4707-56-6Relevant academic research and scientific papers
Radical Carbonylation under Low CO Pressure: Synthesis of Esters from Activated Alkylamines at Transition Metal-Free Conditions
Zhao, Fengqian,Ai, Han-Jun,Wu, Xiao-Feng
supporting information, p. 927 - 932 (2021/03/03)
High CO pressure (> 40 bar) is usually needed in radical carbonylation reactions in the absence of metal catalyst. In this communication, we developed a transition-metal-free radical carbonylation of activated alkylamines with phenols and alcohols under low CO pressure (1—6 bar). Various esters were obtained in moderate to excellent yields under simple reaction conditions with good functional group compatibility.
Photoswitching the Efficacy of a Small-Molecule Ligand for a Peptidergic GPCR: from Antagonism to Agonism
Gómez-Santacana, Xavier,de Munnik, Sabrina M.,Vijayachandran, Prashanna,Da Costa Pereira, Daniel,Bebelman, Jan Paul M.,de Esch, Iwan J. P.,Vischer, Henry F.,Wijtmans, Maikel,Leurs, Rob
, p. 11608 - 11612 (2018/09/10)
For optical control of GPCR function, we set out to develop small-molecule ligands with photoswitchable efficacy in which both configurations bind the target protein but exert distinct pharmacological effects, that is, stimulate or antagonize GPCR activation. Our design was based on a previously identified efficacy hotspot for the peptidergic chemokine receptor CXCR3 and resulted in the synthesis and characterization of five new azobenzene-containing CXCR3 ligands. G protein activation assays and real-time electrophysiology experiments demonstrated photoswitching from antagonism to partial agonism and even to full agonism (compound VUF16216). SAR evaluation suggests that the size and electron-donating properties of the substituents on the inner aromatic ring are important for the efficacy photoswitching. These compounds are the first GPCR azo ligands with a nearly full efficacy photoswitch and may become valuable pharmacological tools for the optical control of peptidergic GPCR signaling.
Electrophilicity and nucleophilicity of commonly used aldehydes
Pratihar, Sanjay
, p. 5781 - 5788 (2014/07/22)
The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.
APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
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Paragraph 1483-1484, (2013/04/24)
Disclosed are compounds which inhibit the activity of anti-apoptotic Bc1-xL proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bc1-xL protein.
Study on the scope of tert-amino effect: New extensions of type 2 reactions to bridged biaryls
Bottino, Paola,Dunkel, Petra,Schlich, Michele,Galavotti, Lorenzo,Deme, Ruth,Regdon Jr., Geza,Benyei, Attila,Pintye-Hodi, Klara,Ronsisvalle, Giuseppe,Matyus, Peter
, p. 1033 - 1041 (2014/01/06)
Thermal isomerization of aminomethyl- or oxygen-bridged biphenyl systems possessing dicyanovinyl and sec-amino groups in ortho- and ortho0-positions was investigated. Both systems underwent cyclization via tert-amino effect. Thus, 2-(2-{[2-(sec-amino)benz
Mono-N-methylation of functionalized anilines with alkyl methyl carbonates over NaY faujasites. 4. Kinetics and selectivity
Selva, Maurizio,Tundo, Pietro,Foccardi, Tommaso
, p. 2476 - 2485 (2007/10/03)
(Chemical Equation Presented) In the presence of NaY faujasite as the catalyst, the reaction of bifunctional anilines (1-4: XC6H 4-NH2; X = OH, CO2H, CH2OH, and CONH2) with methyl alkyl carbonates [MeOCO2R′: R′ = Me or MeO(CH2)2O(CH2)2] proceeds with a very high mono-N-methyl selectivity (XC6H 4NHMe up to 99%), and chemoselectivity as well, with other nucleophilic functions (OH, CO2H, CH2OH, CONH2) fully preserved from alkylation and/or transesterification reactions. Aromatic substituents, however, modify the relative reactivity of amines 1-4: good evidence suggests that, not only steric and electronic effects, but, importantly, direct acid-base interactions between substituents and the catalyst are involved. Weakly acidic groups (OH, CH2OH, CONH2, pKa ≥ 10) may help the reaction, while aminobenzoic acids (pK a of 4-5) are the least reactive substrates. The solvent polarity also affects the reaction, which is faster in xylene than in the more polar diglyme. The mono-N-methyl selectivity is explained by the adsorption pattern of reagents within the zeolite pores: a BAl2 displacement of the amine on methyl alkyl carbonate should occur aided by the geometric features of the NaY supercavities. Different factors account for the reaction chemoselectivity. Evidence proves that the polarizability of the two nucleophilic terms (NH 2 and X groups) of anilines is relevant, although adsorption and confinement phenomena of reagents promoted by the zeolite should also be considered.
2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6- tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors
Yamada,Yura,Morimoto,Harada,Yamada,Honma,Kinoshita,Sugiura
, p. 596 - 604 (2007/10/03)
Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K+- ATPase. Structure-activity relationships indicate that the substitution of 2- pyridyl groups at the 1-position of the imidazole moiety combined with (2- aminobenzyl)sulfinyl groups at the 2-position leads to highly active compounds with a favorable chemical stability. Other substitution patterns in the imidazole moiety result in reducing biological activities. 2-[(2- Aminobenzyl)sulfinyl]-1-[2-(3-methylpyridyl)]-1,4,5,6- tetrahydrocyclopent[d]imidazole (12h, T-776) was selected for further development as a potential clinical candidate. Extensive study on the acid degradation of 12h indicates a mechanism of action different from that of omeprazole, the first H+/K+-ATPase inhibitor introduced to the market.
Synthesis and structure-activity relationships of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines as a new class of gastric H+/K+-ATPase inhibitors
Yamakawa,Matsukura,Nomura,Yoshioka,Masaki,Igata,Okabe
, p. 1746 - 1752 (2007/10/02)
A series of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines was synthesized and evaluated for its biological activity against H+/K+-ATPase prepared from rabbit stomach and gastric acid secretions in Heidenhain pouch dogs. Monoalkyl substituents on the nitrogen atom of the aniline moiety markedly inhibited the enzyme activity to the same degree as omeprazole, a representative H+/K+-ATPase inhibitor. Most of these compounds, administered at 3 mg/kg i.v. inhibited histamine-stimulated gastric acid secretion. The inhibitory activity of these derivatives on the enzymes at pH 6.0 was more potent than that at pH 7.4, and was distinctly correlated to stability in aqueous solution at pH 5.0.
A New Reduction of Some Carboxylic Esters with Sodium Borohydride and Zinc Chloride in the Presence of a Tertiary Amine
Yamakawa, Tomio,Masaki, Mitsuo,Nohira, Hiroyuki
, p. 2730 - 2734 (2007/10/02)
In the presence of a tertiary amine, sodium borohydride (NaBH4) combined with zinc chloride (ZnCl2) showed powerful reducing properties and carboxylic esters were smoothly reduced to their corresponding alcohols which were not obtained by reduction with NaBH4 and ZnCl2 alone.Tetrahydrofuran (THF) was an efficient solvent, and the effective molar ratio of the reducing agents, NaBH4:ZnCl2:tertiary amine, was 2:1:1.In particular, aminobenzoates such as anthranilic esters, were reduced to aminobenzyl alcohols with high yields without the addition of a tertiary amine.Further, it was also found that this combination reduced nitro, cyano, and amido groups to their corresponding amino groups.
