74732-00-6

Basic information

• Product Name: N-(2-CHLOROETHYL)-1,8-NAPHTHALIMIDE
• Synonyms: 2-(2-Chloroethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione;AKOS BBS-00007398;N-(2-CHLOROETHYL)-1,8-NAPHTHALIMIDE;2-(2-chloroethyl)benzo[de]isoquinoline-1,3-dione
• CAS NO: 74732-00-6
• Molecular Formula: C₁₄H₁₀ClNO₂
• Molecular Weight: 259.69
• Mol File: 74732-00-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 205 °C (dec.)(lit.)
• Boiling Point: 433.7°C at 760 mmHg
• Flash Point: 216.1°C
• Appearance: /
• Density: 1.398g/cm³
• Vapor Pressure: 1.01E-07mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: N-(2-CHLOROETHYL)-1,8-NAPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-CHLOROETHYL)-1,8-NAPHTHALIMIDE(74732-00-6)
• EPA Substance Registry System: N-(2-CHLOROETHYL)-1,8-NAPHTHALIMIDE(74732-00-6)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 74732-00-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H10ClNO2/c15-7-8-16-13(17)10-5-1-3-9-4-2-6-11(12(9)10)14(16)18/h1-6H,7-8H2

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 2896-23-3 N-ethyl-1,8-naphthalimide 
• 5450-40-8 2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 

Downstream Products

• 131729-18-5 1-[2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-ethyl]-4-(phenyl-propionyl-amino)-piperidine-4-carboxylic acid methyl ester 

Relevant articles and documents

Antitumor efficacy and apoptotic activity of substituted chloroalkyl 1H-benz[de]isoquinoline-1,3-diones: A new class of potential antineoplastic agents

A series of ten chloroalkyl 1H-benz[de]isoquinoline-1,3-diones (naphthalimides) were synthesized and evaluated for antitumor activity. Amongst them, new compounds 2d and 2i carrying a 6-NO2 substituent in the aromatic portion of the molecule possessed significant antineoplastic activity. The most active compound 2i had elicited significant cytotoxicity in 15 human tumor cell lines namely Leukemia: MOLT-4, HL-60; Lymphoma: U-937; Colon: 502713, HT-29, SW-620, HCT-15, COLO-205; Liver: Hep-2; Prostate DU-145, PC-3; Breast: MCF-7; Neuroblastoma: IMR-32, SK-N-SH and Ovary: OVCAR-5 out of the 17 cell lines screened. Flow cytometric analysis performed to study the effect of compound 2i on the progression of cell cycle of MOLT-4 cells, revealed rise in sub-G1 fraction and concomitant accumulation of cells in S and G 2/M phases, indicating apoptosis, mitotic arrest and/or delay in exit of daughter cells from mitotic cycle respectively. It also induced caspase-mediated apoptosis of MOLT-4 cells in a dose dependant manner. Light and electron microscopic studies revealed characteristic morphology of apoptotic MOLT-4 cells after in vitro treatment with 10 μM concentration of the compound. Apoptosis induction was also observed in HL-60 cells by compounds 2d and 2i to an extent much greater than camptothecin and cis-platin at 10 μM concentration. Both the compounds have shown minimal suppressive effect on human PBMC having high IC50 values of 3,582 and 1,536 μM respectively. These compounds inhibited DNA and RNA synthesis in murine ascites Sarcoma-180 tumor cells in vitro at 8 μM concentration. Above results indicate promising chemotherapeutic potential of the key compound 2i.

Stereoelectronic effects in the halogenation of N-alkylnaphthalimides

The greater rate of bromination of N-methylnaphthalimide compared to N-ethylnaphthalimide, and the relative ease of chlorination of these compounds, provide convincing evidence of stereoelectronic effects in the free-radical halogenation of N-alkylimides.