- Thermally Sensitive Protecting Groups for Cysteine, and Manufacture and Use Thereof
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In a preferred embodiment, there is provided a protecting group for protecting the thiol side chain of a cysteine residue, the protecting group comprising a Diels-Alder cycloadduct of a furan and a maleimide, and optionally, a linker interposed between the thiol side chain and the Diels-Alder cycloadduct.
- -
-
Paragraph 0085; 0090
(2021/02/12)
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- Novel p-nitrophenyl maleanilic acid and its organometallic chelates of Cr, Mo and W carbonyls structure evaluation using different techniques and chromium chelate cytotoxicity
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Novel p-nitrophenyl maleanilic acid bidentate free ligand (PNMA) was synthesized eco-friendly by solvent free reaction between 4-nitroaniline and maleic anhydride. Some novel mixed ligand organometallic chelates of formulae [M(CO)4L] (M = Cr, Mo, or W and
- Zayed,Oraby, Khloud R.,Hassan, Fatma S.M.
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p. 4327 - 4340
(2020/12/09)
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- 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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-
- Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction
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A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).
- Xu, Wen-Lei,Tang, Lei,Ge, Chen-Yu,Chen, Jie,Zhou, Ling
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supporting information
p. 2268 - 2273
(2019/04/10)
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- Acetylcholinesterase inhibition by products generated in situ from the transformation of N-arylisomaleimides
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When N-arylisomaleimides were transformed under enzymatic reaction conditions, the transformation reaction proved to be influenced by electronic effects. This was demonstrated qualitatively by 1H NMR spectroscopy and quantitatively by monitoring the kinetic of isomerization of N-phenylisomaleimide to N-phenylmaleimide. Subsequently, the first pseudo-order and activation energy (Ea) of the process were determined. The compounds showed in situ influence on AChE inhibition. The derivatives with electron-withdrawing groups exhibited a better effect than those having electron-donating groups. The in silico experiments show that the ligands evaluated established interactions with the CAS site. This suggests that these compounds could be useful for generating better reversible and competitive inhibitors of AChE.
- Guevara, Juan A.,Trujillo, José G.,Quintana, Delia,Jiménez, Hugo A.,Arellano, Mónica G.,Bahena, José R.,Tamay, Feliciano,Ciprés, Fabiola J.
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p. 989 - 1003
(2017/12/18)
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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)
-
- 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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- The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes
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The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acid (4) derivatives containing structural characteristics that can be used for the synthesis of several active molecules, is presented. Some of the butenoic acid derivatives (4a, 4c, 4e, 4i, 4j, 4k) are
- Oktay, Koray,K?se, Leyla Polat,?endil, K?v?lc?m,Gültekin, Mehmet Serdar,Gül?in, ?lhami,Supuran, Claudiu T.
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p. 939 - 945
(2016/10/09)
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- An approach to "escape from flatland": Chemo-enzymatic synthesis and biological profiling of a library of bridged bicyclic compounds
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A major reason for the low success rate in current drug development through chemical synthesis has been ascribed to the large fraction of quasi planar candidate molecules. Therefore, an "escape from flatland" strategy has been recommended for the generation of bioactive chemical entities. In a first attempt to test this recommendation, we synthesized a small collection of bridged bicyclic compounds possessing a rigid spherical core structure by combining a group of cyclic dienes with a collection of dienophiles. We started from planar biphenyl analogues and, by enzymatic dioxygenation, transformed them into hydroxylated diene structures. Using a small library of newly synthesized dienophiles, the dienes were converted into bridged bicycles via the Diels-Alder reaction. The resulting collection of 78 structures was first tested for bioactivity in a generic assay based on interference with the proliferation of mammalian cells. A more mechanism-targeted bioactivity profiling method, exploiting cellular impedance monitoring, was subsequently used to obtain suggestions for the mode of action exerted by those compounds that were the most active in the proliferation assay. Proteasome inhibition could be confirmed for 8 of a series of 9 respective candidates. Whilst 7 of these molecules showed relatively weak interference with proteasome activity, one candidate exerted a moderate but distinct inhibition. This result appears remarkable in view of the small size of the compound library, which was synthesized following a few basic considerations. It encourages the application of diverse synthetic approaches to further investigate the role of spherical shape for the success of compound libraries.
- Suryanarayana Birudukota,Franke, Raimo,Hofer, Bernd
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p. 3821 - 3837
(2016/05/09)
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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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- Triethylamine-catalyzed synthesis of oxazepine from maleamic acids
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2-Thioxo-1,3-oxazepine-4,7-dione compounds were obtained via triethylamine-catalyzed condensation of maleamic acids with thiophosgene under anhydrous conditions. This method features relatively a simple methodology, use of inexpensive reagents, convenient operating conditions and high yields.
- Badru, Rahul,Singh, Baldev
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p. 635 - 640
(2015/05/13)
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- DABCO-catalyzed [3+2] cycloaddition reactions of azomethine imines with N-aryl maleimides: Facile access to dinitrogen-fused heterocycles
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DABCO-catalyzed [3+2] cycloaddition of azomethine imines with maleimides has been developed. This method could efficiently furnish dinitrogen-fused tetracyclic heterocycles in high levels of regioselectivity and with good yields.
- Jia, Qianfa,Chen, Lei,Yang, Gongming,Wang, Jian,Wei, Jia,Du, Zhiyun
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supporting information
p. 7150 - 7153
(2015/12/12)
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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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- Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides
-
Itaconic anhydride reacts with aryl amines to give a substituent controlled equilibrium mixture of regioisomeric (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4- (arylamino)but-2-enoic acids. Electron-donating groups favor nucleophilic attack on C-5 carbonyl, while the presence of electron-withdrawing groups enhances the bias for attack on C-2 carbonyl. The treatment of (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl2-Et 3N in THF provided the corresponding maleimides in high yields while under the same conditions the maleic anhydride aryl amine addition products gave predominately the corresponding 3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent dependent ratio. TUeBITAK, 2012.
- Faturaci, Yeliz,Coskun, Necdet
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p. 749 - 758
(2013/02/25)
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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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- Chlorin photosensitizers sterically designed to prevent self-aggregation
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The synthesis and photophysical evaluation of new chlorin derivatives are described. The Diels-Alder reaction between protoporphyrin IX dimethyl ester and substituted maleimides furnishes endo-adducts that completely prevent the self-aggregation of the chlorins. Fluorescence, resonant light scattering (RLS) and 1H NMR experiments, as well as X-ray crystallographic have demonstrated that the configurational arrangement of the synthesized chlorins prevent π-stacking interactions between macrocycles, thus indicating that it is a nonaggregating photosensitizer with high singlet oxygen (ΦΔ) and fluorescence (Φf) quantum yields. Our results show that this type of synthetic strategy may provide the lead to a new generation of PDT photosensitizers.
- Uchoa, Adjaci F.,De Oliveira, Kleber T.,Baptista, Mauricio S.,Bortoluzzi, Adailton J.,Iamamoto, Yassuko,Serra, Osvaldo A.
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experimental part
p. 8824 - 8832
(2011/12/21)
-
- 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.
-
scheme or table
p. 1510 - 1515
(2010/06/16)
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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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- Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides
-
NMR spectra of a series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides were examined to estimate the electronic effect of the amide and imide groups on the chemical shifts of the hydrogen and carbon nuclei of the benzene ring.
- Lee, Hye Sun,Yu, Ji Sook,Lee, Chang Kiu
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scheme or table
p. 711 - 715
(2010/07/05)
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- Synthesis and copolymerization study of new polyimide precursors with potential application in optical and photonic field
-
New polyimide precursors were synthesized by simple one step procedure. (Z)-3-(4-Nitro-phenylcarbamoyl)-acrylic acid (A2), (Z)-3-(4-Ciano- phenylcarbamoyl)-acrylic acid (A3), (Z)-3-(4-Diethyl-phenylcarbamoyl)-acrylic acid (A4) and (Z)-3-[N'-(2,4-Dinitro-phenyl)-hydrazinocarbonyl]-acrylic acid (A6) were characterized by FT-IR, FT-NMR and UV-VIS spectroscopy. Test copolymerization successfully yielded copolymers that were characterized by FT-IR and FT-NMR spectroscopy. Improved solubility of these copolymers make them candidates for potential NLO applications.
- Nicolescu, Adriana Florica,Jerca, Victor Valentin,Albu, Ana-Maria,Vuluga, Dumitru Mircea,Draghici, Constantin
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experimental part
p. 38/[1080]-49/[1091]
(2009/10/11)
-
- Preparation, polymerization and characterization of some new maleimides
-
This article described the synthesis of poly N-arylmaleimides and copolymaleimides. The maleimides monomer N- (2-nitrophenyl)maleimide (2-NPMI), N-(3-nitrophenyl)maleimide (3-NPMI) and N-(4-nitrophenyl)maleimide (4-NPMI) were prepared from corresponding s
- Hiran,Paliwal,Chaudhary, Jyoti,Meena, Suresh
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p. 385 - 388
(2008/04/03)
-
- Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide
-
A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.
- Gupta,Wagh
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p. 697 - 702
(2007/10/03)
-
- Synthesis and antimicrobial activity of some succinimides
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A series of substituted succinimides 3 are prepared from hydrazides and maleimides. The compounds are characterized and screened for their antimicrobial activities.
- Shetgiri,Nayak
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p. 1933 - 1936
(2007/10/03)
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- α-chlorosuccinimides - A new source for maleimides and succinimides
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N-Arylmaleimides and N-arylsuccinimides were prepared by dehydrochlorination reaction of N-aryl α-chlorosuccinimides in the presence of a base and by reduction of 2-chlorosuccinimide in the presence of zinc, respectively. N-Aryl α-chlorosuccinimides were obtained by dehydration of N-aryl substituted maleamic acids in the presence of thionyl chloride. The structure of the synthesized compounds was confirmed by IR, 1H-NMR and 13C-NMR spectra.
- Gǎinǎ, Constantin,Gǎinǎ, Viorica
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p. 655 - 661
(2007/10/03)
-
- Synthesis and characterization of new compounds containing 1,4-dithiintetracarboxydiimide units
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New compounds containing 1,4-dithiintetracarboxydiimide units were synthesized by the disubstitution reaction of N-substituted 2,3- dichloromaleimide with sodium sulflde nonahydrate or thiourea. IR, UV-vis and 1H-NMR spectroscopy, as well as elemental analysis, confirmed their structures. Thermal conversion of 1,4-dithiine ring to thiophene was monitored by differential calorimetry (DSC) and thermogravimetric (TGA) measurements.
- Gǎinǎ, Constantin
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p. 601 - 607
(2007/10/03)
-
- Syntheses of 4-(3,5-bisphenylmethylene-4-oxopiperidin-1-yl)-4-oxo-but-2Z-enoic acid arylamides as candidate cytotoxic agents
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The title compounds were designed and synthesized as candidate cytotoxic agents. They were synthesized by reacting 3,5-bisphenylmethylene-piperidin-4-one with the appropriate 3-arylcarbamoylacrylic acids. These reactions follow an unusual mechanism and deviate from the previously reported reactions on similar substrates.
- Jha, Amitabh,Dimmock, Jonathan R.
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p. 1211 - 1223
(2007/10/03)
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- The electronic effects on the formation of N-aryl-maleimides and isomaleimides
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The synthesis of a range of aromatic maleimides and isomaleimides is reported. The effect of different substituents on the aromatic system and the products formed is also discussed.
- Fruk, Ljiljana,Graham, Duncan
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p. 2305 - 2313
(2007/10/03)
-
- Synthesis and antimicrobial activities of N-substituted imides
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In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.
- Zentz, Frederic,Valla, Alain,Le Guillou, Regis,Labia, Roger,Mathot, Anne-Gabrielle,Sirot, Danielle
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p. 421 - 426
(2007/10/03)
-
- Solid-state reaction between maleic anhydride and p-nitroaniline
-
p-Nitroaniline in the solid state reacts with maleic anhydride forming maleimic acid. Spectroscopic techniques supported the formation of this reaction product. The reaction products obtained from solution and solid-state have same stoichiometry but diffe
- Singh,Pathak
-
p. 1012 - 1015
(2007/10/03)
-
- Investigation of arene-arene interaction in stereoselective MCPBA epoxidation
-
Effect of arene-arene interaction in stereoselective MCPBA epoxidation was investigated using 5,6-dimethyl-2-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-diones 1. From the good correlation between the stereoselectivity of the products and Hammett's coefficients of para-substituents (σP) on the phenyl group, it was found that polar/π interaction between the phenyl group and MCPBA is the main interaction for controlling the stereoselectivity in the reaction. Other arene-arene interactions, charge-transfer complexation and edge-to-face interaction, were assumed to be much weaker than polar/π interaction in this reaction.
- Kishikawa, Keiki,Naruse, Mamoru,Kohmoto, Shigeo,Yamamoto, Makoto,Yamaguchi, Kentaro
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p. 462 - 468
(2007/10/03)
-
- Reactions of cyclic anhydrides with aromatic primary amines: Part 3 - Synthesis of novel 3-(N-arylcarbamoyl)- and 3-(N-naphthylcarbamoyl)carboxylic acids
-
Some hitherto unreported 3-(N-arylcarbamoyl)propenoic acids 7a-h and 3-(N-naphthylcarbamoyl)propenoic acid 9 have been synthesized in excellent yields, together with some propanoic acid analogues 11a-h and 12 as potential pesticides. Structural assignments of the products are based on elemental analyses and spectral (IR, 1H NMR, mass) data.
- Omuaru, V. O. T.
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p. 814 - 816
(2007/10/03)
-
- INFLUENCE OF MEDIUM AND SUBSTITUENTS ON ACYLATION OF AROMATIC AMINES AND THEIR POLYMERIC ANALOGS WITH MALEIC ANHYDRIDE
-
Correlation relationships describing the influence of substituents and solvents on the rate of acylation of aromatic amines and their polymeric analogs with maleic anhydride have been derived.
- Donya, A. P.,Pakter, M. K.,Sokhina, S. I.
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p. 2093 - 2097
(2007/10/02)
-
- Preparation and Characterisation of Chromium(III) Complexes of Maleanilic and Phthalanilic Acids
-
The complexes of the type , where A-A - maleanilic and phthalanilic acids, and their 4-methyl, 4-chloro, 4-nitro and 1-naphthyl derivatives have been prepared.The magnetic, conductance, ir and electronic spectral studies indicate their octahedral structure.
- Sharma, C. L.,Arya, R. S.,Narvi, S. S.
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p. 267 - 269
(2007/10/02)
-
- 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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- Antitumor chemotherapy. XIV. Cytotoxic activity of compounds possessing an ethylenic double bond substituted at the α and β positions with an electron attracting group
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The authors have previously shown that molecules possessing an ethylene double bond, activated by one or 2 electron attracting substituents, show a cytotoxic activity which must be connected with the addition of a cellular nucleophil to their double bond. This correlation has been extended to N alkylmaleinimides and different compounds with paraquinonine structure. The compounds examined possess a distinct cytotoxic antitumor activity which is, however, inferior to that of α nitro stilbenes and β nitro styrenes, the simplified analogs of aristolochic acid.
- Dore Ch.,Viel
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