245092-42-6

Basic information

• Product Name: (3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
• Synonyms: (3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
• CAS NO: 245092-42-6
• Molecular Weight: 211.218
• Mol File: 245092-42-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione(245092-42-6)
• EPA Substance Registry System: (3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione(245092-42-6)

Safety Data

• Hazardous Substances Data: 245092-42-6(Hazardous Substances Data)

Upstream product

• 141-43-5 ethanolamine 
• 29745-04-8 norcantharidin 
• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 847757-03-3 (+/-)-(3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 
• 5426-09-5 4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 

Downstream Products

• 1338378-73-6 4-(2-(diphenyloxyphosphoryloxy)ethyl)-4-aza-10-oxatricyclo[5.2.1.0(2,6)]decane-3,5-dione 

Relevant articles and documents

In situ ATRP-mediated hierarchical formation of giant amphiphile bionanoreactors

(Figure Presented) Functional giants: Amphiphilic bioconjugates can be synthesized in situ by grafting polystyrene from a protein (see scheme). The resulting giant amphiphiles display low polydispersities and the characteristic aggregation properties of amphiphilic biomacromolecules. A second, catalytically active guest protein can also be included within the superstructures.

Norcantharimide analogues possessing terminal phosphate esters and their anti-cancer activity

A family of norcantharidin analogues possessing a terminal alcohol (ethanol, propanol, butanol, pentanol, hexanol and cyclohexanol) moiety were treated with either chlorodiethyl, chlorodiphenyl or chloro-bis-trichloroethyl- phosphate to afford highly focused libraries of the corresponding phosphate esters. Subsequent biological screening against a panel of nine human cancer cell lines identified a trend between the ease of phosphate unmasking (phosphate ester hydrolysis) and cell death. The most potent analogues possessed either a diphenyl or a bis-trichloroethyl moiety. The effect of alkyl spacer was also examined with the hexyl analogues typically more potent. 4-Aza-4-(3-{bis(2,2,2- trichloroethyl)phosphate}propyl)-10-oxatricyclo[5.2.1.0]decane-3,5-dione (10b) was the most potent analogue synthesised with an average GI50 of 11 μM across a panel of nine human carcinoma cell lines: colon carcinoma (HT29 and SW480); breast carcinoma (MCF-7); ovarian carcinoma (A2780); lung carcinoma (H460); skin carcinoma (A431); prostate carcinoma (DU145); neuronal carcinoma (BE2-C) and brain carcinoma (SJ-G2). This represents a fivefold improvement in anti-proliferative activity relative to the lead, norcantharidin.

Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation

A range of amines was reacted with norcantharidin (2) to provide the corresponding norcantharimides (9-43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (20) which was amenable to epoxidation (mCPBA, 22) and