- Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2-Symmetric Biaryls
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We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue β-dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling naphthols and ester-bearing quinones to yield non-C2-symmetric BINOL-type scaffolds with good yields and enantioselectivity. The study culminates in the asymmetric synthesis of backbone-substituted scaffolds similar to 3,3′-disubstituted BINOLs, such as (R)-TRIP, with good (94:6 e.r.) to excellent (>99.9:0.1 e.r.) enantioselectivity after recrystallization, and a diastereoselective net arylation of the minimally modified nonsteroidal anti-inflammatory drug (NSAID) naproxen.
- Coombs, Gavin,Sak, Marcus H.,Miller, Scott J.
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supporting information
p. 2875 - 2880
(2020/01/24)
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- Design, Synthesis, and Cytotoxic Activity of 3-Aryl-N-hydroxy-2-(sulfonamido)propanamides in HepG2, HT-1080, KB, and MCF-7 Cells
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A new series of (sulfonamido)propanamides (6a1–6a13, 6b1–6b15, 7c1–7c5, 6d1–6d5, 6e1–6e6) was designed and synthesized. All the synthesized compounds were characterized by NMR and mass spectrometry. The target compounds were evaluated for their in vitro c
- Shao, Duanyang,Zhang, Guo-Ning,Niu, Weixiao,Li, Ziqiang,Zhu, Mei,Wang, Juxian,Li, Donghui,Wang, Yucheng
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- Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes
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The rhodium-catalyzed asymmetric ring opening reaction of oxabicyclic alkenes is shown to be an efficient method for synthesizing chiral heterocycles. We demonstrate that the pairwise combination of chiral catalyst with chiral amino-acid-derived pronucleophiles results in a stereodivergent synthesis of diastereomeric hydroxyesters. A favorable conformational preference induces the subsequent lactonization of one diastereomer leading to the highly enantioselective synthesis of oxazinones.
- Yen, Andy,Pham, Anh Hoang,Larin, Egor M.,Lautens, Mark
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supporting information
p. 7549 - 7553
(2019/10/02)
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- Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids
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Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C=O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.
- Amer, Mostafa M.,Carrasco, Ana C.,Leonard, Daniel J.,Ward, John W.,Clayden, Jonathan
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supporting information
p. 7977 - 7981
(2019/01/04)
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- Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
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We report the development of a new class of guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates. Our mechanistic studies suggest that distal stereocontrol is achieved through a Cs-bridged interaction between the Lewis-basic C-terminal carboxylate of the peptides with the distal arene of the substrate.
- Kim, Byoungmoo,Chinn, Alex J.,Fandrick, Daniel R.,Senanayake, Chris H.,Singer, Robert A.,Miller, Scott J.
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supporting information
p. 7939 - 7945
(2016/07/07)
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- Compounds and compositions for treating obesity
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Described herein are novel and useful compounds of the general formula Compounds of this invention can advantageously exhibit melanocortin receptor agonist activity. New and useful compounds comprising such a chemical structure and methods of modulating melanocortin receptor activity in a subject (and promoting, inducing, and/or enhancing the treatment or prevention of related diseases) by administering such a compound or composition also are described.
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Page/Page column 27
(2010/11/28)
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- SULFONAMIDE COMPOUNDS
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Certain sulfonamide compounds are dual CCK1/CCK2 inhibitors useful in the treatment of CCK1/CCK2 mediated diseases.
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Page/Page column 23
(2010/10/20)
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- COMPOUNDS FOR USE IN TREATING OBESITY
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The present invention relates to novel compounds of the general formula (I) as well as any optical or geometric isomer or tautomer form thereof, or a pharmaceutically acceptable salt thereof, as agonists of melanocortin receptors, such as agonists of the MC4 receptor. The compounds may for instance be used in the treatment of obesity.
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- A new chiral catalyst for the enantioselective reduction of prochiral ketones with borane
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A new chiral β-amino alcohol, (s)-2-amino-1,1-diphenyl-3-(2-naphthyl)-1-propanol and its use as a catalyst in the enantioselective reduction of prochiral ketones with borane were described.
- Zhang,Shen,Liu,Chen
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p. 3407 - 3411
(2007/10/03)
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- Variations of the Nature of the Chiral Auxiliary with a Highly Enantioselective Chiral NADH Model
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Various chiral amine alcohols have been used as chiral auxiliares for a highly enantioselective NADH model.Some of these are new reagents which have been obtained by an enzymic resolution method.
- Combret, Yves,Duflos, Jack,Dupas, Georges,Bourguignon, Jean,Queguiner, Guy
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p. 1635 - 1644
(2007/10/02)
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- Synthesis and Conformation of Aromatic Cyclic Dipeptides. Cyclo(phenylalanyl)2, Cyclo(1-naphthylalanyl)2, and Cyclo(2-naphthylalanyl)2
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Cyclic dipeptides of aromatic amino acids, cyclo(L-phenylalanyl)2, cyclo(L-1-naphthylalanyl)2, and cyclo(L-2-naphthylalanyl)2 were synthesized and subjected to spectroscopic analyses using 1H NMR, absorption, circular dichroism (CD), fluorescence, and fluoroscence-detected circular dichroism (FDCD).The 1H NMR data suggested that the 2,5-piperazinedione rings of the three cyclic dipeptides are in planar or nearly planar bowsplitboat-type conformation.The aromatic side groups of cyclo(1- and 2-naphthylalanyl)2's were found to take asymmetric configurations, one naphthyl group being folded onto the 2,5-piperazinedione ring, the order being unfolded.Strong exciton couplet was observed in CD spectra of the three compounds.The signs of the exciton splitting were opposite in the two naphthyl cyclic dipeptides.Fluorescence spectra of the two naphthyl cyclic dipeptides showed no excimer emission.The absence of strong interchromophoric interaction in the lowest excited state was also suggested by the virtual coincidence of CD spectrum with FDCD spectrum.From the above spectroscopic data, probable conformations were proposed for the naphthyl cyclic dipeptides.
- Egusa, Syun,Takagi, Jun,Sisido, Masahiko,Imanishi, Yukio
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p. 2195 - 2202
(2007/10/02)
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