Novel steroid mimics directed towards the estradiol skeleton

Eve Bridgeman; Julie L. Cavill; Daniel J. Schofield; Derek S. Wilkins; Nicholas C. O. Tomkinson

doi:10.1016/j.tetlet.2005.10.005

Novel steroid mimics directed towards the estradiol skeleton

Eve Bridgeman, Julie L. Cavill, Daniel J. Schofield, Derek S. Wilkins, Nicholas C. O. Tomkinson

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

A series of non-sym. tri- and tetra-substituted ureas, e.g. I (R = H, Me) were prepd. to mimic the rigid tetracyclic core of estradiol. Tetra-substituted ureas were prepd. by a five-step protocol, involving activation and displacement of a carbonyldiimidazole adduct in 48-67% overall yield. This method was unsuccessful for tri-substituted ureas, which were prepd. in 42-74% yields by an alternative four-step method, which included a one-pot 4-nitrophenyl carbamate formation/displacement sequence.

Original language	Undefined/Unknown
Pages (from-to)	8521-8524
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2005.10.005
Publication status	Published - 2005

Keywords

estradiol skeleton
steroid
carbonyldiimidazole adduct
tetra-substituted ureas

Access to Document

10.1016/j.tetlet.2005.10.005

Cite this

@article{b7fa5ba388494cefb2ccf43221d5891b,

title = "Novel steroid mimics directed towards the estradiol skeleton",

abstract = "A series of non-sym. tri- and tetra-substituted ureas, e.g. I (R = H, Me) were prepd. to mimic the rigid tetracyclic core of estradiol. Tetra-substituted ureas were prepd. by a five-step protocol, involving activation and displacement of a carbonyldiimidazole adduct in 48-67% overall yield. This method was unsuccessful for tri-substituted ureas, which were prepd. in 42-74% yields by an alternative four-step method, which included a one-pot 4-nitrophenyl carbamate formation/displacement sequence.",

keywords = "estradiol skeleton , steroid, carbonyldiimidazole adduct , tetra-substituted ureas",

author = "Eve Bridgeman and Cavill, {Julie L.} and Schofield, {Daniel J.} and Wilkins, {Derek S.} and Tomkinson, {Nicholas C. O.}",

year = "2005",

doi = "10.1016/j.tetlet.2005.10.005",

language = "Undefined/Unknown",

volume = "46",

pages = "8521--8524",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - Novel steroid mimics directed towards the estradiol skeleton

AU - Bridgeman, Eve

AU - Cavill, Julie L.

AU - Schofield, Daniel J.

AU - Wilkins, Derek S.

AU - Tomkinson, Nicholas C. O.

PY - 2005

Y1 - 2005

N2 - A series of non-sym. tri- and tetra-substituted ureas, e.g. I (R = H, Me) were prepd. to mimic the rigid tetracyclic core of estradiol. Tetra-substituted ureas were prepd. by a five-step protocol, involving activation and displacement of a carbonyldiimidazole adduct in 48-67% overall yield. This method was unsuccessful for tri-substituted ureas, which were prepd. in 42-74% yields by an alternative four-step method, which included a one-pot 4-nitrophenyl carbamate formation/displacement sequence.

AB - A series of non-sym. tri- and tetra-substituted ureas, e.g. I (R = H, Me) were prepd. to mimic the rigid tetracyclic core of estradiol. Tetra-substituted ureas were prepd. by a five-step protocol, involving activation and displacement of a carbonyldiimidazole adduct in 48-67% overall yield. This method was unsuccessful for tri-substituted ureas, which were prepd. in 42-74% yields by an alternative four-step method, which included a one-pot 4-nitrophenyl carbamate formation/displacement sequence.

KW - estradiol skeleton

KW - steroid

KW - carbonyldiimidazole adduct

KW - tetra-substituted ureas

U2 - 10.1016/j.tetlet.2005.10.005

DO - 10.1016/j.tetlet.2005.10.005

M3 - Article

SN - 0040-4039

VL - 46

SP - 8521

EP - 8524

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -