58610-63-2

Basic information

• Product Name: 7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE
• Synonyms: 7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE;1,2,3,5-Tetrahydro-7-Methyl-1,5-dioxo-6-indolizinecarbonitrile
• CAS NO: 58610-63-2
• Molecular Formula: C10H8N2O2
• Molecular Weight: 188.18
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 58610-63-2.mol

Chemical Properties

• Boiling Point: 450.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -3.91±0.60(Predicted)
• CAS DataBase Reference: 7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE(58610-63-2)
• EPA Substance Registry System: 7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE(58610-63-2)

Safety Data

• Hazardous Substances Data: 58610-63-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE is used as a key intermediate in the preparation of Camptothecin derivatives. These derivatives are known for their therapeutic use as antitumor agents, making 7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE an essential component in the development of cancer-fighting drugs.
Used in Cancer Treatment:
7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE contributes to the synthesis of Camptothecin derivatives, which are employed as potent antitumor agents. These derivatives target and inhibit essential cellular processes in cancer cells, leading to their destruction and ultimately aiding in the treatment of various types of cancer.

Upstream product

• 73427-92-6 methyl 6-cyano-1-hydroxy-7-methyl-5-oxo-3,5-dihydroindolizine-2-carboxylate 
• 66917-18-8 2-(methoxycarbonyl)-6-cyano-7-methyl-1,5-dioxo-Δ6(8)-tetrahydroindolizine 
• 58610-61-0 ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate 

Downstream Products

• 110742-81-9 (R)-((S)-2-(6′-cyano-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-1-ethoxy-1-oxobutan-2-yl) 1-tosylpyrrolidine-2-carboxylate 
• 110714-45-9 (R)-((S)-2-(6′-(acetamidomethyl)-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-1-ethoxy-1-oxobutan-2-yl) 1-tosylpyrrolidine-2-carboxylate 
• 110714-46-0 (R)-((S)-2-(6′-(acetoxymethyl)-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-1-ethoxy-1-oxobutan-2-yl) 1-tosylpyrrolidine-2-carboxylate 
• 110714-44-8 (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate 
• 31456-25-4 camptothecin 
• 64439-81-2 dl-10-hydroxycamptothecin 
• 58610-64-3 7’-methyl-5’-oxo-3’,5’-dihydro-2’H-spiro[[1,3]dioxolane-2,1‘-indolizine]-6’-carbonitrile 

Relevant articles and documents

COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF

The present disclosure relates to a compound of formula I, a pharmaceutical composition thereof and the use thereof as an anti-tumor drug.

COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF

The present disclosure relates to a compound of formula I, a pharmaceutical composition thereof and the use thereof as an anti-tumor drug.

Phosphate ester derivatives of homocamptothecin: Synthesis, solution stabilities and antitumor activities

Homocamptothecins (hCPTs) represents a new promising class of topoisomerase I inhibitors with enhanced stability and superior antitumor activity. Some phosphodiesters and phosphotriesters homocamptothecin derivatives were designed and synthesized based on our previous synthetic route. The cytotoxicity in vitro on three cancer cell lines and antitumor activity in vivo, and inhibitory properties of topoisomerase I of these derivatives were evaluated. Among them compounds 24e and 24f exhibited higher cytotoxic activity than IRT and the former exhibited the best antitumor activity in vivo and solution stability both at pH 7.4 and pH 3.0.

Process for the preparation of tetrahydroindolizines

Described is a process for the preparation of Compound (7) in accordance with the following reaction scheme by reacting Compound (5) with ethylene glycol in a solvent in the presence of a Lewis acid, thereby obtaining Compound (6), and then reacting the resulting compound with a carbonate diester in a solvent in the presence of a metal alkoxide (R1, R6each represents a C1-6alkyl group or the like and R5represents H or C1-5alkyl group). Compound (7) so obtained is useful as an intermediate for camptothecins useful as antitumor agents.

Plant antitumor agents: Synthesis and biological activity of camptothecin analogues

Four analogues, 10-methoxy (20), 12-aza (29), benz[j] (36), and 18-methoxy (38), of camptothecin were obtained by total synthesis. The two water-soluble analogues, 10-[(carboxymethyl)oxy] (24) and 10-[2'-(diethylamino)-ethoxy]-20(S)-camptothecin (26), wit