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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
  • 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
  • A: 44586905
  • B: 44586906
  • C: 25058081
  • A: DTXSID501110140
  • B: DTXSID601121211
  • 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).

References edit

  1. ^ a b 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. ^ a b 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.

chaetoxanthone, class, chemical, compounds, which, classified, xanthones, they, have, been, isolated, from, marine, derived, fungi, genus, chaetomium, there, four, compounds, class, that, designated, chaetoxanthones, through, laboratory, synthesis, chaetoxanth. 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 CAS Number A 1052639 24 3B 1052639 25 4C 1052639 26 5D 1843267 68 4 3D model JSmol A Interactive imageB Interactive imageC Interactive imageD Interactive image ChEBI A CHEBI 65611B CHEBI 65612C CHEBI 65613 ChEMBL A ChEMBL501998B ChEMBL527064C ChEMBL499872 ChemSpider A 24711218B 24720687C 24707899 PubChem CID A 44586905B 44586906C 25058081 CompTox Dashboard EPA A DTXSID501110140B 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 s1Key PYEDKAHYOPGAKC PDXJJUDESA NB 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 2H3Key ZUEKQPJBVORAFH UHFFFAOYSA NC 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 s1Key MWYMVCYBLZZWPG BXKDBHETSA ND 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 s1Key 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 OB CC12CCCC O1 C3 C O2 C C4C C3O C O C5 C O4 C CC C5OCC C C H 1CCC C H O1 C2 C C C3C C2O C O C4 C O3 C CC C4OC Cl OD 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 referencesReferences edit a b Pontius Alexander Krick Anja Kehraus Stefan Brun Reto Konig 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 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 a b 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 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Chaetoxanthone amp oldid 1179541272, wikipedia, wiki, book, books, library,

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