Norzoanthamine

Norzoanthamine
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
CAS Number	164991-65-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3139348
ChemSpider	10220837^Y
PubChem CID	10767108
CompTox Dashboard (EPA)	DTXSID10893768
InChI 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^Y Key: RNNGFZNWONBXEI-JHPOJCJNSA-N^Y 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
SMILES 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
Chemical formula	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). Y verify (what is ^YN ?) Infobox references

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

^ 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.
^ 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.
^ 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.

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This page was last edited on 24 August 2023, at 00:36

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References