203923-89-1

Basic information

• Product Name: Karenitecin
• Synonyms: Karenitecin;(4S)-4-Ethyl-4-hydroxy-11-(2-trimethylsilyl)ethyl)-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;BNP 1350;Cositecan;DB 172;MCC 12824
• CAS NO: 203923-89-1
• Molecular Formula: C25H28N2O4Si
• Molecular Weight: 448.592
• Mol File: 203923-89-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 727.2°Cat760mmHg
• Flash Point: 393.6°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.36E-22mmHg at 25°C
• Refractive Index: 1.644
• PKA: 11.27±0.20(Predicted)
• CAS DataBase Reference: Karenitecin(CAS DataBase Reference)
• NIST Chemistry Reference: Karenitecin(203923-89-1)
• EPA Substance Registry System: Karenitecin(203923-89-1)

Safety Data

• Hazardous Substances Data: 203923-89-1(Hazardous Substances Data)

Usage

General Description

Karenitecin is a synthetic topoisomerase I inhibitor that has shown promising anti-cancer activity in preclinical studies. It belongs to the camptothecin family of chemotherapeutic agents and works by binding to the topoisomerase I enzyme, preventing it from repairing DNA damage in cancer cells, ultimately leading to cell death. Karenitecin has demonstrated potent anti-tumor activity in various cancer models, including colon, breast, and lung cancer. Its unique chemical structure and mode of action make it a potential candidate for the development of novel cancer therapies, particularly in combination with other chemotherapy agents. Further research and clinical trials are needed to fully understand the efficacy and safety profile of karenitecin in the treatment of cancer.

InChI:InChI=1/C25H28N2O4Si/c1-5-25(30)19-12-21-22-17(13-27(21)23(28)18(19)14-31-24(25)29)15(10-11-32(2,3)4)16-8-6-7-9-20(16)26-22/h6-9,12,30H,5,10-11,13-14H2,1-4H3/t25-/m0/s1

Upstream product

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• 1072913-33-7 1-(2-nitrophenyl)-3-(trimethylsilyl)prop-2-yn-1-ol 
• 1609257-35-3 1-(2-nitrophenyl)-3-trimethylsilanyl-propenone 
• 1066-54-2 trimethylsilylacetylene 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 1609257-44-4 tert-butyl 2-[3-(trimethylsilyl)propioloyl]phenylcarbamate 
• 1609257-40-0 Weinreb amide 

Relevant articles and documents

Methods for the total chemical synthesis of enantiomerically-pure 7-(2′-trimethylsilyl)ethyl camptothecin

The present invention discloses and claims five (5) novel, highly efficient synthetic routes for the total synthesis of enantiomerically-pure (i.e., 99%) 7-(2′-trimethylsilyl)ethyl camptothecin (BNP1350; Karenitecin; Cositecan). These aforementioned synthetic schemes are the first to disclose the total syntheses of 7-(2′-trimethylsilyl)ethyl camptothecin using a highly novel direct, non-linear and convergent synthetic strategy which involves annealing the key C7-(trimethylsilyl)ethyl side chain-bearing A ring key synthons to an enantiomerically-pure tricyclic pyridone; rather than through the conventional methodology which incorporates the C7-(trimethylsilyl)ethyl side chain as the final synthetic step on a totally synthesized camptothecin parent compound. The current novel synthetic approaches reported herein since utilize desirably functionalized A-ring with preinstalled trimethyl silyl ethyl side chain, the aforementioned synthetic methodologies have a wider scope of making wide range of pharmaceutically relevant A-ring substituted BNP1350 analogs by substituting desirably functionalized nitro or protected amino phenyl carboxy A-ring as the starting material.

Process for making camptothecin derivatives

A process for synthesizing highly lipophilic derivatives of camptothecin. The process includes reacting dissolved, underivatized camptothecin with a silylated heterocyclic compound in a modified Minisci-type alkylation reaction to produce 7-substituted derivatives of camptothecin.

PROCESS FOR MAKING CAMPTOTHECIN DERIVATIVES

A process for synthesizing highly lipophilic derivatives of camptothecin. The process includes reacting dissolved, underivatized camptothecin with a silylated heterocyclic compound in a modified Minisci-type alkylation reaction to produce 7-substituted derivatives of camptothecin.