Circumdatin H

Circumdatin H is an alkaloid. It was isolated, along with related compounds, from the fungus Aspergillus ochraceus.[1]

Circumdatin H
Names
Preferred IUPAC name
(5bS)-2-Methoxy-5b,6,7,8-tetrahydro-10H,16H-pyrrolo[2,1-c]quinazolino[3,2-a][1,4]benzodiazepine-10,16-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H17N3O3/c1-26-12-8-9-15-14(11-12)20(25)23-16-6-3-2-5-13(16)19(24)22-10-4-7-17(22)18(23)21-15/h2-3,5-6,8-9,11,17H,4,7,10H2,1H3/t17-/m0/s1
    Key: MLEAYJRUKNTODR-KRWDZBQOSA-N
  • InChI=1/C20H17N3O3/c1-26-12-8-9-15-14(11-12)20(25)23-16-6-3-2-5-13(16)19(24)22-10-4-7-17(22)18(23)21-15/h2-3,5-6,8-9,11,17H,4,7,10H2,1H3/t17-/m0/s1
    Key: MLEAYJRUKNTODR-KRWDZBQOBN
  • COc1ccc2c(c1)c(=O)n-3c(n2)[C@@H]4CCCN4C(=O)c5c3cccc5
Properties
C20H17N3O3
Molar mass 347.374 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Circumdatin C, and circumdatin F are prototypical members, while other members such as circumdatin D, circumdatin E and circumdatin H have an additional tetrahydropyrrole ring.

The compounds of this group are considered to be useful chemotaxonomic markers. Among these circumdatin H and circumdatin E are able to inhibit the mitochondrial respiratory chain in submitochondrial particles from beef heart, presumable by interfering with NADH oxidase activity (IC50 1.5 μM and 2.5 μM, respectively).

First total synthesis of circumdatin H was reported starting from anthranilic acid.[2]

References
  1. López-Gresa, M Pilar; González, M Carmen; Primo, Jaime; Moya, Pilar; Romero, Vanessa; Estornell, Ernesto (1 June 2005). "Circumdatin H, a New Inhibitor of Mitochondrial NADH Oxidase, from Aspergillus ochraceus". The Journal of Antibiotics. 58 (6): 416–419. doi:10.1038/ja.2005.54. PMID 16156520.
  2. Bose, D.; Chary, M. (2009). "First Total Synthesis of (-)-Circumdatin H, a Novel Mitochondrial NADH Oxidase Inhibitor". Synthesis. 2010 (4): 643. doi:10.1055/s-0029-1218606.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.