Solid phase synthesis of aryl ethers via the mitsunobu reaction

Rano, Thomas A.; Chapman, Kevin T.

doi:10.1016/0040-4039(95)00607-e

Cited by 111 publications

(36 citation statements)

References 10 publications

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“…For each diversity step, the mean purity of all of the compounds arising from a reagent in that step permits an assessment of how well that reagent performed in the library synthesis. These data are summarized in Tables 1-3. This analysis shows that certain reagents used at R1, 4{6, 11,12,17,19,23}, worked very well, exhibiting a mean purity >90%. Although this set displays a variety of electronic and steric effects, there is no clear reactivity trend.…”

Section: Resultsmentioning

confidence: 92%

Solid-Phase Synthesis of a Tyrphostin Ether Library

Guo¹,

Arvanitis²,

Pottorf³

et al. 2003

J. Comb. Chem.

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The solid-phase synthesis of a 4500-member (30 x 15 x 10) tyrphostin library is demonstrated utilizing the Irori-directed sorting system. Fmoc-protected PL-Rink resin was used as the solid support. After Fmoc-deprotection, aryl aldehydes were attached to the resin through reductive amination. Acylation of the resulting secondary amines with cyanoacetic acid was followed by a Knoevenagel condensation with phenolic aldehydes. Mitsunobu coupling of primary alcohols to the resin-bound phenols yielded the final library of compounds 1.

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Section: Resultsmentioning

confidence: 92%

Solid-Phase Synthesis of a Tyrphostin Ether Library

Guo¹,

Arvanitis²,

Pottorf³

et al. 2003

J. Comb. Chem.

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“…The key intermediate in this protocol was the resin-bound 3-vinyl-b-lactam 65. The attachment of Fmoc protected p-aminophenol to Wang resin was however achieved by using tetramethylamine azodicarboxylate (TMAD) and Bu 3 P [107] instead of classical Mitsunobu conditions [108] (DEAD, Ph 3 P). The resin-bound aniline 62 was deprotected following standard procedure and converted to the aldimine 64 by condensation with aldehyde 63.…”

Section: Solid-phase Techniques For B-lactam Synthesismentioning

confidence: 99%

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Mandal

Ghosh

Basu

2010

Heterocyclic Scaffolds I

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Since the discovery of penicillin in 1929, b-lactam antibiotics have been recognized as potentially chemotherapeutic drugs of incomparable effectiveness, conjugating a broad spectrum of activity with very low toxicity. The primary motif azetidin-2-one ring (b-lactam) has been considered as specific pharmacophores and scaffolds. With the advent of combinatorial chemistry and automated parallel synthesis coupled with ample interests from the pharmaceutical industries, recent trends have been driven mostly by adopting solid phase techniques and polymersupported synthesis of b-lactams. The present survey will present an overview of the developments on the polymer-supported and solid phase techniques for the preparation of b-lactam ring or b-lactam containing antibiotics published over the last decade. Both unsubstituted and substitutions with different functional groups at various positions of b-lactams have been synthesized using solid phase technology. However, Wang resin and application of Staudinger [2+2] cycloaddition reaction have remained hitherto the major choice. It may be expected that other solid phase approaches involving different resins would be developed in the coming years.

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“…The linear peptides were prepared manually using standard solid-phase procedure on the p-alkoxybenzylalcohol (Wang) resin. Fmoc-Ile attached to Wang resin was prepared through esterification reaction using Mitsunobu methods [47,48]. Unreacted hydroxyl groups were acetylated with the aid of acetic anhydride, pyridine, and DCM (1 : 2 : 3).…”

Section: Solid-phase Peptide Synthesismentioning

confidence: 99%

Synthesis and immunosuppressive activity of new cyclolinopeptide A analogs modified with β‐prolines

Katarzyńska

Mazur

Bilska

et al. 2008

Journal of Peptide Science

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Immune response suppressors are used in the medical praxis to prevent graft rejection after organ transplantation and in the therapy of some autoimmune diseases. As a continuation of our previous work searching for new, effective suppressors devoid of toxicity, we present the synthesis, conformational analysis, and biological activity of nonapeptides 1-6, analogs of naturally existing immunomodulatory peptide CLA. New CLA analogs were modified with (S)-beta(2)-iso-proline 7 or (S)-beta(3)-homo-proline 8, respectively. The conformational influence of the beta-iso-proline and beta-homo-proline building blocks was analyzed by NMR spectroscopy. Peptides 1-6 exist as a mixture of four isomers due to cis/trans isomerization of the Xxx-Pro peptide bond. The major isomers of peptides 1, 3, and 4 contain all peptide bonds of the trans geometry. The geometry of the proline-proline bond of the second populated isomer of peptides 3 and 4 is cis. The proline-proline peptide bond is cis for the major isomers of peptides 2, 5, and 6. The peptides were tested for their ability to suppress the proliferative response of mouse splenocytes to T- and B-cell mitogens and the secondary humoral immune response to sheep erythrocytes in vitro in parallel with a reference drug-cyclosporine A. The immunoregulatory actions of the peptides depended on the position and content of proline isomers and were, with some exceptions, strongly inhibitory at the highest dose tested (100 microg/ml). In addition, the peptides were practically devoid of toxicity at that dose. In conclusion, the replacement of Pro by beta-Pro may be useful for fine-tuning CLA immunosuppressive potency and undesirable toxicity.

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Solid phase synthesis of aryl ethers via the mitsunobu reaction

Cited by 111 publications

References 10 publications

Solid-Phase Synthesis of a Tyrphostin Ether Library

Solid-Phase Synthesis of a Tyrphostin Ether Library

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Synthesis and immunosuppressive activity of new cyclolinopeptide A analogs modified with β‐prolines

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