53531-16-1Relevant articles and documents
N-Acylated and N-Alkylated 2-Aminobenzothiazoles Are Novel Agents That Suppress the Generation of Prostaglandin E2
Theodoropoulou, Maria A.,Psarra, Anastasia,Erhardt, Martin,Nikolaou, Aikaterini,Gerogiannopoulou, Anna-Dimitra D.,Hadjipavlou-Litina, Dimitra,Hayashi, Daiki,Dennis, Edward A.,Huwiler, Andrea,Kokotos, George
, (2022/02/09)
The quest for novel agents to regulate the generation of prostaglandin E2 (PGE2) is of high importance because this eicosanoid is a key player in inflammatory diseases. We synthesized a series of N-acylated and N-alkylated 2-aminobenzothiazoles and related heterocycles (benzoxazoles and benzimidazoles) and evaluated their ability to suppress the cytokine-stimulated generation of PGE2 in rat mesangial cells. 2-Aminobenzothiazoles, either acylated by the 3-(naphthalen-2-yl)propanoyl moiety (GK510) or N-alkylated by a chain carrying a naphthalene (GK543) or a phenyl moiety (GK562) at a distance of three carbon atoms, stand out in inhibiting PGE2 generation, with EC50 values ranging from 118 nM to 177 nM. Both GK510 and GK543 exhibit in vivo anti-inflammatory activity greater than that of indomethacin. Thus, N-acylated or N-alkylated 2-aminobenzothiazoles are novel leads for the regulation of PGE2 formation.
ANTICANCER 1,3-DIOXANE-4,6-DIONE DERIVATIVES AND METHOD OF COMBINATORIAL SYNTHESIS THEREOF
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, (2020/12/14)
Compounds, methods of synthesis, and methods of cancer treatment by arylidene-1,3-dioxane-4,6-diones. A Meldrum's acid-based chemistry and hybrid solid-liquid method. The method includes protection of ketone and aldehyde components and simultaneous immobilization on the solid phase, introduction of substituents, grafts and derivatives compatible with the protection, detachment and restoration of active carbonyl reactivity, reaction of ketone library with malonate, reacting of the products with the aldehyde library in liquid phase and separation of the products by preparative HPLC.
Transition-Metal-Free Synthesis of Electron Rich 1,3-Dienes via Base Promoted Isomerization of Propargylic Ethers
Liu, Chunxiang,Deng, Guogang,Li, Xin,Xu, Yiren,Yu, Kaili,Chen, Wen,Zhang, Hongbin,Yang, Xiaodong
supporting information, p. 483 - 487 (2020/01/25)
Herein, a novel and scalable synthesis of electron rich 1,3-dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition-metal-free isomerization, high isolated yields, and most of all, it could be used for modification of natural products at late stage functionalizations.
Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives
Qu, Bo,Tan, Renchang,Herling, Madison R.,Haddad, Nizar,Grinberg, Nelu,Kozlowski, Marisa C.,Zhang, Xumu,Senanayake, Chris H.
, p. 4915 - 4920 (2019/03/19)
Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are compatible with both electron-rich and electron-poor substituents.
Switchable Site-Selective Catalytic Carboxylation of Allylic Alcohols with CO2
van Gemmeren, Manuel,B?rjesson, Marino,Tortajada, Andreu,Sun, Shang-Zheng,Okura, Keisho,Martin, Ruben
supporting information, p. 6558 - 6562 (2017/05/29)
A switchable site-selective catalytic carboxylation of allylic alcohols has been developed in which CO2 is used with dual roles, both facilitating C?OH cleavage and as a C1 source. This protocol is characterized by its mild reaction conditions, absence of stoichiometric amounts of organometallic reagents, broad scope, and exquisite regiodivergency which can be modulated by the type of ligand employed.
Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols
Yun, Jihee,Park, Jungmin,Kim, Jaehyun,Lee, Kooyeon
, p. 1045 - 1048 (2015/02/19)
Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions.
Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes
Bourne, Samuel L.,O'Brien, Matthew,Kasinathan, Sivarajan,Koos, Peter,Tolstoy, Paeivi,Hu, Dennis X.,Bates, Roderick W.,Martin, Benjamin,Schenkel, Berthold,Ley, Steven V.
, p. 159 - 172 (2013/03/13)
Two tandem flow chemistry processes have been developed. A single palladium-catalysed Heck reaction with ethylene gas provides an efficient synthesis for functionalised styrenes. Through further elaboration the catalyst becomes multi-functional and performs a second Heck reaction providing a single continuous process for the synthesis of unsymmetrical stilbenes. In addition, the continuous, rhodium-catalysed, hydroformylation of styrene derivatives with syngas affords branched aldehydes with good selectivity. Incorporation of an in-line aqueous wash and liquid-liquid separation allowed for the ethylene Heck reaction to be telescoped into the hydroformylation step such that a single flow synthesis of branched aldehydes directly from aryl iodides was achieved. The tube-in-tube semi-permeable membrane-based gas reactor and liquid-liquid separator both play an essential role in enabling these telescoped flow processes.
C-X (X=Br, I) bond-tolerant aerobic oxidative cross-coupling: A strategy to selectively construct β-aryl ketones and aldehydes
Chen, Mao,Wang, Jie,Chai, Ziyi,You, Cai,Lei, Aiwen
supporting information; experimental part, p. 341 - 346 (2012/05/04)
Using moelcular oxygen as the terminal oxidant, various aryl halide-containing β-aryl ketones and aldehydes can be synthesized directly from readily available allyic alcohols and boronic acids via palladium-catalyzed oxidative cross-coupling reactions. The dual roles of copper, including electron-carrier and Lewis acid functions, are supposed to be critical for the high reactivity and selectivity of this aerobic oxidative coupling transformation. Copyright
Synthesis of 2-alkyl-substituted chromone derivatives using microwave irradiation
Friden-Saxin, Maria,Pemberton, Nils,Da Silva Andersson, Krystle,Dyrager, Christine,Friberg, Annika,Grotli, Morten,Luthman, Kristina
supporting information; experimental part, p. 2755 - 2759 (2009/08/15)
A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using
2,5-Disubstituted tetrahydrofurans as selective serotonin re-uptake inhibitors
Voelker, Troy,Xia, Haiji,Fandrick, Keith,Johnson, Robert,Janowsky, Aaron,Cashman, John R.
experimental part, p. 2047 - 2068 (2009/06/06)
Enhancement of 5-hydroxytryptamine (5-HT, serotonin) neurotransmission is a viable means of treating depression. On the basis of this observation, agents that inhibit re-uptake of 5-HT were prepared based on (-)-cocaine and aryltropanes as lead compounds
