ChemInform Abstract: Catalytic Asymmetric Synthesis of tert‐Butanesulfinamide. Application to the Asymmetric Synthesis of Amines.

Liu, G.; Cogan, Derek A.; Ellman, Jonathan A.

doi:10.1002/chin.199805026

Cited by 22 publications

(29 citation statements)

References 1 publication

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“…Surprisingly, the sterically encumbering benzhydryl amide (27) with an IC 50 = 26 nM and an EC 50 = 1 nM is also well tolerated, perhaps giving an indication of the size of the binding pocket. Lastly, aryl groups are not required for potency, as simple cycloalkyl groups (28,29) afford potent partial agonists as well.…”

mentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

Asteian

Blayo

et al. 2015

ACS Med. Chem. Lett.

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The thiazolidinediones (TZD) typified by rosiglitazone are the only approved therapeutics targeting PPARγ for the treatment of type-2 diabetes (T2DM). Unfortunately, despite robust insulin sensitizing properties, they are accompanied by a number of severe side effects including congestive heart failure, edema, weight gain, and osteoporosis. We recently identified PPARγ antagonists that bind reversibly with high affinity but do not induce transactivation of the receptor, yet they act as insulin sensitizers in mouse models of diabetes (SR1664).1 This Letter details our synthetic exploration around this novel series of PPARγ antagonists based on an N-biphenylmethylindole scaffold. Structure-activity relationship studies led to the identification of compound 46 as a high affinity PPARγ antagonist that exhibits antidiabetic properties following oral administration in diet-induced obese mice.

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confidence: 99%

Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

Asteian

Blayo

et al. 2015

ACS Med. Chem. Lett.

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“…As groups for further elaboration, we chose the olefin 7 and the azide 11. Similar to our previous synthesis of N 4 -Alloc-1,4-diamino-1-(1-naphthyl)-butane, 55 we applied a diastereoselective Ellman-type Mannich reaction 67,[72][73][74] to achieve control of the stereochemistry.…”

Section: Resultsmentioning

confidence: 99%

Increasing the Functional Group Diversity in Helical β-Peptoids: Achievement of Solvent- and pH-Dependent Folding

et al. 2020

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We report the synthesis of a series of bis-functionalized -peptoid oligomers of the hexamer length. This was achieved by synthesizing and incorporating protected amino-or azido-functionalized chiral building blocks into precursor oligomers by a trimer segment coupling strategy. The resulting hexamers were readily elaborated to provide target compounds displaying amino groups, carboxy groups, hydroxy groups, or triazolo-pyridines, which should enable metal ion binding. Analysis of the novel hexamers by CD spectroscopy and HSQC NMR spectroscopy revealed robust helical folding propensity in acetonitrile. CD analysis showed solvent-dependent degree of helical content in the structural ensembles when adding different ratios of protic solvents including aqueous buffer. These studies were enabled by the substantial increase in solubility compared to previously analyzed -peptoid oligomers. This also allowed for investigation of the effect of pH on folding propensity of the amino-and carboxy-functionalized oligomers, respectively. Interestingly, we could demonstrate a reversible effect of sequentially adding acid and base, resulting in a switching between compositions of folded ensembles with varying helical content. We envision that the present discoveries can form the basis for the development of functional peptidomimetic materials responsive to external stimuli.

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“…In 1997, Ellman and co-workers developed an enantioselective method of preparation of tert -butane tert -butyl thiosulfinate 42 by oxidation of the corresponding disulfide 39 with hydrogen peroxide in a biphasic system in the presence of chiral vanadium complex (Schiff base 40 introduced by Bolm and Bienewald 183 was used, Scheme 21 ). 178 , 184 In subsequent studies, it was proven that slow addition of 30% aqueous H 2 O 2 and the use of cosolvent with low miscibility with water (CHCl 3 was found optimal) were of importance for the observed stereoselectivity (up to 91% ee was reached), which is otherwise limited by a nonenantioselective oxidation. 185 Later, change of chiral ligand to the one derived from cis -1-aminoindan-2-ol and 3,5-di- tert -butylsalicylaldehyde ( 41 ) allowed to exchange the two-phase solvent system to acetone, and to apply the protocol on a kilogram scale (99% conversion, 85–86% ee ).…”

Section: Synthesis Of Optically Active Thiosulfinatesmentioning

confidence: 99%

Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

2020

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Chiral sulfinyl compounds, sulfoxides, sulfoximines, sulfinamides, and other derivatives, play an important role in asymmetric synthesis as versatile auxiliaries, ligands, and catalysts. They are also recognized as pharmacophores found in already marketed and well-sold drugs (e.g., esomeprazole) and used in drug design. This review is devoted to the modern methods of preparation of sulfinyl derivatives in enantiopure or enantiomerically enriched form. Selected new approaches leading to racemic products for which the asymmetric variant can be developed in the future are mentioned as well.

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ChemInform Abstract: Catalytic Asymmetric Synthesis of tert‐Butanesulfinamide. Application to the Asymmetric Synthesis of Amines.

Cited by 22 publications

References 1 publication

Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

Increasing the Functional Group Diversity in Helical β-Peptoids: Achievement of Solvent- and pH-Dependent Folding

Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

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