21994-40-1

Usage

Structure

Consists of a triaza-1,2-dien-2-ium core with a 3-cyanopropyl substituent

Application

Commonly used in organic synthesis and as a building block for the preparation of various organic compounds

Reactivity

Exhibits unique reactivity

Usage

Often employed in the synthesis of complex molecules and pharmaceutical intermediates

Research interest

Investigated for its potential biological and pharmacological properties

Field of study

Subject of interest in medicinal chemistry research

Upstream product

• 628-20-6 4-Chlorobutyronitrile 
• 5332-06-9 4-bromobutanenitrile 

Downstream Products

• 5817-87-8 Trimethylenetetrazole 
• 407-83-0 4-fluorobutanenitrile 
• 58793-93-4 3-Fluorbutannitril 
• 32754-99-7 4-aminobutyronitrile 
• 616-45-5 2-pyrrolidinon 
• 56-12-2 4-amino-n-butyric acid 
• 1571095-62-9 4-(4-benzoyl-1H-1,2,3-triazol-1-yl)butanenitrile 

Relevant academic research and scientific papers

An improved synthesis of 4-aminobutanenitrile from 4-azidobutanenitrile and comments on room temperature stability

4-Aminobutanenitrile (1) is an important synthetic intermediate for neurological disorder therapeutics including Parkinson’s and Alzheimer’s diseases, and is an industrial precursor to pyrroline and pyrrolidine. Synthesis of 1 by Co(II) catalyzed reduction of 4-azidobutanenitrile (2) with NaBH4, or by a one-pot Staudinger reduction of 2 in THF, was low yielding. 1H-NMR analysis of the Staudinger reduction revealed the formation of iminophosphorane intermediate (3) after 22 h at rt, and that increasing the reaction temperature from rt to 40 °C promoted hydrolysis of 3 to 1. A modified Staudinger reduction of 2 involving pyridine as solvent, addition of water 3 h after triphenylphosphine, and a temperature increase to 40 °C, gave rise to 1 in 69% yield. 1 is unstable at rt, thus the hydrochloride salt of 1 (1?HCl) was prepared by bubbling HCl(g) through a solution of 1 in chloroform. 1?HCl is stable at rt and is hence the preferred form for storage.

Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles

The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)3 and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.

Identification of Phenylphthalazinones as a New Class of Leishmania infantum Inhibitors

Leishmaniasis is a neglected parasitic disease caused by over 20 different Leishmania species. Current treatments often rely on harsh regimes of pentavalent antimonials such as sodium stibogluconate, while more recent drugs suffer other shortcomings such

Copper complexes bearing an NHC-calixarene unit: Synthesis and application in click chemistry

The synthesis of N-heterocyclic carbene (NHC) copper complexes supported by calix[4]arene is reported. Mono-substituted calix[4]arene was prepared through conventional procedures, followed by the attachment of an imidazolyl group to create the precursor o

SPIROHYDANTOIN COMPOUNDS AND THEIR USE AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

The present invention relates to a compound of formula (1-1 ) in free form or in pharmaceutically acceptable salt form in which the substituents are as defined in the specification; to its preparation, to its use as a medicament and to medicaments comprising it. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

A novel potent nicotinamide phosphoribosyltransferase inhibitor synthesized via click chemistry

The inhibition of NAD synthesis or salvage pathways has been proposed as a novel target for antitumoral drugs. Two molecules with this mechanism of action are at present undergoing clinical trials. In searching for similar novel molecules, we exploited co

[(NHC)2Cu]X complexes as efficient catalysts for azide-alkyne click chemistry at low catalyst loadings

(Chemical Equation Presented) La click, c'est chic! A catalytic system based on an [(NHC)2Cu]X complex (NHC=N-heterocyclic carbene) was developed for the [3+2] cycloaddition of azides with alkynes under click conditions (see scheme). This syste

Rigidified Compounds for Modulating Heparanase Activity

Disclosed are novel rigidified compounds having a rhodanine-like residue and at least one aryl or heteroaryl residue linked to the rhodanine-like residue, whereby a core structure of these compounds, as defined in the specification, is characterized as having one or zero free-to-rotate bonds. Also disclosed are pharmaceutical compositions containing these rigidified compounds and uses thereof for modulating the activity of heparanase and hence in the treatment of heparanase-associated diseases and disorders, and uses thereof for modulating the activity of heparin-binding proteins and hence in the treatment of heparin-binding proteins-associated diseases and disorders as well as in the treatment of medical conditions that are at least partially treatable by rhodanine or a rhodanine analog.

VIGABATRIN BIOISOTERES AND RELATED METHODS OF USE

Compounds bioisoteric to vigabatrin and related methods of use.

New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity

A series of potential substrates of γ-aminobutyric acid aminotransferase (GABA-AT) with lipophilic bioisosteres of the carboxylic acid group (2-7) were synthesized and tested. Most of the synthesized compounds showed substrate activities with GABA-AT; 1H-tetrazole-5-propanamine (6) was the best of those tested. The potential time-dependent inhibitor of GABA-AT, 1H-tetrazole-5-(α-vinyl-propanamine) (8), was designed based on the structures of 6 and the antiepilepsy drug vigabatrin (4-aminohex-5-enoic acid, 1). The synthesized compound 8 showed time-dependent inhibition of GABA-AT, but its potency is lower than that of vigabatrin. Methylation of the tetrazole group in 8 resulted in loss of time-dependent activity, suggesting that the tetrazole ring, the carboxylate bioisostere, exists in its deprotonated form in the enzyme active site.