- Design and discovery of 2-oxochromene derivatives as liver X receptor β-selective agonists
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In an attempt to molecularly design liver X receptor (LXR) β-selective agonists, we discovered that the combination of the 2-oxochromene moiety (head) and the imidazoline-2,4-dione moiety (tail) plays an important role in the expression potency and select
- Matsuda, Takayuki,Okuda, Ayumu,Watanabe, Yuichiro,Miura, Tohru,Ozawa, Hidefumi,Tosaka, Ayako,Yamazaki, Koichi,Yamaguchi, Yuki,Kurobuchi, Sayaka,Koura, Minoru,Shibuya, Kimiyuki
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p. 1274 - 1278
(2015/03/14)
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- An expedient synthesis of bis-fused benzofuran and a two-directional ring- closing metathesis for the synthesis of bisbenzoxepines and bisbenzoxocines
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Synthesis of bis-fused benzofuran derivatives by the implementation of palladium-mediated intramolecular cyclization is described. To our knowledge, this is the first report of the synthesis of bis-fused benzofuran by this protocol. Bisbenzoxepine and bis
- Majumdar, Krishna C.,Chattopadhyay, Buddhadeb,Chakravorty, Santanu
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experimental part
p. 674 - 680
(2009/07/03)
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- Effect of ortho-SR groups on O-H bond strength and H-atom donating ability of phenols: A possible role for the tyr-cys link in galactose oxidase active site?
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Rotation about the Ar-S bond in ortho-(alkylthio)phenols strongly affects the bond dissociation enthalpy (BDE) and the reactivity of the OH group. Newly synthesized sulfur containing heterocycles 3 and 4, where the -SR group is almost coplanar with the phenolic ring, are characterized by unusually low BDE(O-H) values (79.6 and 79.2 kcal/mol, respectively) and by much higher reactivities toward peroxyl radicals than the ortho-methylthio derivative 1 (82.0 kcal/mol). The importance of the intramolecular hydrogen bond (IHB) in determining the BDE(O-H) was demonstrated by FT-IR experiments, which showed that in heterocycles 3 and 4 the IHB between the phenolic OH group and the S atom is much weaker than that present in 1. Since the IHB can be formed only if the -SR group adopts an out-of-plane geometry, this interaction is possible only in the methylthio derivative 1 and not in 3 and 4. The additive contribution to the phenolic BDE(O-H) of the -SR substituent therefore varies from -3.1 to +2.8 kcal/mol for the in-plane and out-of-plane conformations, respectively. These results may be relevant to understanding the role of the tyrosine-cysteine link in the active site of galactose oxidase, an important enzyme that catalyzes the two-electron aerobic oxidation of primary alcohols to aldehydes. The switching of the ortho -SR substituent between perpendicular and planar conformations may account for the catalytic efficiency of this enzyme.
- Amorati, Riccardo,Catarzi, Francesca,Menichetti, Stefano,Pedulli, Gian Franco,Viglianisi, Caterina
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p. 237 - 244
(2008/09/21)
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- Novel synthesis of medium-sized oxa-heterocycles by palladium-catalyzed intramolecular Heck reaction
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An efficient and high yielding method for the synthesis of eight-membered heterocyclic skeletons has been developed via palladium-catalyzed intramolecular Heck reaction.
- Majumdar,Chattopadhyay,Ray
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p. 7633 - 7636
(2008/03/14)
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- Palladium-catalyzed, triethylborane-promoted C-allylation of naphthols and benzene polyols by direct use of allyl alcohols
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The combination of a catalytic amount of Pd(0) species and triethylborane promotes the C-allylation of benzene polyols and naphthols at room temperature to 50 °C by the direct use of a variety of allylic alcohols; Exhaustive allylation of 1,3-benzenediol and 1,3,5-benzenetriol provides penta-allylation and hexa-allylation products, respectively, in good yields. Georg Thieme Verlag Stuttgart.
- Kimura, Masanari,Fukasaka, Miki,Tamaru, Yoshinao
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p. 3611 - 3616
(2008/03/13)
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- Discovery of a novel series of peroxisome proliferator-activated receptor α/γ dual agonists for the treatment of type 2 diabetes and dyslipidemia
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A series of 2-aryloxy-2-methyl-propionic acid compounds and related analogues were designed, synthesized, and evaluated for their PPAR agonist activities. 2-[(5,7-Dipropyl-3-trifluoromethyl)-benzisoxazol-6-yloxy]-2- methylpropionic acid (4) was identified
- Liu, Kun,Xu, Libo,Berger, Joel P.,MacNaul, Karen L.,Zhou, Gauchao,Doebber, Thomas W.,Forrest, Michael J.,Moller, David E.,Jones, A. Brian
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p. 2262 - 2265
(2007/10/03)
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- Aryloxyacetic acids for diabetes and lipid disorders
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A class of aryloxyacetic acids comprises compounds that are potent agonists of PPAR alpha and/or gamma, and are therefore useful in the treatment, control or prevention of non-insulin dependent diabetes mellitus (NIDDM), hyperglycemia, dyslipidemia, hyper
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- Aryloxyacetic acids for diabetes and lipid disorders
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A class of aryloxyacetic acids comprises compounds that are potent agonists of PPAR alpha and/or gamma, and are therefore useful in the treatment, control or prevention of non-insulin dependent diabetes mellitus (NIDDM), hyperglycemia, dyslipidemia, hyper
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