Roseophilin

Roseophilin is an antibiotic isolated from Streptomyces griseoviridis shown to have antitumor activity.[1] The chemical structure can be considered in terms of two components, a macrotricyclic segment and a heterocyclic side-chain. Several laboratory syntheses of roseophilin (e.g., those of Trost, Fürstner, Salamone) are based upon the Paal-Knorr synthesis, and two others are based on the Nazarov cyclization reaction (those of Tius, Frontier). The compound is related to the prodiginines.[2]

Roseophilin
Names
IUPAC name
15-[5-(3-Chloro-1H-pyrrol-2-yl)-3-methoxy-furan-2-yl]-13-isopropyl-2-aza-tricyclo[10.2.1.13,14]hexadeca-1(15),2-triene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C27H33ClN2O2/c1-16(2)23-18-11-9-7-5-4-6-8-10-17-14-19(23)25(30-17)24(18)27-22(31-3)15-21(32-27)26-20(28)12-13-29-26/h12-16,18,23,30H,4-11H2,1-3H3/b26-21-,27-24- checkY
    Key: XEQIXGXEBJYNMG-OLPWBVPVSA-N checkY
  • InChI=1/C27H33ClN2O2/c1-16(2)23-18-11-9-7-5-4-6-8-10-17-14-19(23)25(30-17)24(18)27-22(31-3)15-21(32-27)26-20(28)12-13-29-26/h12-16,18,23,30H,4-11H2,1-3H3/b26-21-,27-24-
    Key: XEQIXGXEBJYNMG-OLPWBVPVBQ
  • CC(C)[C@H]1[C@@H]\2CCCCCCCCC3=CC1=C(/C2=C\4/C(=C/C(=C/5\C(=CC=N5)Cl)/O4)OC)N3
Properties
C27H33ClN2O2
Molar mass 453.02 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Fürstner, A. (2003). "Chemistry and Biology of Roseophilin and the Prodigiosin Alkaloids: A Survey of the Last 2500 Years". Angew. Chem. Int. Ed. 42 (31): 3582–3603. doi:10.1002/anie.200300582. PMID 12916029.
  2. Hu, Dennis X.; Withall, David M.; Challis, Gregory L.; Thomson, Regan J. (2016). "Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products". Chemical Reviews. 116 (14): 7818–7853. doi:10.1021/acs.chemrev.6b00024. PMC 5555159. PMID 27314508.


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