24431-17-2Relevant academic research and scientific papers
Compound, preparation method thereof and application of compound as fluorescent probe
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Paragraph 0131-0132; 0137, (2021/11/10)
The invention discloses a compound, a preparation method thereof and application of the compound as a fluorescent probe, wherein the compound I is selected from at least one compound of the chemical formula shown I. I In formula R1 . R2 Independently selected C1 - C5 Alkyl, C1 - C5 Alkoxy and substituted C1 - C5 At least one of the alkyl I of the alkyl group. R3 Be selected from C1 - C5 Alkyl groups. Substituted C1 - C5 At least one of the alkyl II groups of the alkyl group. The fluorescence probe provided by the invention can detect the morphology and the position of protein aggregation states through fluorescent imaging in living cells.
Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines
Gudun, Kristina A.,Slamova, Ainur,Hayrapetyan, Davit,Khalimon, Andrey Y.
, p. 4963 - 4968 (2020/04/17)
The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.
Preparation of homoallylic amines via a three-component coupling process
Battilocchio, Claudio,Labes, Ricardo,Ley, Steven V.,Ou, Xiaoxu
supporting information, p. 6652 - 6654 (2018/09/29)
A three-component synthesis of homoallylic amines is described. The allylboronic species were generated in situ by homologation of vinyl boroxines with trimethylsilyldiazomethane, then followed by trapping of the allylboron intermediate with imines. Twenty-seven compounds were successfully prepared in moderate to high yields. Imines bearing various functional groups were tolerated, including aliphatic, aromatic and heteroaromatic substituents. Further elaboration of some of the homoallylic amines to form azeditines is also reported.
Dynamic Covalent Metathesis in the C=C/C=N Exchange between Knoevenagel Compounds and Imines
Gu, Ruirui,Flidrova, Karolina,Lehn, Jean-Marie
supporting information, p. 5560 - 5568 (2018/05/01)
Fast and reversible dynamic covalent C=C/C=N exchange takes place without catalyst in nonpolar solvents between barbiturate-derived Knoevenagel (Kn) compounds and imines. A detailed study of the reaction indicates that it proceeds by an associative organo-metathesis mechanism involving the formation of a four-membered ring azetidine intermediate by addition of the imine C=N group to the C=C bond of the Kn compound. This intermediate could be generated cleanly and stabilized at low temperature by condensation of the o,p-dinitrophenyl Kn derivative with the cyclic imine 1-azacyclohexene. It was characterized by extensive NMR and mass spectrometric studies. The process described represents a genuine dynamic covalent organo-metathesis through a four-membered ring adduct as intermediate. It paves the way for the exploration of a wide set of dynamic systems involving (strongly) polarized C=C bonds and various imines, extending also into covalent dynamic polymers and polymolecular assemblies.
Organocatalyzed and uncatalyzed C=C/C=C and C=C/C=N exchange processes between knoevenagel and imine compounds in dynamic covalent chemistry
Kulchat, Sirinan,Meguellati, Kamel,Lehn, Jean-Marie
, p. 1219 - 1236 (2015/04/14)
Molecular diversity generation through reversible component exchange has acquired great importance in the last decade with the development of dynamic covalent chemistry. We explore here the recombination of components linked by C=C and C=N bonds through reversible double-bond formation, and cleavage in C=C/C=C and C=C/C=N exchange processes. The reversibility of the Knoevenagel reaction has been explored, and C=C/C=C C/C exchanges have been achieved among different benzylidenes, under organocatalysis by secondary amines such as L-proline. The substituents of these benzylidenes were shown to play a very important role in the kinetics of the exchange reactions. L-Proline is also used to catalyze the reversible C=C/C=C exchange between Knoevenagel derivatives of barbituric acid and malononitrile. Finally, the interconversion between Knoevenagel derivatives of dimethylbarbituric acid and imines (C=C/C=N exchange) has been studied and was found to occur rapidly in the absence of catalyst. The results of this study pave the way for the extension of dynamic combinatorial chemistry based on C=C/C=C and C=C/C=N exchange systems.
Trisubstituted sulfonamides: A new chemotype for development of potent and selective CB2 receptor inverse agonists
Ouyang, Qin,Tong, Qin,Feng, Rentian,Myint, Kyaw-Zeyar,Yang, Peng,Xie, Xiang-Qun
supporting information, p. 387 - 392 (2013/06/26)
An extensive exploration of the structure-activity relationship of a trisubstituted sulfonamide series led to the identification of 39, which is a potent and selective CB2 receptor inverse agonist [K i(CB2) = 5.4 nM, and Ki(CB1) = 500 nM]. The functional properties measured by cAMP assays indicated that the selected compounds were CB2 inverse agonists with high potency values (for 34, EC50 = 8.2 nM, and for 39, EC50 = 2.5 nM). Furthermore, an osteoclastogenesis bioassay indicated that trisubstituted sulfonamide compounds showed great inhibition of osteoclast formation.
Organocatalysis of c?￡/c?￡N and C?￡C/ C?￡N exchange in dynamic covalent chemistry
Wilhelms, Nadine,Kulchat, Sirinan,Lehn, Jean-Marie
, p. 2635 - 2651 (2013/03/13)
The reversibly formed C?￡N bond plays a very important role in dynamic covalent chemistry and the C?￡N/C?￡N exchange of components between different imine constituents to create dynamic covalent libraries has been extensively used. To facilitate diversity generation, we have investigated an organocatalyzed approach, using L-proline as catalyst, to accelerate the formation of dynamic libraries of [n×n] imine components. The organocatalysis methodology has also been extended, under somewhat modified conditions, to reversible C?￡C/C?￡N exchange processes between Knoevenagel derivatives of barbituric acid and imines, allowing for the generation of increased diversity. Copyright
1D and 2D Nuclear magnetic resonance of new silver(I) complexes with achiral and chiral bases as ligands: Crystal structure of [Ag{(S)-(6-CH3)C5H3N-CHN-CH(α-CH 3)C6H5}(PPh3)2](O 3SCF3)
Cifuentes, Olga,Contreras, Raul,Laguna, Antonio,Crespo, Olga
experimental part, p. 81 - 89 (2012/02/02)
Treatment of equimolar amounts of substituted aniline or amine with substituted benzaldehyde leads to the corresponding achiral or chiral Schiff bases (L). The reaction of the bases with [Ag(O3SCF 3)(PPh3)] leads to the preparation of three or four coordinated cationic complexes, [Ag(k1-L)(PPh3) n]+ (n = 1 or 2) which have been characterized by IR, 1D and 2D NMR spectroscopy. The crystal structure of [Ag{(S)-(6-CH3)C5H3N-CHN-CH(α-CH 3)C6H5}(PPh3)2](O 3SCF3) is reported.
Application of sequential Cu(I)/Pd(0)-catalysis to solution-phase parallel synthesis of combinatorial libraries of dihydroindeno[1,2-c]isoquinolines
Kumar, Sarvesh,Painter, Thomas O.,Pal, Benoy K.,Neuenswander, Benjamin,Malinakova, Helena C.
scheme or table, p. 466 - 477 (2011/11/06)
Parallel solution-phase synthesis of combinatorial libraries of dihydroindenoisoquinolines employing a sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol was realized. The scope and limitations of the protocol with respect to the substitution pattern in the aryl ring of the indene core, as well as the N-substituent have been defined, revealing that the methodology is compatible with a wide-range of aliphatic linear, branched, and ester functionalized N-substituents. Unexpectedly, the formation of regioisomers featuring a 1,2,3-contiguous substitution pattern in the aromatic ring of the indene core was observed. Three distinct combinatorial libraries with a total of 111 of members were synthesized, and 80 highly substituted dihydroindenoisoquinolines structurally related to known medicinal agents including some consisting of mixtures of two regioisomers were made available for biological activity testing.
Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation Protocol for the synthesis of indenoisoquinolines
Jayanth, Thiruvellore Thatai,Zhang, Lei,Johnson, Thomas S.,Malinakova, Helena C.
supporting information; experimental part, p. 815 - 818 (2009/07/18)
Copper-catalyzed coupling of imines, vinylstannanes, or alkynes and o-bromoaroyl chlorides followed by Pd(0)-catalyzed annulations afforded indenoisoquinolines. Protocols requiring minimal purifications were developed, providing new methods for the construction of combinatorial libraries.
