114113-99-4Relevant academic research and scientific papers
Synthesis of lipophilic bisanthracene fluorophores: Versatile building blocks toward the synthesis of new light-harvesting dendrimers
Takahashi, Masaki,Yamamoto, Ayato,Inuzuka, Toshiyasu,Sengoku, Tetsuya,Yoda, Hidemi
experimental part, p. 9484 - 9490 (2011/12/15)
Lipophilic bisanthracene-based fluorophore and its derivatives were synthesized by the Suzuki-Miyaura cross-coupling reaction of 9-anthrylboronic acid with a substituted dibromobenzene. In addition to desirable fluorescent properties, these molecular systems were demonstrated to serve as versatile building blocks toward the synthesis of two types of new light-harvesting dendrimers due to their chemical stability.
A substructure combination strategy to create potent and selective transthyretin kinetic stabilizers that prevent amyloidogenesis and cytotoxicity
Choi, Sungwook,Reixach, Natalia,Connelly, Stephen,Johnson, Steven M.,Wilson, Ian A.,Kelly, Jeffery W.
supporting information; experimental part, p. 1359 - 1370 (2010/04/01)
Transthyretin aggregation-associated proteotoxicity appears to cause several human amyloid diseases. Rate-limiting tetramer dissociation and monomer misfolding of transthyretin (TTR) occur before its aggregation into cross-β-sheet amyloid fibrils. Small molecule binding to and preferential stabilization of the tetrameric state of TTR over the dissociative transition state raises the kinetic barrier for dissociation, imposing kinetic stabilization on TTR and preventing aggregation. This is an effective strategy to halt neurodegeneration associated with polyneuropathy, according to recent placebo-controlled clinical trial results. In three recent papers, we systematically ranked possibilities for the three substructures composing a typical TTR kinetic stabilizer, using fibril inhibition potency and plasma TTR binding selectivity data. Herein, we have successfully employed a substructure combination strategy to use these data to develop potent and selective TTR kinetic stabilizers that rescue cells from the cytotoxic effects of TTR amyloidogenesis. Of the 92 stilbene and dihydrostilbene analogues synthesized, nearly all potently inhibit TTR fibril formation. Seventeen of these exhibit a binding stoichiometry of >1.5 of a maximum of 2 to plasma TTR, while displaying minimal binding to the thyroid hormone receptor (2 crystal structures (1.31-1.70 A) confirmed the anticipated binding orientation of the 3,5-dibromo-4-hydroxyphenyl substructure and revealed a strong preference of the isosteric 3,5-dibromo-4-aminophenyl substructure to bind to the inner thyroxine binding pocket of TTR.
Stereoselective synthesis of new conformationally restricted analogues of a potent CGRP receptor antagonist
Zuev, Dmitry,Michne, Jodi A.,Huang, Hong,Beno, Brett R.,Wu, Dedong,Gao, Qi,Torrente, John R.,Xu, Cen,Conway, Charles M.,Macor, John E.,Dubowchik, Gene M.
, p. 2465 - 2468 (2007/10/03)
(Chemical Equation Presented) A stereocontrolled racemic synthesis of conformationally restricted analogues 2a and 2b of a potent CGRP receptor antagonist 1 by novel functionalization of 2-substituted octahydropyrido[1,2-a] pyrazin-6-ones is described. Th
STUDIES ON A BIOMIMETIC APPROACH TO AEROTHIONIN AND PSAMMAPLYSIN-A
Okamoto, Kelvin T.,Clardy, Jon
, p. 4969 - 4972 (2007/10/02)
Oxidation of a plausible biological precursor for the spirocyclic systems of aerothionin (1) and psammaplysin-A (2) is described.
