- Comparison of the Photochemistry of Acyclic and Cyclic 4-(4-Methoxy-phenyl)-4-oxo-but-2-enoate Ester Derivatives
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To clarify the cis-trans isomerization mechanism of simple alkenes on the triplet excited state surface, the photochemistry of acyclic and cyclic vinyl ketones with a p-methoxyacetophenone moiety as a built-in triplet sensitizer (1 and 2, respectively) wa
- Abdelaziz, Nayera M.,Day, Heidi A.,Gudmundsdottir, Anna D.,Krause, Jeanette A.,Merugu, Rajkumar,Robinson, Jendai,Sarkar, Sujan K.,Upul Ranaweera, Ranaweera A. A.
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Read Online
- Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF2CO2Et toward 2,2-Difluorinated 2,3-Dihydrofurans
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A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been established via the [4 + 1] annulation of enaminones and BrCF2CO2Et with Na2CO3 promotion. This new protocol does not employ any transition metal reagent and enables the annulative difluoromethylation by the partial cleavage of the C═C double bond. In addition, the further treatment with hydrochloric acid in one pot leads to β-keto enoic acids (4-oxo-2-butenoic acids) via a formal enaminone C-N carboxylation.
- Ying, Jinbiao,Liu, Ting,Liu, Yunyun,Wan, Jie-Ping
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p. 2404 - 2408
(2022/04/07)
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- Microwave-assisted synthesis of 4-oxo-2-butenoic acids by aldol-condensation of glyoxylic acid
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4-Oxobutenoic acids are useful as biologically active species and as versatile intermediates for further derivatisation. Currently, routes to their synthesis can be problematic and lack generality. Reaction conditions for the synthesis of 4-oxo-2-butenoic
- Gai, Conghao,Leach, Andrew G.,Liu, Hang,Sprenger, Lukas J.,Uguen, Mélanie,Waring, Michael J.
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p. 30229 - 30236
(2021/10/20)
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- Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives
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The highly diastereoselective synthesis of perfluoroalkyl-containing pyrano[3,4-c]pyrroles has been accomplished via a cascade process involving Michael addition, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction. This domino tra
- Yang, Shanxue,Yao, Lan,Fan, Zhenhua,Han, Jing,Chen, Jie,He, Weimin,Deng, Hongmei,Shao, Min,Zhang, Hui,Cao, Weiguo
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supporting information
(2021/02/03)
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- Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
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A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.
- Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian
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p. 539 - 543
(2019/01/09)
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- Molecular diversity in cyclization of Ugi-products leading to the synthesis of 2,5-diketopiperazines: computational study
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Abstract: Ugi-adducts were obtained via a one-pot four-component reaction of divergent aldehydes, amines, aroylacrylic acids and isocyanide in methanol. These products were subjected to intramolecular Michael addition in the presence of K2COsu
- Zadsirjan, Vahideh,Shiri, Morteza,Heravi, Majid M.,Hosseinnejad, Tayebeh,Shintre, Suhas A.,Koorbanally, Neil A.
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p. 2119 - 2142
(2017/03/22)
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- Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
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Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.
- Xu, Changliang,Bai, Xiaoguang,Xu, Jian,Ren, Jinfeng,Xing, Yun,Li, Ziqiang,Wang, Juxian,Shi, Jingjing,Yu, Liyan,Wang, Yucheng
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p. 4763 - 4775
(2017/02/05)
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- (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone-aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization
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Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations.
- Vitorovic-Todorovic, Maja D.,Eric-Nikolic, Aleksandra,Kolundzija, Branka,Hamel, Ernest,Ristic, Slavica,Juranic, Ivan O.,Drakulic, Branko J.
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- Efficient synthesis of uracil-derived hexa- and tetrahydropyrido[2,3-d] pyrimidines
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A reaction of 6-amino-1,3-dimethyluracil with 3-(hetero)aroylacrylic acids and their methyl esters leads to hexahydropyrido[2,3-d]pyrimidine-5-carboxylic acids or the corresponding methyl esters in high to excellent yields. One-pot oxidation of the acid d
- Tolstoluzhsky, Nikita,Nikolaienko, Pavlo,Gorobets, Nikolay,Van Der Eycken, Erik V.,Kolos, Nadezhda
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supporting information
p. 5364 - 5369
(2013/09/02)
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- A simple, diversity oriented synthesis of highly substituted pyridines
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Figure represented. A particularly straightforward and efficient protocol for the synthesis of highly substituted pyridines, based on a condensation reaction of β-aminocrotonitrile and easily accessible (E)-2-oxo-4-aryl-but- 3-enoic acids and (E)-4-oxo-4-
- Kaczanowska, Katarzyna,Eickhoff, Holger,Albert, Klaus,Wiesmueller, Karl-Heinz,Schaffner, Arnaud-Pierre
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experimental part
p. 792 - 798
(2011/09/16)
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- Stereoselective syntheses of fluorescent non-natural aromatic amino acids based on asymmetric michael additions
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Four fluorescent non-natural aromatic amino acids have been synthesized based on a key stereoselective Michael addition reaction. S-1-Phenylethylamine was employed as both the source of amine and the stereoselectivity controller. The overall yields were m
- Chen, Heru,Zhong, Xianbin,Wei, Jin
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p. 1170 - 1182
(2008/02/05)
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- An efficient synthesis of β-Aroylacrylic acid ethyl ester by the Friedel-Crafts reaction in the presence of diethyl sulfate
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An β-Aroylacrylic acid ethyl ester such as ethyl (E)-4-(3,4- dimethoxyphenyl)-4-oxo-2-butenoate (1) can be obtained in good yield and with excellent purity by way of the Friedel-Crafts reaction in which 1,2-dimethoxybenzene (2) is treated with maleic anhydride (3) and aluminum chloride in the presence of diethyl sulfate (4) under mild conditions. Copyright
- Onoue, Ken-Ichi,Shintou, Taichi,Zhang, Chang Shan,Itoh, Isamu
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- Synthesis of 1,3,5-trisubstituted hydantoins by regiospecific domino condensation/aza-Michael/O→N acyl migration of carbodiimides with activated α,β-unsaturated carboxylic acids
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(Chemical Equation Presented) Carbodiimides and suitably activated α,β-unsaturated carboxylic acids react effectively to afford a vast array of 1,3,5-trisubstituted hydantoins by means of a regiospecific domino condensation/aza-Michael/N→O acyl migration. The reaction works well in very mild conditions (20°C, dichloromethane) with fumaric acid derivatives bearing an electron-withdrawing group in the β position. Good results have been obtained also with less activated substrates bearing only one electron-withdrawing group in the β position, using more polar solvents (acetonitrile, DMF), and in the presence of a base (2,4,6-trimethylpyridine). Reactions with asymmetric carbodiimides are generally highly chemo- and regioselective, giving rise to the formation of a single regioisomeric hydantoin. However, asymmetric carbodiimides bearing one alkyl group and one aryl group can produce variable amounts of N-acylurea byproducts. The latter could be easily recovered and transformed into the corresponding hydantoins. A detailed study of the influence of key reaction parameters such as solvent, base, and structure of the reactants on the reaction outcome and mechanism is presented. This methodology is particularly convenient for the synthesis of trifluoromethyl-substituted hydantoins, which could be interesting as bioactive compounds in medicinal chemistry, as well as precursors of the corresponding α-amino acids.
- Volonterio, Alessandro,De Arellano, Carmen Ramirez,Zanda, Matteo
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p. 2161 - 2170
(2007/10/03)
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- Mesomorphic compound, liquid crystal composition, liquid crystal device, display apparatus and display method
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A mesomorphic compound represented by the following formula (I): STR1 wherein R1 denotes a linear or branched alkyl group having 2-16 carbon atoms capable of including one or non-neighboring two methylene groups which can be replaced with --O--
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- Synthetic Studies on O-Heterocycles via Cycloadditions. Part 2. Adducts from Styrene Oxides
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The styrene oxides (14) and (15), bearing electron-withdrawing functions, readily undergo thermal and photochemical (triplet sensitised) dipolar cycloadditions with simple electron-deficient olefins, regioselectively in the case of methyl acrylate.However, cycloadditions with 5-arylbutenolides as dipolarophiles, required for lignan synthesis, could not be effected in significant yield.A new short route to 5-arylbut-2-enolides was devised.The dihydro- and tetrahydro-furan adducts (18d), (19d), and (20d) all fragment in base to the dienol nitrile (25).
- Clawson, Paul,Lunn, Patricia M.,Whiting, Donald A.
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p. 159 - 162
(2007/10/02)
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- Gastric anti-secretory, anti-ulcer and cytoprotective properties of substituted (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids
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A class of anti-secretory, anti-ulcer and cytoprotective agents, the substituted (E)-4-phenyl and heteroaryl-4-oxo-2-butenoic acids, is described.This chemical structure is not related to those of any known anti-cholinergic drugs, histamine H2-receptor antagonists or prostaglandins.Five compounds, 4-(2-methoxyphenyl)- 15, 4-(4-methoxyphenyl)- 22, 4-(3,4-dimethoxyphenyl)- 32, 4-(3,4,5-trimethoxyphenyl)- 40, and 4-(2-furanyl)-4-oxo-2-butenoic acid 44, have cytoprotective activity at a very low dose (0.6 mg/kg, p.o.) and anti-secretory and anti-ulcer activities at higher doses.One of these compounds, RU 38086 40, has been selected for clinical evaluation.Keywords - anti-ulcer agents / cytoprotective agents / (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids.
- Bianchi, Mario,Butti, Alina,Christidis, Yani,Perronnet, Jacques,Barzaghi, Fernando,et al.
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- 3-benzoyl-2-mercaptopropionic acid derivatives
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3-Benzoyl-2-mercaptopropionic acid derivatives represented by the general formula STR1 (wherein, X represents a hydrogen atom, a halogen atom, hydroxy group, a lower alkyl group or a lower alkoxy group, Y represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, Z represents a hydrogen atom or an acyl group, and R represents a hydrogen atom or a lower alkyl group). These compounds have immunomodulative function and are effective for the treatment of diseases caused by abnormal immunofunction.
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- Mercaptoacyldihydropyrazole carboxylic acid derivatives
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Hypertension can be treated using compounds having the formula or a basic salt thereof, wherein R1 is hydrogen, alkyl, aryl, arylalkyl or STR1 wherein R5 is alkyl or aryl; R2 is hydrogen or alkyl; R3 is aryl; R4 is hydrogen, alkyl or arylalkyl and n is 0, 1 or 2.
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