1405-46-5

Usage

Uses

Used in Pharmaceutical Applications:
(3R,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[(dimethylcarbamoyl)amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentylmethyl 2-hydroxy-6-methylbenzoate is used as a potential therapeutic agent for various medical conditions due to its complex structure and multiple functional groups. (3R,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[(dimethylcarbamoyl)amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentylmethyl 2-hydroxy-6-methylbenzoate's ability to interact with different biological targets may contribute to its efficacy in treating specific diseases or disorders.
Used in Drug Delivery Systems:
In the field of drug delivery, (3R,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[(dimethylcarbamoyl)amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentylmethyl 2-hydroxy-6-methylbenzoate could be utilized as a component in the design of novel drug delivery systems. Its functional groups may facilitate the development of targeted drug carriers, enhancing the bioavailability and therapeutic outcomes of associated pharmaceuticals.
Used in Chemical Synthesis:
(3R,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[(dimethylcarbamoyl)amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentylmethyl 2-hydroxy-6-methylbenzoate may also find use in chemical synthesis, particularly as a building block or intermediate for the creation of other complex molecules with specific applications in various industries, such as materials science, agrochemicals, or specialty chemicals.
Used in Research and Development:
(3R,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[(dimethylcarbamoyl)amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentylmethyl 2-hydroxy-6-methylbenzoate's unique structure and functional groups make it an interesting candidate for research and development in the fields of chemistry and biology. It could be used in the study of molecular interactions, drug design, and the development of new therapeutic strategies.

Upstream product

• 1295471-56-5 C₁₇H₂₀N₄O₅ 
• 1295471-59-8 C₁₇H₂₂N₄O₆ 
• 1295471-19-0 C₃₃H₄₀N₄O₆Si 
• 1295471-20-3 C₃₃H₃₈N₄O₅Si 
• 1295471-25-8 C₄₂H₄₉N₅O₅Si 
• 1295471-26-9 C₄₂H₅₁N₅O₆Si 
• 1295471-61-2 C₂₆H₃₃N₅O₆ 
• 1295471-27-0 C₂₉H₃₇N₅O₆ 
• 1295471-62-3 C₃₀H₃₅N₅O₇ 
• 1295471-28-1 C₃₂H₄₂N₆O₇ 
• 1295471-63-4 C₂₄H₃₆N₆O₅ 
• 1295471-65-6 C₂₃H₃₄N₆O₆ 
• 1295471-34-9 C₂₈H₃₆N₆O₈ 
• 1449329-21-8 benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-oxo-6-oxabicyclo[3.1.0] hexan2-yl)carbamate 

Downstream Products

• 69313-72-0 Pactamycin-Aceton-Addukt 

Relevant academic research and scientific papers

Preparation and biological evaluation of synthetic and polymer-encapsulated congeners of the antitumor agent pactamycin: Insight into functional group effects and biological activity

The synthesis and biological analysis of a number of novel congeners of the aminocyclopentitol pactamycin is described. Specific attention was paid to the preparation of derivatives at crucial synthetic branch points of the parent structure, and biological assays revealed a number of insights into the source of pactamycin's biological activity. Additionally, the encapsulation of pactamycin and select derivatives into the PRINT

SYNTHETIC ROUTE TO PACTAMYCIN AND PACTAMYCIN ANALOGS

Methods and intermediates useful for making compounds of Formula (I) are described, including a general method of making an alpha, beta-diamino ketone by reacting an imine with a 2-amino-substituted 1,3-dicarbonyl in a Mannich addition reaction to produce said alpha,beta-diamino ketone.

Enantioselective synthesis of pactamycin, a complex antitumor antibiotic

Medicinal application of many complex natural products is precluded by the impracticality of their chemical synthesis. Pactamycin, the most structurally intricate aminocyclopentitol antibiotic, displays potent antiproliferative properties across multiple phylogenetic domains, but it is highly cytotoxic. A limited number of analogs produced by genetic engineering technologies show reduced cytotoxicity against mammalian cells, renewing promise for therapeutic applications. For decades, an efficient synthesis of pactamycin amenable to analog derivatizations has eluded researchers. Here, we present a short asymmetric total synthesis of pactamycin. An enantioselective Mannich reaction and symmetry-breaking reduction sequence was designed to enable assembly of the entire carbon core skeleton in under five steps and control critical three-dimensional (stereochemical) functional group relationships. This modular route totals 15 steps and is immediately amenable for structural analog synthesis.

Asymmetric synthesis of the aminocyclitol pactamycin, a universal translocation inhibitor

An asymmetric total synthesis of the aminocyclopentitol pactamycin is described. The title compound is delivered in 15 steps from 2,4-pentanedione. Critical to this approach was the exploitation of a complex symmetry-breaking reduction strategy to assemble the C1, C2, and C7 relative stereochemistry within the first four steps of the synthesis. Multiple iterations of this reduction strategy are described, and a thorough analysis of stereochemical outcomes is detailed. In the final case, an asymmetric Mannich reaction was developed to install a protected amine directly at the C2 position. Symmetry-breaking reduction of this material gave way to a remarkable series of stereochemical outcomes leading to the title compound without recourse to nonstrategic downstream manipulations. This synthesis is immediately accommodating to the preparation of structural analogs.

Total synthesis of pactamycin and pactamycate: A detailed account

This article describes synthetic studies that culminated in the first total synthesis of pactamycin and pactamycate and, in parallel, the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate, lacking the 6-methylsalicylyl moiety. Starting with l-threonine as a chiron, a series of stereocontrolled condensations led to a key cyclopentenone harboring a spirocyclic oxazoline. A series of systematic functionalizations led initially to the incorrect cyclopentanone epoxide, which was "inverted" under solvolytic conditions. Installation of the remaining groups and manipulation of the oxazoline eventually led to pactamycin, pactamycate, and their desalicylyl analogues.

Total synthesis of pactamycin

Lest we forget: 50 years after pactamycin was first isolated from a fermentation broth of Streptomyces pactum var pactum, this highly functionalized aminocyclopentitol natural product has finally succumbed to total synthesis. The modular and stereocontrolled introduction of functional groups should lead to the synthesis of less toxic congeners that maintain the antibacterial and cytotoxic activities. Copyright