Amonafide

Base Information

• Chemical Name: Amonafide
• CAS No.: 69408-81-7
• Molecular Formula: C16H17N3O2
• Molecular Weight: 283.33
• NSC Number: 308847
• UNII: 1Q8D39N37L
• DSSTox Substance ID: DTXSID30219562
• Nikkaji Number: J22.768D
• Wikipedia: Amonafide
• Wikidata: Q4747531
• NCI Thesaurus Code: C71628
• Metabolomics Workbench ID: 149376
• ChEMBL ID: CHEMBL428676
• Mol file: 69408-81-7.mol

Synonyms:5-Amino-2-[2-(dimethylamino)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione;FA 142;M-FA 142;MADE-FA 142;NCI 308847;NSC 308847;Nafidimide;

Chemical Property of Amonafide

Chemical Property:

• Vapor Pressure: 3.89E-10mmHg at 25°C
• Melting Point: 162-164 °C
• Refractive Index: 1.681
• Boiling Point: 500.2 °C at 760 mmHg
• PKA: 8.83±0.28(Predicted)
• Flash Point: 256.3 °C
• PSA: 68.33000
• Density: 1.306 g/cm³
• LogP: 1.67770
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 283.132076794
• Heavy Atom Count: 21
• Complexity: 437

Purity/Quality:

99% ^*data from raw suppliers

Amonafide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(=C32)C1=O)N
• Recent ClinicalTrials: A Pharmacokinetic and Efficacy Study of Amonafide L-malate (AS1413) in Combination With Cytarabine in Patients With Acute Myeloid Leukemia (AML)
• Recent EU Clinical Trials: Phase 3 Open-Label Randomized Study of Amonafide L-Malate in Combination with
• Uses: Amonafide is a DNA intercalator and topoisomerase II inhibitor in clinical development for the treatment of neoplastic diseases. Antitumor agent.

Technology Process of Amonafide

There total 8 articles about Amonafide 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: 99.0%

mitonafide (54824-17-8) → amonafide (69408-81-7)

Guidance literature:

With formic acid; palladium 10% on activated carbon; triethylamine; In ethanol; Inert atmosphere; Reflux;

DOI:10.1016/j.bmc.2013.08.039

Reference yield: 90.0%

3-amino-naphthalene-1,8-dicarboxylic acid-anhydride (23204-38-8) + N,N-dimethylethylenediamine (108-00-9) → amonafide (69408-81-7)

Guidance literature:

In ethanol; at 35 - 45 ℃; for 2h; Inert atmosphere;

DOI:10.3390/ijms22052772

Reference yield:

3-nitro-1,8-naphthalic anhydride (3027-38-1) → amonafide (69408-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / ethanol / 0.5 h / Heating

2: 91 percent / formic acid; triethylamine / Pd/C / ethanol / 0.67 h / Heating

With formic acid; triethylamine; palladium on activated charcoal; In ethanol;

DOI:10.1021/jm070315q

upstream raw materials:

3-amino-naphthalene-1,8-dicarboxylic acid-anhydride

N,N-dimethylethylenediamine

mitonafide

3-nitro-1,8-naphthalic anhydride

Downstream raw materials:

2-[2-(dimethylamino)ethyl]-5-{[(1Z)-(2,5-dihydroxyphenyl)methylene]amino}-1H-benzo[de]isoquinoline-1,3(2H)-dione

5-{[(1Z)-benzo-(3,5-bis(acetoxy)-2-[(acetoxy)methyl]-6-oxy-tetrahydro-2H-pyran-4-ylacetate)-5-ylmethylene]amino}-N-(2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinolin-1,3(2H)-dione)

Refernces

• 1、 Rykowski, Sebastian,Gurda-Wo?na, Dorota,Orlicka-P?ocka, Marta,Fedoruk-Wyszomirska, Agnieszka,Giel-Pietraszuk, Ma?gorzata,Wyszko, Eliza,Kowalczyk, Aleksandra,St?czek, Pawe?,Bak, Andrzej,Kiliszek, Agnieszka,Rypniewski, Wojciech,Olejniczak, Agnieszka B.. "Design, synthesis, and evaluation of novel 3-carboranyl-1,8-naphthalimide derivatives as potential anticancer agents". . p. 1 - 43. Retrieved 2021/03/15.
• 2、 Ma, Jing,Li, Linrong,Yue, Kexin,Zhang, Zhansheng,Su, Shihao,Chen, Yutong,Yu, Lu,Zhang, Pengfei,Ma, Ruijuan,Li, Yingguang,Ma, Yinxia,Jia, Huinan,Wang, Chaojie,Wang, Jiajia,Xie, Songqiang. "A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent". . . Retrieved 2021/05/10.