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Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

6.5K
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...
6.5K
Transducer Mechanism: Nuclear Receptors01:31

Transducer Mechanism: Nuclear Receptors

1.4K
Nuclear receptors, or NRs, are unique transcription factors that regulate gene transcription and affect the cellular pathways involved in reproduction, development, or metabolism. Their ability to be stimulated by small lipophilic ligands and control vital cellular processes makes them ideal drug targets. Nearly 10-15% of currently prescribed drugs target these receptors.
About 48 different soluble family members of nuclear receptors are identified that can be divided into two main classes:
1.4K
Preparation of Epoxides03:00

Preparation of Epoxides

7.8K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
7.8K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.4K
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...
7.4K
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

3.1K
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
3.1K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

8.6K
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...
8.6K

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Updated: Jul 18, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K

Bioactive Steroids Bearing Oxirane Ring.

Valery M Dembitsky1

  • 1Centre for Applied Research, Innovation and Entrepreneurship, Lethbridge College, 3000 College Drive South, Lethbridge, AB T1K 1L6, Canada.

Biomedicines
|August 26, 2023
PubMed
Summary

Natural steroids with oxirane rings exhibit diverse biological activities, including anti-inflammatory and anti-cancer properties. This review synthesizes research on these compounds from various natural sources.

Keywords:
anti-inflammatoryantibacterialantifungalantineoplasticantiviralfungal endophytesisoprenoid lipidsmarine invertebratesplantssteroidstriterpenoids

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

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Area of Science:

  • Natural Products Chemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Steroids and related isoprenoid lipids are crucial natural compounds.
  • Oxirane ring-containing steroids are found in diverse organisms like fungi, plants, algae, and marine invertebrates.
  • Understanding their biological activities is vital for drug discovery.

Purpose of the Study:

  • To review the biological activity and structural diversity of natural steroids containing an oxirane ring.
  • To explore compounds derived from fungi, fungal endophytes, plants, algae, and marine invertebrates.
  • To provide insights into their pharmacological and medical applications.

Main Methods:

  • Extensive literature review of refereed sources.
  • Inclusion of in vivo and in vitro studies.
  • Utilization of the Quantitative Structure-Activity Relationship (QSAR) method.

Main Results:

  • Compounds exhibit a wide range of biological activities, including anti-inflammatory, antineoplastic, antiproliferative, anti-hypercholesterolemic, antiparkinsonian, diuretic, anti-eczematic, and anti-psoriatic effects.
  • 3D graphs illustrate steroid activity, complemented by images of source organisms.
  • Explanations for specific biological activities are provided.

Conclusions:

  • Natural steroids with oxirane rings possess significant and diverse biological activities.
  • These findings have implications for pharmacology and medicine, contributing to theoretical and applied research.
  • The review compiles valuable data on the biological activity of these natural compounds.