485385-79-3Relevant academic research and scientific papers
Model reactions for the synthesis of azacorannulenes and related heteroaromatic compounds
Dix, Ina,Doll, Christian,Hopf, Henning,Jones, Peter G.
, p. 2547 - 2556 (2007/10/03)
4-(2-Ethynylphenyl)pyridine (10), 3-(2-ethynylphenyl)pyridine (11), 2-(2-trimethylsilylethynylphenyl)pyridine (26), and 3-ethynyl-2-phenylpyridine (13) were prepared from readily available pyridine precursors by standard coupling reactions. Pyrolysis of 10 at 810 °C/0.5 Torr provided benzo[f]isoquinoline (45) and the benzopentalene dimer 47. Pyrolysis of 11 (820 °C/0.5 Torr) afforded benzo[f]quinoline (50), benzo[h]i-soquinoline (52), and a mixture of isomers of 47. Pyrolysis of 13 (820 °C/0.3 Torr) provided benzo[h]quinoline (56) and the novel azulene derivative azuleno[1,2-b]pyridine (58). When 26 was desilylated by treatment with TBAF in THF/water, the unusual "dimerization" product 37 was produced; its structure was confirmed by X-ray structural analysis. The mechanisms of these transformations are discussed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Terphenyl cyclooxygenase-2 (COX-2) inhibitors: Optimization of the central ring and o-biphenyl analogs
Pinto, Donald J. P.,Batt, Douglas G.,Pitts, William J.,Petraitis, Joseph J.,Orwat, Michael J.,Wang, Shuaige,Jetter, James W.,Sherk, Susan R.,Houghton, Gregory C.,Copeland, Robert A.,Covington, Maryanne B.,Trzaskos, James M.,Magolda, Ronald L.
, p. 919 - 924 (2007/10/03)
The discovery of terphehyl derivatives as highly selective COX-2 inhibitors resulted from our efforts to overcome poor pharmacokinetics demonstrated by the COX-2 selective diarylthiophene DuP 697 [2-bromo-4-(4'- sulfonylmethyl)phenyl-5-(4'-fluoro)phenylthiophene]. Detailed SAR related to the ortho-biphenyls and variants of the central ring are described herein.
