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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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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...
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Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Bioactive heterocycles containing endocyclic N-hydroxy groups.

Reshma Rani1, Carlotta Granchi1

  • 1Dipartimento di Farmacia, Università di Pisa, Via Bonanno 6, 56126 Pisa, Italy.

European Journal of Medicinal Chemistry
|December 4, 2014
PubMed
Summary

N-hydroxy heterocycles, often overlooked due to drug-likeness rules, show therapeutic potential. This review highlights their bioactivities, expanding options for novel pharmaceutical development.

Keywords:
BioactivityMetabolismN-Hydroxy-heterocycles

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Drug-likeness rules often flag N-O bonds as structural alerts, associated with reactive metabolites and side effects.
  • This concern primarily applies when the nitrogen atom is outside a cyclic structure; endocyclic N-hydroxy groups may behave differently.
  • Heterocycles with endocyclic N-hydroxy moieties remain underexplored for therapeutic applications.

Purpose of the Study:

  • To review N-hydroxy-containing heterocycles with reported bioactivities.
  • To assess their potential as therapeutic agents.
  • To expand the chemical space for pharmaceutical development.

Main Methods:

  • Systematic literature review of N-OH-containing heterocycles.
  • Analysis of reported bioactivities and therapeutic relevance.
  • Discussion of chemical classes and key examples.

Main Results:

  • Identified various classes of N-OH-containing heterocycles with significant bioactivities.
  • Demonstrated that endocyclic N-hydroxy groups may not share the same reactivity concerns as exocyclic ones.
  • Highlighted the therapeutic potential of these understudied chemical classes.

Conclusions:

  • N-hydroxy heterocycles represent a promising, yet underexplored, area for drug discovery.
  • Re-evaluation of drug-likeness rules may be warranted for heterocycles with endocyclic N-hydroxy groups.
  • This review provides a foundation for future research into novel pharmaceuticals based on these scaffolds.