas RNA transcription inhibitor to study its effects on euchromatin coarsening in zebrafish embryo

Technology Process of Flavopiridol hydrochloride

There total 5 articles about Flavopiridol hydrochloride 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:

C25H26ClNO6 → cis-5,7-dihydroxy-2-[2-chlorophenyl]-8-[4-(3-hydroxy-1-methylpiperidinyl)]-4H-1-benzopyran-4-one hydrochloride (131740-09-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water; methanol / 1 h / 20 °C

2: pyridine hydrochloride / 4 h / 210 - 220 °C / Industrial scale

3: hydrogenchloride / diethyl ether; chloroform / 0.25 h / Reflux; Industrial scale

With hydrogenchloride; pyridine hydrochloride; sodium hydroxide; In methanol; diethyl ether; chloroform; water;

DOI:10.1021/op980215h

Reference yield:

flavopiridol → cis-5,7-dihydroxy-2-[2-chlorophenyl]-8-[4-(3-hydroxy-1-methylpiperidinyl)]-4H-1-benzopyran-4-one hydrochloride (131740-09-5)

Guidance literature:

With hydrogenchloride; In diethyl ether; chloroform; for 0.25h; Reflux; Industrial scale;

DOI:10.1021/op980215h

Reference yield:

C18H25NO6 → cis-5,7-dihydroxy-2-[2-chlorophenyl]-8-[4-(3-hydroxy-1-methylpiperidinyl)]-4H-1-benzopyran-4-one hydrochloride (131740-09-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 4 h / 0 - 20 °C

2.1: pyridine; potassium hydroxide / 0.5 h / 55 °C

2.2: 0.5 h

3.1: acetic acid; sulfuric acid / 20 - 100 °C

4.1: sodium hydroxide / water; methanol / 1 h / 20 °C

5.1: pyridine hydrochloride / 4 h / 210 - 220 °C / Industrial scale

6.1: hydrogenchloride / diethyl ether; chloroform / 0.25 h / Reflux; Industrial scale

With pyridine; hydrogenchloride; sulfuric acid; pyridine hydrochloride; acetic acid; potassium hydroxide; sodium hydroxide; In methanol; diethyl ether; chloroform; water;

DOI:10.1021/op980215h

upstream raw materials:

C₂₅H₂₈ClNO₇

Refernces