82938-20-3Relevant academic research and scientific papers
Discovery of Novel 3-Amino-4-alkoxyphenylketones as PDE4 Inhibitors with Improved Oral Bioavailability and Safety against Spatial Memory Impairments
Feng, Kai-Wen,He, Jia-Peng,Liu, Lu,Wang, Hai-Tao,Xia, Chuang,Xu, Jiang-Ping,Zheng, Lei,Zhou, Zhong-Zhen
, p. 390 - 405 (2022/02/07)
To realize PDE4 inhibitors with good developmental potentiality for the treatment of dementia, structure-based optimizations of lead compound FCPR03 resulted in novel aminophenylketones 9c and 9H with low nanomolar potency, which displayed comparable acti
Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products
Zhang, Xiao,Rovis, Tomislav
, p. 21211 - 21217 (2021/12/27)
Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.
Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols
Bhattacharyya, Dipanjan,Sarmah, Bikash Kumar,Nandi, Sekhar,Srivastava, Hemant Kumar,Das, Animesh
supporting information, p. 869 - 875 (2021/02/06)
Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.
DABCO-promoted photocatalytic C-H functionalization of aldehydes
Cardozo, Thiago Messias,Da Silva Santos, Bruno Maia,Finelli, Fernanda Gadini,de Souza, Cauê Paula,dos Santos Dupim, Mariana
supporting information, p. 2959 - 2967 (2022/01/12)
Herein we present a direct application of DABCO, an inexpensive and broadly accessible organic base, as a hydrogen atom transfer (HAT) abstractor in a photocatalytic strategy for aldehyde C-H activation. The acyl radicals generated in this step were arylated with aryl bromides through a well stablished nickel cross-coupling methodology, leading to a variety of interesting aryl ketones in good yields. We also performed computational calculations to shine light in the HAT step energetics and determined an optimized geometry for the transition state, showing that the hydrogen atom transfer between aldehydes and DABCO is a mildly endergonic, yet sufficiently fast step. The same calculations were performed with quinuclidine, for comparison of both catalysts and the differences are discussed.
Aminophenone compounds as well as preparation method and application thereof
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, (2021/02/06)
The invention belongs to the technical field of medicinal chemistry, and particularly relates to aminophenone compounds as well as a preparation method and application thereof. The aminophenone compounds provided by the invention have a good inhibition effect on PDE4, also have good bioavailability, can be applied to preparation of drugs for treating PDE4-related diseases, and increase the optionsof drugs for treating PDE4-related diseases; and the effect of a part of the aminophenone compounds is equivalent to the effect of positive drugs, and the aminophenone compounds have good developmentpotential.
Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 7624 - 7629 (2019/10/02)
A highly reactive catalytic system for the carbonylative coupling of aryl iodides with alkenylaluminum reagents has been developed. Various β-substituted γ,δ-unsaturated ketones were produced under mild conditions in good to excellent yields even under ppm level of palladium catalyst. Notably, this also represents the first example on carbonylative transformation of alkenylaluminum compounds. Additionally, by the addition of zinc salt, the selectivity of the product can be modified.
Pd-catalyzed Oxidative Cross-coupling of Alkyl Chromium(0) Fischer Carbene Complexes with Organoboronic Acids
Wang, Kang,Yang, Jinghui,Yao, Xingqi,Wang, Jianbo
supporting information, p. 3165 - 3168 (2018/10/15)
Alkyl chromium(0) carbene complexes have been explored as the cross-coupling partners in the palladium-catalyzed reaction with aryl or alkenyl boronic acids. This coupling reaction displays the versatile reactivities of alkyl chromium(0) carbenes under palladium catalysis. Mechanistically, this transformation is proposed to involve deprotonation of the alkyl chromium carbene substrate to generate a vinyl chromium anion intermediate that undergoes transmetalation to organopalladium species and reductive elimination.
A new approach to the synthesis of peptidomimetic renin inhibitors: Palladium-catalyzed asymmetric allylation of acyclic alkyl aryl ketones
Hanessian, Stephen,Chénard, Etienne
supporting information; experimental part, p. 3222 - 3225 (2012/08/08)
A new approach to the synthesis of Tekturna, a recently marketed drug for hypertension, takes advantage of a modified protocol of the Stoltz palladium-catalyzed asymmetric allylation with a t-BuPHOX ligand for the synthesis of allylated acyclic alkyl aryl
Direct acylation of aryl chlorides with aldehydes by palladium-pyrrolidine Co-catalysis
Colbon, Paul,Ruan, Jiwu,Purdie, Mark,Xiao, Jianliang
supporting information; experimental part, p. 3670 - 3673 (2010/10/20)
A palladium catalyst system has been developed that allows for the direct acylation of aryl chlorides with aldehydes. The choice of ligand, as well as the presence of pyrrolidine and molecular sieves is shown to be critical to the catalysis, which appears to proceed via an enamine intermediate. The reaction was successful for a wide range of aryl chlorides and tolerant of functionality on the aldehyde component, giving easy access to alkyl aryl ketones in modest to good yields.
3-(2-Aminocarbonylphenyl)propanoic acid analogs as potent and selective EP3 receptor antagonists. Part 2: Optimization of the side chains to improve in vitro and in vivo potencies
Asada, Masaki,Iwahashi, Maki,Obitsu, Tetsuo,Kinoshita, Atsushi,Nakai, Yoshihiko,Onoda, Takahiro,Nagase, Toshihiko,Tanaka, Motoyuki,Yamaura, Yoshiyuki,Takizawa, Hiroya,Yoshikawa, Ken,Sato, Kazutoyo,Narita, Masami,Ohuchida, Shuichi,Nakai, Hisao,Toda, Masaaki
experimental part, p. 1641 - 1658 (2010/04/29)
A series of 3-[2-{[(3-methyl-1-phenylbutyl)amino]carbonyl}-4-(phenoxymethyl)phenyl]propanoic acid analogs were synthesized and evaluated for their in vitro potency. In most cases, introduction of one or two substituents into the two phenyl moieties resulted in the tendency of an increase or retention of in vitro activities. Several compounds, which showed excellent subtype selectivity, were evaluated for their inhibitory effect against PGE2-induced uterine contraction in pregnant rats, which is thought to be mediated by the EP3 receptor subtype. The structure-activity relationships (SARs) are also discussed.
