Rodiasine

Rodiasine is a cyclic bisbenzylisoquinoline alkaloid that was first isolated from the South American greenheart tree Chlorocardium rodiei.[1] The synthesis of O-demethylrodiasine (antioquine) and its derivatives, and the possible application of these compounds as anti-cancer, calcium channel blockers, and anti-parasitic drugs has been described.[2][3]

Rodiasine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C38H42N2O6/c1-39-13-11-24-19-33(43-4)34-21-26(24)29(39)17-22-7-9-31(41)27(15-22)28-16-23(8-10-32(28)42-3)18-30-36-25(12-14-40(30)2)20-35(44-5)37(45-6)38(36)46-34/h7-10,15-16,19-21,29-30,41H,11-14,17-18H2,1-6H3/t29-,30+/m1/s1 checkY
    Key: HIQZXOFBXJICTD-IHLOFXLRSA-N checkY
  • InChI=1/C38H42N2O6/c1-39-13-11-24-19-33(43-4)34-21-26(24)29(39)17-22-7-9-31(41)27(15-22)28-16-23(8-10-32(28)42-3)18-30-36-25(12-14-40(30)2)20-35(44-5)37(45-6)38(36)46-34/h7-10,15-16,19-21,29-30,41H,11-14,17-18H2,1-6H3/t29-,30+/m1/s1
    Key: HIQZXOFBXJICTD-IHLOFXLRBV
  • O(c1ccc5cc1c2c(O)ccc(c2)C[C@H]7N(CCc6cc(OC)c(Oc3c4c(cc(OC)c3OC)CCN(C)[C@H]4C5)cc67)C)C
Properties
C38H42N2O6
Molar mass 622.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Grundon, M.F.; McGarvey, J.E.B. (1966). "Alkaloids from greenheart. Part III. The structure of rodiasine. Mass spectra of bisbenzylisoquinoline alkaloids". Journal of the Chemical Society C: Organic. 1966: 1082–1084. doi:10.1039/J39660001082.
  2. Bentley, K. W. (1996). "β-Phenylethylamines and the isoquinoline alkaloids" (PDF). Natural Product Reports. 13 (2): 127–150. doi:10.1039/NP9961300127.
  3. D'Ocon MP, Candenas ML, Anselmi E, Zafra-Polo MC, Cortes D (1989). "Antioquine: a new bisbenzylisoquinoleine alkaloid with calcium antagonist activity". Arch Int Pharmacodyn Ther. 297: 205–16. PMID 2730236.


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