Voreloxin

Base Information

• Chemical Name: Voreloxin
• CAS No.: 175414-77-4
• Molecular Formula: C18H19N5O4S
• Molecular Weight: 401.44723
• UNII: K6A90IIZ19
• DSSTox Substance ID: DTXSID50938662
• Nikkaji Number: J1.625.332D
• Wikipedia: Vosaroxin
• Wikidata: Q18395775
• NCI Thesaurus Code: C95148
• Metabolomics Workbench ID: 153065
• ChEMBL ID: CHEMBL68117
• Mol file: 175414-77-4.mol

Synonyms:1,4-dihydro-7-(3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid;AG 7352;AG-7352;AG7352;SNS-595;voreloxin;vosaroxin

Chemical Property of Voreloxin

Chemical Property:

• PSA: 137.82000
• LogP: 1.41930
• Solubility.: insoluble in H2O; insoluble in EtOH; insoluble in DMSO
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 401.11577528
• Heavy Atom Count: 28
• Complexity: 662

Purity/Quality:

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

Voreloxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CN(CC1OC)C2=NC3=C(C=C2)C(=O)C(=CN3C4=NC=CS4)C(=O)O
• Isomeric SMILES: CN[C@H]1CN(C[C@@H]1OC)C2=NC3=C(C=C2)C(=O)C(=CN3C4=NC=CS4)C(=O)O
• Recent ClinicalTrials: Vosaroxin and Azacitidine in Treating Patients With Myelodysplastic Syndromes
• Recent EU Clinical Trials: A Phase II Study with a Safety Run-in Phase Evaluating Vosaroxin With Azacitidine in Older Patients with Newly Diagnosed Acute Myeloid Leukemia and Intermediate/Adverse Genetic Risk or Myelodysplastic Syndrome with Excess Blasts-2 (MDS-EB-2) - AMLSG 24-15
• Uses: Voreloxin is a potent Topoisomerase II inhibitor with broad-spectrum anti-tumor activity.

Technology Process of Voreloxin

There total 17 articles about Voreloxin 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: 86.3%

ethyl 1,4-dihydro-7-[(S,S)-3-methoxy-4-methylamino-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate (685880-17-5) → vosaroxin (175414-77-4)

Guidance literature:

ethyl 1,4-dihydro-7-[(S,S)-3-methoxy-4-methylamino-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate; With water; sodium hydroxide; In ethanol;

With acetic acid; In ethanol; at 60 ℃; for 2h; pH=7.5;

Reference yield:

ethyl 1,4-dihydro-7-(trans-3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate → 1,4-dihydro-7-(3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid (175414-77-4)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 24h;

DOI:10.1021/jm0304966

Reference yield:

ethyl 7-chloro-4-oxo-1-(1,3-thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate (174726-87-5) → vosaroxin (175414-77-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Et₃N / acetonitrile / 24 h / 20 °C

2: aq. NaOH; EtOH / 24 h / 20 °C

With sodium hydroxide; ethanol; triethylamine; In acetonitrile;

DOI:10.1021/jm0304966

upstream raw materials:

ethyl 1,4-dihydro-7-[(S,S)-3-methoxy-4-methylamino-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate

(3S,4S)-3-methoxy-4-(N-methylammmonio)pyrrolidinium

ethyl 7-chloro-4-oxo-1-(1,3-thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

ethyl 2-(2,6-dichloro-3-nicotinoyl)-3-(2-thiazolylamino)acrylate

Refernces

• 1、 -. "COMPOUNDS AND COMPOSITIONS FOR TREATMENT OF CANCER". Page/Page column 16. . Retrieved 2010/03/02.
• 2、 Tsuzuki, Yasunori,Tomita, Kyoji,Shibamori, Koh-Ichiro,Sato, Yuji,Kashimoto, Shigeki,Chiba, Katsumi. "Synthesis and Structure-Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 2". . p. 2097 - 2109. Retrieved 2007/10/03.