89597-97-7Relevant academic research and scientific papers
Stereoselectivity in Reactions of Metal Complexes. Part XVII. Synthesis of Three New Optically Active Triamines: 2,6-Bismethyl>pyridine, 2,6-Bismethyl>pyridine, and 2,6-Bispyrro...
Bernauer, Klaus,Chuard, Thierry,Stoeckli-Evans, Helen
, p. 2263 - 2273 (1993)
The three new optically active triamines derived from 2,6-bis(aminomethyl)pyridine, i.e. 2,6-bis1melhyl>pyridine (3a), 2,6-bismethyl>-pyridine (3b), and 2,6-bispyrrolidin-1-yl>methyl>pyridine (3c), were synthesized.The equilibrium behaviour in solution and Cu(II) complex formation were studied by acidimetric titration and by UV/VIS and CD measurements.It was found that in aqueous solution, 3a can coordinate one of the CH2OH groups to Cu(II) upon deprotonation.X-Ray crystal structures were determined for the complexes ClO4*H2O, ClO4, and ClO4.In the solid state, coordination of both the OH and the alkoxy goups was observed, and the three ligands are pentacoordinated.
KRAS G12C INHIBITORS
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, (2019/05/24)
The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.
Rhodium-Catalyzed Asymmetric Synthesis of β-Branched Amides
Wu, Zhao,Laffoon, Joshua D.,Nguyen, Trang T.,McAlpin, Jacob D.,Hull, Kami L.
, p. 1371 - 1375 (2017/01/24)
A general asymmetric route for the one-step synthesis of chiral β-branched amides is reported through the highly enantioselective isomerization of allylamines, followed by enamine exchange, and subsequent oxidation. The enamine exchange allows for a rapid and modular synthesis of various amides, including challenging β-diaryl and β-cyclic.
Transition-metal-free synthesis of 3-(1-pyrrolidinyl)quinolines and 3-(1-pyrrolidinyl)quinoline 1-oxides via a one-pot reaction of 3-(1-pyrrolidinyl)crotonates with nitrobenzenes
Bujok, Robert,Cmoch, Piotr,Wróbel, Zbigniew,Wojciechowski, Krzysztof
, p. 2397 - 2402 (2017/03/20)
A carbanion of tert-butyl 3-(1-pyrrolidinyl)crotonate adds to nitrobenzenes to form σH-adducts, which in the presence of pivaloyl chloride and triethylamine are converted into 3-(1-pyrrolidinyl)quinolines or 3-(1-pyrrolidinyl)quinoline 1-oxides depending on the nitrobenzene structure. This is the first methodology in which a quinoline ring is constructed from a substrate bearing a pyrrolidinyl ring. Starting from optically pure enamines, the method allows synthesis of the corresponding chiral products without racemisation.
KRAS G12C INHIBITORS
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, (2017/12/18)
The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.
Direct evidence of significantly different chemical behavior and excited-state dynamics of 1,7- and 1,6-regioisomers of pyrrolidinyl-substituted perylene diimide
Dubey, Rajeev K.,Niemi, Marja,Kaunisto, Kimmo,Efimov, Alexander,Tkachenko, Nikolai V.,Lemmetyinen, Helge
, p. 6791 - 6806 (2013/07/11)
Novel bay-functionalized perylene diimides with additional substitution sites close to the perylene core have been prepared by the reaction between 1,7(6)-dibromoperylene diimide 6 (dibromo-PDI) and 2-(benzyloxymethyl) pyrrolidine 5. Distinct differences in the chemical behaviors of the 1,7- and 1,6-regioisomers have been discerned. While the 1,6-dibromo-PDI produced the corresponding 1,6-bis-substituted derivative more efficiently, the 1,7-dibromo-PDI underwent predominant mono-debromination, yielding a mono-substituted PDI along with a small amount of the corresponding 1,7-bis-substituted compound. By varying the reaction conditions, a controlled stepwise bis-substitution of the bromo substituents was also achieved, allowing the direct synthesis of asymmetrical 1,6- and 1,7-PDIs. The compounds were isolated as individual regioisomers. Fullerene (C60) was then covalently linked at the bay region of the newly prepared PDIs. In this way, two separate sets of perylene diimide-fullerene dyads, namely single-bridged (SB-1,7-PDI-C60 and SB-1,6-PDI-C60) and double-bridged (DB-1,7-PDI-C60 and DB-1,6-PDI-C60), were synthesized. The fullerene was intentionally attached at the bay region of the PDI to achieve close proximity of the two chromophores and to ensure an efficient photoinduced electron transfer. A detailed study of the photodynamics has revealed that photoinduced electron transfer from the perylene diimide chromophore to the fullerene occurs in all four dyads in polar benzonitrile, and also occurs in the single-bridged dyads in nonpolar toluene. The process was found to be substantially faster and more efficient in the dyads containing the 1,7-regioisomer, both for the singly- and double-bridged molecules. In the case of the single-bridged dyads, SB-1,7-PDI-C60 and SB-1,6-PDI-C60, different relaxation pathways of their charge-separated states have been discovered. To the best of our knowledge, this is the first observation of photoinduced electron transfer in PDI-C60 dyads in a nonpolar medium. Copyright
Chiral aminophosphines as catalysts for enantioselective double-michael indoline syntheses
Khong, San N.,Kwon, Ohyun
, p. 5626 - 5650 (2012/07/03)
The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogencontaining heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an asymmetric variant of the reaction were to be developed. Aminophosphines can also facilitate the double-Michael reaction and chiral amines are more readily available in Nature and synthetically; therefore, in this study we prepared several new chiral aminophosphines. When employed in the asymmetric double-Michael reaction between ortho-tosylamidophenyl malonate and 3-butyn-2-one, the chiral aminophosphines produced indolines in excellent yields with moderate asymmetric induction.
3,4-Dihydropyrimido(1,2-a)indol-10(2H)-ones as potent non-peptidic inhibitors of caspase-3
Havran, Lisa M.,Chong, Dan C.,Childers, Wayne E.,Dollings, Paul J.,Dietrich, Arlene,Harrison, Boyd L.,Marathias, Vasilios,Tawa, Gregory,Aulabaugh, Ann,Cowling, Rebecca,Kapoor, Bhupesh,Xu, Weixin,Mosyak, Lidia,Moy, Franklin,Hum, Wah-Tung,Wood, Andrew,Robichaud, Albert J.
experimental part, p. 7755 - 7768 (2010/03/03)
Cysteine-dependant aspartyl protease (caspase) activation has been implicated as a part of the signal transduction pathway leading to apoptosis. It has been postulated that caspase-3 inhibition could attenuate cell damage after an ischemic event and thereby providing for a novel neuroprotective treatment for stroke. As part of a program to develop a small molecule inhibitor of caspase-3, a novel series of 3,4-dihydropyrimido(1,2-a)indol-10(2H)-ones (pyrimidoindolones) was identified. The synthesis, biological evaluation and structure-activity relationships of the pyrimidoindolones are described.
Dpp-IV Inhibitors
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Page/Page column 21, (2008/12/07)
The invention relates to compounds of formula (I) wherein R1-9, Z, n, X, A, and Rb have the meaning as cited in the description and the claims. Said compounds are useful as DPP-IV inhibitors. The invention also relates to the pre
Analogs and derivatives of (S,S,R)-(-)-actinonin and uses therefor
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, (2008/06/13)
The present invention provides analog and derivative compounds of (S,S,R)-(?)-actinonin and methods of asymmetric synthesis thereof having a structure: where R1 is hydrogen, C(O)R6 or R1 in combination with N is 2-oxomorph
