86639-62-5

Basic information

• Product Name: 9-Nitrocamptothecin
• Synonyms: RUBETICAN;CAMPTOTHECIN, 9-NITRO-20(S)-;9-NITRO-CPT;9-Nitrocamptothecin (Rubitecan);9-Nitrocamptothecin;4α-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;9-Nitro-20(S)-camptothecine;(S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• CAS NO: 86639-62-5
• Molecular Formula: C₂₀H₁₅N₃O₆
• Molecular Weight: 393.35
• Product Categories: Natural Anti-cancer Medical Materials and It's Derivatives
• Mol File: 86639-62-5.mol

Chemical Properties

• Boiling Point: 827.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.63±0.1 g/cm3(Predicted)
• PKA: 11.17±0.20(Predicted)
• CAS DataBase Reference: 9-Nitrocamptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Nitrocamptothecin(86639-62-5)
• EPA Substance Registry System: 9-Nitrocamptothecin(86639-62-5)

Safety Data

• Hazardous Substances Data: 86639-62-5(Hazardous Substances Data)

Usage

Uses

Used in Oncology:
9-Nitrocamptothecin is used as an anticancer agent for its demonstrated anti-tumor activity in preclinical studies. It is particularly effective against various types of cancer, including lung, breast, and ovarian cancers. 9-Nitrocamptothecin modulates the activity of topoisomerase I, leading to the accumulation of DNA strand breaks and inducing cell death, which makes it a potential treatment option for cancer patients.
Used in Cancer Research:
9-Nitrocamptothecin is used as a research tool in cancer biology to study the mechanisms of action of topoisomerase I inhibitors and their effects on DNA replication and transcription. This helps in understanding the molecular pathways involved in cancer cell death and can guide the development of new therapeutic strategies for cancer treatment.
Used in Drug Development:
9-Nitrocamptothecin is used as a lead compound in the development of new cancer therapies. Its potent inhibitory effect on topoisomerase I and its demonstrated anti-tumor activity make it a valuable starting point for the design and synthesis of novel anticancer drugs with improved efficacy and reduced side effects.

Upstream product

• 56008-61-8 2-amino-5-nitrobenzaldehyde 
• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 86639-72-7 (4R,5bS,11aS)-4-Ethyl-4-hydroxy-9-nitro-1,5b,6,11,11a,12-hexahydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione 
• 86639-48-7 Camptothecin 1-oxide 
• 53544-22-2 1,2,6,7-tetrahydrocamptothecin 
• 7689-03-4 camptothecin 

Downstream Products

• 86639-63-6 10-amino-20(S)-camptothecin 
• 19685-10-0 10-methoxycamptothecin 
• 19685-09-7 (S)-10-hydroxycamptothecin 

Relevant articles and documents

Plant Antitumor Agents. 30. Synthesis and Structure Activity of Novel Camptothecin Analogs

A large number of camptothecin (CPT) analogs have been prepared in the 20S, 20RS, and 20R configurations with a number of ring A substituents.Topoisomerase I (T-I) inhibition data (IC50) have been obtained by standard procedures.In general, substitution at the 9 or 10 positions with amino, halogeno, or hydroxyl groups in compounds with 20S configuration results in compounds with enhanced T-1 inhibition.Compounds in the 20RS configuration were less active in vitro and in vivo and those in the 20R configuration were inactive.Compounds with 10,11-methylenedioxy substitution on ring A displayed a marked increase in potency in the T-I inhibition assay.The activities of some of the analogs as determined in a variety of in vivo assays including the L-1210 mouse leukemia assay were, in general, in accord with T-I inhibition.A number of water-soluble analogs such as 20-glycinate esters, 9-glycinamides, or hydrolyzed lactone salts were prepared and tested in in vitro and in vivo assays.In general, these compounds were less active than CPT both in terms of T-I inhibition and life prolongation in the L-1210 assay.However, certain 20-glycinate esters showed good in vivo activity after iv administration.

Synthesis and antitumor activity of 20(S)-camptothecin derivatives: A-ring modified and 7,10-disubstituted camptothecins

20(S)-Camptothecin derivatives having nitro, amino, chloro, bromo, hydroxyl and methoxyl groups in the A-ring were synthesized. B-Ring hydrogenated camptothecin (2a) was converted into 10-hydroxycamptothecin (6e) by treatment with lead tetraacetate in trifluoroacetic acid. 10-Substituted derivatives (6) were obtained by a photoreaction of N-oxides (9). The cytotoxicity of the A-ring modified camptothecins was evaluated against KB cells in vitro and leukemia L1210 in mice. 7-Ethyl-10-hydroxycamptothecin (6i) was identified as a potential derivative for further modification.