7-Ethylcamptothecin Chemical Properties

Melting point:

236-241°C

Boiling point:

752.9±60.0 °C(Predicted)

Density 

1.43

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform and Methanol Mixture (Slightly, Heated, Sonicated), DMSO (Slightly, Heated)

pka

11.24±0.20(Predicted)

form 

Solid

color 

Pale Yellow to Light Orange

InChI

InChI=1S/C22H20N2O4/c1-3-12-13-7-5-6-8-17(13)23-19-14(12)10-24-18(19)9-16-15(20(24)25)11-28-21(26)22(16,27)4-2/h5-9,27H,3-4,10-11H2,1-2H3/t22-/m0/s1

InChIKey

MYQKIWCVEPUPIL-JOCHJYFZSA-N

SMILES

N1C2C(=CC=CC=2)C(CC)=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O

CAS DataBase Reference

78287-27-1(CAS DataBase Reference)

Safety Information

Risk Statements 

23/34/35

Safety Statements 

3/14-6-36/37/39

RIDADR 

1544

HazardClass 

6.1

PackingGroup 

III

HS Code 

29349990

7-Ethylcamptothecin Usage And Synthesis

Chemical Properties

Light Pink Solid

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.

Definition

ChEBI: 7-ethylcamptothecin is a pyranoindolizinoquinoline.

Biological Activity

7-Ethylcamptothecin is one of the camptothecin analogs. Camptothecin (CPT), a cytotoxic alkaloid isolated from camptothecin analogues, has strong antitumor activity against L1210 leukemia and Walker 256 carcinosarcoma models.

Synthesis

To a 5L reactor were added 80 g of (S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (camptothecin), 840 g of glacial acetic acid, and 368 g of concentrated sulfuric acid, and mechanical stirring was initiated until complete dissolution. Subsequently, 80 g of propionaldehyde was slowly added and 102 g of hydrogen peroxide was added dropwise. The reaction temperature was controlled in the range of -5 to 5°C for 10 minutes. After completion of the reaction, 10 kg of pure water was added to the system and stirring was continued for 2 hours. The precipitate was collected by filtration to give 72.5 g of (S)-4,11-diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolo[1,2-b]quinoline-3,14(4H,12H)-dione (7-ethylcamptothecin) in 95.4% yield.

References

[1] Patent: CN108484624, 2018, A. Location in patent: Paragraph 0031; 0039; 0043; 0044
[2] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 6, p. 1446 - 1454
[3] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 10, p. 2574 - 2580
[4] Patent: WO2006/16203, 2006, A1. Location in patent: Page/Page column 9-10
[5] European Journal of Pharmaceutical Sciences, 2018, vol. 123, p. 546 - 559

7-Ethylcamptothecin(78287-27-1)Related Product Information

• Irinotecan Hydroxyl Acid
• Irinotecan IMpurity G
• Irinotecan Impurity 18
• 12-Hydroxy Irinotecan
• Irinotecan Lactone IMpurity
• 12-ethyl-8-methyl-9-oxo-7-propionyl-9,11-dihydroindolizino[1,2-b]quinolin-2-yl [1,4'-bipiperidine]-1'-carboxylate
• 10-Nitrocamptothecin
• (+)-Camptothecin
• 10-Hydroxycamptothecin
• 4-Ethyl-4,10-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• Irinotecan Impurity 19
• Irinotecan Impurity 29
• [1,4'-Bipiperidine]-1'-carboxylic acid
• sodium:(2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-(4-piperidin-1-ylpiperidine-1-carbonyl)oxy-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate
• 11-Desethyl Irinotecan
• Irinotecan Impurity 26
• Irinotecan
• 7,11-Diethyl-10-hydroxycaMptothecin