Alvocidib

Base Information

• Chemical Name: Alvocidib
• CAS No.: 146426-40-6
• Deprecated CAS: 358739-39-6
• Molecular Formula: C21H20ClNO5
• Molecular Weight: 401.847
• Hs Code.: 2934999090
• UNII: 45AD6X575G
• DSSTox Substance ID: DTXSID20904970
• Nikkaji Number: J564.052K
• Wikipedia: Alvocidib
• Wikidata: Q4063441
• NCI Thesaurus Code: C74940
• Pharos Ligand ID: DZT8FZQTCAZT
• Metabolomics Workbench ID: 133953
• ChEMBL ID: CHEMBL428690
• Mol file: 146426-40-6.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 Alvocidib

Chemical Property:

• Appearance/Colour: Yellow powder
• Melting Point: 52.5 °C
• Refractive Index: 1.708
• Boiling Point: 603.6 °C at 760 mmHg
• PKA: 6.16±0.40(Predicted)
• Flash Point: 318.8 °C
• PSA: 94.14000
• Density: 1.448 g/cm³
• LogP: 3.24250
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; ≥40.2 mg/mL in DMSO; ≥85.4 mg/mL in EtOH with gentle warming and ultrasonic
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 401.1030004
• Heavy Atom Count: 28
• Complexity: 628

Purity/Quality:

98% ^*data from raw suppliers

Flavopiridol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC(C(C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O
• Isomeric SMILES: CN1CC[C@@H]([C@@H](C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)O
• Recent ClinicalTrials: Study of Alvocidib in Patients With Relapsed/Refractory AML Following Treatment With Venetoclax Combination Therapy
• 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
• Recent NIPH Clinical Trials: A Phase 1 Clinical Study of DSP-2033 (Alvocidib) in Combination with Cytarabine/Mitoxantrone or Cytarabine/Daunorubicin (7+3) in Patients with Acute Myeloid Leukemia
• Uses: Antineoplastic (cyclin-dependent kinase inhibitor)[Note—The trivial name, flavopiridol, has appeared in literature]. Flavopiridol is a synthetic flavonoid derivative, potent inhibitor of CDKs. Inhibitor of CDK9 as a postexposure drug target for adenoviruses.

Technology Process of Alvocidib

There total 2 articles about Alvocidib 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%

2-(2-chlorophenyl)-5,7-dimethoxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-benzopyran-4-one hydrochloride (358739-92-1) → flavopiridol (146426-40-6)

Guidance literature:

With boron tribromide; In chlorobenzene; at 80 - 103 ℃; for 15h;

Reference yield: 56.0%

→ flavopiridol (146426-40-6) + (3S-cis)-1-Methyl-4-(2,4,6-trimethyoxyphenyl)-3- piperidinol

Guidance literature:

Reference yield: 70.0%

flavopiridol (146426-40-6) + 3-(2-methoxyethyloxy)propionic acid (149577-05-9,125220-94-2) → (3S,4R)-4-(2-(2-chlorophenyl)-5-hydroxy-7-((3-(2-methoxyethoxy)propanoyl)oxy)-4-oxo-4H-chromen-8-yl)-1-methylpiperidin-3-yl 3-(2-methoxyethoxy)propanoate

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;

upstream raw materials:

2-(2-chlorophenyl)-5,7-dimethoxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-benzopyran-4-one hydrochloride

Downstream raw materials:

flavopiridol 3'-O-β-D-glucoside

Refernces

• 1、 -. "CDK9 INHIBITORS AND POLYMORPHS THEREOF FOR USE AS AGENTS FOR TREATMENT OF CANCER". Paragraph 00346; 00369; 00370. . Retrieved 2020/07/05.
• 2、 -. "PROCESS FOR THE PREPARATION OF CHIRAL KETONE INTERMEDIATES USEFUL FOR THE PREPARATION OF FLAVOPIRIDOL AND ANALOGS". . . Retrieved 2008/06/13.