10133-20-7Relevant articles and documents
Synthesis of Thia-Analogues of Calothrixin B Involving FeCl3-Mediated Domino Reaction
Ramalingam, Bose Muthu,Moorthy, Nachiappan Dhatchana,Vellaichamy, Elangovan,Mohanakrishnan, Arasambattu K.
, p. 133 - 137 (2017)
The total synthesis of thiacalothrixins, an isostere of the biologically important carbazoloquinone alkaloid calothrixin B, was achieved from ethyl benzo[b]thiophene-2-carboxylate. Alternatively, the multi-step synthesis of thiaisocalothrixins could be achieved from 3-methylbenzo[b]thiophene. A preliminary in vitro cytotoxicity evaluation of the synthesized thia analogues of calothrixins displayed promising potential against cancer cell cultures.
The design and synthesis of novel, phosphonate-containing transient receptor potential melastatin 8 (TRPM8) antagonists
Matthews, Jay M.,Qin, Ning,Colburn, Raymond W.,Dax, Scott L.,Hawkins, Mike,McNally, James J.,Reany, Laura,Youngman, Mark A.,Baker, Judith,Hutchinson, Tasha,Liu, Yi,Lubin, Mary Lou,Neeper, Michael,Brandt, Michael R.,Stone, Dennis J.,Flores, Christopher M.
supporting information; experimental part, p. 2922 - 2926 (2012/06/04)
A series of benzothiophene-based phosphonates was synthesized and many analogs within the series were shown to be potent antagonists of the TRPM8 channel. The compounds were obtained as a racemic mixture in 5 synthetic steps, and were tested for TRPM8 antagonist activity in a recombinant, canine TRPM8-expressing cell line using a fluorometric imaging plate reader (FLIPR) assay. Structure-activity relationships were developed initially by modification of the core structure and subsequently by variation of the aromatic substituents and the phosphonate ester. Compound 9l was administered intraperitoneally to rats and demonstrated engagement of the TRPM8 target in both prevention and reversal-modes in an icilin-induced 'wet-dog' shake model.
NOVEL HETEROCYCLIC ACRYLAMIDES AND THEIR USE AS PHARMACEUTICALS
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Page/Page column 139, (2011/06/19)
The invention relates to novel heterocyclic acrylamide compounds (I), to the preparation of the compounds and intermediates used therein, to the use of the compounds as antibacterial medicaments and pharmaceutical compositions containing the compounds.
Potent and selective inhibitors of long chain l-2-hydroxy acid oxidase reduced blood pressure in DOCA salt-treated rats
Barawkar, Dinesh A.,Meru, Ashwin,Bandyopadhyay, Anish,Banerjee, Abir,Deshpande, Anil M.,Athare, Chandrashekhar,Koduru, Chandrasekhar,Khose, Goraksha,Gundu, Jayasagar,Mahajan, Koshu,Patil, Pradeep,Kandalkar, Sachin R.,Niranjan, Sanjay,Bhosale, Shubhangi,De, Siddhartha,Mukhopadhyay, Sudit,Chaudhary, Sumit,Koul, Summon,Singh, Umesh,Chugh, Anita,Palle, Venkata P.,Mookhtiar, Kasim A.,Vacca, Joseph,Chakravarty, Prasun K.,Nargund, Ravi P.,Wright, Samuel D.,Roy, Sophie,Graziano, Michael P.,Singh, Sheo B.,Cully, Doris,Cai, Tian-Quan
supporting information; experimental part, p. 919 - 923 (2012/02/15)
l-2-Hydroxy acid oxidase (Hao2) is a peroxisomal enzyme with predominant expression in the liver and kidney. Hao2 was recently identified as a candidate gene for blood pressure quantitative trait locus in rats. To investigate a pharmacological role of Hao
Tandem free-radical addition/substitution chemistry and its application to the preparation of novel AT1 receptor antagonists
Staples, Maree K.,Grange, Rebecca L.,Angus, James A.,Ziogas, James,Tan, Nichole P. H.,Taylor, Michelle K.,Schiesser, Carl H.
experimental part, p. 473 - 479 (2011/03/17)
Benzothiophene and benzoselenophene analogues of the thiophene-containing antihypertensives milfasartan and eprosartan were prepared and tested for AT1 receptor antagonist properties. While the sulfur-containing systems were prepared following
Synthesis and biological evaluation of new nanomolar competitive inhibitors of Helicobacter pylori type II dehydroquinase. Structural details of the role of the aromatic moieties with essential residues
Prazeres, Verónica F. V.,Tizón, Lorena,Otero, José M.,Guardado-Calvo, Pablo,Llamas-Saiz, Antonio L.,Van Raaij, Mark J.,Castedo, Luis,Lamb, Heather,Hawkins, Alastair R.,González-Bello, Concepción
experimental part, p. 191 - 200 (2010/05/19)
The shikimic acid pathway is essential to many pathogens but absent in mammals. Enzymes in its pathway are therefore appropriate targets for the development of novel antibiotics. Dehydroquinase is the third enzyme of the pathway, catalyzing the reversible dehydratation of 3-dehydroquinic acid to form 3-dehydroshikimic acid. Here we present the synthesis of novel inhibitors with high affinity for Helicobacter pylori type II dehydroquinase and efficient inhibition characteristics. The structure of Helicobacter pylori type II dehydroquinase in complex with the most potent inhibitor shows that the aromatic functional group interacts with the catalytic Tyr22 by π-stacking, expelling the Arg17 side chain, which is essential for catalysis, from the active site. The structure therefore explains the favorable properties of the inhibitor and will aid in design of improved antibiotics.
Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626
Vangveravong, Suwanna,Taylor, Michelle,Xu, Jinbin,Cui, Jinquan,Calvin, Wesley,Babic, Sonja,Luedtke, Robert R.,MacH, Robert H.
experimental part, p. 5291 - 5300 (2010/09/09)
A series of indole, 7-azaindole, benzofuran, and benzothiophene compounds have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds share structural elements with the classical D 2-like dopamine rec
Benzothiophene derivatives and medicinal use thereof
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, (2008/06/13)
A benzothiophene derivative represented by formula (1): can activate a peroxisome proliferator-activated receptor (PPAR) α or γ which is an intranuclear transcription factor. The compound may be used as an active ingredient to give a drug for preventing o
4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity
De Dios, Alfonso,Prieto, Lourdes,Martín, Jose Alfredo,Rubio, Almudena,Ezquerra, Jesus,Tebbe, Mark,López De Uralde, Beatriz,Martín, Justina,Sánchez, Ana,LeTourneau, Deborah L.,McGee, James E.,Boylan, Carole,Parr Jr., Thomas R.,Smith, Michele C.
, p. 4559 - 4570 (2007/10/03)
The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.
Design, synthesis, and evaluation of nonpeptidic inhibitors of human rhinovirus 3C protease
Webber, Stephen E.,Tikhe, Jayashree,Worland, Stephen T.,Fuhrman, Shella A.,Hendrickson, Thomas F.,Matthews, David A.,Love, Robert A.,Patick, Amy K.,Meador, James W.,Ferre, Rose Ann,Brown, Edward L.,Delisle, Dorothy M.,Ford, Clifford E.,Binford, Susan L.
, p. 5072 - 5082 (2007/10/03)
The design, synthesis, and biological evaluation of reversible, nonpeptidic inhibitors of human rhinovirus (HRV) 3C protease (3CP) are reported. A novel series of 2,3-dioxindoles (isatins) were designed that utilized a combination of protein structure-bas
