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Physical Properties of Amines01:26

Physical Properties of Amines

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Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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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.
Due to the absence of continuous...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Isolation of Mandibular Gland Reservoir Contents from Bornean 'Exploding Ants' Formicidae for Volatilome Analysis by GC-MS and MetaboliteDetector
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Isolation of Mandibular Gland Reservoir Contents from Bornean 'Exploding Ants' Formicidae for Volatilome Analysis by GC-MS and MetaboliteDetector

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Acetogenins from Annonaceae.

Chih-Chuang Liaw1, Jing-Ru Liou2, Tung-Ying Wu3

  • 1Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, 804, Taiwan. ccliaw@mail.nsysu.edu.tw.

Progress in the Chemistry of Organic Natural Products
|December 15, 2015
PubMed
Summary

Annonaceous acetogenins, natural compounds from plants, are explored for their potential in cancer treatment and pest control. This review covers their chemistry and diverse biological activities since 1997.

Keywords:
Acetogenin mimicsAcetogeninsAnnonaceaeAnti-cancer activityApoptosisAtypical ParkinsonismIonophoresMitochondria complex I inhibitionNeurotoxicityPesticidal activity

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Area of Science:

  • Phytochemistry
  • Natural Products Chemistry
  • Pharmacology

Background:

  • Annonaceous acetogenins are a class of plant-derived secondary metabolites with complex structures.
  • These compounds have garnered significant research interest due to their diverse biological properties.
  • Previous studies have focused on their isolation, synthesis, and mechanisms of action.

Purpose of the Study:

  • To provide a comprehensive summary of research on annonaceous acetogenins and their synthetic mimics published since 1997.
  • To consolidate information on the chemical and biological aspects of these compounds.
  • To highlight their potential applications in medicine and agriculture.

Main Methods:

  • Literature review of scientific reports from 1997 onwards.
  • Systematic search for studies detailing isolation, structure elucidation, and synthesis.
  • Analysis of biological evaluations, including cytotoxicity, neurotoxicity, and pesticidal effects.

Main Results:

  • An extensive body of literature exists on the isolation and synthesis of annonaceous acetogenins and mimics.
  • Demonstrated significant cytotoxicity against various cancer cell lines.
  • Reported neurotoxic, pesticidal, and other miscellaneous biological activities.

Conclusions:

  • Annonaceous acetogenins represent a promising class of compounds with therapeutic and agricultural potential.
  • Continued research into their mechanisms of action and toxicity is warranted.
  • Synthetic acetogenin mimics offer avenues for developing novel bioactive agents.