- Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles
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An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.
- Ni, Qijian,Wang, Xuyang,Zeng, Da,Wu, Qianling,Song, Xiaoxiao
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p. 2273 - 2278
(2021/04/05)
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- Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase
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Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.
- Chen, Haifeng,Guo, Yanrong,Han, Xinya,Hu, Wei,Huang, Yunyuan,Ren, Yanliang,Tang, Zilong,Wang, Qi,Wei, Lin,Xia, Qinfei,Yan, Jufen
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- Synthesis of novel 3-halo-3-nitroflavanones and their activities as DNA methyltransferase inhibitors in cancer cells
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The implication of DNA methylation in cancer is today clearly established. Despite that nucleoside analogues are currently used for leukaemia treatment, their low stability in physiological conditions and their lack of selectivity arise the need for the i
- Pechalrieu, Dany,Dauzonne, Daniel,Arimondo, Paola B.,Lopez, Marie
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- Cinnamic acid derivative and preparation method and application thereof
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The invention provides a cinnamic acid derivative. The cinnamic acid derivative is of the structure as shown in the formula I. The invention also provides two methods for preparing the cinnamic acid derivative. The two methods depend on a single bond or double bonds in the structure shown in the formula I. The invention further provides a pesticide. The pesticide comprises the cinnamic acid derivative. In addition, the invention provides a sterilization method. The sterilization method includes the step of applying the cinnamic acid derivative or the pesticide to crops. The crops include rice,wheat, fruit trees and vegetables. The low-toxicity, low-residue-content and high-activity environment-friendly cinnamic acid derivative is developed, and the cinnamic acid derivative pesticide can replace traditional high-toxicity and high-residue-content pesticides.
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- Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes
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Drug resistance has become a major concern in the field of infection management, therefore searching for new antibacterial agents is getting more challenging. Our study presents an optimized and eco-friendly synthesis scheme for a panel of nitroalkenes be
- Boguszewska-Czubara, Anna,Lapczuk-Krygier, Agnieszka,Rykala, Konrad,Biernasiuk, Anna,Wnorowski, Artur,Popiolek, Lukasz,Maziarka, Agata,Hordyjewska, Anna,Jasiński, Radomir
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p. 900 - 907
(2016/10/09)
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- A novel tandem sequence to pyrrole syntheses by 5-endo-dig cyclization of 1,3-enynes with amines
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The synthesis of pentasubstituted pyrroles has been described using molecular iodine from 1,3-enynes and amines via a sequential tandem aza-Michael addition, iodocyclization, and oxidative aromatization. The protocol is simple and efficient to afford the target products at ambient conditions.
- Bharathiraja, Ganesan,Sakthivel, Sekarpandi,Sengoden, Mani,Punniyamurthy, Tharmalingam
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p. 4996 - 4999
(2013/10/22)
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- Synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones utilizing pyrrole weinreb amides
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A regiocontrolled synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1,2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated: (1) modified Henry reaction between arylnitromethanes and arylimines; and (2) Suzuki-Miyaura cross-coupling reaction of 2-aryl-1-bromo-1-nitroethenes with arylboronic acids. Some difficulty was encountered in the preparation of arylnitromethanes, thus leading to the exploration of a cross-coupling strategy that proved more useful. A Barton-Zard pyrrole cyclocondensation reaction between 1,2-diaryl-1-nitroethenes and N-methoxy-N-methyl-2-isocyanoacetamide gave the corresponding pyrrole Weinreb amides, which were then converted into the desired 3-pyrrolin-2-ones in two steps. Overall, this method allowed for the construction of 3,4-diaryl-3- pyrrolin-2-ones with complete regiocontrol of the substituents with respect to the lactam carbonyl. The utility of this synthetic methodology was demonstrated by the preparation of eight unsymmetrical and symmetrical 3,4-diaryl-3-pyrrolin- 2-ones including the N-H lactam analogue of the selective COX-II inhibitor, rofecoxib.
- Greger, Jessica G.,Yoon-Miller, Sarah J. P.,Bechtold, Nathan R.,Flewelling, Scott A.,MacDonald, Jacob P.,Downey, Catherine R.,Cohen, Eric A.,Pelkey, Erin T.
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p. 8203 - 8214
(2011/12/04)
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- Synthesis and [3+2] cycloadditions of 3-bromo-5,6-dihydro-4 H -1,2-oxazine N -oxides
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A number of 3-bromo-5,6-dihydro-4H-1,2-oxazine N-oxides have been synthesized and subjected to [3+2] cycloaddition with alkenes affording various types of products: 3-vinyloxazolines, isoxazoline N-oxides, and 3-functionalized 1,2-oxazine N-oxides. Georg Thieme Verlag Stuttgart - New York.
- Romashov, Leonid V.,Khomutova, Yulya A.,Danilenko, Vitaliy M.,Ioffe, Sema L.,Lesiv, Alexey V.
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experimental part
p. 407 - 414
(2010/05/18)
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- Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes
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(Z)-α-Bromo-β-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)4 as catalyst to afford (E)-α,β-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of α-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful α,β-disubstituted nitroethylenes.
- Ganesh, Madhu,Namboothiri, Irishi N.N.
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p. 11973 - 11983
(2008/03/13)
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- Elimination reaction over solid supports under microwave irradiation: Synthesis of functionalized alkenes
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Treatment of 1,2-dibromocompounds with KF supported on alumina, or bentonite/E13N under microwave irradiation leads to an elimination reaction which produces functionalized alkenes in fair yields.
- Saoudi, Aicha,Hamelin, Jack,Benhaoua, Hadj
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p. 4035 - 4038
(2007/10/03)
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- Aqueous isothiazolone formulation
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An aqueous isothiazolone formulation useful for antiseptic or antifungal treatment of various synthetic polymeric emulsions, which comprises (a) a specific isothiazolone compound, (b) water or an aqueous solvent and (c) a specific nitrobromo or cyanobromo compound.
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- SYNTHESIS OF 2-HALOGENO-2-NITROETHENYLARENES
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A series of 2-halogeno-2-nitroethenylarenes were obtained as a result of the condensation of halogenonitromethanes with aromatic (heterocyclic) aldehydes in the presence of catalytic amounts of ethylenediamine and also by the addition of halogenonitromethanes to butylarylimines in acetic anhydride.
- Aleksiev, D. I.,Ivanova, S. M.
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p. 1845 - 1848
(2007/10/02)
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- Insecticidal and acaricidal diarylpyrrolecarbonitrile and diarylnitropyrrole compounds
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This invention relates to new diarylpyrrolecarbonitrile and new diarylnitropyrrole compounds. It also relates to the use of said compounds as insecticidal and acaricidal agents and to a method of protecting plants, particularly crop plants, from attack by
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- A convenient synthesis of substituted 1-bromo-1-nitroalkenes
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The reaction of aldehydes with bromonitromethane in the presence of tri-n-butylarsine affording substituted 1-bromo-1-nitroalkenes in good yields is described.
- Shen,Yang
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- Pathways in the Reactions of Nitronate Ions with Sulphonyl Halides
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Primary and tertiary nitronate ions and sulphonyl bromides and iodides rapidly equilibrate with the nitrohalides and sulphinate ion.Products are determined by solvent and by the occurence of cross-equilibrum reactions, some of which have single-electron-transfer mechanism.The reaction of arene-sulphinate and thiolate ions with 1,2-dibromo-2-nitro-1-phenylethane gave E-β-nitrostyrene by Z-philic elimination in both cases, but the more basic thiolate ion also gave, by protophilic elimination, 2-bromo-2-nitro-1-phenylethene.
- Pigou, Paul E.,Stirling, Charles J. M.
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p. 725 - 730
(2007/10/02)
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- Research on antitumor chemotherapy: X. β Nitrostyrene and nitrovinyl derivatives
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In previous work, the antitumoral cytotoxicity of β nitrostyrenes obtained by simplification of the aristolochic acid molecule was demonstrated. The effect of modifying the 3 characteristic parts of the β nitrostyrene molecule was then investigated. Results in vitro and in vivo indicate a probable mechanism of action for the β nitrostyrene and nitrovinyl compounds studied, and permit definition of the maximum simplification compatible with retention of biological activity.
- Dore,Viel
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