Design, synthesis and evaluation of novel steroid mimics

Robert Strevens, Nicholas C. O. Tomkinson

Research output: Contribution to journalConference Contribution

Abstract

Steroids ellicit their diverse biol. actions via different functionality located around the periphery of their rigid tetra-cyclic core. For example, estradiol (1) can be viewed as a phenolic and a secondary alc. that are spatially fixed by a central lipophilic scaffold (3). Although steroids are chem. quite simple mols., with relatively few functional groups, their stereochem. and architectural complexity renders them an exceedingly difficult target for chem. synthesis. We will report on a program of work to prep. mimics for both androgenic (5) and estrogenic (4) activators that posess a central dicarbonyl moiety where the opposed dipole moments of the carbonyl groups spacially fix the A and D ring mimics in space. The mols. are simple to prep. and therefore amenable to the generation of a diverse range of compds. for biol. evaluation. The synthesis and comprehensive SAR of both the A and D ring mimics of 4 and 5 will be presented. [on SciFinder(R)]

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Steroids
Dipole moment
Scaffolds
Functional groups
Estradiol

Keywords

  • design
  • synthesis
  • evaluation
  • novel steroid mimics

Cite this

@article{11b8cc33e708441289280ec4bd94327f,
title = "Design, synthesis and evaluation of novel steroid mimics",
abstract = "Steroids ellicit their diverse biol. actions via different functionality located around the periphery of their rigid tetra-cyclic core. For example, estradiol (1) can be viewed as a phenolic and a secondary alc. that are spatially fixed by a central lipophilic scaffold (3). Although steroids are chem. quite simple mols., with relatively few functional groups, their stereochem. and architectural complexity renders them an exceedingly difficult target for chem. synthesis. We will report on a program of work to prep. mimics for both androgenic (5) and estrogenic (4) activators that posess a central dicarbonyl moiety where the opposed dipole moments of the carbonyl groups spacially fix the A and D ring mimics in space. The mols. are simple to prep. and therefore amenable to the generation of a diverse range of compds. for biol. evaluation. The synthesis and comprehensive SAR of both the A and D ring mimics of 4 and 5 will be presented. [on SciFinder(R)]",
keywords = "design, synthesis, evaluation, novel steroid mimics",
author = "Robert Strevens and Tomkinson, {Nicholas C. O.}",
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year = "2006",
month = "3",
day = "26",
language = "English",
volume = "231",
pages = "MEDI--043",
journal = "Abstracts of papers - American Chemical Society",
issn = "0065-7727",
publisher = "American Chemical Society",

}

Design, synthesis and evaluation of novel steroid mimics. / Strevens, Robert; Tomkinson, Nicholas C. O.

In: Abstracts of papers - American Chemical Society, Vol. 231, 26.03.2006, p. MEDI-043.

Research output: Contribution to journalConference Contribution

TY - JOUR

T1 - Design, synthesis and evaluation of novel steroid mimics

AU - Strevens, Robert

AU - Tomkinson, Nicholas C. O.

N1 - CAPLUS AN 2006:248196(Conference; Meeting Abstract; Computer Optical Disk)

PY - 2006/3/26

Y1 - 2006/3/26

N2 - Steroids ellicit their diverse biol. actions via different functionality located around the periphery of their rigid tetra-cyclic core. For example, estradiol (1) can be viewed as a phenolic and a secondary alc. that are spatially fixed by a central lipophilic scaffold (3). Although steroids are chem. quite simple mols., with relatively few functional groups, their stereochem. and architectural complexity renders them an exceedingly difficult target for chem. synthesis. We will report on a program of work to prep. mimics for both androgenic (5) and estrogenic (4) activators that posess a central dicarbonyl moiety where the opposed dipole moments of the carbonyl groups spacially fix the A and D ring mimics in space. The mols. are simple to prep. and therefore amenable to the generation of a diverse range of compds. for biol. evaluation. The synthesis and comprehensive SAR of both the A and D ring mimics of 4 and 5 will be presented. [on SciFinder(R)]

AB - Steroids ellicit their diverse biol. actions via different functionality located around the periphery of their rigid tetra-cyclic core. For example, estradiol (1) can be viewed as a phenolic and a secondary alc. that are spatially fixed by a central lipophilic scaffold (3). Although steroids are chem. quite simple mols., with relatively few functional groups, their stereochem. and architectural complexity renders them an exceedingly difficult target for chem. synthesis. We will report on a program of work to prep. mimics for both androgenic (5) and estrogenic (4) activators that posess a central dicarbonyl moiety where the opposed dipole moments of the carbonyl groups spacially fix the A and D ring mimics in space. The mols. are simple to prep. and therefore amenable to the generation of a diverse range of compds. for biol. evaluation. The synthesis and comprehensive SAR of both the A and D ring mimics of 4 and 5 will be presented. [on SciFinder(R)]

KW - design

KW - synthesis

KW - evaluation

KW - novel steroid mimics

M3 - Conference Contribution

VL - 231

SP - MEDI-043

JO - Abstracts of papers - American Chemical Society

T2 - Abstracts of papers - American Chemical Society

JF - Abstracts of papers - American Chemical Society

SN - 0065-7727

ER -