88939-75-7Relevant articles and documents
Synthesis and biological evaluation of fluoro-substituted 3,4-dihydroquinazoline derivatives for cytotoxic and analgesic effects
Kim, Jin Han,Jeong, Hui Rak,Jung, Da Woon,Yoon, Hong Bin,Kim, Sun Young,Kim, Hyoung Ja,Lee, Kyung-Tae,Gadotti, Vinicius M.,Huang, Junting,Zhang, Fang-Xiong,Zamponi, Gerald W.,Lee, Jae Yeol
, p. 4656 - 4664 (2017)
As a bioisosteric strategy to overcome the poor metabolic stability of lead compound KYS05090S, a series of new fluoro-substituted 3,4-dihydroquinazoline derivatives was prepared and evaluated for T-type calcium channel (Cav3.2) block, cytotoxi
Preparation method of 3-(2-aminophenyl)-2-acrylate
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Paragraph 0020-0021, (2022/01/12)
The present invention relates to the field of pharmaceutical preparation technology, in particular a 3-(2-aminophenyl)-2-acrylate preparation method, comprising the following steps: 1) under the action of a base, o-nitrobenzaldehyde and malonate derivativ
Synthesis of 2-(N-cyclicamino)quinoline combined with methyl (E)-3-(2/3/4-aminophenyl)acrylates as potential antiparasitic agents
Bokosi, Fostino R. B.,Beteck, Richard M.,Laming, Dustin,Hoppe, Heinrich C.,Tshiwawa, Tendamudzimu,Khanye, Setshaba D.
, (2021/03/16)
A rationally designed series of 2-(N-cyclicamino)quinolines coupled with methyl (E)-3-(2/3/4-aminophenyl)acrylates was synthesized and subjected to in vitro screening bioassays for potential antiplasmodial and antitrypanosomal activities against a chloroquine-sensitive (3D7) strain of Plasmodium falciparum and nagana Trypanosoma brucei brucei 427, respectively. Substituent effects on activity were evaluated; meta-acrylate 24 and the ortho-acrylate 29 exhibited the highest antiplasmodial (IC50 = 1.4 μM) and antitrypanosomal (IC50 = 10.4 μM) activities, respectively. The activity against HeLa cells showed that the synthesized analogs are not cytotoxic at the maximum tested concentration. The ADME (absorption, distribution, metabolism, and excretion) drug-like properties of the synthesized compounds were predicted through the SwissADME software.
Pd salen complex@CPGO as a convenient, effective heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions
Ghabdian, Mahdieh,Nasseri, Mohammad Ali,Allahresani, Ali,Motavallizadehkakhky, Alireza
, p. 1713 - 1728 (2018/05/25)
A Pd(II) Schiff base complex supported on graphene oxide nanosheets (Pd(II) salen@CPGO) has been synthesized and characterized by FT-IR, ICP-AES, XRD, SEM/EDX and TEM. The synthesized nanocatalyst has been found to be an efficient heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki coupling reactions. Pd(II) salen@CPGO could be separated and recovered easily from the reaction mixture and recycled several times without a discernible decrease in its catalytic activity. The construction of a solid sheet-supported Pd catalyst would be expected to be a promising system to perform heterogeneous catalytic reactions.
One-Pot, Three-Step Synthesis of Benzoxazinones via Use of the Bpin Group as a Masked Nucleophile
Larin, Egor M.,Torelli, Alexa,Loup, Joachim,Lautens, Mark
supporting information, p. 2720 - 2725 (2021/04/05)
The utilization of the Bpin group as a pronucleophile to facilitate the assembly of cyclic carbamates has been achieved. This one-pot process involves an initial copper-catalyzed borylation, a subsequent C-B bond oxidation to generate the reactive alcohol
Design and application of intramolecular vinylogous Michael reaction for the construction of 2-alkenyl indoles
Harish, Battu,Yadav, Sanjay,Suresh, Surisetti
supporting information, p. 231 - 234 (2021/01/14)
A base-mediated transformation based on a designed intramolecular vinylogous Michael addition (intra-VMA) is presented to access 3-substituted 2-alkenyl indole derivatives. The reaction represents the first example of the intra-VMA for the construction of
Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.
supporting information, p. 9413 - 9418 (2021/12/09)
β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.
Photoredox Catalysis toward 2-Sulfenylindole Synthesis through a Radical Cascade Process
Betim, Hugo L. I.,Campos Delgado, Jose Antonio,Corrêa, Arlene G.,Kisukuri, Camila M.,Paix?o, Márcio W.,Santos, Marilia S.
supporting information, p. 4266 - 4271 (2020/06/27)
A radical cascade process initiated through visible-light induced thiyl radical coupling with ortho-substituted arylisocianides followed by an intramolecular cyclization and subsequent aromatization to access 2-sulfenylindoles is described. The key thiyl radicals are promptly generated via a hydrogen atom transfer event. The redox-neutral protocol features broad substrate scope, excellent functional group tolerance, and mild reaction conditions. Furthermore, the implementation of a continuous flow variant allows smooth scalability with a short residence time through process intensification.
Divergent Syntheses of Indoles and Quinolines Involving N1-C2-C3 Bond Formation through Two Distinct Pd Catalyses
San Jang, Su,Kim, Young Ho,Youn, So Won
supporting information, p. 9151 - 9157 (2020/11/03)
Pd-catalyzed annulative couplings of 2-alkenylanilines with aldehydes using alcohols as both the solvent and hydrogen source have been developed. These domino processes allow divergent syntheses of two significant N-heterocycles, indoles and quinolines, from the same substrate by tuning reaction parameters, which seems to invoke two distinct mechanisms. The nature of the ligand and alcoholic solvent had a profound influence on the selectivity and efficiency of these protocols. Particularly noteworthy is that indole formation was achieved by overcoming two significant challenges, regioselective hydropalladation of alkenes and subsequent reactions between the resulting Csp3-Pd species and less reactive imines.
Synthesis and characterization of mesoporous organosilica supported palladium (SBA-Pr-NCQ-Pd) as an efficient nanocatalyst in the Mizoroki–Heck coupling reaction
Moradi, Razieh,Mohammadi Ziarani, Ghodsi,Badiei, Alireza,Mohajer, Fatemeh
, (2020/10/02)
In the present study, the modification of a mesoporous organosilica nanocomposite SBA-15 (Santa Barbara Amorphous 15) was carried out in two steps, first through the surface functionalization of SBA-Pr-NH2 with 2-chloroquinoline-3-carbaldehyde to form SBA-Pr-NCQ, and then through a post-modification process with palladium ions. The target nanocompound structure of SBA-Pr-NCQ-Pd was characterized by different techniques (thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, Energy-dispersive X-ray spectroscopy (EDX), and Fourier transform infrared spectroscopy). The catalytic performance of the porous inorganic–organic hybrid nanocomposite (SBA-Pr-NCQ-Pd) in one of the most important carbon–carbon bond-forming processes, the Mizoroki–Heck coupling reaction of aryl halides and methacrylate in water/ethanol media, was examined. Compared to previous reports, this protocol afforded some advantages, such as high yields of products, short reaction times, catalyst stability without leaching, simple methodology, easy workup, and greener conditions. Also, the nanocatalyst can be easily separated from the reaction mixture and reused several times without a significant decrease in activity and promises economic as well as environmental benefits.
