1076-96-6Relevant articles and documents
-
Emerson et al.
, p. 674 (1946)
-
Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands
Chu, Wenhua,Tu, Zhude,McElveen, Elizabeth,Xu, Jinbin,Taylor, Michelle,Luedtke, Robert R.,MacH, Robert H.
, p. 77 - 87 (2005)
The synthesis of a series of N-(2-methoxyphenyl)piperazine and N-(2,3-dichlorophenyl)piperazine analogs and their in vitro binding affinities for dopamine D2, D3, D4 are presented. A series of N-(2-methoxyphenyl)piperazine
Improved Julia-Kocienski conditions for the methylenation of aldehydes and ketones
Aissa, Christophe
, p. 360 - 363 (2006)
The scope of the methylenation of aldehydes and ketones under optimized Julia-Kocienski conditions is broadened by using 1-tert-butyl-1H-tetrazol-5- ylmethyl sulfone. Two different Barbier-type procedures are applied with NaHMDS at -78 °C or Cs2CO3 at 70 °C. The latter conditions are also adapted for the preparation of 1,2-disubstituted olefins and intramolecular olefination reactions.
One-pot Suzuki-Heck relay to prepare industrially valuable intermediates using the Pd-Cy?Phine catalyst system
Das, Uttam K.,Clément, Roxanne,Johannes, Charles W.,Robins, Edward G.,Jong, Howard,Baker, R. Tom
, p. 4599 - 4603 (2017)
A rare example of a one-pot, palladium-catalyzed Suzuki-Heck sequence has been developed with applicability to APIs and organoelectronic materials. High throughput screening was used to expedite development and survey strategies. Interchangeability of the coupling partners and the avoidance of intermediate isolation gives operational flexibility, which can be used to improve process efficiency and suppress by-product formation.
Discovery of 5-{2-[5-Chloro-2-(5-ethoxyquinoline-8-sulfonamido)phenyl]ethynyl}-4-methoxypyridine-2-carboxylic Acid, a Highly Selective in Vivo Useable Chemical Probe to Dissect MCT4 Biology
Heinrich, Timo,Sala-Hojman, Ada,Ferretti, Roberta,Petersson, Carl,Minguzzi, Stefano,Gondela, Andrzej,Ramaswamy, Shivapriya,Bartosik, Anna,Czauderna, Frank,Crowley, Lindsey,Wahra, Pamela,Schilke, Heike,B?pple, Pia,Dudek, ?ukasz,Le?, Marcin,Niedziejko, Paulina,Olech, Kamila,Pawlik, Henryk,W?oszczak, ?ukasz,Zuchowicz, Karol,Suarez Alvarez, Jose Ramon,Martyka, Justyna,Sitek, Ewa,Mikulski, Maciej,Szcz??niak, Joanna,J?ckel, Sven,Krier, Mireille,Król, Marcin,Wegener, Ansgar,Ga??zowski, Micha?,Nowak, Mateusz,Becker, Frank,Herhaus, Christian
, p. 11904 - 11933 (2021)
Due to increased lactate production during glucose metabolism, tumor cells heavily rely on efficient lactate transport to avoid intracellular lactate accumulation and acidification. Monocarboxylate transporter 4 (MCT4/SLC16A3) is a lactate transporter that plays a central role in tumor pH modulation. The discovery and optimization of a novel class of MCT4 inhibitors (hit 9a), identified by a cellular screening in MDA-MB-231, is described. Direct target interaction of the optimized compound 18n with the cytosolic domain of MCT4 was shown after solubilization of the GFP-tagged transporter by fluorescence cross-correlation spectroscopy and microscopic studies. In vitro treatment with 18n resulted in lactate efflux inhibition and reduction of cellular viability in MCT4 high expressing cells. Moreover, pharmacokinetic properties of 18n allowed assessment of lactate modulation and antitumor activity in a mouse tumor model. Thus, 18n represents a valuable tool for investigating selective MCT4 inhibition and its effect on tumor biology.
A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus
Masunari, Andrea,Tavares, Leoberto Costa
, p. 4229 - 4236 (2007)
Hospital-acquired methicillin-resistant Staphylococcus aureus (MRSA) has been an increasing problem worldwide since the initial reports over 40 years ago. To examine new drug leads with potential antibacterial activities, 14 p-substituted benzoic acid [(5-nitro-thiophen-2-yl)-methylene]-hydrazides were designed, synthesized, and tested against standard and multidrug-resistant S. aureus strains by serial dilution tests. All compounds exhibited significant bacteriostatic activity and some of them also showed bactericidal activity. The results confirmed the potential of this class of compounds as an alternative for the development of selective antimicrobial agents.
Pyrene-benzoylthiophene exciplexes as selective catalysts for the [2+2] cycloaddition between cyclohexadiene and styrenes
Gonzalez-Bejar, Maria,Bentama, Abdeslem,Miranda, Miguel Angel,Stiriba, Salah-Eddine,Perez-Prieto, Julia
, p. 2067 - 2070 (2007)
Efficient intramolecular fluorescence quenching in pyrene-benzoylthiophene systems leads to formation of exciplexes. These species interact with 1,3-cyclohexadiene (or styrenes), leading to reactive excited triplexes. The overall process affords [2+2] cro
Catalytic α-Selective Deuteration of Styrene Derivatives
Puleo, Thomas R.,Strong, Alivia J.,Bandar, Jeffrey S.
, p. 1467 - 1472 (2019)
We report an operationally simple protocol for the catalytic α-deuteration of styrenes. This process proceeds via the base-catalyzed reversible addition of methanol to styrenes in DMSO-d6 solvent. The concentration of methanol is shown to be critical for high yields and selectivities over multiple competing side reactions. The synthetic utility of α-deuterated styrenes for accessing deuterium-labeled chiral benzylic stereocenters is demonstrated.
PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation
Wu, Xiaofang,Zhou, Lei,Li, Fangshao,Xiao, Jing
, p. 491 - 497 (2021/01/20)
A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.
Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids
Bai, Junxue,Li, Miao,Zhou, Cong,Sha, Yu,Cheng, Jiang,Sun, Jianwei,Sun, Song
supporting information, p. 9654 - 9658 (2021/12/14)
A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.