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Related Concept Videos

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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Mixtures of Acids03:27

Mixtures of Acids

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The pH of a solution containing an acid can be determined using its acid dissociation constant and its initial concentration. If a solution contains two different acids, then its pH can be determined using one of several methods depending upon the relative strength of the acids and their dissociation constants.
A Mixture of a Strong Acid and a Weak Acid
In a mixture of a strong acid and a weak acid, the strong acid dissociates completely and becomes a source of almost all the hydronium ions...
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Mixtures of Acids01:19

Mixtures of Acids

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The pH of a solution containing an acid can be determined using its acid dissociation constant and initial concentration. If a solution contains two different acids, then its pH can be determined using one of several methods depending on the relative strength of the acids and their dissociation constants.
In a strong and weak acid mixture, the strong acid dissociates completely and becomes a source of almost all the hydronium ions present in the solution. In contrast, the weak acid shows...
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Coordination Compounds and Nomenclature02:54

Coordination Compounds and Nomenclature

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In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
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Position of Equilibrium in Acid-Base Reactions02:05

Position of Equilibrium in Acid-Base Reactions

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In any solution, the value of pKa indicates whether an acid is completely dissociated or not. A negative pKa corresponds to a stronger acid, whereas a positive pKa corresponds to a weaker acid. Consider the reaction between ammonia and an ethoxide ion. In this reaction, ethanol with a pKa of 15.9 is a stronger acid than ammonia with a pKa of 38. Recall that the strong acid forms a weak conjugate base, and a weak acid forms a strong conjugate base. Hence, the ethoxide ion is a weak base.
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Leaky Scanning02:28

Leaky Scanning

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During most eukaryotic translation processes, the small 40S ribosome subunit scans an mRNA from its 5' end until it encounters the first start AUG codon. The large 60S ribosomal subunit then joins the smaller one to initiate protein synthesis. The location of the translation initiation is largely determined by the nucleotides near the start codon as there may be multiple translation initiation sites present on the mRNA.  Marilyn Kozak discovered that the sequence RCCAUGG (where R...
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Identification of Bis-Cyclic Guanidines as Antiplasmodial Compounds from Positional Scanning Mixture-Based Libraries.

David L Perry1, Bracken F Roberts2, Ginamarie Debevec3

  • 1Division of Molecular Biology and Microbiology, Burnett School of Biomedical Sciences, University of Central Florida, Orlando, FL 32826, USA. dperryII@Knights.ucf.edu.

Molecules (Basel, Switzerland)
|March 23, 2019
PubMed
Summary

Researchers screened over 30 million compounds, identifying a pyrrolidine bis-cyclic guanidine library (TPI-1955) as highly active and selective against malaria parasites. Further analysis pinpointed key structural features for potent antiplasmodial drug discovery.

Keywords:
antiplasmodialcombinatorial chemistryguanidinesheterocyclic peptidomimeticsmalariaparallel synthesissolid-phase synthesis

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Area of Science:

  • Medicinal Chemistry
  • Parasitology
  • Drug Discovery

Background:

  • Antiplasmodial drug discovery is crucial for combating malaria.
  • Small molecule libraries are vital for identifying novel therapeutic agents.
  • Pyrrolidine bis-cyclic guanidines represent a promising scaffold for anti-infective agents.

Purpose of the Study:

  • To identify potent and selective antiplasmodial compounds from a large chemical library.
  • To explore the structure-activity relationships within the pyrrolidine bis-cyclic guanidine scaffold.
  • To guide the development of new antimalarial drugs.

Main Methods:

  • High-throughput screening of over 30 million compounds from 81 diverse small molecule libraries.
  • Systematic screening of a positional scanning library (TPI-1955) comprising 120 sublibraries.
  • Deconvolution of the positional scanning library and parallel synthesis of individual compounds.

Main Results:

  • The pyrrolidine bis-cyclic guanidine library (TPI-1955) emerged as a highly active and selective antiplasmodial library.
  • Positional scanning provided critical information on key structural features for antiplasmodial activity.
  • Identification of active and selective antiplasmodial pyrrolidine bis-cyclic guanidines through deconvolution and synthesis.

Conclusions:

  • Pyrrolidine bis-cyclic guanidines are a promising class of compounds for antimalarial drug development.
  • The identified compounds demonstrate significant potential as selective antiplasmodial agents.
  • This study provides a foundation for further optimization and development of novel antimalarial therapies.