Ring-Closing Metathesis Strategies to Cyclic Sulfamide Peptidomimetics

Dougherty, Jack; Probst, Donald A.; Robinson, Randall E.; Moore, Joel D.; Klein, Thomas A.; Snelgrove, Kelley A; Hanson, Paul R.

doi:10.1016/s0040-4020(00)00885-1

Cited by 67 publications

(41 citation statements)

References 85 publications

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“…Symmetric N,N 0 -disubstituted sulfamides and tetra-substituted sulfamides were prepared in concordance with the typical procedures by condensation of an excess of amine with sulfuryl chloride (compounds 7 to 15). [24][25][26][27][28][29] Similarly, N,N 0 -di-substituted aminoacid derived sulfamides 16-18 were prepared by reaction of the corresponding salts of amino esters with sulfuryl chloride in presence of triethylamine. 30 Mono-substituted sulfamides (compounds 3-4) were synthesized following the standard method that involves the preparation of N-alkoxycarbonyl sulfamides as intermediates of the reaction.…”

Section: Synthesis Of Sulfamides and Sulfamatesmentioning

confidence: 99%

Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV

Gavernet

Funes

Palestro

et al. 2013

Bioorganic & Medicinal Chemistry

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A set of sulfamides and sulfamates were synthesized and tested against several isoforms of carbonic anhydrase: CA I, CA II, CA VII, CA XII and CA XIV. The biological assays showed a broad range of inhibitory activity, and interesting results were found for several compounds in terms of activity (Ki <1μm) and selectivity: some aromatic sulfamides are active against CA I, CA II and/or CA VII; while they are less active in CA XII and CA XIV. On the other hand, bulky sulfamides are selective to CA VII. To understand the origin of the different inhibitory activity against each isozyme we used molecular modeling techniques such as docking and molecular dynamic simulations.

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Section: Synthesis Of Sulfamides and Sulfamatesmentioning

confidence: 99%

Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV

Gavernet

Funes

Palestro

et al. 2013

Bioorganic & Medicinal Chemistry

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“…Equally problematic is the scarcity of these starting materials in the repertoire of commercially available chemicals, [41] thereby resulting in only a limited collection of sulfamides. While these issues have led to the development of several alternative protocols for sulfamide synthesis, [42] these additional technologies have proven amenable only to specific substrate classes and have not yet alleviated the need for multistep protocols. Most significantly, none of these methods has enabled the efficient and selective synthesis of nonsymmetrical N,N'-disubstituted cyclosulfamides (see XIX, Scheme 8), perhaps the most versatile class of these compounds for generating pharmaceutically relevant molecular diversity.…”

Section: Entrymentioning

confidence: 99%

New Uses for the Burgess Reagent in Chemical Synthesis: Methods for the Facile and Stereoselective Formation of Sulfamidates, Glycosylamines, and Sulfamides

Nicolaou

Snyder

Longbottom

et al. 2004

Chemistry A European J

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Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic tasks when applied to appropriate substrates, such as the formation of sulfamidates from 1,2-diols or epoxyalcohols, alpha- and beta-glycosylamines from carbohydrates, and cyclic sulfamides from 1,2-aminoalcohols. Beyond delineating the power of these new reaction manifolds, we also describe the construction of a group of alternative Burgess-type reagents that extends the scope of these new reactions even further.

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“…The first set of sulfamides 1 – 5 used for preliminary analysis were synthesized by treating sulfuryl chloride with the appropriate amino acid methyl esters (see Scheme S1 in the Supporting Information) . Of these sulfamide compounds, 1 and 2 were crystallized from EtOAc/hexanes (1:1) in a monoclinic system under the P 2(1) space group with Z =2.…”

Section: Resultsmentioning

confidence: 99%

Sulfamide‐Lattice Restructuring To Form Dimensionally Controlled Molecular Arrays and Gel‐Forming Systems

Raghava

Gopinath

Srivastava

et al. 2017

Chemistry A European J

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A design approach that incorporates structural requirements for the formation of a 1D assembly, fibril stability, and fibril-fibril interactions for gelation was attempted by using amino acid-based sulfamides with the general structure Aa-NH-SO -NH-Aa (Aa=amino acid). A preference for 1D assembly alone was not a sufficient condition for gelation, which became evident from studies involving sulfamide esters 1-5. Reducing the crystallization tendency without hindering unidirectional growth was executed through diacids of the sulfamide precursors with various amines that form an envelope around the sulfamide core through salt bridges. This strategy was fruitful, and gels of a wide variety of solvents could be formed by varying the acid and amine components. The use of dodecylamine or benzylamine, which could stabilize the molecular layers through alkyl-chain segregation or π-π interactions improved the gelation tendency, whereas the nature of the amino acid side chain, especially the rotational freedom and hydrophobicity, had a direct role in dictating the solvent preference. Crystallographic studies of these two-component systems gave molecular-level insight into the assembly and showed the importance of anisotropy in the distribution of secondary interactions in gelation.

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Ring-Closing Metathesis Strategies to Cyclic Sulfamide Peptidomimetics

Cited by 67 publications

References 85 publications

Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV

Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV

New Uses for the Burgess Reagent in Chemical Synthesis: Methods for the Facile and Stereoselective Formation of Sulfamidates, Glycosylamines, and Sulfamides

Sulfamide‐Lattice Restructuring To Form Dimensionally Controlled Molecular Arrays and Gel‐Forming Systems

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