Spectroscopic and theoretical studies of some N-methoxy-N-methyl-2-[(4′-substituted) phenylsulfonyl]propanamides

Olivato, Paulo R.; Domingues, Nélson; Reis, Adriana Karla Cardoso Amorim; Vinhato, Elisângela; Mondino, Mirta G.; Zukerman-Schpector, Júlio; Rittner, Roberto; Colle, Maurizio Dal

doi:10.1016/j.molstruc.2009.06.038

Cited by 9 publications

(8 citation statements)

References 22 publications

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“…A notable feature of the parallel β-sheet is the nitrogen pyramidalization in each N -(hydroxy)amide (ω(OH 1 ) 171.5° and ω(OH 2 ) 170.9°). A similar pyramidalization was previously reported by Kirshenbaum and others for N -alkoxy peptoids. This phenomenon is likely responsible for decreasing the nitrogen lone pair resonance in the N -(hydroxy)amide, which in turn accentuates the basicity of the vicinal carbonyl.…”

Section: Resultssupporting

confidence: 84%

Structure–Property Relationship Study of N-(Hydroxy)Peptides for the Design of Self-Assembled Parallel β-Sheets

Richaud

Roche

2020

J. Org. Chem.

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The design of novel and functional biomimetic foldamers remains a major challenge in creating mimics of native protein structures. Herein, we report the stabilization of a short b-sheet by incorporating N-(hydroxy)glycine (Hyg) residues into the backbone of peptides. These short peptide−peptoid hybrids form unique parallel b-sheet structures by self-assembly. Spectroscopic and crystallographic data collected suggest that the local conformational perturbations induced by N-(hydroxy)amides are outweighed by a network of strong interstrand hydrogen-bonds. File list (2) download file view on ChemRxiv Manuscript-Roche.pdf (796.16 KiB) download file view on ChemRxiv SI-Roche.pdf (8.92 MiB) Structure-Property Relationship Study of N-(Hydroxy)Peptides for the Design of Self-Assembled Parallel -Sheets.

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Section: Resultssupporting

confidence: 84%

Structure–Property Relationship Study of N-(Hydroxy)Peptides for the Design of Self-Assembled Parallel β-Sheets

Richaud

Roche

2020

J. Org. Chem.

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“…Geometry optimization of 7 constrained to a planar nitrogen results in a structure 1.66–2.65 kcal/mol less favorable than the freely minimized pyramidal geometry according to B3LYP/6‐311+G(2d,p)//HF/6‐31G* and MP2(full)/6‐311+G(d,p)//HF/6‐31G*, respectively (Supporting Information Table S1). Nitrogen pyramidalization has been previously observed in N ‐methoxy‐ N ‐methylamides both computationally and experimentally 44–49. The pyramidalization has been attributed to the increased affinity of nitrogen for its lone pair (relative to an N , N ‐dialkyl amide), which decreases N n to CO π* interactions and also reduces the extent of resonance within the amide group 45.…”

Section: Resultsmentioning

confidence: 89%

Oligo(N‐alkoxy glycines): Trans substantiating peptoid conformations

et al. 2011

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Peptoid oligomers possess many desirable attributes bioactive peptidomimetic agents, including their ease of synthesis, chemical diversity, and capability for molecular recognition. Ongoing efforts to develop functional peptoids will necessitate improved capability for control of peptoid structure, particularly of the backbone amide conformation. We introduce alkoxyamines as a new reagent for solid phase peptoid synthesis. Herein, we describe the synthesis of N-alkoxy peptoids, and present NMR data indicating that the oligomers adopt a single stable conformation featuring trans amide bonds. These findings, combined with results from computational modeling, suggest that N-alkoxy peptoid oligomers have a strong propensity to adopt a polyproline II type secondary structure.

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“…In addition, the conformational analysis were carried out to confirm the minimum energy structure to molecules 12 and 20, by carrying out a series of partial optimizations constraining the concerned dihedral angle step by step within the appropriate range, with a step size of 5°, these calculations were carried out using the B3LYP/6-31G* basis set, the dihedral angles analyzed were C1-C7-C8-O and C4'-O-C8-C7 for molecule 12 and C1-C7-C8-S and C4'-S-C8-C7 for molecule 20. Previous studies about conformational preferences in solid state (crystal) and in solution has been published [55][56][57] for a large number of compounds analogues of the compounds 12 and 20, studied in the present paper. The geometrical structures of the radicals studied were optimized independently from the neutral molecules prior to the calculations of energies, treated as open shell systems DFT/UB3LYP.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Nascimento¹,

Santos²,

Santos³

et al. 2010

J. Braz. Chem. Soc.

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A síntese e a estrutura cristalina por difração de raios-X de dois análogos de neolignanas, 2-(4-clorofenil)-1-feniletanona (20) e 2-[tio(4-clorofenil)]-1-(3,4-dimetoxifenil)propan-1-ona (12) são descritas. O composto 12 apresenta atividade intracelular contra Leishmania donovani e Leishmania amazonensis de amastigotas que causam a leishmaniose tegumentar e visceral. Além disso, a teoria do funcional de densidade (DFT) com o funcional híbrido B3LYP foi empregado para calcular um conjunto de descritores moleculares para dezenove análogos sintéticos de neolignanas com atividades antileishmaniose. Posteriormente, a análise discriminante stepwise foi realizada para investigar possíveis relações entre a estrutura molecular e atividades biológicas. Por meio dessa análise os compostos foram classificados em dois grupos ativos e inativos de acordo com seu grau de atividade biológica, e as propriedades mais importantes foram as cargas de alguns átomos, a afinidade eletrônica e o ClogP.The synthesis and X-ray crystal diffraction structure of two analogues of neolignans, 2-(4-chlorophenyl)-1-phenylethanone (20) and 2-[(4-chlorophenyl)thio]-1-(3,4-dimethoxyphenyl) propan-1-one (12) is described. The compound 12 presents activity against intracellular Leishmania donovani and Leishmania amazonensis amastigotes that cause cutaneous and visceral leishmaniasis. In addition, the density functional theory (DFT) with the B3LYP hybrid functional was employed to calculate a set of molecular descriptors for nineteen synthetic analogues of neolignans with antileishmanial activities. Afterwards, the stepwise discriminant analysis was performed to investigate possible relationship between the molecular descriptors and biological activities. Through this analysis the compounds were classified into two groups active and inactive according to their degree of biological activities, and the more important properties were charges on some key atoms, electronic affinity and ClogP.

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Spectroscopic and theoretical studies of some N-methoxy-N-methyl-2-[(4′-substituted) phenylsulfonyl]propanamides

Cited by 9 publications

References 22 publications

Structure–Property Relationship Study of N-(Hydroxy)Peptides for the Design of Self-Assembled Parallel β-Sheets

Structure–Property Relationship Study of N-(Hydroxy)Peptides for the Design of Self-Assembled Parallel β-Sheets

Oligo(N‐alkoxy glycines): Trans substantiating peptoid conformations

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

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