ROCAGLAMIDE

For Research Use Only.
Category
Alkaloids
Cat.No.
NP0466
CAS
84573-16-0
Product Name
ROCAGLAMIDE
Structure

Product Details

Description
Rocaglamide is the first cyclopenta[b]benzofuran derivative extracted from Aglaia elliptifolia in 1982 by King and colleagues. Its IC50 value is ~50 nM for the heat shock reporter. It has antileukemic activity and displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. It is an immunosuppressant that inhibits activation of NF-kB and NF-AT. It markedly inhibited tumor growth from Huh-7 cells propagated in severe combined immunodeficient mice. It induces apoptosis in various human leukemia cell lines and in acute lymphoblastic leukemia, chronic myeloid leukemia and acute myeloid leukemia cells. It inhibit protein synthesis without affecting DNA or RNA synthesis.
Synonyms
Rocaglamide; Rocaglamide A; RocA; NSC 326408. (1R,2R,3S,3aR,8bS)-2,3,3a,8b-Tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxamide;NSC 326408;Roc-A;Rocaglamide A;1H-Cyclopenta(b)benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)-;[1R-(1α,2α,3β,3aβ,8bβ)]-2,3,3a,8b-Tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxamide
IUPAC Name
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
Molecular Weight
505.56
Molecular Formula
C29H31NO7
Canonical 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
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
Boiling Point
667.3±55.0 °C | Condition: Press: 760 Torr
Melting Point
117-118 °C
Purity
95%
Density
1.321±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
Solubility
10 mM in DMSO
Appearance
Solid powder
Application
Rocaglamide has antileukemic activity and displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. It is an immunosuppressant that inhibits activation of NF-kB and NF-AT. It inhibit protein synthesis without affecting DNA or RNA synthesis.
Shelf Life
2 month in rt, long time
Storage
-20°C Freezer
Color
Colorless
Definition
ChEBI: An organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at
position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity.
Form
Film
NACRES
NA.77
Packaging
1 mg
pKa
11.70±0.70(Predicted)
Quality Level
100
Stability
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. Protect from exposure to light and moisture.
Uses
Rocaglamide is derived from a Chinese medicinal plant Aglaia. Rocaglamide induces apoptosis in various human leukemia cell lines and in acute lymphoblastic leukemia, chronic myeloid leukemia and acute myeloid leukemia cells freshly isolated from patients.
WGK Germany
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