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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Basicity of Heterocyclic Aromatic Amines01:25

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Structure of Amines01:19

Structure of Amines

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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
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Basicity of Aromatic Amines01:18

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

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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...
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Amines: Introduction01:07

Amines: Introduction

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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Structural and Functional Characterization of Indane-Core CD4-Mimetic Compounds Substituted with Heterocyclic Amines.

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ACS Medicinal Chemistry Letters
|January 19, 2023
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Researchers explored modifications to a CD4-mimetic compound (CD4mc) to enhance its effectiveness against HIV-1. They discovered that various ring structures at a specific position significantly impact antiviral activity and immune response, paving the way for more potent HIV therapies.

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Area of Science:

  • Virology
  • Drug Discovery
  • Structural Biology

Background:

  • Human immunodeficiency virus (HIV-1) entry relies on the envelope glycoprotein (Env) interacting with host receptors CD4 and CCR5/CXCR4.
  • CD4-mimetic compounds (CD4mcs) inhibit HIV-1 by binding to the Env gp120, blocking CD4 interaction and neutralizing the virus.
  • A specific moiety at the C5 position of a lead CD4mc, BNM-III-170, was previously linked to its antiviral potency.

Purpose of the Study:

  • To investigate the impact of modifying the C5 position of BNM-III-170 with different ring systems on antiviral activity.
  • To assess the tolerance of the C5 position to various ring sizes and substitutions.
  • To explore the potential for optimizing CD4mcs for enhanced potency and immune sensitization.

Main Methods:

  • Synthesis of novel CD4mc analogues by replacing the C5 chain with pyrrolidine, piperidine, and piperazine ring systems.
  • Evaluation of antiviral activity against HIV-1.
  • Structural and computational analyses, including crystallographic studies of pyrrolidine analogues.

Main Results:

  • The C5 position of BNM-III-170 demonstrated remarkable tolerance to diverse ring systems and substitutions, maintaining antiviral activity.
  • Crystallographic analysis revealed that C5 substituents can form hydrogen bonds with the gp120 Env residue Thr 283.
  • These findings suggest a structure-activity relationship where specific interactions at the C5 position influence potency.

Conclusions:

  • The C5 position of CD4mcs is a versatile site for chemical modification, allowing for the development of novel antiviral agents.
  • Optimizing hydrogen bonding interactions at the C5 position, particularly with Thr 283, holds significant promise for designing more potent HIV-1 inhibitors.
  • This research contributes to the ongoing effort to develop effective therapeutics against HIV-1 infection.