The Chemistry of Vicinal Tricarbonyls: Total Syntheses of Elastase Inhibitors YM-47141 and YM-47142

Wasserman, Harry H.; Chen, Jyun-Hung; Xia, Mingde

doi:10.1002/1522-2675(20000906)83:9<2607::aid-hlca2607>3.0.co;2-b

Cited by 23 publications

(18 citation statements)

References 4 publications

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“…They showed potent HLE inhibition with IC 50 values of 1.5 µM and 3.0 µM, respectively (Orita et al, 1995;Yasumuro et al, 1995). Their total synthesis has also been reported (Wasserman et al, 1999;Wasserman et al, 2000).…”

Section: Polypeptides Of the Bacteriummentioning

confidence: 90%

The Natural Polypeptides as Significant Elastase Inhibitors

et al. 2020

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Human neutrophil elastase (HNE) is a major cause of the destruction of tissues in cases of several different chronic andinflammatory diseases. Overexpression of the elastase enzyme plays a significant role in the pathogenesis of various diseases including chronic obstructive pulmonary disease (COPD), acute respiratory distress syndrome, rheumatoid arthritis, the rare disease cyclic hematopoiesis (or cyclic neutropenia), infections, sepsis, cystic fibrosis, myocardial ischemia/reperfusion injury and asthma, inflammation, and atherosclerosis. Human neutrophil elastase is secreted by human neutrophils due to different stimuli. Medicine-based inhibition of the over-activation of neutrophils or production and activity of elastase have been suggested to mend inflammatory diseases. Although the development of new elastase inhibitors is an essential strategy for treating the different inflammatory diseases, it has been a challenge to specifically target the activity of elastase because of its overlapping functions with those of other serine proteases. This review article highlights the reported natural polypeptides as potential inhibitors of elastase enzyme. The mechanism of action, structural features, and activity of the polypeptides have also been correlated wherever they were available.

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Section: Polypeptides Of the Bacteriummentioning

confidence: 90%

The Natural Polypeptides as Significant Elastase Inhibitors

et al. 2020

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“…Similar results were observed when Yamaguchi's mixed anhydride method21 and the p ‐nitrophenol22 activated ester procedure were employed (entries 4 and 5). Other activated esters, such as succinimide23 and imidazolyl24 ester, did not work either (data not shown). At this stage we moved our attention to more reactive acyl chlorides.…”

Section: Resultsmentioning

confidence: 95%

Asymmetric Total Syntheses of Marine Cyclic Depsipeptide Halipeptins A–D

Yu¹,

Pan²,

Ma³

2006

Chemistry A European J

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Halipeptins A-D (1 a-d) are a family of natural cyclic depsipeptides isolated from marine sponges. Total syntheses of these four compounds are detailed in this report. The key elements in this synthesis include the elaboration of the polysubstituted decanoic acid parts by two asymmetric aldol reactions, assembly of the N-methyl-delta-hydroxyisoleucine residue by using either aza-Claisen rearrangement or methylation of aspartates as the key steps, and macrocyclization at the polysubstituted decanoic acid alanine site.

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“…The existence of three vicinal carbonyl groups act as an abnormal turn‐promoting structural element in macrolide natural products, such as the YM47141–2 (elastate inhibitors), [ 169,170 ] FK‐506 (immunosuppressant) [ 171 ] and rapamycin (active against all strains of Candida albicans examined). [ 172 ] Hulme et al [ 169 ] synthesized a group of secondary‐amide‐containing α,β‐diketoamides through U‐3CRs by oxidative deamination.…”

Section: Post Modifications Of the U‐3crmentioning

confidence: 99%

The Ugi Three‐Component Reaction; a Valuable Tool in Modern Organic Synthesis

2020

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The Ugi three component reaction (U‐3CR) is a variation of the famous Ugi reaction, discovered almost 60 years ago. Today it is somehow neglected, compared to the classical variation, although the α‐aminoamides, derived from this reaction, have been utilized as inhibitors for various targets and even commercial drugs, offering improved pharmacokinetic properties. In this review, we are describing the scope and limitations of the reaction with a special focus on the developed catalytic protocols, the bioactive compounds, and drugs which are based on the reaction and finally the post modifications that have been reported in order to access drug‐like and privileged scaffolds. A special focus is given to the 3D solid state conformations of the U‐3CR derivatives.

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The Chemistry of Vicinal Tricarbonyls: Total Syntheses of Elastase Inhibitors YM-47141 and YM-47142

Cited by 23 publications

References 4 publications

The Natural Polypeptides as Significant Elastase Inhibitors

The Natural Polypeptides as Significant Elastase Inhibitors

Asymmetric Total Syntheses of Marine Cyclic Depsipeptide Halipeptins A–D

The Ugi Three‐Component Reaction; a Valuable Tool in Modern Organic Synthesis

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