6502-22-3Relevant articles and documents
BCL-2 INHIBITOR
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Paragraph 0182-0184, (2021/10/22)
Disclosed herein is a compound of Formula (I) for inhibiting both Bcl-2 wild type and mutated Bcl-2, in particular, Bcl-2 G101V and D103Y, and a method of using the compound disclosed herein for treating dysregulated apoptotic diseases.
Room Temperature Deoxyfluorination of Benzaldehydes and α-Ketoesters with Sulfuryl Fluoride and Tetramethylammonium Fluoride
Melvin, Patrick R.,Ferguson, Devin M.,Schimler, Sydonie D.,Bland, Douglas C.,Sanford, Melanie S.
supporting information, p. 1350 - 1353 (2019/03/08)
A method for the room temperature deoxyfluorination of benzaldehydes and α-ketoesters using sulfuryl fluoride and Me4NF is described. A large scope of aryl and heteroaryl substrates is demonstrated, and this method compares favorably to other common deoxyfluorination methods for many substrates.
Bridged bicyclic 2,3-dioxabicyclo[3.3.1]nonanes as antiplasmodial agents: Synthesis, structure-activity relationships and studies on their biomimetic reaction with Fe(II)
D'Alessandro, Sarah,Alfano, Gloria,Di Cerbo, Luisa,Brogi, Simone,Chemi, Giulia,Relitti, Nicola,Brindisi, Margherita,Lamponi, Stefania,Novellino, Ettore,Campiani, Giuseppe,Gemma, Sandra,Basilico, Nicoletta,Taramelli, Donatella,Baratto, Maria Camilla,Pogni, Rebecca,Butini, Stefania
supporting information, (2019/06/13)
Despite recent advancements in its control, malaria is still a deadly parasitic disease killing millions of people each year. Progresses in combating the infection have been made by using the so-called artemisinin combination therapies (ACTs). Natural and synthetic peroxides are an important class of antimalarials. Here we describe a new series of peroxides synthesized through a new elaboration of the scaffold of bicyclic-fused/bridged synthetic endoperoxides previously developed by us. These peroxides are produced by a straightforward synthetic protocol and are characterized by submicromolar potency when tested against both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains. To investigate their mode of action, the biomimetic reaction of the representative compound 6w with Fe(II) was studied by EPR and the reaction products were characterized by NMR. Rationalization of the observed structure-activity relationship studies was performed by molecular docking. Taken together, our data robustly support the hypothesized mode of activation of peroxides 6a-cc and led to the definition of the key structural requirements responsible for the antiplasmodial potency. These data will pave the way in future to the rational design of novel optimized antimalarials suitable for in vivo investigation.
Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes
Xiao, Peihong,Tang, Zhixing,Wang, Kai,Chen, Hua,Guo, Qianyou,Chu, Yang,Gao, Lu,Song, Zhenlei
, p. 1687 - 1700 (2018/02/23)
A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combination of EtOTf/2,6-DTBMP and LiAlH(O-t-Bu)3 was found to be optimal for reducing alkyl, alkenyl, alkynyl, and 2-monosubstituted aryl N,N-diisopropylamides. In contrast, EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodology was demonstrated with N,N-diisopropylamide-directed ortho-metalation and C-H bond activation.
Benzothiazepine CGP37157 and its 2′-isopropyl analogue modulate Ca2+ entry through CALHM1
Moreno-Ortega, Ana J.,Martínez-Sanz, Francisco J.,Lajarín-Cuesta, Rocío,De Los Rios, Cristóbal,Cano-Abad, María F.
, p. 503 - 510 (2015/06/17)
CALHM1 is a Ca2+ channel discovered in 2008, which plays a key role in the neuronal electrical activity, among other functions. However, there are no known efficient blockers able to modulate its Ca2+ handling ability. We herein desc
GLYCOSIDE DERIVATIVES AND USES THEREOF
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Page/Page column 139; 142, (2011/05/06)
This invention relates to compounds represented by formula (I): wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment
Glycoside Derivatives and Uses Thereof
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Page/Page column 70-71, (2011/08/02)
This invention relates to compounds represented by formula (I): wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment.
Correlated rotations in benzylfluorene derivatives: Structure, conformation, and stereodynamics
Casarini, Daniele,Lunazzi, Lodovico,Mazzanti, Andrea
, p. 2811 - 2818 (2008/09/19)
(Graph Presented) Fluorene derivatives, having substituted benzyl groups bonded to position 9, have been investigated by variable temperature NMR spectroscopy. Stereodynamic processes involving restricted rotation about the fluorenyl-CH2 and ar
Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol·SnCl4 complexes. Optimization, substrate scope and mechanistic investigations
Rauniyar, Vivek,Zhai, Huimin,Hall, Dennis G.
supporting information; experimental part, p. 8481 - 8490 (2009/02/02)
We report a novel class of C2-symmetric chiral diols derived from the hydrobenzoin skeleton. The combination of these diols with SnCl 4 under Yamamoto's concept of Lewis acid assisted Bronsted acidity (LBA catalysis) leads to high levels of asymmetric induction in the allylboration of aldehydes by commercially available allylboronic acid pinacol ester 1a. The corresponding homoallylic alcohol products of synthetically useful aliphatic aldehydes are obtained in excellent yields with up to 98:2 er. This combined acid manifold is also efficient in catalyzing the diastereo- and enantioselective crotylboration of aldehydes, thus providing the propionate units in >95:5 dr and up to 98:2 er. The X-ray crystal structure of the optimal diol·SnCl4 complex, Vivol (4m)·SnCl 4, unambiguously shows the Bronsted acidic character of this LBA catalyst and its highly dissymmetrical environment. Further controls have ruled out a possible boron transesterification mechanism with the chiral diol and point to LBA catalyst-derived activation of the pinacol allylic boronates 1. Due to slow dissociation of the diol·SnCl4 complex, a small excess of diol is required in order to suppress a competing racemic cycle catalyzed by free SnCl4.
Synthesis and structure of optically active 1,12-diethyl-and 1,12-diisopropylbenzo[c]phenanthrenes: An isopropyl group can be smaller than a methyl group
Sugiura, Hiroki,Sakai, Daisuke,Otani, Harunori,Teranishi, Kazuhiro,Takahira, Yusuke,Amemiya, Ryo,Yamaguchi, Masahiko
, p. 72 - 73 (2007/10/03)
1,12-Diethyl- and 1,12-diisopropylbenzo[c]phenanthrene-5,8-dicarboxylic acids were synthesized, and resolved. The dihedral angles formed by the A and D rings increased in the order of diisopropyl diethyl dimethyl as indicated by X-ray analysis, which showed that the strain decreased with the increase of the bulkiness at the 1,12-groups. Copyright
