摘要 :
Isatins are valuable intermediates for heterocyclic chemistry. Most of the common methods for their production are less than adequate when the number and lipophilicjty of substituents on the targeted isatin are increased. Our grou...
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Isatins are valuable intermediates for heterocyclic chemistry. Most of the common methods for their production are less than adequate when the number and lipophilicjty of substituents on the targeted isatin are increased. Our group desired such molecules and identified an alternative method for their production.
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Using an optical biosensor Biacore 3000 the interaction of human recombinant cytokeratins (CK)with isatin analogues (5-aminocaproyl-isatin and 5-aminoisatin) immobilized on the CM5 chip has beeninvestigated. CK-14 effectively inte...
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Using an optical biosensor Biacore 3000 the interaction of human recombinant cytokeratins (CK)with isatin analogues (5-aminocaproyl-isatin and 5-aminoisatin) immobilized on the CM5 chip has beeninvestigated. CK-14 effectively interacted with 5-aminocaproyl-isatin immobilized on the carboxymethyldextran chip surface, but not with a "shorter" analogue (5-aminoisatin). In contrast to CK14, CK8 effectivelyinteracted only with 5-aminoisatin. In both cases cytokeratin binding with the immobilized isatin analogueswas characterized by rather high affinity (K_dof 0.7 μM for the pair CK14/immobilized 5-aminocaproyl-isatin and 1.7 μM for the pair CK8/immobilized 5-aminoisatin). CK20 did not interact with both immobi-lized isatin analogues. Taking into consideration non-specific binding of mouse CK14 and rat CK8 with5-aminocaproyl-isatin Sepharose we have performed comparative analysis of amino acid sequences ofhuman, mouse, and rat CK8 and CK14. The data obtained suggest that in the case of human, mouse, and ratCK14 the N-terminal domain is the most variable among these species, whereas the major differencesbetween amino acid sequences of human, mouse, and rat CK8 have been found both in N-terminal andC-terminal regions
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A general method for the construction of trifluoromethylated 2-quinolinones has been established herein by using a trifluoromethylative ring expansion of isatin with trifluorodiazoethane. The strategy provides a platform for the r...
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A general method for the construction of trifluoromethylated 2-quinolinones has been established herein by using a trifluoromethylative ring expansion of isatin with trifluorodiazoethane. The strategy provides a platform for the rapid synthesis of a wide range of substituted 3-hydroxy-4-trifluoromethyl-2-quinolinones. This operationally simple and robust Ag-catalyzed protocol successfully transforms isatin ketimines to 3-amino-4-trifluoromethylquinolinones in excellent yields. The utility of this novel method is further illustrated by the conversion of the products into various synthetically and medicinally relevant molecules.
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A simple, inexpensive, environmentally friendly, and high yield protocol is described for the synthesis of (5-methylfuran/thiophene-2-yl)isatin by the reaction of 2-methylfuran/2-methylthiophene with isatin/isatin imine in the pr...
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A simple, inexpensive, environmentally friendly, and high yield protocol is described for the synthesis of (5-methylfuran/thiophene-2-yl)isatin by the reaction of 2-methylfuran/2-methylthiophene with isatin/isatin imine in the presence of FeCl3. The present protocol is ideal for the direct introduction of 2-methylfuran/2-methylthiophene onto isatin at 3-position with complete regioselectivity.
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This paper describes the preparation of a series of 16 anthranilic acids in yields ranging from 51 to 97%, by treating the isatins with NaOH and H2O2. Independently of the nature of the substituent on the aromatic ring, the reacti...
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This paper describes the preparation of a series of 16 anthranilic acids in yields ranging from 51 to 97%, by treating the isatins with NaOH and H2O2. Independently of the nature of the substituent on the aromatic ring, the reactions were complete in 15 min at room temperature, whereas those of isatins containing a substituent on the nitrogen atom required longer reaction time for completion (45 min) under the same reaction conditions.
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Isatin is an endogenous compound identified in humans that possesses a wide range of biological activities. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide r...
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Isatin is an endogenous compound identified in humans that possesses a wide range of biological activities. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro. A series of p-substituted isatin semicarbazones have shown anticonvulsant activity in MES, scPTZ and scSTY tests. Various isatin-N-Mannich bases of isatin-3-thiosemicarbazones have shown antiviral and tuberculostatic activity. Methisazone is an effective compound against variola and vaccinia viruses. The N-dimethyl and morpholino derivative of 5-methyl isatin and trimethoprim exhibited an EC50 of more than 4.3 and 17.7 mg mL(-1), respectively. Isatin (3-o-nitrophenyl) hydrazone has shown activity against Walker carcinoma-256. Various substituted indolinones showed antitubercular activity against M. tuberculosis H37Rv with MIC ranging from 10-20 microg mL(-1). Isatin derivatives of Mannich bases had fibrinolytic, muscle relaxant, antiallergic, immunosuppressant, and antithrombotic activity. Isatin showed cardioinhibitory effect on frog heart, and hypotensive, respiratory depression and antidiuretic effects.
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The reactions of N-acetyl isatin and N-propionyl isatin with morpholine, piperazine and diethylamine in acetonitrile underwent nucleophilic substitution reactions at the amide linkage with ring opening process to give N-[2-(2-amin...
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The reactions of N-acetyl isatin and N-propionyl isatin with morpholine, piperazine and diethylamine in acetonitrile underwent nucleophilic substitution reactions at the amide linkage with ring opening process to give N-[2-(2-amino-2-oxo-acetyl)phenyl]acetamide derivatives and N-[2-(2-amino-2-oxoacetyl)phenyl]propionamide derivatives, respectively. The rate constants of the titled reactions were studied spectrophotometerically in pure acetonitrile and acetonitrile-water mixed solvent. The reactions in pure acetonitrile obeyed third order kinetics. The activation parameters suggest that the mechanism of the reaction proceeds by parallel specific base and dimer mechanisms depending on temperature and the nature of amine. The reaction of isatin with piperazine in acetonitrile-water mixed solvent passes through formation of solvated intermediate which in turn gives zwitterionic ion intermediate that leads to the final product in a slow step. The nonlinear plots of log k_N versus 1/D of the binary solvent as well as the plot of log k_N versus X_(H2O), indicate a specific solvation. The plot of log k_N versus log [H20] gives the number of water molecules (n) contaminated in the transition state. The inversely proportional correlation between E_T~N and log k_A values agrees with the formation of solvated zwitterionic (tetrahedral) intermediates in the rate determined step. The application of multiparameter approach of α,β and π* indicates that the rate of the reaction is influenced by both specific and nonspecific solute-solvent interactions.
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Seven isatin derivatives have been designed, and their chemical structures were characterized by single crystal X-ray diffraction studies, H-1 NMR, MS, and elemental analysis. Structural stabilization followed by intramolecular as...
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Seven isatin derivatives have been designed, and their chemical structures were characterized by single crystal X-ray diffraction studies, H-1 NMR, MS, and elemental analysis. Structural stabilization followed by intramolecular as well as intermolecular H-bonds makes these molecules as perfect examples in molecular recognition with self-complementary donor and acceptor units within a single molecule. These compounds were evaluated for antimicrobial activities. Docking simulations have been performed to position compounds into the FtsZ active site to determine their probable binding models. All of the compounds exhibited better antibacterial activities. Interestingly, compound 5c and 5d exhibited better antibacterial activities with IC50 values of 0.03 and 0.05 mu mol/mL against Staphylococcus aureus, respectively. Compound 5g displays antibacterial activity with IC50 values of 0.672 and 0.830 mu mol/ml, against Escherichia coli and Pseudomonas aeruginosa, respectively. (C) 2016 Elsevier B.V. All rights reserved.
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The mol-ecule of the title compound, C8H4ClNO2, is planar, with the non-H atoms possessing an r.m.s. deviation from planarity of 0.062??. In the crystal, mol-ecules are linked through N—H?O hydrogen bonds, forming chains along [0...
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The mol-ecule of the title compound, C8H4ClNO2, is planar, with the non-H atoms possessing an r.m.s. deviation from planarity of 0.062??. In the crystal, mol-ecules are linked through N—H?O hydrogen bonds, forming chains along [010]. The chains are further linked through C—H?O hydrogen bonds, forming layers parallel to (001).
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A convenient, one-pot synthesis of N-isatinylmethylthioacetic acid and several of its derivatives, as potential anticancer agents, by reactions of N-(hydroxymethyl)isatins with Bunte salts in TFA is described. The reactions involv...
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A convenient, one-pot synthesis of N-isatinylmethylthioacetic acid and several of its derivatives, as potential anticancer agents, by reactions of N-(hydroxymethyl)isatins with Bunte salts in TFA is described. The reactions involve attack of these salts on the S(II) atom by C-electrophilic species generated from hydroxy derivatives.
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