- Synthesis, characterization crystal structures and DNA binding studies of zinc complexes with oxygen and nitrogen donor ligands
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Three zinc metal complexes viz, [Zn(L1)2phen] (1), [Zn2(L2)4(bipy)2] (2) and [Zn(L2)2bipy·H2O] (3) where HL1 = 4-(o-toluidino)-4-oxobutanoic acid
- Mehr-un-Nisa,Sirajuddin, Muhammad,Ali, Saqib,Tahir, Muhammad Nawaz,Iqbal, Muhammad
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- Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents
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A series of 3,4-dihydro-2(1H)-quinolinone derivatives contained butenediamide fragment were designed and synthesized. Their inhibition potency against chitin synthase and antimicrobial activities were screened in vitro. The enzymatic assays showed that all the synthesized compounds had inhibition potency against chitin synthase at concentration of 300 μg/mL. Compound 2d displayed excellent potency with inhibition percentage (IP) value of 82.3%, while IP value of the control polyoxin B was 87.5%. Compounds 2b, 2e and 2s whose IP values were above 70% showed good inhibition potency against chitin synthase. Moreover, the IC50 value of 2b was comparable with that of polyoxin B (0.09 mM). The Ki of compound 2b was 0.12 mM and the result from Lineweaver-Burk plot showed that 2b was non-competitive inhibitor to bind chitin synthase. The antifungal experiment showed that these compounds had excellent antifungal activity against fungal strains, especially for candida albicans. The antifungal activities against C .albicans of compounds 2b, 2d, 2e and 2l were comparable with that of fluconazole and were superior to that of polyoxin B. Meanwhile, the other compounds against C. albicans showed better antifungal activity (MIC 2 μg/mL) than polyoxin B except for compound 2n (MIC 4 μg/mL). The trial of drug combination use showed that these synthesized compounds had synergistic effects with fluconazole and polyoxin B. It indicated that these compounds were not competing with polyoxin B to bind with chitin synthase, which was also consistence with the result of enzymatic assays. The antibacterial experiment showed that these compounds had no activity against selected strains including three Gram-positive and three Gram-negative bacteria. These results showed that the designed compounds were chitin synthase inhibitors and had selective antifungal activity.
- Ji, Qinggang,Li, Baihui,Shen, Yangli,Wu, Hu,Wu, Xiaobo,Yuan, Lvjiang
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- Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation
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A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.
- Hosseini-Sarvari, Mona,Koohgard, Mehdi,Firoozi, Somayeh,Mohajeri, Afshan,Tavakolian, Hosein
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supporting information
p. 6880 - 6888
(2018/05/04)
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- Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds
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Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.
- Firoozi, Somayeh,Hosseini-Sarvari, Mona,Koohgard, Mehdi
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supporting information
p. 5540 - 5549
(2019/01/03)
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- Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium
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The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.
- Girish, Yarabhally R.,Pandit, Subrata,Pandit, Subhendu,De, Mrinmoy
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supporting information
p. 2393 - 2398
(2017/09/11)
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- Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita
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Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.
- Eloh, Kodjo,Demurtas, Monica,Mura, Manuel Giacomo,Deplano, Alessandro,Onnis, Valentina,Sasanelli, Nicola,Maxia, Andrea,Caboni, Pierluigi
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p. 4876 - 4881
(2016/07/06)
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- Study of the diels-alder and retro-diels-alder reaction between furan derivatives and maleimide for the creation of new materials
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The Diels-Alder reaction leads to a mixture of two diastereomers, one called endo and the other one exo. The cyclo-reversion temperature of the first one is lower than the exo adduct and the ratio between endo and exo adducts varies according to the substituents of the Diels-Alder partners and experimental parameters. Therefore, the influence of some reaction parameters such as the substituents of furan and maleimide derivatives, the reaction temperature and the presence of a nucleophile on the endo/exo Diels-Alder ratio and/or the retro-Diels-Alder reaction have been studied. For instance, furan and maleimide derivatives with electron withdrawing substituents induced the creation of the endo adduct preferentially. Also the presence of a far electron withdrawing substituent on furan and/or an electron attracting mesomeric substituent on maleimide resulted in a faster reversibility of the endo adduct. Finally, a high temperature and the presence of a nucleophile (thiol) also induced faster retro-Diels-Alder kinetics. Moreover, it was proved that isomerization from the endo to the exo diastereomer is preceded by a retro-Diels-Alder reaction of the endo adduct. The presence of a nucleophile in the mixture confirmed this result. This study allowed the highlighting of different parameters of the Diels-Alder reaction to obtain as much endo adduct as possible, and a fast and/or full retro-Diels-Alder reaction of this adduct.
- Froidevaux,Borne,Laborbe,Auvergne,Gandini,Boutevin
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p. 37742 - 37754
(2015/05/13)
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- Chemical reactivity and antimicrobial activity of N-substituted maleimides
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Several N-substituted maleimides containing substituents of varying bulkiness and polarity were synthesised and tested for antimicrobial and cytostatic activity. Neutral maleimides displayed relatively strong antifungal effect minimum inhibitory concentrations (MICs in the 0.54 g ml-1 range); their antibacterial activity was structure dependent and all were highly cytostatic, with IC50 values below 0.1 g ml-1. Low antimicrobial but high cytostatic activity was noted for basic maleimides containing tertiary aminoalkyl substituents. Chemical reactivity and lipophilicity influenced antibacterial activity of neutral maleimides but had little if any effect on their antifungal and cytostatic action. N-substituted maleimides affected biosynthesis of chitin and β(1,3)glucan, components of the fungal cell wall. The membrane enzyme, β(1,3)glucan synthase has been proposed as a putative primary target of N-ethylmaleimide and some of its analogues in Candida albicans cells.
- Salewska, Natalia,Boros-Majewska, Joanna,Lcka, Izabela,Chylinska, Katarzyna,Sabisz, Michal,Milewski, Slawomir,Milewska, Maria J.
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scheme or table
p. 117 - 124
(2012/04/18)
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- Total synthesis of (±)-dysibetaine CPa and analogs
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The syntheses of the marine sponge-derived γ-amino carboxylic acid dysibetaine CPa and five analogs in their racemic forms were successfully performed by taking advantage of an electron-withdrawing N-(4-nitrophenyl) group in the cyclopropanation reaction,
- Oikawa, Masato,Sasaki, Shota,Sakai, Michihiro,Ishikawa, Yuichi,Sakai, Ryuichi
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p. 5789 - 5802,14
(2020/09/15)
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- A facile synthesis of N-substituted maleimides
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A simple and efficient method for the synthesis of N-substituted maleimides from the corresponding maleamic acids under the phase transfer catalysis has been described.
- Deshpande, Sunita R.,Maybhate, Shailaja P.,Likhite, Anjali P.,Chaudhary, Preeti M.
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body text
p. 487 - 488
(2010/10/18)
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- Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore
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Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 cells. Methyl N-arylfumaramates showed the highest cytotoxic potencies and, in particular, methyl N-(3,4-dichlorophenyl)fumaramate is six times more potent than melphalan towards L1210 cells and is equipotent with this drug in the Molt 4/C8 assay. Electrophilicity of compounds under investigation was demonstrated by carrying out thiolation using model benzyl mercaptan on representative compounds. Methyl N-(3,4-dichlorophenyl)fumaramate and methyl N-(4-chlorophenyl)maleamate inhibited human N-myristoyltransferase, a possible molecular target, in high micromolar range. QSAR and molecular modeling revealed some correlations between different structural features of a number of the molecules and cytotoxic potencies. Methyl N-arylfumaramates were well tolerated in mice in comparison to the analogs in other series of compounds tested. The data obtained in this investigation affords guidelines for preparing new series of molecules with greater potencies.
- Jha, Amitabh,Mukherjee, Chandrani,Prasad, Ashok K.,Parmar, Virinder S.,Vadaparti, Manjula,Das, Umashankar,De Clercq, Erik,Balzarini, Jan,Stables, James P.,Shrivastav, Anuraag,Sharma, Rajendra K.,Dimmock, Jonathan R.
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scheme or table
p. 1510 - 1515
(2010/06/16)
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- Chemospecific allylation and domino metathesis of 7-oxanorbornenes for skeletal and appendage diversity
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We report a synthetic strategy for skeletally diverse heterocycles featuring appendage diversity based on a tandem Ugi/ Diels-Alder reaction followed by domino metathesis. An associating effect of the amide carbonyl functionality to the ruthenium metal ce
- Ikoma, Minoru,Oikawa, Masato,Sasaki, Makoto
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experimental part
p. 72 - 84
(2009/06/18)
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- Reactions of Cyclic Anhydrides: Part VI - Transesterification of Maleanilic and Fumaranilic Acids with Phosphorus Pentoxide-Alkanol
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Mixed phosphorus esters obtained from alkanols and phosphorus pentoxide furnish the corresponding esters in 80-90percent yield when refluxed with maleanilic and fumaranilic acids.
- Wagh, S. B.,Balasubramaniyan, P.,Balasubramaniyan, V.
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p. 577 - 578
(2007/10/02)
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