An efficient substitution reaction for the preparation of thyroid hormone analogues

Hikari A I Yoshihara, Grazia Chiellini, Timothy J. Mitchison, Thomas (Tom) Scanlan

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich aromatic compounds, providing a convenient route to the synthesis of new thyroid hormone analogues. Copyright (C) 1998 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1179-1183
Number of pages5
JournalBioorganic and Medicinal Chemistry
Volume6
Issue number8
DOIs
StatePublished - Aug 1998
Externally publishedYes

Fingerprint

Thyroid Hormones
Substitution reactions
Silanes
Nucleophiles
Aromatic compounds
Sulfhydryl Compounds
Hydroxyl Radical
Carbon
Alcohols
Electrons
GC 1 compound
allyl alcohol

Keywords

  • S(N)1
  • Thyroid hormone
  • Thyromimetic

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

An efficient substitution reaction for the preparation of thyroid hormone analogues. / Yoshihara, Hikari A I; Chiellini, Grazia; Mitchison, Timothy J.; Scanlan, Thomas (Tom).

In: Bioorganic and Medicinal Chemistry, Vol. 6, No. 8, 08.1998, p. 1179-1183.

Research output: Contribution to journalArticle

Yoshihara, Hikari A I ; Chiellini, Grazia ; Mitchison, Timothy J. ; Scanlan, Thomas (Tom). / An efficient substitution reaction for the preparation of thyroid hormone analogues. In: Bioorganic and Medicinal Chemistry. 1998 ; Vol. 6, No. 8. pp. 1179-1183.
@article{66cbba7b8b7f43e688fdac5c64835c3e,
title = "An efficient substitution reaction for the preparation of thyroid hormone analogues",
abstract = "The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich aromatic compounds, providing a convenient route to the synthesis of new thyroid hormone analogues. Copyright (C) 1998 Elsevier Science Ltd.",
keywords = "S(N)1, Thyroid hormone, Thyromimetic",
author = "Yoshihara, {Hikari A I} and Grazia Chiellini and Mitchison, {Timothy J.} and Scanlan, {Thomas (Tom)}",
year = "1998",
month = "8",
doi = "10.1016/S0968-0896(98)00085-6",
language = "English (US)",
volume = "6",
pages = "1179--1183",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "8",

}

TY - JOUR

T1 - An efficient substitution reaction for the preparation of thyroid hormone analogues

AU - Yoshihara, Hikari A I

AU - Chiellini, Grazia

AU - Mitchison, Timothy J.

AU - Scanlan, Thomas (Tom)

PY - 1998/8

Y1 - 1998/8

N2 - The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich aromatic compounds, providing a convenient route to the synthesis of new thyroid hormone analogues. Copyright (C) 1998 Elsevier Science Ltd.

AB - The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich aromatic compounds, providing a convenient route to the synthesis of new thyroid hormone analogues. Copyright (C) 1998 Elsevier Science Ltd.

KW - S(N)1

KW - Thyroid hormone

KW - Thyromimetic

UR - http://www.scopus.com/inward/record.url?scp=0031687370&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0031687370&partnerID=8YFLogxK

U2 - 10.1016/S0968-0896(98)00085-6

DO - 10.1016/S0968-0896(98)00085-6

M3 - Article

C2 - 9784860

AN - SCOPUS:0031687370

VL - 6

SP - 1179

EP - 1183

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 8

ER -