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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Cycloalkanes02:28

Cycloalkanes

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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.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
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Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Charting Biologically Relevant Spirocyclic Compound Space.

Gerhard Müller1, Tim Berkenbosch1, Jorg C J Benningshof1

  • 1Mercachem, Kerkenbos 1013, 6546 BB Nijmegen, P.O. Box 6747, 6503 GE, Nijmegen, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 19, 2016
PubMed
Summary
This summary is machine-generated.

This study analyzes bioactive spirocycles for drug discovery, identifying thousands of compounds active against numerous targets, including G protein-coupled receptors (GPCRs). Findings reveal potential for expanding novel spirocyclic scaffolds in pharmaceutical research.

Keywords:
compound distributioncomputational analysisscaffold synthesisspiro compoundsstructural biology

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Area of Science:

  • Medicinal Chemistry
  • Drug Discovery
  • Chemical Biology

Background:

  • Spirocycles are prevalent in natural products and increasingly important in drug discovery due to their sp3-rich and three-dimensional nature.
  • Exploring existing bioactive spirocycles is crucial for identifying new therapeutic leads.

Purpose of the Study:

  • To systematically explore and analyze the chemical space of bioactive spirocycles.
  • To identify opportunities for expanding spirocyclic chemical space for pharmaceutical research.
  • To design and synthesize novel spirocyclic scaffolds.

Main Methods:

  • Systematic exploration and classification of spirocyclic compounds.
  • Analysis of spirocycle scaffolds and ring combinations.
  • Identification of bioactive compounds and their targets.
  • Design and synthesis of novel spirocyclic scaffolds.

Main Results:

  • Nearly 47,000 spirocyclic compounds active against approximately 200 targets were identified.
  • Several pharmaceutically relevant G protein-coupled receptors (GPCRs) were among the identified targets.
  • Notable scaffold diversity was observed, but limited combinations of differently sized rings were found.
  • Three novel spirocyclic scaffolds were designed and synthesized.

Conclusions:

  • Significant potential exists to expand spirocyclic chemical space for drug discovery using the privileged substructure concept.
  • The identified novel scaffolds offer new avenues for pharmaceutical research and library synthesis.
  • This work provides a foundation for developing new spirocycle-based therapeutics.