The synthesis of 'tyrosyl' peptidomimetics by acid-catalyzed N(1)-C(4) ring opening of 4-(4′-hydroxyphenyl)-azetidine-2-ones

Pijus Kumar Mandal; Larry A. Cabell; John S. McMurray

doi:10.1016/j.tetlet.2005.03.141

The synthesis of 'tyrosyl' peptidomimetics by acid-catalyzed N(1)-C(4) ring opening of 4-(4′-hydroxyphenyl)-azetidine-2-ones

Pijus Kumar Mandal
, Larry A. Cabell
, John S. McMurray

Experimental Therapeutics

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

12 Scopus citations

Abstract

Under acidic conditions, the N(1)-C(4) bond of 4-(4′-hydroxyphenyl)- azetidine-2-ones are cleaved with the formation of a stabilized benzylic carbocation intermediates. The intermediates were reduced by silanes or participated in intramolecular or intermolecular Friedel-Crafts reactions to produce tyrosine mimetics.

Original language	English (US)
Pages (from-to)	3715-3718
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.141
State	Published - May 23 2005

Keywords

4-(4′-Hydroxyphenyl)-azetidine-2-one
Friedel-Crafts alkylation
N(1)-C(4) bond
Peptidomimetic
Trifluoroacetic acid
β-Lactam

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.03.141

Cite this

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title = "The synthesis of 'tyrosyl' peptidomimetics by acid-catalyzed N(1)-C(4) ring opening of 4-(4′-hydroxyphenyl)-azetidine-2-ones",

abstract = "Under acidic conditions, the N(1)-C(4) bond of 4-(4′-hydroxyphenyl)- azetidine-2-ones are cleaved with the formation of a stabilized benzylic carbocation intermediates. The intermediates were reduced by silanes or participated in intramolecular or intermolecular Friedel-Crafts reactions to produce tyrosine mimetics.",

keywords = "4-(4′-Hydroxyphenyl)-azetidine-2-one, Friedel-Crafts alkylation, N(1)-C(4) bond, Peptidomimetic, Trifluoroacetic acid, β-Lactam",

author = "Mandal, \{Pijus Kumar\} and Cabell, \{Larry A.\} and McMurray, \{John S.\}",

note = "Funding Information: We are grateful to the National Cancer Institute for support of this work (CA096652). We also acknowledge the NCI Cancer Center Support Grant CA016672 for the support of our NMR facility and the M. D. Anderson Cancer Center Proteomics Facility for mass spectrometry.",

year = "2005",

month = may,

day = "23",

doi = "10.1016/j.tetlet.2005.03.141",

language = "English (US)",

volume = "46",

pages = "3715--3718",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "21",

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TY - JOUR

T1 - The synthesis of 'tyrosyl' peptidomimetics by acid-catalyzed N(1)-C(4) ring opening of 4-(4′-hydroxyphenyl)-azetidine-2-ones

AU - Mandal, Pijus Kumar

AU - Cabell, Larry A.

AU - McMurray, John S.

N1 - Funding Information: We are grateful to the National Cancer Institute for support of this work (CA096652). We also acknowledge the NCI Cancer Center Support Grant CA016672 for the support of our NMR facility and the M. D. Anderson Cancer Center Proteomics Facility for mass spectrometry.

PY - 2005/5/23

Y1 - 2005/5/23

N2 - Under acidic conditions, the N(1)-C(4) bond of 4-(4′-hydroxyphenyl)- azetidine-2-ones are cleaved with the formation of a stabilized benzylic carbocation intermediates. The intermediates were reduced by silanes or participated in intramolecular or intermolecular Friedel-Crafts reactions to produce tyrosine mimetics.

AB - Under acidic conditions, the N(1)-C(4) bond of 4-(4′-hydroxyphenyl)- azetidine-2-ones are cleaved with the formation of a stabilized benzylic carbocation intermediates. The intermediates were reduced by silanes or participated in intramolecular or intermolecular Friedel-Crafts reactions to produce tyrosine mimetics.

KW - 4-(4′-Hydroxyphenyl)-azetidine-2-one

KW - Friedel-Crafts alkylation

KW - N(1)-C(4) bond

KW - Peptidomimetic

KW - Trifluoroacetic acid

KW - β-Lactam

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U2 - 10.1016/j.tetlet.2005.03.141

DO - 10.1016/j.tetlet.2005.03.141

M3 - Article

AN - SCOPUS:17844362478

SN - 0040-4039

VL - 46

SP - 3715

EP - 3718

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

The synthesis of 'tyrosyl' peptidomimetics by acid-catalyzed N(1)-C(4) ring opening of 4-(4′-hydroxyphenyl)-azetidine-2-ones

Abstract

Keywords

ASJC Scopus subject areas

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