4-Amino-1,8-naphthalimide

Base Information

• Chemical Name: 4-Amino-1,8-naphthalimide
• CAS No.: 1742-95-6
• Molecular Formula: C12H8N2O2
• Molecular Weight: 212.208
• Hs Code.: 29251995
• European Community (EC) Number: 217-110-1
• UNII: S529AR2S8B
• DSSTox Substance ID: DTXSID6061941
• Nikkaji Number: J203.150G
• Wikidata: Q27096011
• Pharos Ligand ID: B7BLFD9AC5VM
• Metabolomics Workbench ID: 52241
• ChEMBL ID: CHEMBL338790
• Mol file: 1742-95-6.mol

Synonyms:4-amino-1,8-naphthalimide;4-amino1,8-naphthalimide

Chemical Property of 4-Amino-1,8-naphthalimide

Chemical Property:

• Appearance/Colour: orange amorphous powder
• Vapor Pressure: 6.75E-12mmHg at 25°C
• Melting Point: 360 °C
• Refractive Index: 1.764
• Boiling Point: 544.1 °C at 760 mmHg
• PKA: 9.53±0.20(Predicted)
• Flash Point: 282.8 °C
• PSA: 75.95000
• Density: 1.474 g/cm³
• LogP: 1.64270
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO
• Water Solubility.: 354mg/L at 25℃
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 212.058577502
• Heavy Atom Count: 16
• Complexity: 342

Purity/Quality:

99.9% ^*data from raw suppliers

4-Amino-1,8-naphthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC3=C2C(=C1)C(=O)NC3=O)N
• Description: The poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis, particularly in response to reactive oxygen and nitrogen species. 4-amino-1,8-Naphthalimide (4-ANI) is an inhibitor of PARP (IC50 = 180 nM). It blocks radiation-induced PARP in cancer cells, potentiating the cytotoxicity of γ-radiation, although it is not cytotoxic in the absence of radiation. 4-ANI is used to study the role of PARP activity in various cell systems.
• Uses: The poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis, particularly in response to reactive oxygen and nitrogen species. 4-amino-1,8-Naphthalimide (4-ANI) is an inhibitor of PARP (IC50 = 180 nM). It blocks radiation-induced PARP in cancer cells, potentiating the cytotoxicity of γ-radiation, although it is not cytotoxic in the absence of radiation. 4-ANI is used to study the role of PARP activity in various cell systems.

Technology Process of 4-Amino-1,8-naphthalimide

There total 12 articles about 4-Amino-1,8-naphthalimide 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: 67.0%

4-amino-1,8-naphthalic anhydride (6492-86-0) → 4-amino-1,8-naphthalimide (1742-95-6)

Guidance literature:

With ammonium hydroxide; for 5h; Reflux;

Reference yield: 51.0%

4-nitronaphthalic-1,8-anhydride (6642-29-1) → 4-amino-1,8-naphthalimide (1742-95-6)

Guidance literature:

With ammonia; In ethanol; for 48h; sealed tube;

DOI:10.1016/S0040-4039(01)92917-X

Reference yield:

6-(3-methyl-triaz-1-en-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione → 4-amino-1,8-naphthalimide (1742-95-6)

Guidance literature:

With water; In dimethylsulfoxide-d6; at 20 ℃; for 48h;

DOI:10.3390/molecules22071183

upstream raw materials:

4-sulfo-naphthalene-1,8-dicarboxylic acid

4-nitronaphthalic-1,8-anhydride

4-bromonaphthalene-1,8-dicarboximide

4-bromo-1,8-naphthalenedicarboxylic anhydride

Downstream raw materials:

6-Amino-2-(4-nitro-benzyl)-benzo[de]isoquinoline-1,3-dione

6-amino-2-benzyl-1Hbenzo[de]isoquinoline-1,3(2H)-dione

C₃₈H₃₅BN₂O₄

C₃₂H₃₁BN₂O₄

Refernces

• 1、 Lovitt, June I.,Umadevi, Deivasigamani,Raja Lakshmi, Pandi,Twamley, Brendan,Gunnlaugsson, Thorfinnur,Shanmugaraju, Sankarasekaran. "Synthesis, structural characterization, antibiotics sensing and coordination chemistry of a fluorescent 4-amino-1,8-naphthalimide Tr?ger’s base supramolecular scaffold". . p. 620 - 633. Retrieved 2020.
• 2、 Zhou, Jin,Fang, Canliang,Liu, Ying,Zhao, Yao,Zhang, Nan,Liu, Xiangjun,Wang, Fuyi,Shangguan, Dihua. "Visible-light-induced cleavage of 4-α-amino acid substituted naphthalimides and its application in DNA photocleavage". . p. 3931 - 3935. Retrieved 2015/03/30.