104267-73-4

Usage

Uses

Used in Oncology:
10-HYDROXY-9-NITROCAMPTOTHECIN is used as a chemotherapeutic agent for the treatment of various types of cancer. It is particularly effective in inhibiting the growth of cancer cells by disrupting their DNA replication process, leading to cell death.
Used in Cancer Research:
10-HYDROXY-9-NITROCAMPTOTHECIN is utilized in research studies to explore its potential as a treatment for different types of cancer. Ongoing research aims to understand its mechanism of action, efficacy, and safety profile in order to optimize its use as a cancer therapeutic.
Used in Drug Development:
As a promising anti-cancer compound, 10-HYDROXY-9-NITROCAMPTOTHECIN is being investigated for its potential incorporation into novel drug formulations and delivery systems. This research focuses on enhancing its bioavailability, targeting specific cancer cells, and minimizing side effects, thereby improving its therapeutic index.

InChI:InChI=1/C20H15N3O7/c1-2-20(27)12-6-14-16-9(7-22(14)18(25)11(12)8-30-19(20)26)5-10-13(21-16)3-4-15(24)17(10)23(28)29/h3-6,24,27H,2,7-8H2,1H3/t20-/m0/s1

Upstream product

• 870527-52-9 1,2,6,7-tetrahydro-(20S)-camphthotecine 
• 7689-03-4 camptothecin 
• 19685-09-7 (S)-10-hydroxycamptothecin 

Downstream Products

• 164159-91-5 4-fluoro-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 172917-97-4 4-methoxy-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 91421-43-1 9-amino-20(S)-camptothecin 
• 91421-42-0 rubitecan 
• 172917-96-3 4-nitro-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 909094-10-6 4-bromo-benzenesulfonic acid 4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 
• 164159-99-3 9-nitro-10-(p-toluenesulfonyl)camptothecin 
• 172917-94-1 Benzenesulfonic acid (S)-4-ethyl-4-hydroxy-10-nitro-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester 

Relevant academic research and scientific papers

A new high yield semisynthetic approach to (20S)-9-NH2-Camptothecin based on a sequence of palladium-catalysed reductions

A new 5-step synthesis of 9-NH2-Camptothecin starting from natural Camptothecin is described. The approach, centred on a double palladium catalysed reduction of an arylsulfonate and a nitro group, has an overall yield consistently higher than the previously reported ones.

Structure-Based Drug Design and Identification of H2O-Soluble and Low Toxic Hexacyclic Camptothecin Derivatives with Improved Efficacy in Cancer and Lethal Inflammation Models in Vivo

Camptothecin (CPT) has been shown to block disassembly of the topoisomerase I (Topo I)/DNA cleavable complex. However, the poor aqueous solubility, intrinsic instability, and severe toxicity of CPTs have limited their clinical applications. Herein, we report the design and synthesis of H2O-soluble and orally bioavailable hexacyclic CPT derivatives. By analysis of a virtual chemical library and cytotoxicity screening in vitro, 9 and 11 were identified as potential prodrugs and chosen for further characterization in vivo. Both compounds exhibited remarkable anticancer and anti-inflammation efficacies in animals and improved drug-like profiles.

Radiosynthesis of carbon-11-labeled camptothecin derivatives as potential positron emission tomography tracers for imaging of topoisomerase I in cancers

Four carbon-11-labeled camptothecin derivatives, 9-[11C]methoxy- 20(S)-camptothecin ([11C]5), 10-[11C]methoxy-20(S)- camptothecin ([11C]7), 9-nitro-10-[11C]methoxy-20(S)- camptothecin ([11C]9), and 9-[([11C]trimethylamino)methyl] -10-hydroxy-20(S)-camptothecin ([11C]11), have been synthesized as potential positron emission tomography tracers for imaging of topoisomerase I in cancers.

A practical regiospecific synthesis of 9-nitrocamptothecin

9-Nitrocamptothecin has shown potent antitumor activity against many types of human cancers. A practical scale-up procedure for this compound is reported by selective reduction of corresponding sulfonate. Georg Thieme Verlag Stuttgart.

Synthesis and antitumor activity of a new class of water soluble camptothecin derivatives

A new family of water soluble camptothecin derivatives is described. Their synthesis, in vitro cytotoxicity, and in vivo antitumor activity is reported. Compounds 5a and 5c displayed excellent in vivo antitumor activity both ip and iv.