86639-63-6

Basic information

• Product Name: 9-amino-20-camptothecin
• Synonyms: 9-amino-20-camptothecin;(4S)-9-Amino-4-ethyl-4-hydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione;10-Aminocamptothecin;1H-Pyrano(3',4':6,7)indolizino(1,2-B)quinoline-3,14(4H,12H)-dione, 9-amino-4-ethyl-4-hydroxy-, (S)-;Camptothecin, 10-amino-
• CAS NO: 86639-63-6
• Molecular Formula: C₂₀H₁₇N₃O₄
• Molecular Weight: 363.37
• Mol File: 86639-63-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9-amino-20-camptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: 9-amino-20-camptothecin(86639-63-6)
• EPA Substance Registry System: 9-amino-20-camptothecin(86639-63-6)

Safety Data

• Hazardous Substances Data: 86639-63-6(Hazardous Substances Data)

Usage

Description

9-amino-20-camptothecin is a derivative of Camptothecin, a potent antitumor alkaloid with significant activity against various types of cancer. 9-amino-20-camptothecin is characterized by the presence of an amino group at the 9th position and a modified structure at the 20th position, which may contribute to its unique properties and potential applications in cancer therapy.

Uses

Used in Oncology:
9-amino-20-camptothecin is used as an antitumor agent for the treatment of hyperproliferative diseases, including various types of cancer. Its mechanism of action involves the inhibition of topoisomerase I, an enzyme essential for DNA replication, which leads to the prevention of cancer cell proliferation and induction of apoptosis.
Used in Drug Development:
9-amino-20-camptothecin serves as a valuable compound in the development of novel anticancer drugs. Its unique structural features and potent antitumor activity make it a promising candidate for further research and optimization to improve its pharmacokinetic properties, bioavailability, and therapeutic index.
Used in Cancer Research:
9-amino-20-camptothecin is also utilized in cancer research to investigate the molecular mechanisms underlying its antitumor effects, as well as to identify potential synergistic interactions with other chemotherapeutic agents. This research can contribute to the development of more effective and targeted cancer therapies.

Upstream product

• 86639-62-5 10-nitro-(20S)-camptothecin 
• 202745-28-6 ((S)-4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl)-carbamic acid tert-butyl ester 
• 173442-34-7 (S)-4-ethyl-4-hydroxy-6-iodo-3-oxo-1H-pyrano[3,4-c]-8-pyridone 
• 174092-80-9 (S)-4-ethyl-4-hydroxy-6-iodo-7-(prop-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione 
• 174092-79-6 (S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one 
• 202745-13-9 4-(tert-butyloxycarbonylamino)phenyl isocyanide 
• 869097-09-6 (+/-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one 
• 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 
• 86639-48-7 Camptothecin 1-oxide 
• 53544-22-2 1,2,6,7-tetrahydrocamptothecin 
• 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 
• 7689-03-4 camptothecin 

Downstream Products

• 19685-09-7 (S)-10-hydroxycamptothecin 
• 19685-10-0 10-methoxycamptothecin 

Relevant articles and documents

A general synthetic approach to the (20s)-camptothecin family of antitumor agents by a regiocontrolled cascade radical cyclization of aryl isonitriles

A general and efficient synthesis of (20S)-camptothecin (1a) is reported. A key common intermediate containing the pyridone and lactone (DE) rings of camptothecin and most derivatives was constructed from 2-trimethylsilyl-6-methoxypyridine by a series of metalation reactions and a Heck cyclization to provide an achiral bicyclic enol ether. Sharpless asymmetric dihydroxylation followed by lactol oxidation and iododesilylation produced the key intermediate in 94% enantiomeric excess. Alkylation with prop-argyl bromide and a cascade radical reaction with phenyl isonitrile then produced 1a. About 20 other penta-and hexacyclic analogues of camptothecin with differing single or multiple substituents at C7, C9, C10, C11, and/or C12 were made by changing the propargylating agent and the isonitrile. Included among these are several drug candidates and the approved drugs topotecan and irinotecan. The synthesis of the prodrug irinotecan is a direct one that does not pass through the active metabolite. The use of ortho-trimethylsilyl-substituted isonitriles allows the regioselective synthesis of camptothecin analogues in cases where isomeric mixtures are formed from the parent isonitriles. The synthesis of the derivatives relies on the broad scope and functional group tolerance of the key cascade radical reaction.

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.