69409-02-5

Basic information

• Product Name: N-[2-(Dimethylamino)ethyl]-3-(acetylamino)-1,8-naphthalenedicarbimide
• Synonyms: 2-[2-(Dimethylamino)ethyl]-5-(acetylamino)-2,3-dihydro-1H-benzo[de]isoquinoline-1,3-dione;5-(Acetylamino)-2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione;N-[2-(Dimethylamino)ethyl]-3-(acetylamino)-1,8-naphthalenedicarbimide;N-Acetylamonafide;MADE-FA 4512;N-[2-[2-(DiMethylaMino)ethyl]-2,3-dihydro-1,3-dioxo-1H-benz[de]isoquinolin-5-yl]acetaMide
• CAS NO: 69409-02-5
• Molecular Formula: C18H19N3O3
• Molecular Weight: 325.36176
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 69409-02-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 210-212°C
• Boiling Point: 570.339 °C at 760 mmHg
• Flash Point: 298.73 °C
• Appearance: /
• Density: 1.314 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• CAS DataBase Reference: N-[2-(Dimethylamino)ethyl]-3-(acetylamino)-1,8-naphthalenedicarbimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(Dimethylamino)ethyl]-3-(acetylamino)-1,8-naphthalenedicarbimide(69409-02-5)
• EPA Substance Registry System: N-[2-(Dimethylamino)ethyl]-3-(acetylamino)-1,8-naphthalenedicarbimide(69409-02-5)

Safety Data

• Hazardous Substances Data: 69409-02-5(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

InChI:InChI=1/C18H19N3O3/c1-11(22)19-13-9-12-5-4-6-14-16(12)15(10-13)18(24)21(17(14)23)8-7-20(2)3/h4-6,9-10H,7-8H2,1-3H3,(H,19,22)

Upstream product

• 61690-44-6 3-acetylaminonaphthalene-1,8-dicarboxylic anhydride 
• 108-00-9 N,N-dimethylethylenediamine 
• 108-24-7 acetic anhydride 
• 69408-81-7 amonafide 
• 54824-17-8 mitonafide 
• 3027-38-1 3-nitro-1,8-naphthalic anhydride 
• 72-89-9 acetylcoenzyme A 
• 23204-38-8 3-amino-naphthalene-1,8-dicarboxylic acid-anhydride 

Relevant articles and documents

Cancer cell-targeted two-photon fluorescence probe for the real-time ratiometric imaging of DNA damage

Real-time imaging of DNA damage in cancer cells could provide valuable information on the formation and development of cancer. Herein, a two-photon fluorescence probe was discovered. Through sequential ICT processes, it allows successful in vivo visualization of DNA damage in cancer cells by one/two-photon microscopic imaging or by the unaided eye and a hand-held ultraviolet lamp.

2,2,2-Trichloro-N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2, 3-dihydro-1H-benzo[de]isoquinolin-5-yl}carbamoyl)acetamide (UNBS3157), a novel nonhematotoxic naphthalimide derivative with potent antitumor activity

Amonafide (1), a naphthalimide which binds to DNA by intercalation and poisons topoisomerase IIα, has demonstrated activity in phase II breast cancer trials, but has failed thus far to enter clinical phase III because of dose-limiting bone marrow toxicity. Compound 17 (one of 41 new compounds synthesized) is a novel anticancer naphthalimide with a distinct mechanism of action, notably inducing autophagy and senescence in cancer cells. Compound 17 (2,2,2-trichloro-N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H- benzo[de]isoquinolin-5-yl}carbamoyl)acetamide (UNBS3157)) was found to have a 3-4-fold higher maximum tolerated dose compared to amonafide and not to provoke hematotoxicity in mice at doses that display significant antitumor effects. Furthermore, 17 has shown itself to be superior to amonafide in vivo in models of (i) L1210 murine leukemia, (ii) MXT-HI murine mammary adenocarcinoma, and (iii) orthotopic models of human A549 NSCLC and BxPC3 pancreatic cancer. Compound 17, therefore, merits further investigation as a potential anticancer agent.