85761-39-3Relevant academic research and scientific papers
CDPK1 INHIBITORS, COMPOSITIONS, AND METHODS RELATED THERETO
-
Paragraph 0407-0410, (2021/11/13)
The invention relates to inhibitors of calcium-dependent protein kinase 1 (CDPK1) and pharmaceutical preparations thereof. The invention further relates to methods of treatment of parasitic infections, such as T. gondii, P. falciparum, C. hominis, or C. parvum infections, using the novel inhibitors of the invention.
Benzoxaborole Catalyst for Site-Selective Modification of Polyols
Kusano, Shuhei,Miyamoto, Shoto,Matsuoka, Aki,Yamada, Yuji,Ishikawa, Ryuta,Hayashida, Osamu
supporting information, p. 1598 - 1602 (2020/02/11)
The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.
Optimizing Pyrazolopyrimidine Inhibitors of Calcium Dependent Protein Kinase 1 for Treatment of Acute and Chronic Toxoplasmosis
Janetka, James W.,Hopper, Allen T.,Yang, Ziping,Barks, Jennifer,Dhason, Mary Savari,Wang, Qiuling,Sibley, L. David
supporting information, p. 6144 - 6163 (2020/07/10)
Calcium dependent protein kinase 1 (CDPK1) is an essential Ser/Thr kinase that controls invasion and egress by the protozoan parasite Toxoplasma gondii. The Gly gatekeeper of CDPK1 makes it exquisitely sensitive to inhibition by small molecule 1H-pyrazolo
Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: Expansion of substrate scope and mechanistic studies
Lee, Doris,Williamson, Caitlin L.,Chan, Lina,Taylor, Mark S.
supporting information; experimental part, p. 8260 - 8267 (2012/07/14)
Synthetic and mechanistic aspects of the diarylborinic acid-catalyzed regioselective monofunctionalization of 1,2- and 1,3-diols are presented. Diarylborinic acid catalysis is shown to be an efficient and general method for monotosylation of pyranoside derivatives bearing three secondary hydroxyl groups (7 examples, 88% average yield). In addition, the scope of the selective acylation, sulfonylation, and alkylation is extended to 1,2- and 1,3-diols not derived from carbohydrates (28 examples); the efficiency, generality, and operational simplicity of this method are competitive with those of state-of-the-art protocols including the broadly applied organotin-catalyzed or -mediated reactions. Mechanistic details of the organoboron-catalyzed processes are explored using competition experiments, kinetics, and catalyst structure-activity relationships. These experiments are consistent with a mechanism in which a tetracoordinate borinate complex reacts with the electrophilic species in the turnover-limiting step of the catalytic cycle.
Asymmetric synthesis of O-protected acyloins using enoate reductases: Stereochemical control through protecting group modification
Winkler, Christoph K.,Stueckler, Clemens,Mueller, Nicole J.,Pressnitz, Desiree,Faber, Kurt
experimental part, p. 6354 - 6358 (2011/02/24)
O-Protected cyclic acyloins were obtained in nonracemic form through asymmetric bioreduction of α,β-unsaturated alkoxy ketones by using 11 different enoate reductases from the "Old Yellow Enzyme" family. The stereochemical outcome of the biotransformation could be switched by variation of the O-protecting group or by the ring size of the substrate, which allows access to both stereoisomers in up to >97 % ee Whereas α-alkoxy enones were readily accepted as substrates, β-analogs were not converted. Overall, α-alkoxy enones represent a novel type of substrate for flavin-dependent ene-reductases. Copyright
Catalytic monoalkylation of 1,2-diols
Maki, Toshihide,Ushijima, Nobuto,Matsumura, Yoshihiro,Onomura, Osamu
experimental part, p. 1466 - 1468 (2009/05/31)
A catalytic monoalkylation of 1,2-diols by using a weak base has been developed. Copper(II) dichloride and boronic acids are effective catalysts for activating 1,2-diols in the presence of potassium carbonate as a base. Various 1,2-diols were selectively monoalkylated with allyl-, benzyl- and alkyl- halides in DMF by choosing a suitable catalyst for each 1,2-diols.
Remaekable effect of subtle structural change of chiral pseudo-18-crown-6 on enantiomer-selectivity in complexation with chiral amino alcohols
Hirose, Keiji,Aksharanandana, Pakatip,Suzuki, Michiko,Wada, Kiyoshi,Naemura, Koichiro,Tobe, Yoshito
, p. 405 - 431 (2007/10/03)
Chiral receptors [(S,S)-1] and [(S,S,S,S)-2] having 1,2-dialkoxy-1-(3,5-dimethylphenyl)ethane and 1,2-dialkoxy-1-(3,5-dimethyl phenyl)cyclohexane as chiral building blocks, respectively, were prepared. Thermodynamic parameters of complexations of these and structurally related receptors [(S,S)-3] and [(S,S,S,S)-4] with 2-amino-l-propanol (5), 2-amino-2-phenylethanol (6), and 3-methylbutan-l-ol (7) in chloroform were determined. It was found that the host-guest systems that have same enantiomer-selectivity at 25°C showed opposite selectivity in the enthalpy term. For example, complexations of both (S,S)-1 and (S,S)-3 with 5 are R-selective at 25°C (ΔΔG = 2.2 and 3.8 kJ mol-1, respectively), whereas in terms of the enthalpy of complexation the former is S-selective (ΔΔH = 22 kJ mol-1) but the latter is R-selective (ΔΔH = 10 kJ mol-1).
Selective electrochemical deprotection of cinnamyl ethers, esters, and carbamates
Hansen, Jeff,Freeman, Stanley,Hudlicky, Tomas
, p. 1575 - 1578 (2007/10/03)
Electrochemical deprotection of the cinnamyl moiety from ethers, esters, and carbamates was studied with the focus on O- versus N- selectivity as well as selectivity over allyl or benzyl systems.
Synthesis of chiral trans-anti-trans-isomers of dicyclohexano-18-crown-6 via an enzymatic reaction and the solid-state structure of one enantiomer
Yamato, Kazuhiro,Bartsch, Richard A.,Broker, Grant A.,Rogers, Robin D.,Dietz, Mark L.
, p. 5805 - 5808 (2007/10/03)
Chiral trans-anti-trans-dicyclohexano-18-crown-6 isomers are synthesized via a lipase-catalyzed reaction. The solid-state structure of the (S)-enantiomer is determined and compared with those reported for 18-crown-6 and trans-syn-trans-dicyclohexano-18-crown-6.
Improved conditions for the addition of alkoxides to di(ethylene glycol) di-p-tosylate: Application to the stereospecific synthesis of the trans-isomers of dicyclohexano-18-crown-6
Huber, Vincent J.,Dietz, Mark L.
, p. 2945 - 2948 (2007/10/03)
Conditions are defined for the efficient preparation of polyethers by direct condensation of ditosylates and alkoxides, and this approach is shown to provide a facile method for the synthesis of the trans-syn-trans (C) and trans-anti-trans (D) isomers of
