255826-36-9Relevant academic research and scientific papers
Synthesis and structure revision of goupiolone A: A benzotropolone natural product
Fukui, Nobuaki,Ohmori, Ken,Suzuki, Keisuke
, p. 2194 - 2217 (2012)
Goupiolone A, a benzotropolone natural product, has been synthesized by assembling a benzocyclobutene derivative and a silyl-substituted cyclopropane unit, followed by thermal ring enlargement. The synthetic sample did not correspond to the reported data. On the basis of biogenetic considerations, an alternative structure with a catechol moiety was proposed, and the synthesis established it as the correct structure.
THIAZOLIDINONE COMPOUNDS AND USE THEREOF
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Paragraph 0351-0352, (2017/09/21)
A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.
Discovery and evaluation of the hybrid of bromophenol and saccharide as potent and selective protein tyrosine phosphatase 1B inhibitors
Zhang, Renshuai,Yu, Rilei,Xu, Qi,Li, Xiangqian,Luo, Jiao,Jiang, Bo,Wang, Lijun,Guo, Shuju,Wu, Ning,Shi, Dayong
supporting information, p. 24 - 33 (2017/04/11)
Protein tyrosine phosphatase 1B (PTP1B) is a key negative regulator of insulin signaling pathway. Inhibition of PTP1B is expected to improve insulin action. Appropriate selectivity and permeability are the gold standard for excellent PTP1B inhibitors. In this work, molecular hybridization-based screening identified a selective competitive PTP1B inhibitor. Compound 10a has IC50 values of 199?nM against PTP1B, and shows 32-fold selectivity for PTP1B over the closely related phosphatase TCPTP. Molecule docking and molecular dynamics studies reveal the reason of selectivity for PTP1B over TCPTP. Moreover, the cell permeability and cellular activity of compound 10a are demonstrated respectively.
The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands
Lim, Kwang Su,Lee, Hobin,Kim, Sung Eun,Ha, Tae-Hwan,Ann, Jihyae,Son, Karam,Choi, Sun,Sun, Wei,Pearce, Larry V.,Deandrea-Lazarus, Ian A.,Blumberg, Peter M.,Lee, Jeewoo
, p. 233 - 243 (2013/10/01)
A series of carbonate analogues of 5′-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with Ki(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism.
Complementary diastereoselectivity in the intermolecular addition of titanium and magnesium naphtholates to asymmetric lactaldehydes
Giles, Robin G. F.,Joll, Cynthia A.,Sargent, Melvyn V.,Tilbrook, D. Matthew G.
, p. 3029 - 3038 (2007/10/03)
Addition of 7-benzyloxy-4,5-dimethoxy-1-naphthol 3 as its triisopropoxytitanium naphtholate to (2R, 1′R or S)-2-(1′-ethoxyethoxy)propanal 4 afforded solely (15, 2R, 1″R or S)-1-(7′-benzyloxy-4′,5′-dimethoxy-1′-hydroxy-2′- naphthyl)-2-(1″-ethoxyethoxy)propan-l-ol 5, being the erythro product arising from anti addition. Complementary reaction of the naphthol 3 as its bromomagnesium naphtholate with aldehyde 4 gave rise solely to the alternative (1R, 2R, 1″R or S) diastereomer 6. The naphthol 3 was prepared through the completely regioselective addition of 2-methoxyfuran 9 to 5-benzyloxy-3-methoxydehydrobenzene 8. This differentially protected bisalkoxybenzyne was conveniently prepared from vanillin. The Royal Society of Chemistry 1999.
