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Related Concept Videos

Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Antifungal Agents

Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to cholesterol contributes to...
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Bacterial Phylum Actinobacteria

Coryneform bacteria are gram-positive, aerobic, nonmotile rods that exhibit irregular, club-shaped, or V-shaped arrangements. Their V-shape results from snapping division, where the inner cell wall layer forms the cross-wall, while the outer layer remains intact until it ruptures on one side, causing the daughter cells to bend away.The primary genera are Corynebacterium and Arthrobacter. Corynebacterium includes diverse species, ranging from saprophytes to pathogens like Corynebacterium...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Production of Antibiotics

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Related Experiment Video

Updated: Jun 21, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Carbocyclic 4'-Epiformycin.

Jian Zhou1, Minmin Yang, Akin Akdag

  • 1Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849-5312.

Tetrahedron
|August 7, 2009
PubMed
Summary
This summary is machine-generated.

Researchers synthesized carbocyclic 4'-epiformycin, a novel C-nucleoside analog. Preliminary antiviral assays showed the compound was inactive and non-toxic to host cells, indicating limited therapeutic potential.

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
05:17

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Virology

Background:

  • Formycin is a biologically active C-nucleoside.
  • Developing novel C-nucleoside analogs is crucial for drug discovery.
  • Carbocyclic nucleosides offer enhanced stability compared to their natural counterparts.

Purpose of the Study:

  • To synthesize carbocyclic 4 -epiformycin, a novel analog of formycin.
  • To evaluate the antiviral activity of carbocyclic 4 -epiformycin.
  • To assess the cytotoxicity of carbocyclic 4 -epiformycin against host cells.

Main Methods:

  • Asymmetric aldol reaction.
  • Ring-closing metathesis.
  • Antiviral assay.
  • Cytotoxicity assay.

Main Results:

  • Carbocyclic 4 -epiformycin was successfully synthesized.
  • The compound exhibited no antiviral activity in preliminary assays.
  • Carbocyclic 4 -epiformycin demonstrated no cytotoxicity to host cells.

Conclusions:

  • The synthesized carbocyclic 4 -epiformycin lacks significant antiviral properties.
  • The compound's lack of cytotoxicity suggests a favorable safety profile, but its inactivity limits therapeutic interest.