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Didesmethylrocaglamide

HCID 397614
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Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
177262-30-5
Standard SMILES
COc1ccc([C@@]23Oc4cc(OC)cc(OC)c4[C@]2(O)[C@H](O)[C@H](C(N)=O)[C@H]3c2ccccc2)cc1
InChIKey
RMNPQEWLGQURNX-PXIJUOARSA-N
Molecular formula
C27H27NO7
Average molar mass
477.5 g/mol
Monoisotopic mass
477.1787522

Overview

Didesmethylrocaglamide is a naturally-occurring derivative of [rocaglamide] and belongs to a class of anti-cancer phytochemicals referred to as "rocaglamides" derived from plants of the genus Aglaia. While traditionally used for their insecticidal benefits, this class of compounds is now being studied for use as chemotherapeutic agents in the treatment of various leukemias, lymphomas, and carcinomas. Of the known derivatives of rocaglamide, didesmethylrocaglamide appears to carry the most potent anti-tumour activity.

Names & identifiers

Preferred name
Didesmethylrocaglamide
IUPAC
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
English name
1H-Cyclopenta[b]benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-, (1R,2R,3S,3aR,8bS)-
Molecular formula
C27H27NO7
Molecular weight
477.51

Names & synonyms

Didesmethylrocaglamide177262-30-5(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta(b)(1)benzofuran-2-carboxamideRefChem:133299RocBNSC705956Didesmethylrocaglamide?CHEMBL583207orb1693474SCHEMBL29520556SCHEMBL31489959
Show more names
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide1H-Cyclopenta[b]benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-, (1R,2R,3S,3aR,8bS)-
HY-19356ANSC825721AKOS040755444DB15496NSC-705956NSC-825721DA-62855MS-28858

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
120 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
7
Rotatable bonds
6
Heavy atoms
35
Formal charge
0
Complexity
767

Physicochemical properties

Boiling point
691.4 · 691.4±55.0 °C(Predicted)
Density
1.379 · 1.379±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
solubility
100 mg/mL · DMSO: 100 mg/mL (209.42 mM)
form
Solid
pka
11.7 · 11.70±0.70(Predicted)
color
White to off-white

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Little research has been conducted specifically regarding didesmethylrocaglamide, but its mechanism of action is likely to be congruent with the rest of the rocaglamide class. Didesmethylrocaglamide’s anti-tumor activity, similar to other rocaglamide derivatives, is driven primarily via inhibition of protein synthesis in tumor cells. Inhibition of protein synthesis is accomplished via inhibition of prohibitin 1 (PHB1) and prohibitin 2 (PHB2) - these proteins are necessary in the proliferation of cancer cells and are implicated in the Ras-mediated CRaf-MEK-ERK signaling pathway responsible for phosphorylating eIF4E, a key factor in the initiation of protein synthesis. There is also some evidence that rocaglamides can act directly on eIF4A, another translation initiation factor of the eIF4F complex ultimately responsible for initiation of protein synthesis. Inhibition of protein synthesis has a number of downstream effects. Many of the proteins that are down-regulated in response to protein synthesis inhibition in tumor cells are short-lived proteins responsible for regulation of the cell cycle, such as Cdc25A. Cdc25A is an oncogene that can become overexpressed in certain cancers and lead to unchecked cell growth. In addition to inhibiting its synthesis via the mechanism described above, rocaglamides promote degradation of Cdc25A via activation of the ATM/ATR-Chk1/Chk2 checkpoint pathway. This pathway is normally activated in response to DNA damage and serves to reduce the expression of proteins responsible for cell cycle progression, thereby inhibiting proliferation of damaged (i.e. tumour) cells. Inhibition of protein synthesis also appears to prevent the actions of the transcription factor heat shock factor 1 (HSF1), leading to an increased expression of thioredoxin-interacting protein (TXNIP) which is negatively regulated by HSF1. TXNIP is a negative regulator of cell glucose uptake, and its increased expression blocks glucose uptake and consequently impairs the proliferation of malignant cells. Rocaglamides also appear to induce apoptosis in tumor cells via activation of the pro-apoptotic proteins p38 and JNK and inhibition of the anti-apoptotic Mcl-1 protein. Similarly, they have been studied as an adjuvant in TRAIL-resistant cancers due to their ability to inhibit the synthesis of c-FLIP and IAP/XIAP - these anti-apoptotic proteins can become elevated in certain cancers, preventing the induction of apoptosis and resulting in resistance to TRAIL-based therapies.

Applications · 1 item

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
177262-30-5
PubChem CID
397614
ChEMBL
CHEMBL583207
Nikkaji
J864.651A

UsesDidesmethylrocaglamide, a derivative of Rocaglamide, is a potent eukaryotic initiation factor 4A (eIF4A) inhibitor. Didesmethylrocaglamide has potent growth-inhibitory activity with an IC50 of 5 nM. Didesmethylrocaglamide suppresses multiple growth-promoting signaling pathways and induces apoptosis in tumor cells. Antitumor activity[1][2].

Suppliers13 total

Aladdin Scientific[email protected]
InvivoChem中国13549236410 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
InvivoChem+1-708-310-1919 +1-13798911105 · [email protected]