17432-37-0Relevant academic research and scientific papers
Differing activity profiles of the stereoisomers of 2,3,5,6TMP-TQS, a putative silent allosteric modulator of a7 nAChR
Papke, Roger L.,Garai, Sumanta,Stokes, Clare,Horenstein, Nicole A.,Zimmerman, Arthur D.,Abboud, Khalil A.,Thakur, Ganesh A.
, p. 292 - 302 (2020)
Many synthetic compounds to which we attribute specific activities are produced as racemic mixtures of stereoisomers, and it may be that all the desired activity comes from a single enantiomer. We have previously shown this to be the case with the a7 nicotinic acetylcholine receptor positive allosteric modulator (PAM) 3a,4,5,9b-Tetrahydro-4-(1-naphthalenyl)-3H-cyclopentan[ c]quinoline-8-sulfonamide (TQS) and the a7 ago-PAM 4BP-TQS. Cis-trans-4-(2,3,5,6-tetramethylphenyl)-3a,4,5,9b-tetrahydro- 3H-cyclopenta[c]quinoline-8-sulfonamide (2,3,5,6TMPTQS), previously published as a "silent allosteric modulator" and an antagonist of a7 allosteric activation, shares the same scaffold with three chiral centers as the aforementioned compounds. We isolated the enantiomers of 2,3,5,6TMP-TQS and determined that the (2) isomer was a significantly better antagonist than the (+) isomer of the allosteric activation of both wild-type a7 and the nonorthosterically activatible C190A a7 mutant by the ago-PAM GAT107 (the active isomer of 4BP-TQS). In contrast, (+)2,3,5,6TMPTQS proved to be an a7 PAM. (2)2,3,5,6TMP-TQS was shown to antagonize the allosteric activation of a7 by the structurally unrelated ago-PAM B-973B as well as the allosteric activation of the TQS-sensitive a4b2L159M mutant. In silico docking of 2,3,5,6TMP-TQS in the putative allosteric activation binding site suggested a specific interaction of the (2) enantiomer with a7T106, and allosteric activation of a7T106 mutants was not inhibited by (2)2,3,5,6TMP-TQS, confirming the importance of this interaction and supporting the model of the allosteric binding site. Comparisons and contrasts between 2,3,5,6TMP-TQS isomers and active and inactive enantiomers of other TQS-related compounds identify the orientation of the cyclopentenyl ring to the plane of the core quinoline to be a crucial determinate of PAM activity.
Blue phosphorescent N-heterocyclic carbene chelated Pt(ii) complexes with an α-duryl-β-diketonato ancillary ligand
Ko, Soo-Byung,Park, Hee-Jun,Gong, Shaolong,Wang, Xiang,Lu, Zheng-Hong,Wang, Suning
, p. 8433 - 8443 (2015/05/20)
C^C chelated Pt(ii) compounds that contain an N-heterocyclic carbene (NHC) donor have recently attracted great interest as blue or white phosphorescent emitters for organic light-emitting devices (OLEDs). To overcome the tendency for excimer formation in Pt(ii) compounds, an α-duryl-β-diketonato ligand was selected as the ancillary ligand for blue phosphorescent C^C chelated Pt(ii) compounds. Using this approach, a series of NHC-based C^C chelated Pt(ii) compounds has been designed and synthesized. The chelate ligands used in the new C^C chelated Pt(ii) compounds include 1-phenylimidazol-2-ylidene in Pt1, 1-phenyl-1,2,4-triazol-5-ylidene in Pt2, p-TMS-1-phenylimidazol-2-ylidene in Pt3, and p-TMS-1-phenyl-1,2,4-triazol-5-ylidene in Pt4. A single-crystal X-ray diffraction analysis revealed that the presence of the α-duryl-β-diketonato ligand in the Pt(ii) compounds effectively suppresses the dimer formation in the crystal lattice. Pt1, Pt2, Pt3, and Pt4 display blue phosphorescence at room temperature. The p-TMS substituted complex Pt3 was found to display the most efficient blue phosphorescence at λem = 468 nm with a ΦPL of 0.68. Spectroscopic and computational studies established that the blue phosphorescence in the phenyl-imidazolylidene chelated complexes originates mainly from a 3MLCT state while that in the phenyl-triazolylidene chelated compounds arises from a 3ILCT state. Electroluminescent devices using Pt1 and Pt3 as the dopant were fabricated which display both monomer and exciplex emission, leading to pure white light electroluminescence with CIE coordinates of (0.32, 0.31).
Aryllithiums with increasing steric crowding and lipophilicity prepared from chlorides in diethyl ether. the first directly prepared room-temperature-stable dilithioarenes
Screttas, Constantinos G.,Steele, Barry R.,Micha-Screttas, Maria,Heropoulos, Georgios A.
supporting information, p. 5680 - 5683 (2013/01/15)
A convenient procedure has been developed for the preparation of synthetically useful, room-temperature-stable aryllithiums starting from aryl chlorides and lithium metal. The method provides a route to aryllithiums which have previously not been accessible cleanly or could only be prepared by using more expensive starting materials.
CHEMICAL ENCODING TECHNOLOGY FOR COMBINATORIAL SYNTHESIS
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Page 10, (2008/06/13)
A chemical tag can include a core and a plurality of substituents attached directly to the core. The substituents of each chemical tag form a subset of a closed set of possible substituents. The tag can be used to track an object.
A new redox system: Trichloromethylarene - Pyridine base. On the mechanism of the synthesis of N-(4-pyridyl)pyridinium dichloride
Belen'kii, Leonid I.,Poddubnyi, Igor S.,Krayushkin, Mikhail M.
, p. 5075 - 5078 (2007/10/02)
A redox reaction of trichloromethylarenes with pyridines results in respective N-(α-chloroarylmethyl)-substituted pyridinium chlorides which give on hydrolysis aromatic aldehydes and 4-chloropyridines or 1,4'- bipyridinium salts.
Dual Reactivity of the Formyl Cation as an Electrophile and a Broensted Acid in Superacids
Tanaka, Mutsuo,Fujiwara, Masahiro,Ando, Hisanori
, p. 3846 - 3850 (2007/10/02)
The nature of the formyl cation in the Gattermann-Koch formylation was studied by comparing the formylation with the acetylation and sulfonation in CF3SO3H-SbF5 and FSO3H-SbF5, respectively.The results of the kinetic studies in CF3SO3H-SbF5 showed that the formyl cation has dual reactivity as an electrophile and as a Broensted acid.Upon comparing the formylation with the sulfonation in FSO3H-SbF5, it was found that the protonated aromatic compounds also act as Broensted acids to produce formyl cations.Therefore, the formylation has a priority over other typical electrophilic substitutions under conditions where most of aromatic compounds are protonated because the formyl cation is reproduced close to the aromatic compounds by the protonation of CO with not only superacids but also protonated aromatic compounds.
THERMAL DISSOCIATION OF DI(ALKYLBENZYL)NAPHTHYL>PEROXYDICARBONATES IN RELATION TO THE STRUCTURE OF THE ALKYL AROMATIC FRAGMENTS
Fomin, V. A.,Etlis, I. V.,Kurskii, Yu. A.,Nozrina, F. D.,Chervyakova, G. N.,Shmuilovich, S. M.
, p. 811 - 819 (2007/10/02)
The kinetics of the thermolysis of di peroxydicarbonates at 40-70 deg C in organic solvents were investigated, the effectiveness of escape of the free radicals from the solvent "cage" was studied, and the final products from thermal dissociation of the peroxydicarbonates were investigated.A scheme was formulated for the thermolysis of peroxides, explaining the relation between the homolysis rate of the O-O group and the reactivity of the obtained free radicals in relation to the structure of the alkylbenzyl fragments in the symmetrical and unsymmetrical peroxydicarbonates.
Formylation and dichloromethylation as alternative directions of rieche reaction. A novel to the synthesis of sterically hindered aromatic dialdhydes
Yakubov, Alexander P.,Tsyganov, Dmitry V.,Belen'kii, Leonid I.,Krayushkin, Mikhail M.
, p. 3397 - 3404 (2007/10/02)
A previously unknown direction of Rieche reaction has been found: formylation of mesitylene, m-xylene, and durene with dichloromethyl methyl ether in the presence of aluminium trichloride and, to lesser extent, of titanium tetrachloride give the respective benzylidene dichlorides besides aldehydes. A novel approach to the synthesis of sterically hindered aromatic dialdehydes has been offered which involves the transformation of a monoaldehyde into the corresponding benzylidene dichloride, Rieche formylation of the latter, and hydrolysis of dichloromethyl aldehyde formed.
Thermal Isomerization of Photochemically Synthesized (Z)-9-Styrylacridines. An Unusuallly High Enthalpy of Z -> E Conversion for Stilbene-like Compounds
Bastianelli, Carlo,Caia, Vincenzo,Cum, Giampietro,Gallo, Raffaele,Mancini, Vittorio
, p. 679 - 683 (2007/10/02)
Eight stable (Z)-9-styrylacridines, have been photochemically synthesized and their enthalpies of thermal isomerization (ΔHZ->E) determined by means of thermal analysis.The enthalpy values were found to be influenced by both electronic and steric effects.The title compounds were used as models in order to gain insight into the energetic implications involved in the Z->E isomerization process and its applicability to photochemical energy conversion by irradiation in the visible wavelength region.
An Unexpected γ-Hydrogen Rearrangement in the Mass Spectra of Di-ortho-substituted Alkylbenzenes
Kingston, Eric E.,Eichholzer, John V.,Lyndon, Paul,MacLeod, John K.,Summons, Roger E.
, p. 42 - 47 (2007/10/02)
In contradiction of long-accepted mass spectrometric dogma, the site-specific γ-hydrogen rearrangement is observed in alkylbenzenes in which both ortho positions are blocked with methyl substituents.Mass spectrometric studies of a series of five trimethyl- and three tetramethylisopentylbenzenes have shown that this rearrangement is only suppressed to a significant degree in those compounds in which all three positions ortho and para to the isopenyl group are blocked.Deuterium labelling has confirmed the γ-site-specific origin of the migrating H atom while metastable studies have been used to investigate the mechanism of the rearrangement process.
