Chaetoxanthone

Chaetoxanthone
Chaetoxanthone A	Chaetoxanthone B
Chaetoxanthone C	Chaetoxanthone D
Identifiers
CAS Number	A: 1052639-24-3; B: 1052639-25-4; C: 1052639-26-5; D: 1843267-68-4;
3D model (JSmol)	A: Interactive image; B: Interactive image; C: Interactive image; D: Interactive image;
ChEBI	A: CHEBI:65611; B: CHEBI:65612; C: CHEBI:65613;
ChEMBL	A: ChEMBL501998; B: ChEMBL527064; C: ChEMBL499872;
ChemSpider	A: 24711218; B: 24720687; C: 24707899;
PubChem CID	A: 44586905; B: 44586906; C: 25058081;
CompTox Dashboard (EPA)	A: DTXSID501110140; B: DTXSID601121211;
	InChI 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;
	SMILES 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

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]

References

1 2 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. Bibcode:2008JNAtP..71.1579P. doi:10.1021/np800294q. PMID 18683985.
↑ 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.
1 2 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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[Pontius-1] 1 2 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. Bibcode:2008JNAtP..71.1579P. 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.

[amber-3] 1 2 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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References