Ellipticine

Ellipticine
Names
Preferred IUPAC name
5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.514 Edit this at Wikidata
EC Number
  • 208-264-0
KEGG
UNII
  • InChI=1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3
  • CC1=C2C(=C(C3=C1C=CN=C3)C)C4=CC=CC=C4N2
Properties
C17H14N2
Molar mass 246.313 g·mol−1
Appearance Yellow crystalline powder[1]
Density 1.257±0.06 g/cm3[2]
Melting point 316–318 °C (601–604 °F; 589–591 K)[2]
Very low[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
GHS labelling:
GHS06: Toxic[4]
H301[4]
P264, P270, P301+P310, P321, P330, P405, P501[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ellipticine is a tetracyclic alkaloid first extracted from trees of the species Ochrosia elliptica and Rauvolfia sandwicensis,[5][6] which inhibits the enzyme topoisomerase II via intercalative binding to DNA.[7]

  1. ^ Miller, R B; Dugar, S (1989). "A regiospecific total synthesis of ellipticine via nitrene insertion". Tetrahedron Letters. 30 (3): 297–300. doi:10.1016/S0040-4039(00)95184-0. ISSN 0040-4039.
  2. ^ a b "Ellipticine | 519-23-3". ChemicalBook. 2016. Retrieved 2017-05-30.
  3. ^ Sbai, M; Ait Lyazidi, S; Lerner, D A; del Castillo, B; Martin, M A (1996). "Use of micellar media for the fluorimetric determination of ellipticine in aqueous solutions". Journal of Pharmaceutical and Biomedical Analysis. 14 (8): 959–965. doi:10.1016/S0731-7085(96)01759-1. ISSN 0731-7085. PMID 8818001.
  4. ^ a b c "Ellipticine | C17H14N2 - PubChem". PubChem. 2016. Retrieved 2017-05-30.
  5. ^ Goodwin, S; Smith, A F; Horning, E C (1959). "Alkaloids of Ochrosia elliptica Labill". Journal of the American Chemical Society. 81 (8): 1903–1908. doi:10.1021/ja01517a031.
  6. ^ Woodward, R B; Iacobucci, G A; Hochstein, I A (1959). "The synthesis of ellipticine". Journal of the American Chemical Society. 81 (16): 4434–4435. doi:10.1021/ja01525a085. ISSN 0002-7863.
  7. ^ Auclair, C (1987). "Multimodal action of antitumor agents on DNA: The ellipticine series". Archives of Biochemistry and Biophysics. 259 (1): 1–14. doi:10.1016/0003-9861(87)90463-2. ISSN 0003-9861. PMID 3318697.