165657-63-6

Basic information

• Product Name: (+)-N-BENZYL-D-MALIMIDE
• Synonyms: (R)-2-HYDROXY-N-BENZYLSUCCINIMIDE;(R)-1-BENZYL-3-HYDROXYPYRROLE-2,5-DIONE;(+)-N-BENZYL-D-MALIMIDE;(R)-1-Benzyl-3-hydroxypyrrolidine-2,5-dione
• CAS NO: 165657-63-6
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 165657-63-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-N-BENZYL-D-MALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-N-BENZYL-D-MALIMIDE(165657-63-6)
• EPA Substance Registry System: (+)-N-BENZYL-D-MALIMIDE(165657-63-6)

Safety Data

• Hazardous Substances Data: 165657-63-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(+)-N-BENZYL-D-MALIMIDE is used as an intermediate in the synthesis of Monocrotaline-d4 (M526002), a labelled version of the toxic pyrrolizidine alkaloid Monocrotaline (M526000). This alkaloid is isolated from Crotalaria spp. and is utilized for inducing pulmonary diseases in rats, contributing to the study and understanding of such conditions.
Used in Chemical Research:
As a chemical intermediate, (+)-N-BENZYL-D-MALIMIDE plays a crucial role in the development and synthesis of new compounds for various applications. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable tool for researchers in the field of chemistry and related disciplines.

Upstream product

• 173353-28-1 3-benzoyloxy-1-benzyl-2,5-pyrrolidinedione 
• 100-46-9 benzylamine 
• 78027-57-3 (RS)-N-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 165388-00-1 methyl (2R,3R)-4-(N-benzylcarbamoyl)-2,3-dihydroxybutyrate 
• 636-61-3 D-Malic acid 
• 156150-59-3 (R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione 
• 115061-63-7 (2R,3R)-2,3-diacetoxy-4-(benzylamino)-4-oxobutanoic acid 
• 173353-27-0 1-benzyl-3-dodecanoyloxy-2,5-pyrrolidinedione 
• 173353-25-8 1-benzyl-3-isobutyryloxy-2,5-pyrrolidinedione 
• 173353-24-7 1-benzyl-3-propionyloxy-2,5-pyrrolidinedione 
• 129823-21-8 3-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 173353-26-9 1-benzyl-3-hexanoyloxy-2,5-pyrrolidinedione 

Downstream Products

• 202743-03-1 (3R)-1-benzyl-3-benzyloxy pyrrolidine-2,5-dione 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 116143-02-3 (3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate 
• 156150-59-3 (R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione 

Relevant articles and documents

Substitutive nicotinamide compound, medicine composition and application of composition

The invention provides a substitutive nicotinamide compound, a composition containing the compound and application of the composition. The substitutive nicotinamide compound is shown in the formula (I) or pharmaceutically acceptable salt, prodrug, hydrate

3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: Inhibition of rat intestinal α-glucosidase

Thirteen pyrrolidine-based iminosugar derivatives have been synthesized and evaluated for inhibition of α-glucosidase from rat intestine. The compounds studied were the non-hydroxy, mono-hydroxy and dihydroxypyrrolidines. All the compounds were N-benzylated apart from one. Four of the compounds had a carbonyl group in the 2,5-position of the pyrrolidine ring. The most promising iminosugar was the trans-3,4-dihydroxypyrrolidine 5 giving an IC50 of 2.97 ± 0.046 and a KI of 1.18 mM. Kinetic studies showed that the inhibition was of the mixed type, but predominantly competitive for all the compounds tested. Toxicological assay results showed that the compounds have low toxicity. Docking studies showed that all the compounds occupy the same region as the DNJ inhibitor on the enzyme binding site with the most active compounds establishing similar interactions with key residues. Our studies suggest that a rotation of ～90° of some compounds inside the binding pocket is responsible for the complete loss of inhibitory activity. Despite the fact that activity was found only in the mM range, these compounds have served as simple molecular tools for probing the structural features of the enzyme, so that inhibition can be improved in further studies.

FUSED BENZENE DERIVATIVE AND USE

The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X1 represents carbon atom, X2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y11 represents a group represented by the formula CR2R3' (wherein R2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R3' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y21 represents a group represented by the formula CR4R5' (wherein R4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R5' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.

Practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate from L-tartaric acid

An efficient method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate is described starting from L-tartaric acid, which affords the desired compounds with 99% ee in good overall yields (63-74%).

Lipase-catalyzed practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its related compounds

A practical method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione (1) was investigated by the use of the enzymatic hydrolysis of its acetate (2a). Among several hydrolases examined here, lipase PS from Pseudomonas cepacia gave the best result: In a mixed solvent (1:1 v/v) of dioxane and a phosphate buffer (pH 7), the hydrolysis took place smoothly with a high enantioselectivity (E > 3000). Several 3-alkanoyl derivatives of 1 were subjected to the lipase PS-catalyzed hydrolysis. The chain length of the alkanoyl does not noticeably influence the reaction rate or the enantioselectivity. In contrast, the hydrolysis of the 1-benzoyl derivative proceeded slowly with a low enantioselectivity (E = 19). The syntheses of optically active 3-hydroxypyrrolidines and 3-hydroxypiperidines were also achieved under the reaction conditions similar to the lipase PS-catalyzed hydrolysis of 2a.