97522-31-1Relevant academic research and scientific papers
Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation
Cardinale, Luana,Jacobi Von Wangelin, Axel,Konev, Mikhail O.,Schmotz, Mattis-Ole W. S.
, (2022/01/20)
An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.
Structure-Based Exploration of Selectivity for ATM Inhibitors in Huntington's Disease
Van De Po?l, Amanda,Toledo-Sherman, Leticia,Breccia, Perla,Cachope, Roger,Bate, Jennifer R.,Angulo-Herrera, Ivan,Wishart, Grant,Matthews, Kim L.,Martin, Sarah L.,Peacock, Marcus,Barnard, Amy,Cox, Helen C.,Jones, Graham,McAllister, George,Vater, Huw,Esmieu, William,Clissold, Cole,Lamers, Marieke,Leonard, Philip,Jarvis, Rebecca E.,Blackaby, Wesley,Eznarriaga, Maria,Lazari, Ovadia,Yates, Dawn,Rose, Mark,Jang, Sung-Wook,Mu?oz-Sanjuan, Ignacio,Dominguez, Celia
supporting information, p. 5018 - 5036 (2021/05/04)
Our group has recently shown that brain-penetrant ataxia telangiectasia-mutated (ATM) kinase inhibitors may have potential as novel therapeutics for the treatment of Huntington's disease (HD). However, the previously described pyranone-thioxanthenes (e.g., 4) failed to afford selectivity over a vacuolar protein sorting 34 (Vps34) kinase, an important kinase involved with autophagy. Given that impaired autophagy has been proposed as a pathogenic mechanism of neurodegenerative diseases such as HD, achieving selectivity over Vps34 became an important objective for our program. Here, we report the successful selectivity optimization of ATM over Vps34 by using X-ray crystal structures of a Vps34-ATM protein chimera where the Vps34 ATP-binding site was mutated to approximate that of an ATM kinase. The morpholino-pyridone and morpholino-pyrimidinone series that resulted as a consequence of this selectivity optimization process have high ATM potency and good oral bioavailability and have lower molecular weight, reduced lipophilicity, higher aqueous solubility, and greater synthetic tractability compared to the pyranone-thioxanthenes.
ATM KINASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF
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Paragraph 0265, (2021/06/11)
Provided are certain ATM kinase inhibitors of Formula (I). Also provided herein are compositions of such compounds, and methods of their use.
METHODS FOR WOUND HEALING AND SCAR PREVENTION
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, (2017/09/29)
The present invention is related to a compound of formula (I) or a pharmaceutically acceptable salt or ester thereof. The present invention is further related to a method of healing and/or inhibiting formation of scar tissue in an external wound of a subj
Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes
Zeng, Wei,Chemler, Sherry R.
, p. 12948 - 12949 (2008/09/17)
The enantioselective oxidative cyclizations of γ-alkenyl arylsulfonamides and a δ-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO2 is used as
Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines
Lebrun, Stephane,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
, p. 2625 - 2632 (2007/10/03)
An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and subsequent reduction complete the synthesis of the title compounds.
A Simple Asymmetric Synthesis of 2-Substituted Pyrrolidines and 5-Substituted Pyrrolidinones
Burgess, Laurence E.,Meyers, A. I.
, p. 1656 - 1662 (2007/10/02)
An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids.Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding γ-keto acid and
A Simple Asymmetric Synthesis of 2-Substituted Pyrrolidines from 3-Acylpropionic Acids
Meyers, A. I.,Burgess, Laurence E.
, p. 2294 - 2296 (2007/10/02)
The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in >98percent enantiomeric excess.The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.
N-(Trifluoroacetyl)-α-amino Acid Chlorides as Chiral Reagents for Friedel-Crafts Synthesis
Nordlander, J. Eric,Njoroge, F. George,Payne, Mark J.,Warman, Dhiraj
, p. 3481 - 3484 (2007/10/02)
Chiral N-(trifluoroacetyl)-α-amino acid chlorides unergo Friedel-Crafts reaction with benzene and 1,2-dimethoxybenzene under mild conditions commonly with complete (>99percent) preservation of configurational identity.The resultant (trifluoroacetyl)amino ketones may be deoxygenated with Et3SiH or H2/Pd-C in acidic media to the corresponding N-(trifluoroacetyl)-β-arylalkylamines likewise without loss of configurational purity.
