6820-95-7

Basic information

• Product Name: N-(3-Morpholinopropyl)phthalimide
• Synonyms: N-(3-Morpholinopropyl)phthalimide;2-(3-Morpholinopropyl)isoindoline-1,3-dione
• CAS NO: 6820-95-7
• Molecular Formula: C₁₅H₁₈N₂O₃
• Molecular Weight: 274.32
• Mol File: 6820-95-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 427.1°C at 760 mmHg
• Flash Point: 212.1°C
• Appearance: /
• Density: 1.239g/cm³
• Vapor Pressure: 1.69E-07mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: N-(3-Morpholinopropyl)phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-Morpholinopropyl)phthalimide(6820-95-7)
• EPA Substance Registry System: N-(3-Morpholinopropyl)phthalimide(6820-95-7)

Safety Data

• Hazardous Substances Data: 6820-95-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H18N2O3/c18-14-12-4-1-2-5-13(12)15(19)17(14)7-3-6-16-8-10-20-11-9-16/h1-2,4-5H,3,6-11H2

Upstream product

• 123-00-2 4-(3-Aminopropyl)morpholine 
• 85-44-9 phthalic anhydride 
• 7357-67-7 4-(3-chloropropyl)morpholine 
• 1074-82-4 potassium phtalimide 
• 110-91-8 morpholine 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 

Downstream Products

• 123-00-2 4-(3-Aminopropyl)morpholine 

Relevant articles and documents

Highly Selective Butyrylcholinesterase Inhibitors with Tunable Duration of Action by Chemical Modification of Transferable Carbamate Units Exhibit Pronounced Neuroprotective Effect in an Alzheimer's Disease Mouse Model

In this study, the carbamate structure of pseudo-irreversible butyrylcholinesterase (BChE) inhibitors was optimized with regard to a longer binding to the enzyme. A set of compounds bearing different heterocycles (e.g., morpholine, tetrahydroisoquinoline, benzimidazole, piperidine) and alkylene spacers (2 to 10 methylene groups between carbamate and heterocycle) in the carbamate residue was synthesized and characterized in vitro for their binding affinity, binding kinetics, and carbamate hydrolysis. These novel BChE inhibitors are highly selective for hBChE over human acetycholinesterase (hAChE), yielding short-, medium-, and long-acting nanomolar hBChE inhibitors (with a half-life of the carbamoylated enzyme ranging from 1 to 28 h). The inhibitors show neuroprotective properties in a murine hippocampal cell line and a pharmacological mouse model of Alzheimer's disease (AD), suggesting a significant benefit of BChE inhibition for a disease-modifying treatment of AD.

Flavonoid derivatives as selective ABCC1 modulators: Synthesis and functional characterization

A series of chromones, bearing substituted amino groups or N-substituted carboxamide moieties in position 2, was synthesized and characterized in cellular assays for modulation of the ABC transporters ABCC1 (MDCKII-MRP1 cells), ABCB1 (Kb-V1 cells) and ABCG2 (MCF-7/Topo cells). The most potent ABCC1 modulators identified among these flavonoid-type compounds were comparable to the reference compound reversan regarding potency, but superior in terms of selectivity concerning ABCB1 and ABCG2 (2-[4-(Benzo[c][1,2,5]oxadiazol-5-ylmethyl)piperazin-1-yl]-5,7-dimethoxy-4H-chromen-4-one (51): ABCC1, IC50 11.3-1/4M; inactive at ABCB1 and ABCG2). Compound 51 was as effective as reversan in reverting ABCC1-mediated resistance to cytostatics in MDCKII-MRP1 cells and proved to be stable in mouse plasma and cell culture medium. Modulators, such as compound 51, are of potential value as pharmacological tools for the investigation of the (patho)physiological role of ABCC1.

Synthesis and biological evaluation of 2,4-diaminoquinazoline derivatives as novel heat shock protein 90 inhibitors

Novel 2,4-diaminoquinazoline derivatives originating from a virtual screening approach were designed, synthesized and their biological activities as heat shock protein 90 (Hsp90) inhibitors were evaluated. The prepared compounds exhibited significant anti-proliferative activities against DU-145, HT-29, HCT-116, A375P and MCF-7 cancer cell lines. The selected compounds were tested against Her2, a client protein of Hsp90, and showed significant reduction in Her2 protein expression. Compound 6b was found the most potent, reduced Her2 protein expression levels and induced Hsp70 protein expression levels significantly.