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Fernando Rodrigues de Sá Alves et al.
Mini reviews in medicinal chemistry, 9(7), 782-793 (2009-06-13)
The indole scaffold probably represents one of the most important structural subunits for the discovery of new drug candidates. The demonstration that many alkaloids contain the indole nucleus, the recognition of the importance of essential amino acid tryptophan in human
Hélène Gérard et al.
The Journal of organic chemistry, 78(18), 9233-9242 (2013-08-07)
The chemo-, regio-, and stereoselectivities of multicomponent [4 + 2]/[3 + 2] domino cycloaddition reactions involving nitroindole derivatives with vinylethers and acrylates are studied computationnally and compared to experimental results. In this process, the nitroarene first reacts as an electron-deficient
Kap-Sun Yeung et al.
Bioorganic & medicinal chemistry letters, 23(1), 198-202 (2012-12-04)
A series of substituted carboxamides at the indole C7 position of the previously described 4-fluoro-substituted indole HIV-1 attachment inhibitor 1 was synthesized and the SAR delineated. Heteroaryl carboxamide inhibitors that exhibited pM potency in the primary cell-based assay against a
Rodolphe Beaud et al.
Angewandte Chemie (International ed. in English), 51(50), 12546-12550 (2012-11-06)
IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3) features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the
Kap-Sun Yeung et al.
Bioorganic & medicinal chemistry letters, 23(1), 203-208 (2012-12-04)
As part of the SAR profiling of the indole-oxoacetic piperazinyl benzamide class of HIV-1 attachment inhibitors, substitution at the C7 position of the lead 4-fluoroindole 2 with various 5- and 6-membered heteroaryl moieties was explored. Highly potent (picomolar) inhibitors of
Aleem Gangjee et al.
Bioorganic & medicinal chemistry, 21(4), 891-902 (2013-01-22)
A series of fourteen N(4)-(substituted phenyl)-N(4)-alkyl/desalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines was synthesized as potential microtubule targeting agents. The synthesis involved a Fisher indole cyclization of 2-amino-6-hydrazinylpyrimidin-4(3H)-one with cyclohexanone, followed by oxidation, chlorination and displacement with appropriate anilines. Compounds 6, 14 and 15 had low
Yasuoki Murakami
Proceedings of the Japan Academy. Series B, Physical and biological sciences, 88(1), 1-17 (2012-01-14)
We found that the Fischer indole synthesis of ethyl pyruvate 2-methoxyphenylhydrazone (5) with HCl/EtOH gave an abnormal product, ethyl 6-chloroindole-2-carboxylate (7), as the main product, with a smaller amount of ethyl 7-methoxyindole-2-carboxylate (6) as the normal product. This abnormal reaction
Nadeesha Ranasinghe et al.
Bioorganic & medicinal chemistry letters, 23(6), 1740-1742 (2013-02-16)
Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted
Arunima Chaudhuri et al.
Biochimica et biophysica acta, 1838(1 Pt B), 419-428 (2013-10-24)
The linear ion channel peptide gramicidin represents an excellent model for exploring the principles underlying membrane protein structure and function, especially with respect to tryptophan residues. The tryptophan residues in gramicidin channels are crucial for the structure and function of
Jean-Pierre H Perchellet et al.
Anticancer research, 34(4), 1643-1655 (2014-04-03)
Synthetic 6,7-annulated-4-substituted indole compounds, which elicit interesting antitumor effects in murine L1210 leukemia cells, were tested for their ability to inhibit human HL-60 tumor cell proliferation, disrupt mitosis and cytokinesis, and interfere with tubulin and actin polymerization in vitro. Various
Takayoshi Hiyama et al.
The FEBS journal, 281(14), 3113-3125 (2014-05-20)
The last two steps of l-tryptophan (Trp) biosynthesis are catalyzed by Trp synthase, a heterotetramer composed of TrpA and TrpB. TrpB catalyzes the condensation of indole, synthesized by TrpA, and serine to Trp. In the hyperthermophilic archaeon Thermococcus kodakarensis, trpA
Gang Li et al.
Microbiology (Reading, England), 159(Pt 2), 402-410 (2013-02-12)
The signalling molecule indole occurs in significant amounts in the mammalian intestinal tract and regulates diverse microbial processes, including bacterial motility, biofilm formation, antibiotic resistance and host cell invasion. In Escherichia coli, the enzyme tryptophanase (TnaA) produces indole from tryptophan
Jörg Fabian et al.
Chemico-biological interactions, 206(2), 356-363 (2013-10-15)
Cytosolic phospholipase A2α (cPLA2α) plays a key role in the pathogenesis of many inflammatory diseases, such as rheumatoid arthritis, atopic dermatitis and Alzheimer's disease. Therefore, inhibition of this enzyme is assumed to provide a novel therapeutic option for the treatment
Xianchang Li et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 105, 593-599 (2013-02-21)
In this essay, three novel nonlinear optical (NLO) azo-materials containing indole and sulfonyl based chromophores were studied in-depth by using Fourier transform (FT) IR, FT-Raman spectra and density functional theory (DFT). The scaled theoretical results were shown to be in
Xueqing Geng et al.
The Plant cell, 24(11), 4763-4774 (2012-12-04)
The phytotoxin coronatine (COR) promotes various aspects of Pseudomonas syringae virulence, including invasion through stomata, growth in the apoplast, and induction of disease symptoms. COR is a structural mimic of active jasmonic acid (JA) conjugates. Known activities of COR are
Jing Zheng et al.
Organic letters, 16(13), 3560-3563 (2014-06-25)
A Rh(III)-catalyzed selective coupling of N-methoxy-1H-indole-1-carboxamide and aryl boronic acids is reported. The coupling is mild and efficient toward diverse product formation, with selective C-C and C-C/C-N bond formation. Kinetic isotope effects studies were conducted to reveal a mechanism of
Gonzalo Blay et al.
The Journal of organic chemistry, 77(23), 10545-10556 (2012-11-07)
Experimental and theoretical studies on the structure of several complexes based on (R)-3,3'-Br(2)-BINOL ligand and group (IV) metals used as catalysts in an enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones have been carried out. NMR spectroscopic studies of these
Sanjay Saikia et al.
Mycological research, 112(Pt 2), 184-199 (2008-02-12)
Indole-diterpenes are a structurally diverse group of secondary metabolites with a common cyclic diterpene backbone derived from geranylgeranyl diphosphate and an indole group derived from indole-3-glycerol phosphate. Different types and patterns of ring substitutions and ring stereochemistry generate this structural
Nirod Kumar Sarangi et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 13(18), 4258-4270 (2012-10-24)
Molecular orientation-dependent electron transport across supported 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) lipid bilayers (SLBs) on semiconducting indium tin oxide (ITO) is reported with an aim towards potential nanobiotechnological applications. A bifunctional strategy is adopted to form symmetric and asymmetric bilayers of DPPC that
Shengnan Shi et al.
Applied biochemistry and biotechnology, 169(4), 1088-1097 (2013-01-12)
Biotransformation of indole to indigo in liquid-liquid biphasic systems was performed in Escherichia coli cells expressing phenol hydroxylase. It was suggested that indole could inhibit the cell growth even at low concentration of 0.1 g/L. The critical Log P for strain
C J van der Horst
Cytobios, 45(181), 85-95 (1986-01-01)
Both in the male and in the female reproductive tract glucose can be converted via either the pentose pathway or the sorbitol pathway. It is shown that a disturbed carbohydrate metabolism can lead to infertility, i.e. in the cow and
Thomas B Parsons et al.
Chemical communications (Cambridge, England), 49(23), 2296-2298 (2013-02-12)
The first synthesis of kottamide E, a marine natural product containing a 5,6-dibromoindole linked via a (Z)-enamide to an unusual 1,2-dithiolane-containing amino acid, is reported.
Can indole-based extracts prevent colorectal cancer via early apoptotic pathways?
Shusuke Toden et al.
Cancer biology & therapy, 9(5), 380-382 (2010-02-20)
Jin-Hyung Lee et al.
FEMS microbiology reviews, 34(4), 426-444 (2010-01-15)
Bacteria can utilize signal molecules to coordinate their behavior to survive in dynamic multispecies communities. Indole is widespread in the natural environment, as a variety of both Gram-positive and Gram-negative bacteria (to date, 85 species) produce large quantities of indole.
Rui Wang et al.
Bioorganic & medicinal chemistry letters, 23(6), 1760-1762 (2013-02-14)
A series of novel indole-imidazole derivatives have been prepared and evaluated in vitro on the aromatase inhibitory activities. The results suggested that proton or a small electron-withdrawing group at para-position of the phenyl ring would enhance the inhibitory activities and
Stephen J Heffernan et al.
Chemical communications (Cambridge, England), 49(23), 2314-2316 (2013-02-13)
The Au(I)-catalysed rearrangement of propargylic esters formed from an ynamide has been studied. The reaction is facile, and when conducted in the presence of a reactive indole nucleophile, leads to a cascade process whereby γ-indolyl α-acyloxyenamides are formed in good
N A Martynova et al.
Gigiena i sanitariia, (6)(6), 61-64 (2013-03-06)
The toxic properties of indole have been studied in terms of LD50 indole was established to refer to moderately hazardous substances: in case of indole introducing into the stomach in rats and mice, DL50 is 1200 mg/kg and 750 mg/kg
Vida Mashayekhi et al.
Chemical & pharmaceutical bulletin, 61(2), 144-150 (2012-11-17)
Based on the existing reports regarding the antiplatelet aggregation activity of hydrazone derivatives, a series of indole hydrazone derivatives were considered as potential antiplatelet agents and synthesized. The structures of the synthesized compounds were confirmed by spectral data and elemental
Israel Alvarado et al.
Journal of bacteriology, 195(5), 1005-1011 (2012-12-25)
Paenibacillus larvae is the causative agent of American foulbrood (AFB), a disease affecting honey bee larvae. First- and second-instar larvae become infected when they ingest food contaminated with P. larvae spores. The spores then germinate into vegetative cells that proliferate
Anton A Toutov et al.
Nature, 518(7537), 80-84 (2015-02-06)
Heteroaromatic compounds containing carbon-silicon (C-Si) bonds are of great interest in the fields of organic electronics and photonics, drug discovery, nuclear medicine and complex molecule synthesis, because these compounds have very useful physicochemical properties. Many of the methods now used
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