Chaetoxanthone

Chaetoxanthones are a class of chemical compounds which are classified as xanthones. They have been isolated from marine-derived fungi in the genus Chaetomium.[1] There are four compounds in the class that are designated as chaetoxanthones A through D.[1][2] A laboratory synthesis of (±)-chaetoxanthone B has been reported.[3] The chaetoxanthones are under investigation as potential antimalarials.[3]

Chaetoxanthone
Chaetoxanthone A
Chaetoxanthone B
Chaetoxanthone C
Chaetoxanthone D
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • A: InChI=1S/C20H18O7/c1-20-8-9(21)6-13(26-20)16-14(27-20)7-12-17(19(16)23)18(22)15-10(24-2)4-3-5-11(15)25-12/h3-5,7,9,13,21,23H,6,8H2,1-2H3/t9-,13+,20+/m1/s1
    Key: PYEDKAHYOPGAKC-PDXJJUDESA-N
  • B: InChI=1S/C20H18O6/c1-20-8-4-7-12(25-20)16-14(26-20)9-13-17(19(16)22)18(21)15-10(23-2)5-3-6-11(15)24-13/h3,5-6,9,12,22H,4,7-8H2,1-2H3
    Key: ZUEKQPJBVORAFH-UHFFFAOYSA-N
  • C: InChI=1S/C20H19ClO6/c1-9-5-3-7-12(26-9)14-18(23)15-17(22)13-10(25-2)6-4-8-11(13)27-20(15)16(21)19(14)24/h4,6,8-9,12,23-24H,3,5,7H2,1-2H3/t9-,12-/m1/s1
    Key: MWYMVCYBLZZWPG-BXKDBHETSA-N
  • D: InChI=1S/C21H22O6/c1-11-6-4-8-15(26-11)19-16(25-3)10-12(22)17-20(23)18-13(24-2)7-5-9-14(18)27-21(17)19/h5,7,9-11,15,22H,4,6,8H2,1-3H3/t11-,15-/m1/s1
    Key: MUBFTAAOQKTFBO-IAQYHMDHSA-N
  • A: C[C@]12C[C@@H](C[C@H](O1)C3=C(O2)C=C4C(=C3O)C(=O)C5=C(O4)C=CC=C5OC)O
  • B: CC12CCCC(O1)C3=C(O2)C=C4C(=C3O)C(=O)C5=C(O4)C=CC=C5OC
  • C: C[C@@H]1CCC[C@@H](O1)C2=C(C(=C3C(=C2O)C(=O)C4=C(O3)C=CC=C4OC)Cl)O
  • D: O(C)C=1C(=C2C(C(=O)C=3C(O2)=CC=CC3OC)=C(O)C1)[C@@H]4O[C@H](C)CCC4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Pontius, Alexander; Krick, Anja; Kehraus, Stefan; Brun, Reto; König, Gabriele M. (1 September 2008). "Antiprotozoal Activities of Heterocyclic-Substituted Xanthones from the Marine-Derived Fungus Chaetomium sp". Journal of Natural Products. 71 (9): 1579–1584. doi:10.1021/np800294q. PMID 18683985.
  2. Wang, Meng-Hua; Li, Li; Jiang, Tao; Wang, Xue-Wei; Sun, Bin-Da; Song, Bo; Zhang, Qiu-Bo; Jia, Hong-Mei; Ding, Gang; Zou, Zhong-Mei (2015). "Stereochemical determination of tetrahydropyran-substituted xanthones from fungus Chaetomium murorum". Chinese Chemical Letters. 26 (12): 1507–1510. doi:10.1016/j.cclet.2015.10.025.
  3. Lennon, Amber C.; Tallen, Sara C.; Dabire, Sadiq W.; Quach, Nhu H.; Gladen, Paul T. (October 2021). "Total synthesis of (±)-chaetoxanthone B". Tetrahedron Letters. 82: 153390. doi:10.1016/j.tetlet.2021.153390. S2CID 240556659.
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