Anthramycin

Not to be confused with anthracimycin.
Anthramycin
Names
Preferred IUPAC name
(2E)-3-[(11S,11aS)-9,11-Dihydroxy-8-methyl-5-oxo-5,10,11,11a-tetrahydro-1H-pyrrolo[2,1-c] [1,4]benzodiazepin-2-yl]prop-2-enamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+/t11-,15-/m0/s1 checkY
    Key: VGQOVCHZGQWAOI-HYUHUPJXSA-N checkY
  • Cc1ccc2C(=O)N3C=C(C[C@H]3[C@H](O)Nc2c1O)\C=C\C(=O)N
Properties
C16H17N3O4
Molar mass 315.329 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anthramycin is a pyrrolobenzodiazepine antibiotic with antitumor activity.[1] First derived from the thermophilic actinomycete Streptomyces refuineus by M. D. Tendler and S Korman in the 1950s, it was first successfully synthesized in a laboratory setting by Leimgruber et al. in 1965. Due to the unstable nature of the chemical structure, characterization of the species was done on its epimer, anthrmycin-11-methyl-ether. This derivative can be formed by recrystallization of anthramycin from hot methanol.

  1. ^ Kitamura, Tsuyoshi; Yoshihiro Sato; Miwako Mori (2004). "Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross-metathesis". Tetrahedron. 60 (43): 9649–57. doi:10.1016/j.tet.2004.07.040.