Rocaglamide

• CAT Number: I005059
• CAS Number: 84573-16-0
• Molecular Formula: C₂₉H₃₁NO₇
• Molecular Weight: 505.56
• Purity: ≥95%
• Synonyms: NSC 326408;Roc-A;Rocaglamide A
• Solubility: 10 mM in DMSO
• Storage: -20°C
• IC50: 50 nM (for the heat shock reporter)
• InChI: 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
• InChIKey: DAPAQENNNINUPW-IDAMAFBJSA-N
• SMILES: CN(C)C(=O)C1C(C2(C(C1O)(C3=C(C=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5

Rocaglamide (CAT: I005059) is a natural product derived from the Aglaia genus of plants. It is known for its potent anticancer activity and has been extensively studied as a potential therapeutic agent. Rocaglamide exhibits a broad range of pharmacological activities, including inhibition of protein synthesis, induction of apoptosis, modulation of signaling pathways, and anti-inflammatory effects. It has shown promising activity against various cancer types, including leukemia, breast cancer, and lung cancer. Rocaglamide’s mechanism of action involves targeting multiple cellular pathways involved in cancer progression, making it a promising candidate for further drug development and research.

Reference

1. Nat Prod Rep. 2014 Jul;31(7):924-39. doi: 10.1039/c4np00006d. Epub 2014 May 2.

Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia
species.

Pan L(1), Woodard JL, Lucas DM, Fuchs JR, Kinghorn AD.

Author information:
(1)Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The
Ohio State University, Columbus, Ohio 43210, United States.

Covering: 2006 to 2013. Investigations on the chemistry and biology of
rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia
species during the period 2006-2013 are reviewed. Included are new phytochemical
studies of naturally occurring rocaglamide derivatives, an update on synthetic
methods for cyclopenta[b]benzofurans, and a description of the recent biological
evaluation and mechanism-of-action studies on compounds of this type.

2. ISRN Org Chem. 2011 Apr 4;2011:239817. doi: 10.5402/2011/239817.

Progress in the total synthesis of rocaglamide.

Cai XH(1), Xie B, Guo H.

Author information:
(1)College of Chemistry and Environmental Science, Guizhou University for
Nationalites, Guiyang 550025, China.

The first cyclopenta[b]benzofuran derivative, rocaglamide, from Aglaia
elliptifolia, was found to exhibit considerable insecticidal activities and
excellent potential as a therapeutic agent candidate in cancer chemotherapy; the
genus Aglaia has been subjected to further investigation. Both the structural
complexity of rocaglamide and its significant activity make it an attractive
synthetic target. Stereoselective synthesis of the dense substitution pattern of
these targets is a formidable synthetic challenge: the molecules bear five
contiguous stereocenters and cis aryl groups on adjacent carbons. In past years
of effort, only a handful of completed total syntheses have been reported,
evidence of the difficulties associated with the synthesis of rocaglate natural
products. The advance on total synthesis of rocaglamide was mainly reviewed from
intramolecular cyclization and biomimetic cycloaddition approach.