9-Aminocamptothecin

Base Information

• Chemical Name: 9-Aminocamptothecin
• CAS No.: 91421-43-1
• Molecular Formula: C20H17N3O4
• Molecular Weight: 363.373
• Hs Code.: 29349990
• NSC Number: 603071
• UNII: 5MB77ICE2Q
• DSSTox Substance ID: DTXSID10873202
• Nikkaji Number: J360.571J
• Wikidata: Q27149808
• NCI Thesaurus Code: C1488
• Pharos Ligand ID: PBQNM1ZS32L3
• Metabolomics Workbench ID: 129982
• ChEMBL ID: CHEMBL274070
• Mol file: 91421-43-1.mol

Synonyms:9-amino-20(S)-camptothecin;9-amino-20-camptothecin, (+-)-isomer;9-amino-20-camptothecin, (R,S)-isomer;9-amino-CPT;9-aminocamptothecin;NSC 603071

Chemical Property of 9-Aminocamptothecin

Chemical Property:

• Appearance/Colour: Orange-yellow powder
• Vapor Pressure: 2.01E-28mmHg at 25°C
• Melting Point: 142.0-145.0 °C
• Refractive Index: 1.771
• Boiling Point: 819.6 °C at 760 mmHg
• PKA: 11.23±0.20(Predicted)
• Flash Point: 449.5 °C
• PSA: 107.44000
• Density: 1.55 g/cm³
• LogP: 2.24300
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: ≤1mg/ml in DMSO;1mg/ml in dimethyl formamide
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 363.12190603
• Heavy Atom Count: 27
• Complexity: 775

Purity/Quality:

99% ^*data from raw suppliers

9-AminoCamptothecin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5N=C4C3=C2)N)O
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5N=C4C3=C2)N)O
• Recent ClinicalTrials: Aminocamptothecin in Treating Patients With Stomach Cancer or Cancer of the Esophagus
• Uses: 9-Amino Camptothecin is a derivative of Camptothecin (C175150), as antitumor agent.

Technology Process of 9-Aminocamptothecin

There total 18 articles about 9-Aminocamptothecin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.2%

rubitecan (91421-42-0) → 9-amino-20(S)-camptothecin (91421-43-1)

Guidance literature:

With hydrogen; platinum(IV) oxide; In 1,4-dioxane; ethanol; for 2h; under 760 Torr;

DOI:10.1248/cpb.39.3183

Reference yield: 89.0%

(S)-4-Ethyl-9-(4-fluoro-benzenesulfonyl)-4-hydroxy-10-nitro-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione → 9-amino-20(S)-camptothecin (91421-43-1)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; formic acid; triethylamine; In 1,4-dioxane; at 90 ℃; for 1.15h;

DOI:10.1016/0040-4039(95)01939-F

Reference yield: 88.0%

9-nitro-10-(p-toluenesulfonyl)camptothecin (164159-99-3) → 9-amino-20(S)-camptothecin (91421-43-1)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; formic acid; triethylamine; In 1,4-dioxane; at 90 ℃; for 1.15h;

DOI:10.1016/0040-4039(95)01939-F

upstream raw materials:

rubitecan

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

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

9-nitro-10-(p-toluenesulfonyl)camptothecin

Downstream raw materials:

methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin

9-methoxycamptothecin

10-hydroxycamptothecin

camptothecin

Refernces

• 1、 -. "Integrin-Mediated drug targeting". Page/Page column 66. . Retrieved 2008/06/13.
• 2、 -. "Antiangiogenic combination therapy for the treatment of cancer". . . Retrieved 2008/06/13.