32754-99-7Relevant articles and documents
An improved synthesis of 4-aminobutanenitrile from 4-azidobutanenitrile and comments on room temperature stability
Capon, Patrick K.,Avery, Thomas D.,Purdey, Malcolm S.,Abell, Andrew D.
, p. 428 - 436 (2020/12/25)
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.
Preparation method N-substituted piperidine -3- ketone (by machine translation)
-
Paragraph 0077-0080, (2020/03/25)
The invention provides N -substituted piperi- 3 3-ketone preparation method, which uses acrylonitrile (II) and nitromethane as raw materials to obtain 4 -substituted-N-alkoxycarbonylmethyl- 4 4-aminobutyronitrile (III), to obtain 4 - substituent - N N-alkoxycarbonylmethyl( (IV),substituted-piperi- 3 3-one N - by addition reaction and decarboxylation to yield (V),substituted-piperidin-3-one according. to the present invention by two-time substituent reaction, reaction, and decarboxylation to obtain, a compound obtained from, N -substituted-piperidin-3-one of, the invention. (I). The method is simple, process and, times of reaction and decarboxylation. (by machine translation)
PYRIMIDINE COMPOUNDS CONTAINING ACIDIC GROUPS
-
Paragraph 1178; 1180, (2018/06/15)
The present disclosure relates to a class of pyrimidine derivatives having immunomodulating properties that act via TLR7 which are useful in the treatment of viral infections and cancers.
Photostimulated reduction of nitriles by SmI2
Rao, Chintada Nageswara,Hoz, Shmaryahu
experimental part, p. 4029 - 4034 (2012/06/29)
Despite their high electron-withdrawing strength, nitriles are not good electron acceptors and therefore are hard to reduce. In this work, using photostimulation in the visible region, we examined the reactivity of aliphatic and aromatic, mono- and dicyano compounds in reaction with SmI2. A proton donor that complexes efficiently with SmI2 must be used. Maximum yield was obtained at ca.0.2 M MeOH. Aromatic nitriles were more reactive than aliphatic nitriles, which exhibited negligible yields. Phenylacetonitrile presents an intermediate reactivity. The mechanism of the reaction involves coordination of the SmI2 to the lone pair of the nitrile nitrogen followed by an inner sphere electron transfer. Surprisingly, m-dicyanobenzene was less reactive than the monocyano derivative benzonitrile. This was traced to the lower ability of the dicyano compound to coordinate to the SmI2 due to, as was shown by quantum mechanical calculations, its lone pair having an energy significantly lower than that of benzonitrile. It is noteworthy that at the SmI2 initial concentration used (0.04M), light penetrates only the 0.4 mm outer layer of the reaction mixture. Therefore the photostimulation effect observed was due to irradiation of only 4% of the total reaction volume, implying that under optimal conditions the effect should be 25 times larger.
Direct stereospecific amination of alkyl and aryl pinacol boronates
Mlynarski, Scott N.,Karns, Alexander S.,Morken, James P.
supporting information, p. 16449 - 16451,3 (2020/09/15)
The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.
ANTIFUNGAL AGENTS
-
Page/Page column 30, (2012/04/23)
Compounds and compositions useful as antifungals are provided, as are methods of use and preparation of such compounds and compositions containing such compounds. In some embodiments, the compounds are bifunctional, comprising two active moieties connected by a linking moiety. The compounds of the invention are useful for treating infections by microorganisms.
Rigidified Compounds for Modulating Heparanase Activity
-
Page/Page column 55-56, (2010/11/30)
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
-
Page/Page column 8; 15, (2010/11/26)
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
Yuan, Hai,Silverman, Richard B.
, p. 1331 - 1338 (2007/10/03)
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.
One-pot sequence for the decarboxylation of α-amino acids
Laval, Gilles,Golding, Bernard T.
, p. 542 - 546 (2007/10/03)
Treatment of an α-amino acid with N-bromosuccinimide in water at pH 5 or in an alcoholic-aqueous ammonium chloride mixture, followed by addition of nickel(II) chloride and sodium borohydride, effected an overall decarboxylation via an intermediate nitrile to afford the corresponding amine in good yield.
