- Synthesis and biological evaluation of 2-heteroarylthioalkanoic acid analogues of clofibric acid as peroxisome proliferator-activated receptor α agonists
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Aseries of 2-heteroarylthioalkanoic acids were synthesized through systematic structural modifications of clofibric acid and evaluated for human peroxisome proliferator-activated receptor α (PPARα) transactivation activity, with the aim of obtaining new hypolipidemic compounds. Some thiophene and benzothiazole derivatives showing a good activation of the receptor α were screened for activity against the PPARγ isoform. The gene induction of selected compounds was also investigated in the human hepatoma cell line. 2009 American Chemical Society.
- Giampietro, Letizia,Ammazzalorso, Alessandra,Giancristofaro, Antonella,Lannutti, Fabio,Bettoni, Giancarlo,De Filippis, Barbara,Fantacuzzi, Marialuigia,Maccallini, Cristina,Petruzzelli, Michele,Morgano, Annalisa,Moschetta, Antonio,Amoroso, Rosa
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- Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering
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In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for -bromoesters.
- Prokop, Zbynek,Sato, Yukari,Brezovsky, Jan,Mozga, Tomas,Chaloupkova, Radka,Koudelakova, Tana,Jerabek, Petr,Stepankova, Veronika,Natsume, Ryo,Van Leeuwen, Jan G. E.,Janssen, Dick B.,Florian, Jan,Nagata, Yuji,Senda, Toshiya,Damborsky, Jiri
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supporting information; experimental part
p. 6111 - 6115
(2010/11/05)
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- Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates
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Enolates of (S)-N,N′-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee.
- Bull, Steven D.,Davies, Stephen G.,Epstein, Simon W.,Garner, A. Christopher,Mujtaba, Nadeam,Roberts, Paul M.,Savory, Edward D.,Smith, Andrew D.,Tamayo, Juan A.,Watkin, David J.
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p. 7911 - 7925
(2007/10/03)
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- Enantiospecific Synthesis of the trans-9-carbazoles
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The compounds in the title, (R,R)- and (S,S)-2, are isomers of the cis-dimethyl compound 1, which is in human trials as an antipsychotic.They were made starting with chiral alanine esters (6) and the 2-bromopropionic esters made from the alanines of opposite chirality (5) and proceeding by cyclization of the ethoxycarbonyl-protected iminodipropionic acids 9, via anhydride 10, with 3-(9-carbazolyl)propylamine and subsequent BH3 reduction of the imides 12 followed by hydrolytic removal of the COOEt.Selection of the reagents necessary to minimize racemization D 20 values at each condensation stage and the 1H and 13C NMR absorption data required for structure proof of 2 are given; a ring inversion rate of 5200 s-1 is calculated based on low and ambient temperature 13C NMR data.
- Harfenist, Morton,Hoerr, David C.,Crouch, Ronald
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p. 1356 - 1359
(2007/10/02)
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