57918-73-7Relevant academic research and scientific papers
Tetrahydroindazole inhibitors of CDK2/cyclin complexes
Lee, Jae Chul,Hong, Kwon Ho,Becker, Andreas,Tash, Joseph S.,Sch?nbrunn, Ernst,Georg, Gunda I.
, (2021/02/09)
Over 50 tetrahydroindazoles were synthesized after 7-bromo-3,6,6-trimethyl-1-(pyridin-2-yl)-5,6,7,7a-tetrahydro-1H-indazol-4(3aH)-one (3) was identified as a hit compound in a high throughput screen for inhibition of CDK2 in complex with cyclin A. The activity of the most promising analogues was evaluated by inhibition of CDK2 enzyme complexes with various cyclins. Analogues 53 and 59 showed 3-fold better binding affinity for CDK2 and 2- to 10-fold improved inhibitory activity against CDK2/cyclin A1, E, and O compared to screening hit 3. The data from the enzyme and binding assays indicate that the binding of the analogues to a CDK2/cyclin complex is favored over binding to free CDK2. Computational analysis was used to predict a potential binding site at the CDK2/cyclin E1 interface.
Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
G?rtner, Dominik,Stein, André Luiz,Grupe, Sabine,Arp, Johannes,Von Wangelin, Axel Jacobi
supporting information, p. 10545 - 10549 (2015/09/02)
Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.
2-Quinoxalinol diamine Cu(II) complex: Facilitating catalytic oxidation through dual mechanisms
Li, Yuancheng,Lee, Taebum,Weerasiri, Kushan,Wang, Tanyu,Buss, Emily E.,McKee, Michael L.,Gorden, Anne E. V.
, p. 13578 - 13583 (2014/11/08)
The Cu(II) complex 1, Cu(II)-6-N-3,5-di-tert-butylsalicylidene-6,7- quinoxalinol-diamine, has been developed to address problems with current methods of catalytic oxidation using tert-butyl hydroperoxide (TBHP). Complex 1 demonstrated an increased capability to utilize TBHP while limiting interference from free radical reactions and was demonstrated to be highly effective in the oxidations of a variety of olefins. the Partner Organisations 2014.
A Machine-assisted flow synthesis of SR48692: A probe for the investigation of neurotensin receptor-1
Battilocchio, Claudio,Deadman, Benjamin J.,Nikbin, Nikzad,Kitching, Matthew O.,Baxendale, Ian R.,Ley, Steven V.
, p. 7917 - 7930 (2013/07/19)
Here we report the direct comparison of a conventional batch mode synthesis of Meclinertant (SR48692, 1), a neurotensin receptor-1 antagonist, with its machine-assisted flow chemistry alternative. By using these enabling tools, combined with solid-supported reagents and scavengers, many process advantages were observed. Care, however, must be taken not to convert these techniques into expensive solutions to problems that do not exist. Copyright
A prototype device for evaporation in batch and flow chemical processes
Deadman, Benjamin J.,Battilocchio, Claudio,Sliwinski, Eric,Ley, Steven V.
supporting information, p. 2050 - 2055 (2013/09/24)
We report a convenient and efficient prototype device for evaporating, concentrating and switching solvents in continuous flow and batch processing and batch mode fashion. One of the main features of this system is the level of recyclability, whereby all solvents removed can be easily collected and reused, with reduced environmental impact.
Allylic C-H activations using Cu(II) 2-quinoxalinol salen and tert-butyl hydroperoxide
Li, Yuancheng,Lee, Tae Bum,Wang, Tanyu,Gamble, Audrey V.,Gorden, Anne E. V.
experimental part, p. 4628 - 4633 (2012/08/08)
Using a Cu(II) 2-quinoxalinol salen complex as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, allylic activations of olefin substrates can be converted to the corresponding enones or 1,4-enediones. Excellent yields can be achieved (up to 99%) within a very short reaction time and with great tolerance for additional functional groups. Possible mechanistic pathways have been characterized using Raman spectroscopy, cyclic voltammetry, and theoretical calculations.
Acyloxybutadiene tricarbonyl iron complexes as enzyme-triggered CO-releasing molecules (ET-CORMs): A structure-activity relationship study
Romanski, Steffen,Kraus, Birgit,Guttentag, Miguel,Schlundt, Waldemar,Rücker, Hannelore,Adler, Andreas,Neud?rfl, J?rg-Martin,Alberto, Roger,Amslinger, Sabine,Schmalz, Hans-Günther
supporting information, p. 13862 - 13875 (2013/01/15)
A series of η4-acyloxycyclohexadiene-Fe(CO)3 complexes was prepared and fully characterized by spectroscopic methods including single crystal X-ray diffraction. For this purpose a new synthetic access to differently acylated 1,3- and 1,5-dienol-Fe(CO)3 complexes was developed. The enzymatically triggered CO release from these compounds was monitored (detection of CO through GC and/or by means of a myoglobin assay) and the anti-inflammatory effect of the compounds was assessed by a cellular assay based on the inhibition of NO-production by inducible NO synthase (iNOS). It was demonstrated that the properties (rate of esterase-triggered CO release, iNOS inhibition, cytotoxicity) of the complexes strongly depend on the substitution pattern of the π-ligand and the nature of the acyloxy substituent.
An unprecedented method for the generation of tert -butylperoxy radical using DIB/TBHP protocol: Solvent effect and application on allylic oxidation
Zhao, Yi,Yeung, Ying-Yeung
supporting information; experimental part, p. 2128 - 2131 (2010/08/05)
Figure presented Tert-Butylperoxy radical was generated with PhI(OAc) 2 and tBuOOH. Ester solvent was found to be critical and the protocol was applied in the allylic oxidation of various olefinic substrates, which gave the corresponding α,β-unsaturated enones in good yield and regioselectivity.
HETEROTRICYCLIC COMPOUNDS AS POSITIVE ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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Page/Page column 30-31, (2010/08/04)
The present invention relates to novel compounds of Formula (I), wherein wherein X1, X2, Y, Z1, Z2, Z3, M and (A)m are defined as in Formula (I); invention compounds are modulators of metab
