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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3139348;
ChemSpider	10220837 ;
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 Key: RNNGFZNWONBXEI-JHPOJCJNSA-N ; 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). verify (what is ?) 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. hdl:10261/213410. PMID 12713841.
^ 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.

[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.

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