143901-96-6Relevant articles and documents
Photoactuators based on the dynamic molecular crystals of naphthalene acrylic acids driven by stereospecific [2+2] cycloaddition reactions
Liu, Jiaxi,Ye, Kaiqi,Shen, Yanbing,Peng, Jiang,Sun, Jingbo,Lu, Ran
supporting information, p. 3165 - 3175 (2020/03/19)
The photomechanical effects of the dynamic molecular crystals of halogen-substituted naphthalene acrylic acids (1FNaAA, 1ClNaAA, 1BrNaAA, 1INaAA and 6BrNaAA) have been investigated. Upon UV irradiation, the needle-like crystal of 1FNaAA curls away from the light source, while the slice-like crystal of 6BrNaAA bends towards the light source. Moreover, the light-induced bending, flipping and bursting are observed for the elongated needle-like crystals of 1FNaAA, and the slice-like crystals of 1ClNaAA and 1BrNaAA show bending, cracking, coiling, rotating and twisting triggered by 365 nm light. It is found that stereospecific [2+2] cycloaddition reactions take place in the crystals to afford one stereoisomer of β-type cyclobutanes, since 1FNaAA, 1ClNaAA, 1BrNaAA and 6BrNaAA pack in a head-to-head mode, which satisfies the Schmidt's topo-photochemical criteria. The strain can be generated and accumulated during the photodimerization, and the release of the strain leads to the photomechanical effects. This provides new clues for the development of photomechanical molecular crystals based on acrylic acids bearing halogen-substituted aromatic units.
N-substituted acrylamide derivatives as DHODH inhibitors and preparation and use of N-substituted acrylamide derivatives
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Paragraph 0371; 0375; 0379, (2019/11/04)
The invention relates to N-substituted acrylamide derivatives as DHODH inhibitors and preparation and use of the N-substituted acrylamide derivatives. In particular, the invention discloses a compoundshown in a general formula I and the preparation and use of the compound. The compound has excellent DHODH inhibitory activation, so the compound can be used for treating or preventing various diseases caused by DHODH, the various diseases include but not limited to cancer, rheumatoid arthritis, lupus erythematosus, organ transplant rejection and other autoimmune diseases, and colitis, rhinitis and other inflammatory diseases.
Tri-substituted imidazole analogues of SB203580 as inducers for cardiomyogenesis of human embryonic stem cells
Low, Joo-Leng,Jürjens, Gerrit,Seayad, Jayasree,Seow, Jasmine,Ting, Sherwin,Laco, Filip,Reuveny, Shaul,Oh, Steve,Chai, Christina L.L.
supporting information, p. 3300 - 3303 (2013/06/27)
The p38α mitogen-activated protein kinase (MAPK) inhibitor SB203580 had been reported to enhance the cardiomyogenesis of human embryonic stem cells (hESCs). To investigate if tri-substituted imidazole analogues of SB203580 are equally effective inducers f
Asymmetric hydrogenation of unsaturated ureas with the BIPI ligands
Busacca, Carl A.,Lorenz, Jon C.,Grinberg, Nelu,Haddad, Nizar,Lee, Heewon,Li, Zhibin,Liang, Mary,Reeves, Diana,Saha, Anjan,Varsolona, Rich,Senanayake, Chris H.
, p. 341 - 344 (2008/09/19)
(Chemical Equation Presented) Asymmetric hydrogenation of unsaturated urea esters with the BIPI Ligands has been examined. Optimization of the P-N ligand structure has led to the development of chiral rhodium catalysts capable of producing the targets wit
Potent 4-aryl- or 4-arylalkyl-substituted 3-isoxazolol GABAA antagonists: Synthesis, pharmacology, and molecular modeling
Fr?lund, Bente,Jensen, Lars S.,Guandalini, Luca,Canillo, Carolina,Vestergaard, Henrik T.,Kristiansen, Uffe,Nielsen, Birgitte,Stensb?l, Tine B.,Madsen, Christian,Krogsgaard-Larsen, Povl,Liljefors, Tommy
, p. 427 - 439 (2007/10/03)
We have previously described a series of competitive GABAA antagonists derived from the low-efficacy partial agonist 5-(4-piperidyl)-3- isoxazolol (4-PIOL, 4). The 2-naphthylmethyl analogue, 4-(2-naphthylmethyl)-5- (4-piperidyl)-3-isoxazolol (5), provided affinity for the GABAA receptor site higher than that of the standard GABAA receptor antagonist, SR 95531 (3). Molecular modeling studies of these compounds exposed a cavity at the receptor recognition site capable of accommodating aromatic groups of substantial size in the 4-position in the 3-isoxazolol ring. Here we present a series of analogues of 5, with various substituents in different positions in the naphthyl ring system (6a-k), and compounds with aromatic substituents directly attached to the 4-position of the 3-isoxazolol ring (71-n). The compounds have been pharmacologically characterized using receptor-binding assays and electrophysiological whole-cell patch-clamp techniques. All of the tested compounds show affinity for the GABAA receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (Ki = 45, 109, and 80 nM, respectively) comparable with that of 5 (Ki = 49 nM), the 1-bromo analogue, 6a, provided the highest receptor affinity of the series (Ki = 10 nM). Introduction of a series of different substituents in the 1-position in the 2-naphthyl ring system led to compounds, 6c-k, with retained high affinity for the GABA A receptor (Ki = 16-250 nM). Introduction of a phenyl ring directly into the 4-position on the 3-isoxazolol ring gave a 41-fold increase in affinity relative to that of 4-PIOL. In whole-cell patch-clamp recordings from cultured cerebral cortical neurons, all of the tested compounds were able to inhibit the effect of the specific GABAA agonist isoguvacine, 6a showing antagonist potency (IC50 = 42 nM) markedly higher than that of 3 (IC50 = 240 nM). Molecular modeling studies, based on the compounds described, emphasized the importance of the distal ring in 5 for receptor affinity and the considerable dimensions of the proposed receptor cavity. Furthermore, the phenyl rings in 71 and in 6k were shown to represent highly favorable positions for an aromatic ring in previously unexplored receptor regions in terms of a pharmacophore model.
The abnormal behavior of an atropisomer: 3,3′-dibromo-1,1′- difluoro-2,2′-binaphthyl reacting with alkyllithium compounds
Leroux, Frederic,Mangano, Giuseppe,Schlosser, Manfred
, p. 5049 - 5054 (2007/10/03)
1-Fluoro-2-(triethylsilyl)naphthalene (1) and other 1-fluoronaphthalenes bearing a metalation-resistant substituent at the 2-position proved to be totally inert toward base attack. 3-Bromo-1-fluoronaphthalene (6), readily prepared from the 2-bromo isomer 5 by deprotonation-triggered heavy halogen migration, was converted into 3,3′-dibromo-1,1′-difluoro-2,2′- binaphthyl (8) by consecutive treatment with lithium diisopropylamide, copper(II) bromide and nitrobenzene. The dilithiated intermediate generated from the atropisomer 8 by treatment with 2 equiv. of butyllithium reacted with a variety of electrophiles to afford products such as the diacid 12 or the bis(phosphanes) 14 and 15 in high yields. The latter compound was also obtained in a straightforward manner from (4-fluoro-2-naphthyl)diphenylphosphane oxide (16). Unexpectedly, neither the 3,3′-dibromobinaphthyl 8 nor its 3,3′-diiodo analogue 18 were amenable to a unilateral but only to a double-sided halogen/metal permutation. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
