A divergent synthesis of minor groove binders with tail group variation

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Abstract

A new synthesis of polyamide minor groove binders in which diversity is introduced by the nucleophilic substitution of a 2-sulfido-1,3,2-diazaphospholidinyloxy substituent by volatile secondary amine nucleophiles is described. Such a method has potential value for economically investigating structure-activity relationships in this important class of compounds through library synthesis. As an example using this method are prepared two new minor groove binders with pyrrolidinyl or piperidinyl tail groups that are close relatives of highly active antibacterial minor groove binders with morpholinyl tail groups. The antibacterial activity found against Staphylococcus aureus and Mycobacterium spp. indicates that the pKa of this set of compounds is not the dominant factor in determining the antibacterial activity
LanguageEnglish
Pages178-186
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number1
DOIs
Publication statusPublished - 2009

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grooves
Binders
Nylons
synthesis
Mycobacterium
Staphylococcus aureus
staphylococcus

Keywords

  • synthesis
  • minor groove binders
  • tail group variation

Cite this

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title = "A divergent synthesis of minor groove binders with tail group variation",
abstract = "A new synthesis of polyamide minor groove binders in which diversity is introduced by the nucleophilic substitution of a 2-sulfido-1,3,2-diazaphospholidinyloxy substituent by volatile secondary amine nucleophiles is described. Such a method has potential value for economically investigating structure-activity relationships in this important class of compounds through library synthesis. As an example using this method are prepared two new minor groove binders with pyrrolidinyl or piperidinyl tail groups that are close relatives of highly active antibacterial minor groove binders with morpholinyl tail groups. The antibacterial activity found against Staphylococcus aureus and Mycobacterium spp. indicates that the pKa of this set of compounds is not the dominant factor in determining the antibacterial activity",
keywords = "synthesis, minor groove binders, tail group variation",
author = "D. Breen and A.R. Kennedy and C.J. Suckling",
year = "2009",
doi = "10.1039/b814452d",
language = "English",
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journal = "Organic and Biomolecular Chemistry",
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T1 - A divergent synthesis of minor groove binders with tail group variation

AU - Breen, D.

AU - Kennedy, A.R.

AU - Suckling, C.J.

PY - 2009

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N2 - A new synthesis of polyamide minor groove binders in which diversity is introduced by the nucleophilic substitution of a 2-sulfido-1,3,2-diazaphospholidinyloxy substituent by volatile secondary amine nucleophiles is described. Such a method has potential value for economically investigating structure-activity relationships in this important class of compounds through library synthesis. As an example using this method are prepared two new minor groove binders with pyrrolidinyl or piperidinyl tail groups that are close relatives of highly active antibacterial minor groove binders with morpholinyl tail groups. The antibacterial activity found against Staphylococcus aureus and Mycobacterium spp. indicates that the pKa of this set of compounds is not the dominant factor in determining the antibacterial activity

AB - A new synthesis of polyamide minor groove binders in which diversity is introduced by the nucleophilic substitution of a 2-sulfido-1,3,2-diazaphospholidinyloxy substituent by volatile secondary amine nucleophiles is described. Such a method has potential value for economically investigating structure-activity relationships in this important class of compounds through library synthesis. As an example using this method are prepared two new minor groove binders with pyrrolidinyl or piperidinyl tail groups that are close relatives of highly active antibacterial minor groove binders with morpholinyl tail groups. The antibacterial activity found against Staphylococcus aureus and Mycobacterium spp. indicates that the pKa of this set of compounds is not the dominant factor in determining the antibacterial activity

KW - synthesis

KW - minor groove binders

KW - tail group variation

UR - http://dx.doi.org/10.1039/b814452d

U2 - 10.1039/b814452d

DO - 10.1039/b814452d

M3 - Article

VL - 7

SP - 178

EP - 186

JO - Organic and Biomolecular Chemistry

T2 - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 1

ER -