101469-91-4

Basic information

• Product Name: N-Benzyl-(3S)-hydroxysuccinimide
• Synonyms: (3S)-N-Benzyl-3-hydroxypyrrolidine-2,5-dione;N-Benzyl-(3S)-hydroxysuccinimide;N-Benzyl-(S)-malimide;(S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione;(S)-1-benzyl-3-hydro×ypyrrolidine-2,5-dione;(R)-benzyl 3-fluoropyrrolidine-1-carboxylate
• CAS NO: 101469-91-4
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.20994
• EINECS: -0
• Mol File: 101469-91-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 110-111℃
• Appearance: /
• Density: 1.385
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-Benzyl-(3S)-hydroxysuccinimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-(3S)-hydroxysuccinimide(101469-91-4)
• EPA Substance Registry System: N-Benzyl-(3S)-hydroxysuccinimide(101469-91-4)

Safety Data

• Hazardous Substances Data: 101469-91-4(Hazardous Substances Data)

Usage

General Description

N-Benzyl-(3S)-hydroxysuccinimide, also known as NBS, is a well-known amine-reactive chemical frequently utilized in organic synthesis and bioconjugation reactions. N-Benzyl-(3S)-hydroxysuccinimide is derived from succinimide and is functionalized with a benzyl group and a hydroxyl group at the 3S position. NBS is commonly used as a mild and selective reagent for the bromination of alcohols and amines, as well as for the introduction of the succinimido group onto amines during peptide synthesis. Its reactivity with amines and its mild reaction conditions have made NBS a versatile tool in the fields of organic chemistry and bioconjugation.

Upstream product

• 97-67-6 (S)-Malic acid 
• 100-46-9 benzylamine 
• 78027-57-3 (RS)-N-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 173353-28-1 3-benzoyloxy-1-benzyl-2,5-pyrrolidinedione 
• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 

Downstream Products

• 101408-94-0 3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 101385-91-5 (S)-tert-butyl 3-acetoxypyrrolidine-1-carboxylate 
• 935550-24-6 C₂₃H₂₉NO₄ 
• 935550-28-0 C₂₃H₂₉NO₄ 
• 935550-23-5 C₁₇H₂₁NO₄ 
• 935550-19-9 C₁₈H₂₃NO₄ 
• 192987-90-9 (4S)-1-benzyl-4,5-dihydroxypyrrolidin-2-one 
• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 122536-94-1 (S)-3-hydroxypyrrolidine hydrochloride 
• 74880-19-6 C₁₂H₁₈N₂ 
• 74880-19-6 methyl-(2S,4R)-4-amino-1-benzylpyrrolidine 

Relevant articles and documents

Synthesis method of (S)-3-pyrrolidinol hydrochloride

The invention discloses a synthesis method of (S)-3-pyrrolidinol hydrochloride, which belongs to the field of drug synthesis, and comprises the following steps: dehydrating and amidating L-malic acidand benzylamine as raw materials to obtain (3S)-N-benzyl-3-hydroxypyrrolidine-2,5-diketone, and carrying out one-pot reduction, debenzylation and salification to synthesize (S)-3-pyrrolidinol hydrochloride. The method is short in synthetic route, simple to operate, high in yield, good in product purity and beneficial to industrial production.

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.

COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY

The present invention is directed to indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which the LRRK2 kinase is involved, such as Parkinson's Disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which LRRK-2 kinase is involved.