965-50-4Relevant academic research and scientific papers
NOVEL CELL METABOLISM MODULATING COMPOUNDS AND USES THEREOF
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Page/Page column 234-235, (2021/07/31)
A class of compounds that bind to fatty acid binding protein (FABP4) and modulate adipocyte metabolism to drive enhanced glucose utilization, as well as pharmaceutical compositions comprising the class of compounds, in combination with a pharmaceutically acceptable diluent or carrier, and optionally, further in combination with a therapeutically active agent, and the use of these compounds in medicine and for the preparation of a medicament in the treatment of disorders acting on the FABP4.
1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides
Vala, Anand,Parmar, Nirali,Soni, Jigar Y.,Kotturi, Sharadsrikar,Guduru, Ramakrishna
, p. 2080 - 2084 (2021/10/07)
Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.
Palladium catalysed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one/pyrazolone derivatives
Krishna Reddy, Singarajanahalli Mundarinti,Prasanna Kumari, Subramaniyan,Selva Ganesan, Subramaniapillai
, (2021/08/03)
Palladium catalysed addition of arylboronic acid to the readily available 2-cyano-(N-aryl)-acetamide or ethyl-2-cyanoacetate followed by subsequent reaction transform them into the biologically significant 4-arylquinolin-2-one or pyrazolone derivatives. The reaction conditions are robust enough to prevent the hydrolysis of ester/amide moiety during arylation. In addition, the unactivated nitrile moiety in the acetonitrile also converted to the corresponding acetophenone derivative.
Selective exploitation of acetoacetate carbonyl groups using imidazolium based ionic liquids: synthesis of 3-oxo-amides and substituted benzimidazoles
Chakraborty, Ankita,Majumdar, Swapan,Maiti, Dilip K.
, p. 3298 - 3302 (2016/07/11)
An unprecedented Br?nsted base ionic liquid tuned selective aminolysis of ester carbonyl of acetoacetates is demonstrated to achieve acetoacetamide derivatives. Other imidazolium ionic liquid performs an efficient cyclization catalysis involving acetoacetate-carbonyl groups and o-phenylenediamine at elevated temperature to produce benzimidazoles via C–C bond cleavage of intermediate 1,5-benzodiazepinones under solvent-free conditions.
Silver(I)-catalyzed tandem approach to β-oxo amides
Vandavasi, Jaya Kishore,Hsiao, Cheng-Tien,Hu, Wan-Ping,Boominathan, Siva Senthil Kumar,Wang, Jeh-Jeng
supporting information, p. 3171 - 3177 (2015/05/13)
A facile and efficient AgI-catalytic approach is reported for the first time to synthesize β-oxo amides from β-oxo esters a with broad substrate scope in good to excellent yields. Crossover and in situ NMR studies confirmed that the reaction occurred through a new pathway and not by the traditional condensation reaction. The key advantages of this method are the readily available starting materials, the air-stable reaction, the simple protocol, and the environmental friendliness. A new, catalytic approach to the synthesis of β-oxo amides from β-oxo esters with a broad substrate scope in good to excellent yields was developed. In situ NMR spectroscopy and crossover experiments confirmed the reaction mechanism.
Multicomponent strategy to indeno[2,1- C ]pyridine and hydroisoquinoline derivatives through cleavage of carbon-carbon bond
Feng, Xian,Wang, Jian-Jun,Xun, Zhan,Huang, Zhi-Bin,Shi, Da-Qing
, p. 1025 - 1033 (2015/01/30)
A concise and efficient three-component domino reaction has been developed for the synthesis of polyfunctionalized indenopyridine and hydroisoquinoline derivatives via the cleavage of a C-C bond under transition-metal-free conditions. This reaction provides facile access to complex nitrogen-containing heterocycles by simply mixing three common starting materials in EtOH in the presence of 20 mol % NaOH under microwave irradiation conditions.
Synthesis and evaluation of 4-aryl-2(1H)-quinolinones as potent amyloid β fibrillogenesis inhibitors
Shimokawa, Yoko,Nakakoshi, Masamichi,Saito, Setsu,Suzuki, Hideharu,Yokoyama, Yuusaku,Ishigami, Akihito,Nishioka, Hideo,Tsubuki, Masayoshi
experimental part, p. 1933 - 1940 (2012/09/25)
4-Aryl-2(1H)-quinolinones were synthesized and evaluated in vitro as inhibitors of Aβ1-42 fibrillogenesis using a thioflavin T fluorescence method. The most potent anti-aggregating molecules (4b and 5c) were found among the derivatives bearing OH and/or OMe groups at C-4' (R4) and/or C-6 (R2) of the 4-aryl-2(1H)-quinolinone moiety. Furthermore, the derivative bearing 4'-F substituent (4f) proved to be a very active inhibitor.
Synthesis and anticonvulsant activity of 5-phenyl-[1,2,4]-triazolo[4,3-a] quinolines
Guan, Li-Ping,Jin, Qing-Hao,Wang, Shou-Feng,Li, Fu-Nan,Quan, Zhe-Shan
scheme or table, p. 774 - 779 (2009/04/14)
A series of novel 5-phenyl-[1,2,4]-triazolo[4,3-a]quinoline derivatives was synthesized by the cyclization of 2-chloro-4-phenyl-1,2-dihydronaphthalene with formohydrazide. The starting material 2-chloro-4-phenyl-1,2-dihydronaphthalene was synthesized from ethyl-3-oxo-3-phenylpropanoate and substituted aniline. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The maximal electroshock test showed that 7-hexyloxy-5-phenyl-[1,2,4]- triazolo[4,3-a]quinoline 4f was found to be the most potent compound with an ED50 value of 6.5 mg/kg and a protective index (PI = ED 50/TD50) value of 35.1, which was much higher than the PI of the reference drug phenytoin.
A new synthesis of β-keto amides by reduction of Passerini adducts
Neo, Ana G.,Delgado, Jose,Polo, Cecilia,Marcaccini, Stefano,Marcos, Carlos F.
, p. 23 - 26 (2007/10/03)
The Passerini reaction between glyoxals, isocyanides and acetic acid forms β-keto acyloxyamides, which are readily transformed in β-keto amides by reductive deacetoxylation with zinc. The versatility of this procedure, which allows introducing different groups both in position-3 and the amide nitrogen, makes it ideal for its use in diversity-oriented synthesis, in combination with subsequent complexity generation reactions.
