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Indole Derivatives (indole + derivative)
Selected AbstractsDeprotonation of Indole Derivatives in Aqueous Cationic SurfactantsEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 5 2004Nicoletta Spreti Abstract Deprotonations of 5-nitroindole, 1a, and its 2-carboxylate ion, 2a, have been monitored in 0.01, 0.1, and 0.5 M NaOH in micellar solutions of cetyl trialkylammonium bromide, alkyl = Me, Et, nPr, nBu, CTABr, CTEABr, CTPABr, CTBABr. Extents of deprotonation (% f) have been fitted using the pseudophase model of micellar effects with interionic competition described by ion exchange or by independent association constants. Both treatments indicate that base dissociation constants in dilute OH, are lower than in water by factors of ca. 3,11, and decrease with increasing bulk of the head groups, and that these factors increase modestly as the OH, concentration increases to 0.5 M. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) [source] Sulfur-Assisted and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Catalyzed Cyclization of 2-Alkynylanilines for the Metal-Free Synthesis of Indole DerivativesADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 13 2010Hongwei Zhou Abstract A sulfur-assisted and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed cyclization of 2-alkynylanilines for the metal-free synthesis of indole derivatives is reported. As a result of the metal-free process, the ready availability of the starting materials and the simple and convenient operation, the type of reaction presented here has potential utility in organic synthesis. A 10-gram scale preparation may demonstrate the possibility of its application in the environmentally friendly synthesis of indole derivatives. [source] Development of Diphenylamine-Linked Bis(imidazoline) Ligands and Their Application in Asymmetric Friedel,Crafts Alkylation of Indole Derivatives with NitroalkenesADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 7 2010Han Liu Abstract The new diphenylamine-linked bis(imidazoline) ligands were prepared through Kelly-You's imidazoline formation procedure mediated by Hendrickson's reagent in good yields. The novel ligands were tested in the asymmetric Friedel,Crafts alkylation of indole derivatives with nitroalkenes. In most cases, good yields (up to 97%) and excellent enantioselectivities (up to 98%) can be achieved. The optimized bis(imidazoline) ligand with trans -diphenyl substitution on the imidazoline ring gave better enantioselectivity than the corresponding bis(oxazoline) ligand. [source] Exciplex-type Behavior and Partition of 3-Substituted Indole Derivatives in Reverse Micelles Made with Benzylhexadecyldimethylammonium Chloride, Water and Benzene,PHOTOCHEMISTRY & PHOTOBIOLOGY, Issue 2 2001Claudio D. Borsarelli ABSTRACT The fluorescence properties of 3-methylindole (MI), 3-indoleacetic acid (IAA), 3-indoleethyltrimethylammonium bromide (IETA), l -tryptophan (Trp) and tryptamine hydrochloride (TA) were studied in reverse micelles solutions made with the cationic surfactant benzylhexadecyldimethylammonium chloride (BHDC) in benzene as a function of the molar ratio water/surfactant R (=[H2O]/[BHDC]). The fluorescence quenching of the model compound MI by benzene in cyclohexane solutions and by BHDC in benzene solutions were also studied in detail. The fluorescence of MI in benzene is characteristic of a charge-transfer exciplex. The exciplex is quenched by the presence of BHDC, due to the interactions of the surfactant ion pairs with the polar exciplex. In reverse micelle solutions at low R values, all the indoles show exciplex-type fluorescence. As R increases, the fluorescence behavior strongly depends on the nature of the indole derivative. The anionic IAA remains anchored to the cationic interface and its fluorescence is quenched upon water addition due to the increases of interface's micropolarity. For IETA, TA and Trp an initial fluorescence quenching is observed at increasing R, but a fluorescence recovery is observed at R > 5, indicating a probe partition between the micellar interface and the water pool. For the neutral MI, the fluorescence changes with R indicate the partition of the probe between the micellar interface and the bulk benzene pseudophase. A simple two-site model is proposed for the calculation of the partition constants K as a function of R. In all cases, the calculation showed that even at the highest R value, about 90% of the indole molecules remain associated at the micellar interface. [source] 2-Aryl-3-(1H -Azol-1-yl)-1H -Indole Derivatives: A New Class of Antimycobacterial Compounds , Conventional Heating in Comparison with MW-Assisted SynthesisARCHIV DER PHARMAZIE, Issue 12 2009Daniele Zampieri Abstract 2-Aryl-3-(1H -imidazol-1-yl and 1H -1,2,4-triazol-1-yl)-1H -indole derivatives were synthesized and tested for their in-vitro antifungal and antimycobacterial activities. These indole derivatives were devoid of antifungal activity against the tested strains of Candida spp. Yet, they exhibited an interesting antitubercular activity against Mycobacterium tuberculosis reference strain H37Rv. [source] Reinvestigation of a Cyclic Dipeptide N -Prenyltransferase Reveals Rearrangement of N-1 Prenylated Indole DerivativesCHEMBIOCHEM, Issue 7 2008Han-Li Ruan Prof. Dr. Converting revere to regular: Reinvestigation of cyclic dipeptide N -prenyltransferase (CdpNPT) revealed that the enzymatic products are derivatives that carry 3,-(3,,3,)-dimethylallyl moieties at the N-1 position of the indole ring, and they undergo rearrangement in the presence of acids, such as trichloroacetic acid, used for termination of enzymatic reactions and protein precipitation (see scheme). The rearrangement can be avoided by using MeOH instead of acid for termination and protein precipitation. [source] Research Letter: New Potent Indole Derivatives as Hyaluronidase InhibitorsCHEMICAL BIOLOGY & DRUG DESIGN, Issue 6 2007Süreyya Ölgen Because of the physiologic importance of hyaluronidases, the identification of potent and selective inhibitors of hyaluronidases has become increasingly important. A variety of assay methods have been used for such a purpose, i.e. classical turbidimetric, viscometric and colorimetric. In this study, a modified enzymatic assay has been used to obtain a microtiter plate-based sensitive activity screening. All inhibitors were tested in a stains-all assay at pH 7 and in a Morgan-Elson assay at pH 3.5. Among the tested compounds, 1, 2, 3, 6, 7, 8, 16, 17 and 18 showed good inhibition of more than 50%, so the IC50 values of these derivatives were determined in the range of 25,41 ,m. The IC50 value of the most active hyaluronidase inhibitor Vcpal (6-palmitoyl- l -ascorbic acid) was measured as 8.36 ,m. All inhibitors including Vcpal showed twofold less activity at pH 3.5 in a Morgan-Elson assay. Examination of substituent effects on the activity showed that para -positions of benzamide needs to be chlorinated or fluorinated to obtain good inhibitory effect. It was found that the introduction of a p -fluoro benzyl ring in the indole nitrogen has a positive effect for the inhibitory effects of both indole-2- and 3-carboxamide derivatives. [source] ChemInform Abstract: tert-Butyl (2S)-(p-Tolylsulfonyloxy)propionate (II) , A Suitable Reagent for the Direct Alkylation of Indole Derivatives.CHEMINFORM, Issue 24 2009A. V. Kurkin Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source] A Novel Palladium Catalyst for the Amination of Electron-Rich Indole Derivatives.CHEMINFORM, Issue 31 2007Nicolle Schwarz Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source] A New Cuburbit[8]uril-Based Fluorescent Receptor for Indole DerivativesCHEMINFORM, Issue 23 2007Yonghua Ling Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source] PTC-Promoted Japp,Klingmann Reaction for the Synthesis of Indole Derivatives (IV).CHEMINFORM, Issue 42 2005Wei He No abstract is available for this article. [source] A New Approach for the Synthesis of 2-Substituted Indole Derivatives via Michael Type Adducts.CHEMINFORM, Issue 29 2005Hueseyin Cavdar Abstract For Abstract see ChemInform Abstract in Full Text. [source] A Facile Synthesis of Various Fluorine-Containing Indole Derivatives via Palladium-Catalyzed Annulation of Internal Alkynes.CHEMINFORM, Issue 33 2004Jungha Chae Abstract For Abstract see ChemInform Abstract in Full Text. [source] Synthesis of 5-Substituted Indole Derivatives.CHEMINFORM, Issue 13 2004Part 5. Abstract For Abstract see ChemInform Abstract in Full Text. [source] ChemInform Abstract: Methyl 3-Amino-1H-indole-2-carboxylates in the Synthesis of 5H-Pyrimido[5,4-b]indole Derivatives.CHEMINFORM, Issue 8 2010A. S. Shestakova Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source] Design and Synthesis of 2,3,4,9-Tetrahydro-1H-carbazole and 1,2,3,4-Tetrahydro-cyclopenta[b]indole Derivatives as Non-Nucleoside Inhibitors of Hepatitis C Virus NS5B RNA-Dependent RNA Polymerase.CHEMINFORM, Issue 31 2006Ariamala Gopalsamy Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source] First Synthesis of Pyrrolo[1,2:1,,2,]azepino[5,6-b]indole Derivatives.CHEMINFORM, Issue 48 2003Julien Perron Abstract For Abstract see ChemInform Abstract in Full Text. [source] Synthesis of Pyrano[3,2-b]indole Derivatives Based on Intramolecular Hetero-Diels,Alder of 2-Benzylidene-2,3-dihydro-1H-indol-3-ones.CHEMINFORM, Issue 46 2003Yann Davion Abstract For Abstract see ChemInform Abstract in Full Text. [source] Rearrangement of Spiro[2H-1-benzopyran-2,2,-[2H]indoles] to Pyrrolo[1,2-a]indole Derivatives.CHEMINFORM, Issue 21 2003Vytas Martynaitis Abstract For Abstract see ChemInform Abstract in Full Text. [source] N -Glucosyl-1H -indole Derivatives from Cortinarius brunneus (Basidiomycetes)CHEMISTRY & BIODIVERSITY, Issue 4 2008Axel Teichert Abstract Two new N -glucosylated indole alkaloids were isolated from fruiting bodies of the basidiomycete Cortinarius brunneus (Pers.) Fr. The structures were elucidated by means of the spectroscopic data. Additionally, the very recently reported compounds N- 1 -,- glucopyranosyl-3-(carboxymethyl)-1H -indole (3) and N- 1 -,- glucopyranosyl-3-(2-methoxy-2-oxoethyl)-1H -indole (4) could be detected. Compound 3 is the N -glucoside of the plant-growth regulator 1H -indole-3-acetic acid (IAA), but, in contrast, it does not exhibit auxin-like activity in an Arabidopsis thaliana tap root elongation assay. [source] One-pot synthesis of the indole derivative 4-chloro-3-sulphamoyl- N -(2,3-dihydro-2-methyl-1H -indol-1-yl)benzamide (indapamide)JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 1 2004Barbara Ziobro New methods for the synthesis the indole derivative, Indapamide (1), using mixed anhydrides of the general formula R1COOCOOR2 (2) or DCC (N,N'-dicyclohexylcarbodiimide) (3), are described. [source] Exciplex-type Behavior and Partition of 3-Substituted Indole Derivatives in Reverse Micelles Made with Benzylhexadecyldimethylammonium Chloride, Water and Benzene,PHOTOCHEMISTRY & PHOTOBIOLOGY, Issue 2 2001Claudio D. Borsarelli ABSTRACT The fluorescence properties of 3-methylindole (MI), 3-indoleacetic acid (IAA), 3-indoleethyltrimethylammonium bromide (IETA), l -tryptophan (Trp) and tryptamine hydrochloride (TA) were studied in reverse micelles solutions made with the cationic surfactant benzylhexadecyldimethylammonium chloride (BHDC) in benzene as a function of the molar ratio water/surfactant R (=[H2O]/[BHDC]). The fluorescence quenching of the model compound MI by benzene in cyclohexane solutions and by BHDC in benzene solutions were also studied in detail. The fluorescence of MI in benzene is characteristic of a charge-transfer exciplex. The exciplex is quenched by the presence of BHDC, due to the interactions of the surfactant ion pairs with the polar exciplex. In reverse micelle solutions at low R values, all the indoles show exciplex-type fluorescence. As R increases, the fluorescence behavior strongly depends on the nature of the indole derivative. The anionic IAA remains anchored to the cationic interface and its fluorescence is quenched upon water addition due to the increases of interface's micropolarity. For IETA, TA and Trp an initial fluorescence quenching is observed at increasing R, but a fluorescence recovery is observed at R > 5, indicating a probe partition between the micellar interface and the water pool. For the neutral MI, the fluorescence changes with R indicate the partition of the probe between the micellar interface and the bulk benzene pseudophase. A simple two-site model is proposed for the calculation of the partition constants K as a function of R. In all cases, the calculation showed that even at the highest R value, about 90% of the indole molecules remain associated at the micellar interface. [source] Raman Spectroscopy Detects Cardiac Allograft Rejection with Molecular SpecificityCLINICAL AND TRANSLATIONAL SCIENCE, Issue 3 2009Yoon Gi Chung B.S. Abstract Spatially resolved Raman spectroscopy is shown here to be capable of molecular-specific detection without exogenous labeling. This molecular specificity is achieved by detecting the strong and characteristic Raman spectral signature of an indole derivative, serotonin, whose selective existence in rejected heart transplants serves as the biomarker. The study also corroborates the increasingly recognized role of serotonin receptors in various immune responses, including cardiac allograft rejection. Combining both medical and physical sciences, this work demonstrates the potential use of Raman spectroscopy in replacing the invasive endomyocardial biopsy as the standard for post-transplantation rejection surveillance and presents a new paradigm in advancing clinical care through interdisciplinary studies. [source] Synthesis of Novel Polycyclic Indole-Annulated Thiopyranocoumarin Derivatives via Domino Knoevenagel,Hetero- Diels,Alder Reaction in Aqueous MediaHELVETICA CHIMICA ACTA, Issue 5 2010Firouz, Matloubi Moghaddam Abstract An efficient synthesis of polycyclic indole derivatives is achieved via domino Knoevenagel,hetero- Diels,Alder reaction of O -acrylated salicylaldehyde derivatives with dihydroindole-2-thiones in H2O as solvent. The products are formed in good-to-excellent yields with high regio- and stereoselectivity. [source] Sulfur-Assisted and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Catalyzed Cyclization of 2-Alkynylanilines for the Metal-Free Synthesis of Indole DerivativesADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 13 2010Hongwei Zhou Abstract A sulfur-assisted and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed cyclization of 2-alkynylanilines for the metal-free synthesis of indole derivatives is reported. As a result of the metal-free process, the ready availability of the starting materials and the simple and convenient operation, the type of reaction presented here has potential utility in organic synthesis. A 10-gram scale preparation may demonstrate the possibility of its application in the environmentally friendly synthesis of indole derivatives. [source] Development of Diphenylamine-Linked Bis(imidazoline) Ligands and Their Application in Asymmetric Friedel,Crafts Alkylation of Indole Derivatives with NitroalkenesADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 7 2010Han Liu Abstract The new diphenylamine-linked bis(imidazoline) ligands were prepared through Kelly-You's imidazoline formation procedure mediated by Hendrickson's reagent in good yields. The novel ligands were tested in the asymmetric Friedel,Crafts alkylation of indole derivatives with nitroalkenes. In most cases, good yields (up to 97%) and excellent enantioselectivities (up to 98%) can be achieved. The optimized bis(imidazoline) ligand with trans -diphenyl substitution on the imidazoline ring gave better enantioselectivity than the corresponding bis(oxazoline) ligand. [source] Trapping of Active Methylene Intermediates with Alkenes, Indoles or Thiols: Towards Highly Selective Multicomponent ReactionsADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 18 2009Yanlong Gu Abstract In this paper, a basic method to access new multicomponent reactions (MCRs) is reported. The mechanism of these MCRs is based on the trapping of methylene intermediates, formed in situ by reaction of formaldehyde with electron-rich carbons, with alkene, thiol or indole derivatives. According to our strategy, a wide range of valuable skeletons has been obtained in a one-pot reaction, thus allowing a minimization of waste, cost and labor. The presented methodology exhibits a broad substrate scope and electron-rich carbons in the ,-position of a hydroxy or carbonyl group were found to be particularly efficient. More generally, this work offers new tools for creating molecular complexity and diversity from one of the simplest organic building blocks, formaldehyde. [source] Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenaseLETTERS IN APPLIED MICROBIOLOGY, Issue 6 2003J.Y. Kim Abstract Aims: To isolate and characterize the phorate [O,O-diethyl-S-(ethylthio)methyl phosphoradiothioate] degrading bacteria from agricultural soil, and their assessment for multifarious biological activities of environmental and agronomic significance. Methods and Results: Based on their morphological and biochemical characteristics, the selected isolates PS-1, PS-2 and PS-3 were presumptively identified as Rhizobium, Pseudomonas and Proteus species, respectively. The HPLC analysis of phorate in bioaugmented soil revealed its complete disappearance within 40 days. The degradation isotherms of the isolates PS-1, PS-2 and PS-3 suggested time-dependent disappearance of phorate following the first-order rate kinetics at the corresponding rate constants of 0.04, 0.05 and 0.04 d,1. Besides, the isolates concurrently exhibited substantial phosphate solubilization, indole acetic acid (IAA) and siderophore production, as well as limited biocontrol activity against fungal phytopathogens. Conclusions, Significance and Impact of the Study: The data revealed the potential of isolates for collateral plant growth promotion, biocontrol and bioremediation. The selected strains may serve as an important bioresource for development of effective super-bioinoculants. [source] Low-temperature study of 3-acetylindole at 110,KACTA CRYSTALLOGRAPHICA SECTION C, Issue 7 2008Barbara Hachu The title compound, C10H9NO, contains an acetyl group that is nearly coplanar with the indole ring system, with an angle between the planes of the heterocyclic ring and the acetyl group of 1.75,(17)°. The planes of the benzene and pyrrole rings in the indole system make a dihedral angle of 2.05,(11)°. Each molecule in the unit cell is linked through N,H...O hydrogen bonds to two other molecules, forming hydrogen-bonded chains in the [101] direction with graph set C(6). The significance of this study lies in the analysis of the interactions occurring via hydrogen bonds in this structure, as well as in the comparison drawn between the molecular structure of the title compound and those of several other indole derivatives possessing a 3-carbonyl group. The correlation between the IR spectrum of this compound and the structural data is also discussed. [source] Highly efficient bimetallic iron-palladium catalyzed Michael-type Friedel,Crafts reactions of indoles with chalconesAPPLIED ORGANOMETALLIC CHEMISTRY, Issue 3 2009Yue-Hua Gao Abstract Iron,palladium is a superior bimetallic catalyst in the presence of acetylacetone (Acac) with remarkable synergistic effect for the Michael-type Friedel,Crafts reactions of indoles with chalcones. This catalytic system has the advantages of mild reaction conditions, smaller amount of metal salts, high yields of the desired products and operational simplicity, which make it a useful and promising process for the synthesis of indole derivatives. Copyright © 2009 John Wiley & Sons, Ltd. [source] | ||||||||||||||||||||||||||||