| Identification | More | [Name]
7-Ethylcamptothecin | [CAS]
78287-27-1 | [Synonyms]
7-ETHYL-CAMPTOTHECIN,HPLC 99%
(S)-4,11-Diethyl-4-hydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione
(4S)-4,11-Diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
SN 22
7-Etyl-camptothecin
(4S)-4,11-Diethyl-4-hydroxy-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione | [Molecular Formula]
C22H20N2O4 | [MDL Number]
29349990 | [Molecular Weight]
376.4 | [MOL File]
78287-27-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Pink Solid | [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) | [form ]
Solid | [pka]
11.24±0.20(Predicted) | [color ]
Pale Yellow to Light Orange | [Usage]
An anticancer drug, showed strong activity against various murine tumors. A Camptothecin (CPT) derivative as antineoplastic agent against drug-resistant tumors. | [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 Data | Back Directory | [Risk Statements ]
23/34/35 | [Safety Statements ]
3/14-6-36/37/39 | [RIDADR ]
1544 | [WGK Germany ]
WGK 3 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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. | [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. | [Cytotoxicity]
7-ethyl Camptothecin is cytotoxic to ADJ/PC6 SN-38-sensitive and PC6/SN2-5H2 SN-38-resistant cells (IC50s = 0.85 and 2.98 nM, respectively).
| [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 |
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