A novel method for the formation of 2-azocanones by lactone-to-lactam ring contraction of 2-oxonanones

Derrer, Sam; Feeder, Neil; Teat, Simon J.; Davies, John E.; Holmes, Andrew B.

doi:10.1016/s0040-4039(98)02093-0

Cited by 20 publications

(9 citation statements)

References 16 publications

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“…Related aminopyrrolidones, aminopiperidones and larger ring heterocycles have recently attracted interest as enzyme inhibitors 29 and peptidomimetic structures. [30][31][32][33] Amination of the enolate of lactam 1a with (PhO) 2 P(O)N 3 followed by treatment with Boc 2 O gave the amino lactam 8 in 50% yield (Scheme 2); surprisingly, the endo product, whose stereochemistry was subsequently established, was obtained exclusively. Acidic release of the protecting groups, and reprotection of the C-4 amino function as its benzyloxycarbonyl (Z) derivative, gave the product 9b in 51% yield over the two steps.…”

mentioning

confidence: 99%

Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid

Goswami¹,

Moloney²

1999

Chem. Commun.

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mentioning

confidence: 99%

Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid

Goswami¹,

Moloney²

1999

Chem. Commun.

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“…Also some substance P derivatives that contain Damino acids e.g. [Arg 6 , D-Trp l0 ]-sp (6)(7)(8)(9)(10)(11) and [Pro 4 , D-Trp 7.9 ]-sp (4-11) act as strongly competitive antagonists [47]. Stavropoulos, George et al [48], synthesized potent agonists of substance P. The analogues [Glp 6 , Glu(OBzl) 11 ]-sp(6-l 1) figure ( 4) and [Glp 5 , Glu(OBzl) 11 ] -SP-(5-l 1) figure (5) of the c-terminal hexapeptide and heptapeptide as shown in figures (4,5).…”

Section: Figure (1): Structure Of Amino Acids United By a Peptide Bond To Form Peptides And Proteinsmentioning

confidence: 99%

“…Neurokinins are peptides show a strong hypotensive effect like substance P. They were isolated from porcine spinal cord extracts and synthesized in 1984 by Munekata et al [49]. They have the sequences figure (6,7).…”

Section: Neurokininsmentioning

confidence: 99%

“…In efforts to address these limitations, peptides are modified by several ways. Previously the scientists modified peptides into mimetics with specific physical, chemical and biological characteristics [6][7][8]. These so-called peptidomimetics are derived from peptides by partly or completely removing amid bonds while retaining essential amino acid side chains (such as -OH, -NH2, -COOH, -SH, phenolic -OH, guanidine…etc) in a defined, spatial relationship.…”

Section: Introductionmentioning

confidence: 99%

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The Importance of Amino Acid and Peptide Chemistry in the Treatment of the Major Diseases: Neuropeptides

Moustafa

Shalaby

2021

Egypt. J. Chem.

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During this review, from the reality of the previously published articles, we explained how the peptide bond is formed. This review was divided and different peptide groups were distinguished according to the mode of action of the various peptides, whether they were linear or cyclic peptides, as well as according to the path from hormonally active cells to the target organ, in addition to their peptide analogs that can develop different treatments. Alternatively, an extensive reference survey was conducted for the peptides family "Neuropeptides" and some examples for this family that are chemically composed of various amino acids and peptides were studied.

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“…An O-N intramolecular benzoyl migration was effectively used to obtain the paclitaxel side chain, phenylisoserine [138]. Moreover, this reaction was applied to: carbohydrate chemistry, because it allowed regioselective modifications of sugars [139][140][141]; in the synthesis of peptide with 2-hydroxy-4-methoxybenzyl (Hmb) or its derivatives as an auxiliary moiety [88,[142][143][144]; in the synthesis of lactams [145,146]; and initially, this rearrangement was also used in peptide ligation [147][148][149].…”

Section: Other Application Of O-n Intramolecular Acyl Migration Reactionmentioning

confidence: 99%

Application of the O-N Intramolecular Acyl Migration Reaction in Medicinal Chemistry

Skwarczynski¹,

Kiso

2007

CMC

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The O-N intramolecular acyl migration, also named as an acyl shift or acyl transfer reaction, is well-known in organic and peptide chemistry as a simple rearrangement which proceeds under very mild aqueous conditions. Despite a long history with this reaction, its application in medicinal chemistry has only lately been proposed. In the last decade, this reaction has been intensively studied and several applications of this rearrangement in medicinal chemistry have appeared. O-N Intramolecular acyl migration has been employed in "no auxiliary, no byproduct" prodrug strategies (prodrugs of paclitaxel and other taxoids, prodrugs of HIV protease inhibitors), for the synthesis of peptides containing difficult sequences via "O-acyl isopeptide method", including Alzheimer's disease related amyloid beta peptide (Abeta) 1-42, and in the design of pH-, photo- or enzyme-triggered click peptides, as a potential powerful tool for identifying the pathological functions of amyloid beta peptides in Alzheimer's disease. This review summarized recent advances in the application of O-N intramolecular acyl migration with special focus on medicinal chemistry.

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A novel method for the formation of 2-azocanones by lactone-to-lactam ring contraction of 2-oxonanones

Cited by 20 publications

References 16 publications

Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid

Novel peptidomimetic structures: enantioselective synthesis of conformationally constrained lysine, ornithine and alanine analogues from pyroglutamic acid

The Importance of Amino Acid and Peptide Chemistry in the Treatment of the Major Diseases: Neuropeptides

Application of the O-N Intramolecular Acyl Migration Reaction in Medicinal Chemistry

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