Synthesis of peptidomimetics: An evaluation of p-nitrophenyl carbamate of ethylenediamine

Wiszniewska, Anna; Kunce, Danuta; Chung, Nga N.; Schiller, Peter W.; Izdebski, Jan

doi:10.1007/bf02443640

Cited by 3 publications

(6 citation statements)

References 14 publications

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“…Compound 9 was prepared in one pot using the bis-p-nitrophenyl carbamate of 1,5-dimethyl-2,4-phenylenediamine; which was reacted in situ with diamine 1. [25,27] This was readily converted to compound 10 by capping with o-tolylene isocyanate.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Urea‐Linked Aromatic Oligomers—A Route Towards Convoluted Foldamers

Mousseau

Xing

Tang

et al. 2009

Chemistry A European J

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Herein we report the design and synthesis of crescent-shaped and helical urea-based foldamers, the curvature of which is controlled by varying the constituent building blocks and their connectivity. These oligomers are comprised of two, three or five alternating aromatic heterocycles (pyridazine, pyrimidine or pyrazine) and methyl-substituted aromatic carbocycles (tolyl, o-xylyl or m-xylyl) connected together through urea linkages. A crescent-shaped conformational preference is encoded within these pi-conjugated urea-linked oligomers based on intramolecular hydrogen bonding and steric interactions; the degree of curvature is tuned by the urea connectivity to the heterocycles and the aryl groups. NMR characterization of these foldamers confirms the intramolecular hydrogen-bonded conformation expected (Z,E configuration of the urea bond) in both the pyridazyl and pyrimidyl foldamers in solution. An X-ray crystal structure of the N(3),N(6)-diisobutylpyridazine-4,6-diamine-o-tolyl urea-linked foldamer (4) confirms the presence of N-H...N hydrogen bonds between the heterocyclic nitrogen atom and the free hydrogen of the urea linkage. Additionally, the tolyl methyl group interacts unfavourably with the urea carbonyl oxygen, thus destabilising the alternate planar conformation.

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Urea‐Linked Aromatic Oligomers—A Route Towards Convoluted Foldamers

Mousseau

Xing

Tang

et al. 2009

Chemistry A European J

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“…Peptidomimetics were obtained recently containing alkylurea units, based on the 1-4 enkephalin sequence [8], which displayed moderate activity in MVD and GPI assays. In this work new peptidomimetics were obtained using p-nitrophenoxycarbonyl derivatives of Boc-protected diaminoalkanes with various lengths of the alkyl chain.…”

Section: Resultsmentioning

confidence: 99%

“…This prompted the use of HCl/dioxane in the synthesis of the [Leu 5 ]-enkephalin analogue containing a C-terminal ethylurea unit (3) (Scheme 2). This deprotection reagent had been used previously with success, in the synthesis of oligoalkylureas [8]. The synthesis was carried out along two synthetic routes.…”

Section: Resultsmentioning

confidence: 99%

“…and analysis for p-nitrophenoxycarbonyl derivative of 1-Boc-1,2-diaminoethane are given in our previous paper [8].…”

Section: P-nitrophenoxycarbonyl Derivative Of Boc-eda Yield Mpmentioning

confidence: 99%

“…We recently obtained biologically active enkephalin analogues, derived from the 1-4 fragment, using the p-nitrophenoxycarbonyl derivative of 1-Boc-1,2diaminoethane [8], and this encouraged us to investigate whether the application of other diaminoalkanes would yield similar results in regard to the activity of synthesized peptidomimetics. In addition, it was of interested to determine whether the presence of a C-terminal leucine in the analogue sequence would enhance the activity of the peptidomimetics and 580 WISZNIEWSKA ET AL.…”

Section: Introductionmentioning

confidence: 99%

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p-Nitrophenoxycarbonyl derivatives of Boc-protected diaminoalkanes in the synthesis of enkephalin peptidomimetics

et al. 2005

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The synthesis of p-nitrophenoxycarbonyl derivatives of 1-Boc-1,2-diaminoethane, 1-Boc-1,3-diaminopropane and 1-Boc-1,4-diaminobutane is described. These derivatives were used to synthesize five peptidomimetics, analogues of enkephalin, containing alkylurea units inside the peptide chain and at the C-terminal. All syntheses were carried out in solid phase on MBHA resin. Peptidomimetics with alkylurea units inserted into the peptide chain were synthesized using the standard method employing the Boc-strategy, with TFA deprotection and HF cleavage. The analogue containing a C-terminal alkylurea unit was synthesized using the Boc-strategy, with HCl/dioxane deprotection and TFA cleavage. All of the analogues were examined for opioid activity in GPI and MVD assays. The activity of the analogue containing a C-terminal alkylurea unit was comparable to that of [Leu5]-enkephalin, while the other analogues were less active.

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Theoretical studies on effective interactions in two‐band system

Nagao

Kawabe

2005

Int J of Quantum Chemistry

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ABSTRACT:We investigate effective interactions in a two-dimensional twosublattice system by using a two-band Hubbard model. We present a t-matrix approach for two-dimensional two-sublattice system and derive expressions of effective interactions by using the t-matrix approach. Expressions of the effective exchange integral in the Heisenberg model are also approximately derived. The results suggest that two-band superconductivity appears in the limit of an almost-empty or almostfilled band and strongly electron-electron correlation in two-band systems. © 2005 Wiley Periodicals, Inc. Int J Quantum Chem 105: [571][572][573][574][575][576][577][578][579] 2005

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Synthesis of peptidomimetics: An evaluation of p-nitrophenyl carbamate of ethylenediamine

Cited by 3 publications

References 14 publications

Design and Synthesis of Urea‐Linked Aromatic Oligomers—A Route Towards Convoluted Foldamers

Design and Synthesis of Urea‐Linked Aromatic Oligomers—A Route Towards Convoluted Foldamers

p-Nitrophenoxycarbonyl derivatives of Boc-protected diaminoalkanes in the synthesis of enkephalin peptidomimetics

Theoretical studies on effective interactions in two‐band system

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