32149-28-3Relevant academic research and scientific papers
Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
, p. 4327 - 4337 (2021/05/31)
A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian
, p. 539 - 543 (2019/01/09)
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.
Base-Controlled Reactions through an Aldol Intermediate Formed between 2-Oxoaldehydes and Malonate Half Esters
Kumar, Atul,Khan, Shahnawaz,Ahmed, Qazi Naveed
supporting information, p. 4730 - 4733 (2017/09/22)
A practical, atom-economical, base-directed, and highly efficient method for the generation of different selective products through a common aldol intermediate of 2-oxoaldehydes and malonate half esters is successfully developed. The addition of a strong basic environment (potassium tert-butoxide) catalyzed the synthesis of stable decarboxylative aldol products (α-hydroxy ketones), while the Doebner modification procedure resulted in decarboxylative elimination to (E)-α,β-unsaturated esters in good yields. The application of this method in one pot and one pot/two steps with azoles helped to develop regioselective α- and β-azolated products in appreciable yields.
Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
Xu, Changliang,Bai, Xiaoguang,Xu, Jian,Ren, Jinfeng,Xing, Yun,Li, Ziqiang,Wang, Juxian,Shi, Jingjing,Yu, Liyan,Wang, Yucheng
, p. 4763 - 4775 (2017/02/05)
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.
Isothiourea-mediated one-pot synthesis of functionalized pyridines
Stark, Daniel G.,Morrill, Louis C.,Yeh, Pei-Pei,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Smith, Andrew D.
, p. 11642 - 11646 (2013/11/06)
Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/ lactamization, thiophenol elimination, and N- to O
ORGANOPHOSPHORUS CHEMISTRY 10. THE BEHAVIOUR OF β-AROYLACRYLIC ACIDS TOWARD NUCLEOPHILIC PHOSPHORUS COMPOUNDS
Mahran, Mohamed R.,Abdou, Wafaa M.,Ganoub, Neven A. F.,Sidky, Mahmoud M.
, p. 19 - 26 (2007/10/02)
The reaction of alkyl phosphites and thiolphosphoric acids with β-aroylacrylic acids 1a,b has been investigated.Dialkyl phosphites (DAP) attacked 1 at the β-carbon atom with respect to the aroyl-carbonyl function, to give phosphonate 1:1 adducts assigned structure 2A.Thiolphosphoric acids (7) attacked 1 at the same centre to give adducts 8.On the other hand, trialkyl phosphites (TAP) converted 1 into the respective esters 5, almost exclusively.Structures of the new products were assigned according to consistent analytical and spectroscopic measurements.Key words: β-aroylacrylic acids; alkylation; phosphorylation; thiophosphorylation.
Preparation and Rearrangement of cis-Methyl 3,4-Epoxy-4-(4'-methylphenyl)butanoate
Bhat, K. S.,Rao, A. S.
, p. 355 - 358 (2007/10/02)
AlCl3 catalysed bromination of methyl 4-keto-4-(4'-methylphenyl)butanoate (2) is regioselective and furnishes methyl 3-bromo-4-keto-4-(4'-methylphenyl)butanoate (3). 3 on NaBH4 reduction in the presence of NaHCO3 furnishes a mixture of cis-methyl 3,4-epoxy-4-(4'-methylphenyl)butanoate (9), methyl (E)-4-hydroxy-4-(4'-methylphenyl)but-2-enoate (12), 4-(4'-methylphenyl)butanolide (26) and 2. 12 can be transformed to 1 on heating with NaOH-ethanol.BF3 catalysed rearrangement of 9 furnishes methyl 3-keto-4-(4'-methylphenyl)butanoate (17).The sequence of reactions 2->3->9->17 constitutes an interesting example of ketone transposition and provides a convenient route for the preparation of 17 from the readily available 2.
Antidiabetic pyrrolecarboxylic acids
-
, (2008/06/13)
Certain pyrrolecarboxylic and pyrroleacetic acid derivatives substituted on the pyrrole ring with thioether groups, acyl groups, phenyl, substituted phenyl, phenoxy, substituted phenoxy, benzyl or halo and optionally substituted on the pyrrole nitrogen with alkyl, and the pharmaceutically acceptable salts thereof, are useful in lowering the blood glucose levels of hyperglycemic animals.
