Rocaglamide
Names
Preferred IUPAC name
(1R,2R,3S,3aR,8bS)-1,8b-Dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
    Key: DAPAQENNNINUPW-IDAMAFBJSA-N
  • InChI=1/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
    Key: DAPAQENNNINUPW-IDAMAFBJBD
  • CN(C)C(=O)[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(C=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5
Properties
C29H31NO7
Molar mass 505.567 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

Rocaglamide is a natural product which belongs to a class of molecules called flavaglines.[1][2] This compound was isolated in 1982 by King, Ming-Lu (金明儒) and colleagues based on its antileukemic activity.[3] The name of Rocaglamide is named from two parts: Roc- and aglamide. Roc- means Republic of China (中華民國), the place in which this product isolated; aglamide indicates this product is isolated from Large-leaved Aglaia (Scientific name: Aglaia rimosa[4]). Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. Rocaglamide A (RocA) inhibits eukaryotic translation initiation by binding to the translation initiation factor eIF4A and converting it into a translational repressor.[5]

Rocaglamide was first synthesized by Barry Trost in 1990.[6] Although other syntheses have been described since, Trost’s remains the only one to afford rocaglamide in an enantio-specific manner.

See also

References

  1. ↑ Ebada SS, Lajkiewicz N, Porco JA, Li-Weber M, Proksch P (2011). "Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae)". Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. 94: 1–58. doi:10.1007/978-3-7091-0748-5_1. ISBN 978-3-7091-0747-8. PMC 4157394. PMID 21833837.
  2. ↑ Ribeiro N, Thuaud F, Nebigil C, Désaubry L (March 2012). "Recent advances in the biology and chemistry of the flavaglines". Bioorganic & Medicinal Chemistry. 20 (6): 1857–64. doi:10.1016/j.bmc.2011.10.048. PMID 22071525.
  3. ↑ King ML, Chiang CC, Ling HC, Fujita E, Ochiai M, McPhail AT (1992). "X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia". Chem. Commun. (20): 1150–1. doi:10.1039/c39820001150.
  4. ↑ "Aglaia rimosa (Blanco) Merr". Plants of the World Online. Retrieved 2022-12-14.
  5. ↑ Iwasaki S, Floor SN, Ingolia NT (June 2016). "Rocaglates convert DEAD-box protein eIF4A into a sequence-selective translational repressor". Nature. 534 (7608): 558–61. Bibcode:2016Natur.534..558I. doi:10.1038/nature17978. PMC 4946961. PMID 27309803.
  6. ↑ Trost BM, Greenspan PD, Yang BV, Saulnier MG (November 1990). "An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (−)-rocaglamide". Journal of the American Chemical Society. 112 (24): 9022–4. doi:10.1021/ja00180a081.
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