| Identification | Back Directory | [Name]
CEPHALOTAXINE | [CAS]
24316-19-6 | [Synonyms]
NSC 128487
NSC 245454
Cephalotaxin
ZINC19795976)
Cephalotaxlen
CEPHALOTAXINE USP/EP/BP
Cephalotaxine 24316-19-6
Cephalotaxine hydrochloride
Cephalotaxlen (ZINC19795976)
Cephalotaxlen ((-)-Cephalotaxine
CEPHALOTAXINE FROM CEPHALOTAXUS &
(1S,3aR,14bβ)-1,5,6,8,9,14b-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1α-ol
[1S-(1a,3aS*,14b)]-1,5,6,8,9,14b-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol
(2S,3S,6R)-4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),4,13,15(19)-tetraen-3-ol
[1S-(1α,3aS*,14bβ)]-1,5,6,8,9,14b-Hexahydro-2-Methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol
(1S,3aR,14bS)-2-Methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-ol
(3aR)-2-Methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-ol
(4R)-7,8-(Methylenebisoxy)-3,4-(trimethylene)-4β,5β-[(3S)-2-methoxy-3-hydroxypropene-1,3-diyl]-1,2,4,5-tetrahydro-3H-3-benzoazepine | [Molecular Formula]
C18H21NO4 | [MDL Number]
MFCD00063372 | [MOL File]
24316-19-6.mol | [Molecular Weight]
315.36 |
| Chemical Properties | Back Directory | [Melting point ]
131-132 °C(Solv: benzene (71-43-2)) | [Boiling point ]
495.2±45.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMF: 10 mg/mL; DMSO: 12 mg/mL; Ethanol: 5 mg/mL | [form ]
powder to crystal | [pka]
13.30±0.40(Predicted) | [color ]
White to Orange to Green | [CAS DataBase Reference]
24316-19-6 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
20/21/22 | [Safety Statements ]
36 | [RIDADR ]
UN 1544 6.1/PG 3
| [WGK Germany ]
3
| [HS Code ]
2939.79.0000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
Antiviral and antitumor agent | [Definition]
ChEBI: A benzazepine alkaloid isolated from Cephalotaxus harringtonia. | [Synthesis]
Sodium borohydride (27 mg, 0.70 mmol, 40 eq.) was added to a stirred solution of (-)-cephathione (S9) (5.5 mg, 18 μmol, 1.0 eq.) in methanol (0.65 mL) at -78 °C. The resulting white mixture was continued to be stirred at -78 °C for 10 minutes, followed by a slow warming to 25 °C and stirring at this temperature for 1 hour. Upon completion of the reaction, the mixture was diluted with water (30 mL) and extracted with dichloromethane (4 x 15 mL). The organic phases were combined, dried with sodium sulfate, gravity filtered, and the filtrate was concentrated by rotary evaporation to afford the target product (-)-1 (5.2 mg, 95% yield) as a light yellow film. Thin layer chromatography (TLC) showed an Rf value of 0.08 (unfolding agent: 10% methanol/dichloromethane). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3), IR and HRMS (ESI): 1H NMR δ 6.68 (s, 1H, ArH), 6.65 (s, 1H, ArH), 5.90 (s, 2H, OCH2O), 4.93 (s, 1H, vinyl H), 4.76 (d, 1H, J = 9Hz, CH(OH )), 3.73 (s, 3H, OCH3), 3.68 (d, 1H, J = 9 Hz, ArCHCH(OH)), 3.35 (m, 1H, CH2), 3.08 (m, 1H, CH2), 2.92 (dd, 1H, J = 12, 11, 7 Hz, CH2), 2.54-2.62 (m, 2H, CH2), 2.36 (ddd, 1H, J = 14, 7Hz, CH2), 2.00 (m, 1H, CH2), 1.60-1.90 (m, 4H, CH2); IR (pure film) 3411 (broad peaks, weak), 2926 (medium), 1651 (medium), 1503 (medium), 1486 (strong), 1222 (strong) cm-1; HRMS (ESI) m/z: C18H22NO4 ([M+H]+) calculated value 316.1549, measured value 316.1559. | [storage]
Store at -20°C | [References]
[1] Journal of the American Chemical Society, 2006, vol. 128, # 32, p. 10370 - 10371
[2] Chemistry - A European Journal, 2008, vol. 14, # 14, p. 4293 - 4306
[3] Patent: WO2009/148654, 2009, A2. Location in patent: Page/Page column 135
[4] Phytochemistry (Elsevier), 1973, vol. 12, p. 2987 - 2991 |
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