7-Ethylcamptothecin

Base Information

• Chemical Name: 7-Ethylcamptothecin
• CAS No.: 78287-27-1
• Molecular Formula: C22H20N2O4
• Molecular Weight: 376.412
• Hs Code.: 29349990
• European Community (EC) Number: 680-163-8
• UNII: LPY7FE51IW
• DSSTox Substance ID: DTXSID60228960
• Nikkaji Number: J448.356A
• Wikipedia: SN-22
• Wikidata: Q72473443
• Mol file: 78287-27-1.mol

Synonyms:7-ethylcamptothecin;SN 22;SN-22

Chemical Property of 7-Ethylcamptothecin

Chemical Property:

• Appearance/Colour: light pink solid
• Vapor Pressure: 8.15E-24mmHg at 25°C
• Melting Point: 236-241oC
• Refractive Index: 1.712
• Boiling Point: 752.867 °C at 760 mmHg
• PKA: 11.24±0.20(Predicted)
• Flash Point: 409.119 °C
• PSA: 81.42000
• Density: 1.436 g/cm³
• LogP: 2.64200
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform and Methanol Mixture (Slightly, Heated, Sonicated), DMSO (Slightly, H
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 376.14230712
• Heavy Atom Count: 28
• Complexity: 787

Purity/Quality:

99% ^*data from raw suppliers

7-EthylCamptothecin ^*data from reagent suppliers

Safty Information:

• Statements: 23/34/35
• Safety Statements: 3/14-6-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=CC=CC=C51
• Isomeric SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=CC=CC=C51
• Uses: An anticancer drug, showed strong activity against various murine tumors. A Camptothecin (CPT) derivative as antineoplastic agent against drug-resistant tumors. Irinotecan USP Related Compound E. An anticancer drug, showed strong activity against various murine tumors. A Camptothecin (CPT) derivative as antineoplastic agent against drug-resistant tumors.

Technology Process of 7-Ethylcamptothecin

There total 17 articles about 7-Ethylcamptothecin 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: 95.4%

propionaldehyde (123-38-6) + camptothecin (7689-03-4,91926-09-9) → 7-ethylcamptothecin (78287-27-1)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; acetic acid; at -5 - 5 ℃; for 0.166667h; Temperature;

Reference yield: 83.3%

tert-amyl hydroperoxide (3425-61-4) + camptothecin (7689-03-4,91926-09-9) → 7-ethylcamptothecin (78287-27-1)

Guidance literature:

With sulfuric acid; iron(II) sulfate; acetic acid; In water; at 0 ℃; for 0.5h;

DOI:10.1080/00397910601038723

Reference yield: 60.0%

Ethyl boronic acid (4433-63-0) + camptothecin (7689-03-4,91926-09-9) → 7-ethylcamptothecin (78287-27-1)

Guidance literature:

With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one; at 30 ℃; for 48h; Inert atmosphere; Irradiation;

DOI:10.1039/c6sc02653b

upstream raw materials:

propionaldehyde

camptothecin

propionic acid

Acetic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

Downstream raw materials:

irinotecan hydrochloirde

7-ethyl-14-aminocamptothecin

4-(4-Methoxy-phenyl)-piperazine-1-carboxylic acid (S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester

4-(2-Chloro-phenyl)-piperazine-1-carboxylic acid (S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester

Refernces

• 1、 -. "A preparation method of irinotecan hydrochloride (by machine translation)". Paragraph 0027-0028; 0034-0035; 0041-0042. . Retrieved 2019/06/27.
• 2、 Li, Guo-Xing,Morales-Rivera, Christian A.,Wang, Yaxin,Gao, Fang,He, Gang,Liu, Peng,Chen, Gong. "Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine". . p. 6407 - 6412. Retrieved 2016/09/28.