67627-99-0Relevant academic research and scientific papers
Straightforward and Highly Stereoselective Synthesis of 3,3,4-Trifluoropyrrolidines Involving 1,3-Dipolar Cycloaddition with 2,3,3-Trifluoroacrylate
Yamada, Shigeyuki,Higashi, Masao,Konno, Tsutomu,Ishihara, Takashi
, p. 4561 - 4568 (2016)
The reactions of benzyl 2,3,3-trifluoroacrylate with azomethine ylides, generated by the treatment of imino esters with lithium diisopropylamide, took place smoothly to give the corresponding 1,3-dipolar cycloadducts, fluorine-containing pyrrolidines, in good yields and with high diastereoselectivities (>95:5). When the fluorinated acrylate bore a chiral auxiliary as a substituent, for instance (l)-(–)-menthyl ester, the 1,3-dipolar cycloaddition reaction was found to give the corresponding fluorinated pyrrolidine derivatives in not only a diastereoselective but also an enantioselective manner.
Copper-Catalyzed Enantioselective Difluoromethylation of Amino Acids via Difluorocarbene
Peng, Lingzi,Wang, Hongyi,Guo, Chang
supporting information, p. 6376 - 6381 (2021/05/29)
Difluoromethyl amino acids (DFAA) exhibit intriguing biological properties, making them highly desirable motifs in agrochemical and pharmaceutical science. However, stereochemical control of direct difluoromethyl transformation via the difluorocarbene spe
Synthesis and Penicillin-binding Protein Inhibitory Assessment of Dipeptidic 4-Phenyl-β-lactams from α-Amino Acid-derived Imines
Decuyper, Lena,Juki?, Marko,Sosi?, Izidor,Amoroso, Ana Maria,Verlaine, Olivier,Joris, Bernard,Gobec, Stanislav,D'hooghe, Matthias
supporting information, p. 51 - 55 (2019/11/28)
Monocyclic β-lactams revive the research field on antibiotics, which are threatened by the emergence of resistant bacteria. A six-step synthetic route was developed, providing easy access to new 3-amino-1-carboxymethyl-4-phenyl-β-lactams, of which the penicillin-binding protein (PBP) inhibitory potency was demonstrated biochemically.
HETEROCYCLIC COMPOUNDS AS HIV PROTEASE INHIBITORS
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, (2018/07/26)
The present invention is directed to compounds of Formula I pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.
HETEROCYCLIC COMPOUNDS AS HIV PROTEASE INHIBITORS
-
, (2018/07/29)
The present invention is directed to compounds of Formula I, pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.
Umpolung of Imines Enables Catalytic Asymmetric Regio-reversed [3+2] Cycloadditions of Iminoesters with Nitroolefins
Feng, Bin,Lu, Liang-Qiu,Chen, Jia-Rong,Feng, Guoqiang,He, Bin-Qing,Lu, Bin,Xiao, Wen-Jing
supporting information, p. 5888 - 5892 (2018/05/14)
A copper-catalyzed regio-reversed asymmetric [3+2] cycloaddition of iminoesters with nitroolefins is disclosed for the first time. This method enables the facile synthesis of polysubstituted chiral pyrrolidines bearing at least one chiral quaternary cente
HETEROCYCLIC COMPOUNDS AS HIV PROTEASE INHIBITORS
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Page/Page column 37-38, (2018/06/30)
The present invention is directed to compounds of Formula (I), pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.
Application of meso-hydrobenzoin-derived chiral auxiliaries for the stereoselective synthesis of highly substituted pyrrolidines by 1,3-dipolar cycloaddition of azomethine ylides
Bica, Katharina,Gaertner, Peter
experimental part, p. 641 - 646 (2010/08/03)
The metal-catalyzed stereoselective 1,3-dipolar cycloaddition of azomethine ylides and acrylates using recyclable meso-hydrobenzoin-derived chiral auxiliaries is described. Cleavage of the auxiliary leads to highly substituted pyrrolidines in up to 87% en
Kinesin Spindle Protein (KSP) inhibitors. 9. Discovery of (2S)-4-(2,5-difluorophenyl)-N-[(3R,4S)-3-fluoro-1-methylpiperidin-4-yl] -2-(hydroxymethyl)-N-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (MK-0731) for the treatment of taxane-refractory cancer
Cox, Christopher D.,Coleman, Paul J.,Breslin, Michael J.,Whitman, David B.,Garbaccio, Robert M.,Fraley, Mark E.,Buser, Carolyn A.,Walsh, Eileen S.,Hamilton, Kelly,Schaber, Michael D.,Lobell, Robert B.,Tao, Weikang,Davide, Joseph P.,Diehl, Ronald E.,Abrams, Marc T.,South, Vicki J.,Huber, Hans E.,Torrent, Maricel,Prueksaritanont, Thomayant,Li, Chunze,Slaughter, Donald E.,Mahan, Elizabeth,Fernandez-Metzler, Carmen,Yan, Youwei,Kuo, Lawrence C.,Kohl, Nancy E.,Hartman, George D.
experimental part, p. 4239 - 4252 (2009/07/04)
Inhibition of kinesin spindle protein (KSP) is a novel mechanism for treatment of cancer with the potential to overcome limitations associated with currently employed cytotoxic agents. Herein, we describe a C2-hydroxymethyl dihydropyrrole KSP inhibitor (11) that circumvents hERG channel binding and poor in vivo potency, issues that limited earlier compounds from our program. However, introduction of the C2-hydroxymethyl group caused 11 to be a substrate for cellular efflux by P-glycoprotein (Pgp). Utilizing knowledge garnered from previous KSP inhibitors, we found that β-fluorination modulated the pK a of the piperidine nitrogen and reduced Pgp efflux, but the resulting compound (14) generated a toxic metabolite in vivo. Incorporation of fluorine in a strategic, metabolically benign position by synthesis of an N-methyl-3-fluoro-4-(aminomethyl)piperidine urea led to compound 30 that has an optimal in vitro and metabolic profile. Compound 30 (MK-0731) was recently studied in a phase I clinical trial in patients with taxane-refractory solid tumors.
Solventless lactam synthesis by intramolecular cyclizations of α-iminoester derivatives under microwave irradiation
Zradni, Fatima-Zohra,Hamelin, Jack,Derdour, Aicha
, p. 439 - 454 (2007/10/03)
We have previously reported a new synthesis of amides from esters and amines under microwave irradiation, offering much higher yields than those achieved with conventional heating [1]. We have now extended these studies to the ring closure of neat iminoes
