Mitonafide

Base Information

• Chemical Name: Mitonafide
• CAS No.: 54824-17-8
• Molecular Formula: C16H15 N3 O4
• Molecular Weight: 349.80
• Hs Code.: 2933990090
• NSC Number: 300288
• UNII: 06Q0V17SI9
• DSSTox Substance ID: DTXSID90203321
• Nikkaji Number: J12.936D
• Wikidata: Q27236211
• NCI Thesaurus Code: C66165
• ChEMBL ID: CHEMBL43482
• Mol file: 54824-17-8.mol

Synonyms:2-(2-(dimethylamino)ethyl)-5-nitro-1H-benz(de)isoquinoline-1,3(2H)-dione;2-dimethylaminoethylbenzo(de)isoquinoline-1,3-dione hydrochloride;5-nitro-2-(2-dimethylaminoethyl)benzo(de)isoquinoline-1,3-dione;M 4212;M-4212;mitonafide;N-(2-dimethylaminoethyl)-3-nitro-naphthalimide;N-(2-dimethylaminoethyl)-3-nitronaphthalimide;NSC 300288

Chemical Property of Mitonafide

Chemical Property:

• Vapor Pressure: 5.22E-10mmHg at 25°C
• Melting Point: 138-139 °C(Solv: ethanol (64-17-5))
• Boiling Point: 496.8°C at 760 mmHg
• PKA: 8.76±0.28(Predicted)
• Flash Point: 254.3°C
• PSA: 88.13000
• Density: 1.384g/cm³
• LogP: 1.94570
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 313.10625597
• Heavy Atom Count: 23
• Complexity: 516

Purity/Quality:

99% ^*data from raw suppliers

Mitonafide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(=C32)C1=O)[N+](=O)[O-]
• Uses: A Naphthalimides with potent anticancer activity.

Technology Process of Mitonafide

There total 3 articles about Mitonafide 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: 97.0%

3-nitro-1,8-naphthalic anhydride (3027-38-1) + N,N-dimethylethylenediamine (108-00-9) → mitonafide (54824-17-8)

Guidance literature:

In ethanol; at 80 ℃; for 4h;

DOI:10.1002/chem.202103858

Reference yield:

1,8-Naphthalic anhydride (81-84-5) → mitonafide (54824-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; nitric acid / 5 - 20 °C

2: ethanol / Reflux

With sulfuric acid; nitric acid; In ethanol;

DOI:10.1016/j.cclet.2014.04.020

Reference yield:

→ mitonafide (54824-17-8)

Guidance literature:

entspr. Naphthylsaeure, entspr. Amin;

upstream raw materials:

3-nitro-1,8-naphthalic anhydride

N,N-dimethylethylenediamine

1,8-Naphthalic anhydride

Downstream raw materials:

2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5-ylacetamide

5-{[(2-(2-phenoxy)-6-hydroxymethyltetrahydropyran-3,4,5-triol)-5-ylmethyl]amino}-N-(2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinolin-1,3(2H)-dione)

C₃₅H₃₉N₃O₁₁

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、 -. "1,8-naphthalimide derivative having selective inhibition effect on non-small cell lung cancer, and synthesis method and application thereof". Paragraph 0023. . Retrieved 2018/07/06.
• 2、 Ma, Zhao,Sun, Wei,Chen, Laizhong,Li, Jing,Liu, Zhenzhen,Bai, Haixiu,Zhu, Mengyuan,Du, Lupei,Shi, Xiaodong,Li, Minyong. "A novel hydrazino-substituted naphthalimide-based fluorogenic probe for tert-butoxy radicals". supporting information. p. 6295 - 6297. Retrieved 2013/08/23.