10-Methoxycamptothecin

Base Information

• Chemical Name: 10-Methoxycamptothecin
• CAS No.: 19685-10-0
• Molecular Formula: C21H18 N2 O5
• Molecular Weight: 378.384
• NSC Number: 111533
• DSSTox Substance ID: DTXSID60941445
• Nikkaji Number: J258.664I
• Wikidata: Q72489417
• ChEMBL ID: CHEMBL75854
• Mol file: 19685-10-0.mol

Synonyms:9-methoxycamptothecin

Chemical Property of 10-Methoxycamptothecin

Chemical Property:

• Vapor Pressure: 3.78E-25mmHg at 25°C
• Melting Point: 254-255℃
• Boiling Point: 773.1°Cat760mmHg
• PKA: 11.21±0.20(Predicted)
• Flash Point: 421.4°C
• PSA: 90.65000
• Density: 1.5g/cm³
• LogP: 2.08820
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 378.12157168
• Heavy Atom Count: 28
• Complexity: 790

Purity/Quality:

98% ^*data from raw suppliers

9-Methoxycamptothecin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)OC)O
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)OC)O
• Description: A minor constituent of Mappia foetida Miers. The alkaloid yields pale yellow crystals when purified from CHC13-MeOH. It is laevorotatory with [α]24D - 77.5° (c 1.0, pyridine). The structure has been established by spectroscopic methods.
• Uses: 10-Methoxycamptothecin is a Camptothecin (C175150) derivative used in the treatment of cancers. Used in the treatment of hyperproliferative diseases. 9-Methoxycamptothecin is an alkaloid derivative of Camptothecin (C175150) derivative used in the treatment of cancers. Camptothecin is a potent anti-cancer agent.

Technology Process of 10-Methoxycamptothecin

There total 55 articles about 10-Methoxycamptothecin 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2) → 10-methoxycamptothecin (19685-10-0)

Guidance literature:

In 1,4-dioxane; methanol; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2010.09.130

Reference yield: 85.0%

p-methoxyphenylisonitrile (10349-38-9) + (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 (174092-80-9) → 10-methoxycamptothecin (19685-10-0)

Guidance literature:

With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate; triethylamine; In acetonitrile; at 20 ℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation;

DOI:10.1002/cjoc.201800358

Reference yield: 82.0%

10-methoxy-21-hydroxycamptothecin (1088402-95-2) → 10-methoxycamptothecin (19685-10-0)

Guidance literature:

With iodine; calcium carbonate; In methanol; water; at 40 ℃; for 24h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol802250y

upstream raw materials:

diazomethane

(S)-10-hydroxycamptothecin

methanol

Camptothecin 1-oxide

Downstream raw materials:

10-methoxycamptothecin-20-O-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid ester

12-amino-20(S)-camptothecin

Topotecan hydrochloride

(S)-10-hydroxycamptothecin

Refernces

• 1、 Greenwald, Richard B.,Choe, Yun H.,Wu, Dechun. "Selective phenolic acylation of 10-hydroxycamptothecin using poly (ethylene glycol) carboxylic acid". . p. 577 - 580. Retrieved 2003.
• 2、 -. "Water-soluble anti-tumor compounds". Paragraph 0228-0233. . Retrieved 2019/05/04.
• 3、 Zhu, Meixuan,Jing, Lijia,Wang, Shaoming,Zhang, Sheng,Wang, Yang. "Synthesis and anticancer evaluation of novel 10-methoxycamptothecin derivatives". . p. 932 - 934. Retrieved 2015/02/05.