56327-24-3Relevant academic research and scientific papers
Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride
Chiba, Shunsuke,Ong, Derek Yiren
, p. 1369 - 1378 (2020/04/27)
A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.
Discovery of disubstituted piperidines and homopiperidines as potent dual NK1 receptor antagonists-serotonin reuptake transporter inhibitors for the treatment of depression
Wu, Yong-Jin,He, Huan,Bertekap, Robert,Westphal, Ryan,Lelas, Snjezana,Newton, Amy,Wallace, Tanya,Taber, Matthew,Davis, Carl,MacOr, John E.,Bronson, Joanne
, p. 2217 - 2228 (2013/05/08)
This report describes the synthesis, structure-activity relationships and activity of piperidine, homopiperidine, and azocane derivatives combining NK1 receptor (NK1R) antagonism and serotonin reuptake transporter (SERT) inhibition. Our studies culminated in the discovery of piperidine 2 and homopiperidine 8 as potent dual NK1R antagonists-SERT inhibitors. Compound 2 demonstrated significant activity in the gerbil forced swimming test, suggesting that dual NK1R antagonists-SERT inhibitors may be useful in treating depression disorders.
Application of flow chemistry to the reduction of nitriles to aldehydes
Mu?oz, Juan De M.,Alcázar, Jesús,De La Antonio, Hoz,Díaz-Ortiz, Angel
experimental part, p. 6058 - 6060 (2011/11/29)
Reduction of nitriles to aldehydes with diisobutylaluminium hydride (DIBAL-H) is an important transformation in organic chemistry. But the use of this reaction is limited for the lack of reproducibility due to the instability of the intermediates formed. In the current article we disclose the improvement of the reaction applying continuous flow technology.
Synthesis and optimization of novel 4,4-disubstituted cyclohexylbenzamide derivatives as potent 11β-HSD1 inhibitors
Sun, Daqing,Wang, Zhulun,Caille, Seb,Degraffenreid, Michael,Gonzalez-Lopez De Turiso, Felix,Hungate, Randall,Jaen, Juan C.,Jiang, Ben,Julian, Lisa D.,Kelly, Ron,McMinn, Dustin L.,Kaizerman, Jacob,Rew, Yosup,Sudom, Athena,Tu, Hua,Ursu, Stefania,Walker, Nigel,Willcockson, Maren,Yan, Xuelei,Ye, Qiuping,Powers, Jay P.
scheme or table, p. 405 - 410 (2011/02/27)
The synthesis and SAR of a series of 4,4-disubstituted cyclohexylbenzamide inhibitors of 11β-HSD1 are described. Optimization rapidly led to potent, highly selective, and orally bioavailable inhibitors demonstrating efficacy in both rat and non-human primate ex vivo pharmacodynamic models.
Benzamide derivatives and uses related thereto
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Page/Page column 44-45, (2008/06/13)
Benzamide derivatives of formula I are described and have therapeutic utility, particularly in the treatment of diabetes, obesity and related conditions and disorders: wherein R1, R2, R3, R4, R5, R6, R7, R8, and n are as defined herein.
4-Arylcyclohexylamines
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, (2008/06/13)
The invention relates to novel 4-hydroxymethyl(acyloxymethyl and methyl)-4-arylcyclohexylamines embraced by the formula SPC1 Wherein Ar is an aromatic ring selected from the group consisting of phenyl and naphthyl, each of which has from zero through three substituents independently selected from the group consisting of fluorine, chlorine, bromine, lower alkyl of one through three carbon atoms, lower alkoxy of one through three carbon atoms, and lower alkylthio of one through three carbon atoms; Z is selected from the group consisting of hydrogen, hydroxy and lower acyloxy of one through four carbon atoms; ? is a generic expression denoting cis and trans stereoconfiguration and mixtures thereof, with the proviso that when the stereoconfiguration of the linkage connecting the cyclohexane ring and CH2 Z is cis to the amino group, the linkage connecting the cyclohexane and Ar rings is trans, and vice versa; R1 is selected from the group consisting of hydrogen and lower alkyl of one through three carbon atoms; R2 is selected from the group consisting of hydrogen, lower alkyl of one through three carbon atoms, EQU1 WHEREIN N IS 2 THROUGH 5 AND Ar has the same meaning as above; R1 and R2 taken together with --N is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and substituted pyrrolidino, piperidino, hexamethylenimino, morpholino and piperazino; and pharmacologically acceptable acid addition salts thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (I) and novel derivatives thereof. The administration to humans and animals of the novel compounds (I) depresses their central nervous systems and lowers their blood pressures.
Benzospiran derivatives
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, (2016/03/09)
This invention relates to novel benzospiran derivatives embraced by the formula SPC1 Wherein the sum of A and B is at least the integer 2; A is selected from the group consisting of --(CH2)n -- wherein n is 1 through 5 and --(Cn H2n --2 XY)-- wherein X is selected from the group consisting of hydroxy, acetoxy, amino and acetamido and Y is hydrogen, and X when taken together with Y is selected from the group consisting of =O and =CR3 R4 wherein R3 and R4 are selected from the group consisting of hydrogen and lower alkyl of 1 through 3 carbon atoms; B is absent or --(CH2)n -- wherein n is 1 through 3; R1 is selected from the group consisting of hydrogen and lower alkyl of 1 through 3 carbon atoms; R2 is selected from the group consisting of hydrogen, lower alkyl of 1 through 3 carbon atoms, EQU1 WHEREIN N IS 2 THROUGH 5 AND Ar is phenyl having zero through three substituents selected from the group consisting of lower alkyl of 1 through 3 carbon atoms, lower alkoxy of 1 through 3 carbon atoms, bromine, chlorine and fluorine; R1 and R2 taken together with --N is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and substituted pyrrolidino, piperidino, and hexamethylenimino; Z is selected from the group consisting of hydrogen, lower alkyl of 1 through 3 carbon atoms, lower alkoxy of 1 through 3 carbon atoms, nitro, amino, monoalkylamino of 1 through 3 carbon atoms, acylamido of 1 through 4 carbon atoms, bromine, chlorine and fluorine; and a pharmacologically acceptable acid addition salt thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (1) and novel derivatives thereof. The administration to humans and animals of the novel compounds (1) depresses their central nervous systems and lowers their blood pressures.
