Norzoanthamine

Last updated
Norzoanthamine
Norzoanthamine.png
Names
IUPAC name
(4aS,6aS,7S,7aS,9aS,11S,13R,15aR,16aS,16bR)-1,4a,5,7,7a,8,9,11,12,13,14,16,16a,16b-Tetradecahydro-2,7,7a,11,16a-pentamethyl-4H,10H-9a,13-epoxy-15a,7-(epoxyethano)azepino[1,2-a]naphtho[2,1-g]quinoline-4,6,18(6aH)-trione
Other names
Norzoanthamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C29H39NO5/c1-16-9-20-19(21(31)10-16)11-22(32)24-25(20,3)15-29-27(5,26(24,4)13-23(33)35-29)6-7-28-12-17(2)8-18(34-28)14-30(28)29/h10,17-20,24H,6-9,11-15H2,1-5H3/t17-,18+,19-,20+,24-,25-,26-,27-,28-,29+/m0/s1 Yes check.svgY
    Key: RNNGFZNWONBXEI-JHPOJCJNSA-N Yes check.svgY
  • InChI=1/C29H39NO5/c1-16-9-20-19(21(31)10-16)11-22(32)24-25(20,3)15-29-27(5,26(24,4)13-23(33)35-29)6-7-28-12-17(2)8-18(34-28)14-30(28)29/h10,17-20,24H,6-9,11-15H2,1-5H3/t17-,18+,19-,20+,24-,25-,26-,27-,28-,29+/m0/s1
    Key: RNNGFZNWONBXEI-JHPOJCJNBZ
  • O=C2C[C@@H]1C(=O)/C=C(/C)C[C@H]1[C@]3(C)C[C@]47OC(=O)C[C@@](C)([C@@H]23)[C@]7(C)CC[C@@]65C[C@@H](C)C[C@H](CN45)O6
Properties
C29H39NO5
Molar mass 481.633 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Norzoanthamine is an alkaloid found in soft corals of the genus Zoanthus

Norzoanthamine has been shown to suppress the loss of bone weight and strength in mice. [1] Some derivatives of norzoanthamine also suppress development of some kind of leukemia cell lines and human platelet aggregation. [2]

A laboratory synthesis of this compound was developed in 2004. [3]

References

  1. ↑ García-García, Patricia; Reyes, Ricardo; Évora, Carmen; Delgado, Araceli; Fernández, José J.; Daranas, Antonio Hernández (March 2022). "Osteoprotective effect of the marine alkaloid norzoanthamine on an osteoporosis model in ovariectomized rat". Biomedicine & Pharmacotherapy. 147: 112631. doi:10.1016/j.biopha.2022.112631. hdl: 10261/258849 .
  2. ↑ Villar, Rosa M; Gil-Longo, José; Daranas, Antonio H; Souto, Marı́a L; Fernández, José J; Peixinho, Solange; Barral, Miguel A; Santafé, Gilmar; Rodrı́guez, Jaime; Jiménez, Carlos (May 2003). "Evaluation of the effects of several zoanthamine-type alkaloids on the aggregation of human platelets". Bioorganic & Medicinal Chemistry. 11 (10): 2301–2306. doi:10.1016/S0968-0896(03)00107-X. hdl: 10261/213410 . PMID   12713841.
  3. ↑ Miyashita, M.; Sasaki, M; Hattori, I; Sakai, M; Tanino, K (2004). "Total Synthesis of Norzoanthamine". Science. 305 (5683): 495–9. Bibcode:2004Sci...305..495M. doi: 10.1126/science.1098851 . PMID   15205476. S2CID   27964116.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.