91421-43-1

Basic information

• Product Name: 9-Aminocamptothecin
• Synonyms: 4':6,7)indolizino(1,2-B)quinoline-3,14(4H,12H)-dione;4':6,7)indolizino(1,2-B)quinoline-3,14(4H,12H)-dione, 10-amino-4-ethyl-4-hydroxy-, (S)-;CAMPTOTHECIN, 9-AMINO-(RG);(S)-10-AMino-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;AMinocaMptothecin;(S)-10-Amino-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-di;CAMPTOTHECIN, 9-AMINO-;9-AMINO-CAMPTOTHECIN
• CAS NO: 91421-43-1
• Molecular Formula: C₂₀H₁₇N₃O₄
• Molecular Weight: 363.37
• Product Categories: Pharmaceutical Raw Materials;Alkaloids;Natural Anti-cancer Medical Materials and It's Derivatives
• Mol File: 91421-43-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 142.0-145.0 °C
• Boiling Point: 819.6 °C at 760 mmHg
• Flash Point: 449.5 °C
• Appearance: /
• Density: 1.55 g/cm³
• Vapor Pressure: 2.01E-28mmHg at 25°C
• Refractive Index: 1.771
• Storage Temp.: 2-8°C(protect from light)
• Solubility: ≤1mg/ml in DMSO;1mg/ml in dimethyl formamide
• PKA: 11.23±0.20(Predicted)
• Merck: 14,431
• CAS DataBase Reference: 9-Aminocamptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Aminocamptothecin(91421-43-1)
• EPA Substance Registry System: 9-Aminocamptothecin(91421-43-1)

Safety Data

• RTECS: UQ0490500
• Hazardous Substances Data: 91421-43-1(Hazardous Substances Data)

Usage

Uses

9-Amino Camptothecin is a derivative of Camptothecin (C175150), as antitumor agent.

Biological Activity

9-amino camptothecin is a topoisomerase i inhibitor [1][2].dna topoisomerases relax dna torsional strain generated during replication, transcription, recombination, repair, and chromosome condensation. the relaxation of dna supercoiling by topoisomerase i is enabled by a mechanism of controlled rotation around a transient dna single-strand break. camptothecin (cpt) is isolated from the bark of the chinese tree camptotheca accuminata [3].9-amino camptothecin, a water-soluble camptothecin analogue, is a topoisomerase i inhibitor. in human ht-29 colon adenocarcinoma, 9-amino camptothecin (9-ac) exhibited cytotoxicity with ic50 value of 19 nm. 9-ac also induced dna damage in whole cells and nuclei at a concenstration of 85 nm and 21 nm, respectively [1].9-amino camptothecin had greater activity than camptothecin against human tumour xenografts, including lewis lung carcinoma and b16 melanoma. 9-ac had entered phase ii trials. in patients with advanced solid tumours, 9-amino camptothecin exhibited anti-tumor activity [1][2].

references

[1]. rothenberg, m.l. topoisomerase i inhibitors: review and update. annals of oncology 8(9), 837-855 (1997).[2]. dancey j, eisenhauer ea. current perspectives on camptothecins in cancer treatment. br j cancer. 1996 aug;74(3):327-38.[3]. drwal mn1, agama k, wakelin lp, et al. exploring dna topoisomerase i ligand space in search of novel anticancer agents. plos one. 2011;6(9):e25150.

InChI:InChI=1/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1

Upstream product

• 151585-77-2 2,6-dinitrobenzaldehyde ethylene acetal 
• 151585-78-3 2-amino-6-nitrobenzaldehyde ethylene acetal 
• 130133-53-8 2-amino-6-nitrobenzaldehyde 
• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 606-31-5 2,6-dinitrobenzaldehyde 
• 104267-73-4 9-nitro-10-hydroxy-20(S)-camptothecin 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 7689-03-4 camptothecin 
• 164159-99-3 9-nitro-10-(p-toluenesulfonyl)camptothecin 
• 172917-95-2 Naphthalene-1-sulfonic 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 
• 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 
• 164159-93-7 Methanesulfonic 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 
• 91421-42-0 rubitecan 

Downstream Products

• 189311-99-7 (S)-4-Ethyl-4-hydroxy-10-((E)-styryl)-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione 
• 246032-59-7 methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin 
• 39026-92-1 9-methoxycamptothecin 
• 67656-30-8 10-hydroxycamptothecin 
• 7689-03-4 camptothecin 

Relevant articles and documents

Integrin-Mediated drug targeting

The present invention relates to cytostatics which have a tumour-specific action as a result of linkage to αvβ3 integrin antagonists via preferred linking units. The preferred linking units guarantee serum stability of the conjugate of cytostatic and αvβ3 integrin antagonist and at the same time the desired intracellular action in tumour cells as a result of their enzymatic or hydrolytic cleavability with release of the cytostatic.

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.

Process for the preparation of 9-amino camptothecin

9-Amino-20(S)-camptothecin (I) is prepared by reducing 12-nitro-20(S)-camptothecin (II); converting the resulting 12-amino-20(S)-camptothecin (III) into a compound of formula (IV) wherein X is a group which can be reductively removed; reacting the compound of formula (IV) with a nitrating agent, to obtain thereby the corresponding 9-nitro-20(S)-camptothecin compound of formula (V) substituted at the 12-position by the group X; reducing in a single step the compound of formula (V), so obtaining the 9-amino-20(S)-camptothecin of formula (I); or reducing the compound of formula (V), so obtaining the corresponding 9-amino-20(S)-camptothecin compound of formula (VI) substituted at the 12-position by the group X and reductively removing the X group from the compound of formula (VI), so obtaining 9-amino-20(S)-camptothecin.