246139-77-5Relevant articles and documents
Bis-Cyclometalated Indazole Chiral-at-Rhodium Catalyst for Asymmetric Photoredox Cyanoalkylations
Steinlandt, Philipp S.,Zuo, Wei,Harms, Klaus,Meggers, Eric
supporting information, p. 15333 - 15340 (2019/11/22)
A new class of bis-cyclometalated rhodium(III) catalysts containing two inert cyclometalated 6-tert-butyl-2-phenyl-2H-indazole ligands and two labile acetonitriles is introduced. Single enantiomers (>99 % ee) were obtained through a chiral-auxiliary-mediated approach using a monofluorinated salicyloxazoline. The new chiral-at-metal complex is capable of catalyzing the visible-light-induced enantioselective α-cyanoalkylation of 2-acyl imidazoles in which it serves a dual function as the chiral Lewis acid catalyst for the asymmetric radical chemistry and at the same time as the photoredox catalyst for the visible-light-induced redox chemistry (up to 80 % yield, 4:1 d.r., and 95 % ee, 12 examples).
Synthesis and Photophysical Properties of a 13,13′-Bibenzo[b]perylenyl Derivative as a π-Extended 1,1′-Binaphthyl Analog
Uchida, Yosuke,Hirose, Takashi,Nakashima, Takuya,Kawai, Tsuyoshi,Matsuda, Kenji
, p. 2118 - 2121 (2016/06/01)
A 13,13′-bibenzo[b]perylenyl derivative-an axially chiral π-extended compound in which two perylene subunits fused to 1,1′-binaphthyl scaffold-has been synthesized from 1,8-dibromophenanthrene using an anionic cyclodehydrogenation reaction in the presence
Asymmetric hydrogenation of ketones with H2 and ruthenium catalysts containing chiral tetradentate S2N2 ligands
Patchett, Ruth,Magpantay, Iris,Saudan, Lionel,Schotes, Christoph,Mezzetti, Antonio,Santoro, Francesco
, p. 10352 - 10355 (2013/10/21)
Getting more for less: In the presence of H2 and a base, air- and moisture-tolerant RuII complexes catalyze the hydrogenation of ketones and aldehydes with excellent activity and chemoselectivity, and with enantioselectivity of up to 95 % under mild conditions. The ratio of substrate to catalyst can be lowered to 106:1. The reactions tolerate scale-up and can be carried out with almost no solvent. A base-free method is available for base-sensitive substrates. Copyright
Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration
Grigg, R. David,Van Hoveln, Ryan,Schomaker, Jennifer M.
supporting information, p. 16131 - 16134,4 (2020/09/09)
A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp2 to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp3 C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.
Discovery of potent, orally available vanilloid receptor-1 antagonists. Structure-activity relationship of N-aryl cinnamides
Doherty, Elizabeth M.,Fotsch, Christopher,Bo, Yunxin,Chakrabarti, Partha P.,Chen, Ning,Gavva, Narender,Han, Nianhe,Kelly, Michael G.,Kincaid, John,Klionsky, Lana,Liu, Qingyian,Ognyanov, Vassil I.,Tamir, Rami,Wang, Xianghong,Zhu, Jiawang,Norman, Mark H.,Treanor, James J. S.
, p. 71 - 90 (2007/10/03)
The vanilloid receptor-1 (TRPV1 or VR1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role in regulating the function of sensory nerves. A growing body of evidence demonstrates the therapeutic potential of TRPV1 modulators, particularly in the management of pain. As a result of our screening efforts, we identified (E)-3-(4-tert- butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (1), an antagonist that blocks the capsaicin-induced and pH-induced uptake of 45Ca2+ in TRPV1-expressing Chinese hamster ovary cells with IC50 values of 17 ± 5 and 150 ± 80 nM, respectively. In this report, we describe the synthesis and structure-activity relationship of a series of N-aryl cinnamides, the most potent of which (49a and 49b) exhibit good oral bioavailability in rats (Foral = 39% and 17%, respectively).
Vanilloid receptor ligands and their use in treatments
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, (2008/06/13)
Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritis, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.
Phenacenes: A family of graphite ribbons. Part 3: Iterative strategies for the synthesis of large phenacenes
Mallory, Frank B,Butler, Kelly E,Bérubé, Amélie,Luzik Jr., Eddie D,Mallory, Clelia W,Brondyke, Emilie J,Hiremath, Rupa,Ngo, Phung,Carroll, Patrick J
, p. 3715 - 3724 (2007/10/03)
Iterative strategies are reported for the synthesis of some large monodisperse [n]phenacenes, which are polycyclic aromatic hydrocarbon derivatives having n benzene rings fused in an extended phenanthrene-like structural motif. The key carbon-carbon bond-
Synthesis of a calix[5]arene receptor having two benzoic acid moieties
Haino, Takeharu,Nitta, Koji,Saijo, Yoshikazu,Matsumura, Kazumi,Hirakata, Masaki,Fukazawa, Yoshimasa
, p. 6301 - 6304 (2007/10/03)
Synthesis and binding behavior of a calix[5]arene receptor possessing two benzoic acids are reported. Two water molecules were bound within the cavity by hydrogen bonding interaction between the two carboxylic acids of the receptor. It also binds 2-aminopyrimidine to form a complex in which the aromatic ring of the guest resides deeply within the cavity.