Self-immolative base-mediated conjugate release from triazolylmethylcarbamates

被引：9

作者：

Blencowe, Christopher A. ^{[1
]}

Thornthwaite, David W. ^{[2
]}

Hayes, Wayne ^{[1
]}

Russell, Andrew T. ^{[1
]}

机构：

[1] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England

[2] Unilever Res Labs, Wirral CH63 3JW, Merseyside, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 32期

基金：

英国工程与自然科学研究理事会;

关键词：

TERMINAL ALKYNES; CLICK CHEMISTRY; DERIVATIVES; PRODRUGS; DENDRIMERS; PLASMIN; DESIGN; AZIDES;

D O I：

10.1039/c5ob00984g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of carbamate functionalized 1,4-disubstituted triazoles featuring a base sensitive trigger residue, plus a model aromatic amine reporter group, were prepared via copper(I) catalysed azide-alkyne cycloaddition and evaluated for their self-immolative characteristics. This study revealed a clear structure-reactivity relationship, via Hammett analysis, between the structure of the 1,4-disubstituted triazole and the rate of self-immolative release of the amine reporter group, thus demonstrating that under basic conditions this type of triazole derivative has the potential to be employed in a range of chemical release systems.

引用

页码：8703 / 8707

页数：5

共 33 条

[1] CHEMICAL ASPECTS OF SELECTIVE TOXICITY [J].

ALBERT, A .

NATURE, 1958, 182 (4633) :421-423

[2] DESIGN, SYNTHESIS, ANTINEOPLASTIC ACTIVITY, AND CHEMICAL-PROPERTIES OF BIS(CARBAMATE) DERIVATIVES OF 4,5-BIS(HYDROXYMETHYL)IMIDAZOLE [J].

ANDERSON, WK ;

BHATTACHARJEE, D ;

HOUSTON, DM .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (01) :119-127

[3]

[Anonymous], 2007, MARCHS ADV ORGANIC C

[4] Modular synthesis of photocleavable peptides using click chemistry [J].

Baccile, Joshua A. ;

Morrell, Mark A. ;

Falotico, Ross M. ;

Milliken, Brandon T. ;

Drew, Daniel L. ;

Rossi, Francis M. .

TETRAHEDRON LETTERS, 2012, 53 (15) :1933-1935

[5] Click chemistry with O-dimethylpropargylcarbamate for preparation of pH-sensitive functional groups.: A case study [J].

Bertrand, Philippe ;

Gesson, Jean Pierre .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3596-3599

[6] Self-immolative linkers in polymeric delivery systems [J].

Blencowe, Christopher A. ;

Russell, Andrew T. ;

Greco, Francesca ;

Hayes, Wayne ;

Thornthwaite, David W. .

POLYMER CHEMISTRY, 2011, 2 (04) :773-790

[7] DIRECTIVE EFFECTS IN AROMATIC SUBSTITUTION .30. ELECTROPHILIC SUBSTITUENT CONSTANTS [J].

BROWN, HC ;

OKAMOTO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (18) :4979-4987

[8] A NOVEL CONNECTOR LINKAGE APPLICABLE IN PRODRUG DESIGN [J].

CARL, PL ;

CHAKRAVARTY, PK ;

KATZENELLENBOGEN, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (05) :479-480

[9] PLASMIN-ACTIVATED PRODRUGS FOR CANCER-CHEMOTHERAPY .2. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PEPTIDYL DERIVATIVES OF DOXORUBICIN [J].

CHAKRAVARTY, PK ;

CARL, PL ;

WEBER, MJ ;

KATZENELLENBOGEN, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (05) :638-644

[10] Rapid preparation of 3-deoxyanthocyanidins and novel dicationic derivatives: New insight into an old procedure [J].

Chassaing, Stefan ;

Kueny-Stotz, Marie ;

Isorez, Geraldine ;

Brouillard, Raymond .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (15) :2438-2448

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