Pyronaridine

Base Information

• Chemical Name: Pyronaridine
• CAS No.: 74847-35-1
• Molecular Formula: C₂₉H₃₂ClN₅O₂
• Molecular Weight: 518.058
• UNII: TD3P7Q3SG6
• DSSTox Substance ID: DTXSID60996354
• Nikkaji Number: J126.219J
• Wikipedia: Pyronaridine
• Wikidata: Q7263674
• NCI Thesaurus Code: C90737
• Metabolomics Workbench ID: 153858
• ChEMBL ID: CHEMBL35228
• Mol file: 74847-35-1.mol

Synonyms:2-methoxy-7-chloro-10-(3',5'-bis(pyrrolin-1-ylmethyl)-4'-hydroxyphenylamino)benzo(b)-1,5-naphthyridine;4-((7-chloro-2-methoxybenzo(b)(1,5)naphthyridin-10-yl)amino)-2,6-bis((pyrrolidin-1-yl)methyl)phenol;4-((7-chloro-2-methoxybenzo(b)-1,5-naphthyridin-10-yl)amino)-2,6-bis(1-pyrrolidinylmethyl)phenol;benzonaphthyridine 7351;malaridine;phenol, 4-((7-chloro-2-methoxybenzo(b)-1,5-naphthyridin-10-yl)amino)-2,6-bis(1-pyrrolidinylmethyl)-, phosphate (1:4);pyronaridine;pyronaridine phosphate salt;pyronaridine tetraphosphate

Chemical Property of Pyronaridine

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.8E-17mmHg at 25°C
• Refractive Index: 1.5650 (estimate)
• Boiling Point: 657.2oC at 760 mmHg
• PKA: 8.20±0.50(Predicted)
• Flash Point: 351.3oC
• PSA: 76.72000
• Density: 1.37g/cm3
• LogP: 5.44880
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 517.2244530
• Heavy Atom Count: 37
• Complexity: 707

Purity/Quality:

99%, ^*data from raw suppliers

Pyronaridine >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC2=C(C3=C(C=C(C=C3)Cl)N=C2C=C1)NC4=CC(=C(C(=C4)CN5CCCC5)O)CN6CCCC6
• Recent ClinicalTrials: Phase IIa Proof of Concept Study of M5717-Pyronaridine in Adults and Adolescents With Acute Uncomplicated Plasmodium Falciparum Malaria (CAPTURE 1)
• Clinical Use: Treatment of uncomplicated P. falciparum and P. vivax malaria A fixed-dose combination with artesunate (Pyramax) is being developed for uncomplicated P. falciparum and P. vivax malaria.

Technology Process of Pyronaridine

There total 17 articles about Pyronaridine 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: 81.76%

pyrrolidine (123-75-1) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-[(7-chloro-2-methoxybenzo[b]-1,5-naphthyridin-10-yl)amino]phenol hemisulphate → pyronaridine (74847-35-1)

Guidance literature:

pyrrolidine; formaldehyd; In ethanol; at -5 - 70 ℃;

4-[(7-chloro-2-methoxybenzo[b]-1,5-naphthyridin-10-yl)amino]phenol hemisulphate; In ethanol; at 45 - 53 ℃; for 15h;

DOI:10.5012/bkcs.2014.35.2.521

Reference yield: 50.0%

pyrrolidine (123-75-1) + 2-methoxy-7-chloro-10-(4'-hydroxyphenyl)aminobenzo[b]-1,5-naphthyridine (81935-60-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → pyronaridine (74847-35-1)

Guidance literature:

pyrrolidine; formaldehyd; In ethanol; at 50 - 60 ℃; for 1h;

2-methoxy-7-chloro-10-(4'-hydroxyphenyl)aminobenzo[b]-1,5-naphthyridine; In ethanol; at 80 ℃; for 1.25h; Further stages.; microwave irradiation;

DOI:10.1002/jlcr.1456

Reference yield:

2-methoxy-7,10-dichloropyrido<3,2-b>quinoline (6626-40-0) + 4-amino-2,6-bis(1-tetrahydropyrrolylmethyl)phenol trishydrochloride → pyronaridine (74847-35-1)

Guidance literature:

In ethanol; at 75 ℃; for 2h; Temperature;

upstream raw materials:

pyrrolidine

2-methoxy-7-chloro-10-(4'-hydroxyphenyl)aminobenzo[b]-1,5-naphthyridine

formaldehyd

6-methoxy-pyridin-3-ylamine

Refernces

• 1、 -. "TLR7/8 ANTAGONISTS AND USES THEREOF". . . Retrieved 2022/02/06.
• 2、 -. "A method of preparing malaridine". . . Retrieved 2017/01/31.