Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE)

被引：36

作者：

Osipyan, Angelina

Sapegin, Alexander

Novikov, Alexander S.

Krasavin, Mikhail

机构：

[1] Saint Petersburg State University, Saint Petersburg

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 17期

基金：

俄罗斯科学基金会;

关键词：

TRIPEPTIDOMIMETIC ANTAGONISTS; MACROCYCLES; DISCOVERY; ARYLATION; PEPTIDES; STRATEGY; LACTAMS; AGONIST; DESIGN; POTENT;

D O I：

10.1021/acs.joc.8b01210

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydrolytic imidazoline ring expansion (HIRE) methodology was extended to readily available tetracyclic [1,4]thiazepines as well as sulfoxide and sulfone analogs thereof. The reactions resulted in the facile formation of a rare medium-sized [1,4,7]thiazecine ring system that has an emerging utility in bioactive compound design. Comparing the HIRE rates for representative compounds in the three groups of substrates allowed drawing some generalizations about the substituent effects on the course of the reaction.

引用

收藏

页码：9707 / 9717

页数：11

相关论文

共 31 条

[1] Ring-Expansion Approach to Medium-Sized Lactams and Analysis of Their Medicinal Lead-Like Properties [J].

Baud, Laetitia G. ;

Manning, Morgan A. ;

Arkless, Helen L. ;

Stephens, Thomas C. ;

Unsworth, William P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (09) :2225-2230

[2] Influence of chain length on the activity of tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4) [J].

Baumann, Markus ;

Hussain, Mohammad Musarraf ;

Henne, Nina ;

Garrote, Daniel Moya ;

Karlshoj, Stefanie ;

Fossen, Torgils ;

Rosenkilde, Mette M. ;

Vabeno, Jon ;

Haug, Bengt Erik .

BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (02) :646-657

[3]

Bliesener J. -U, 1978, LIEBIGS ANN CHEM, V1978, P259

[4] Medium-Sized-Ring Analogues of Dibenzodiazepines by a Conformationally Induced Smiles Ring Expansion [J].

Costil, Romain ;

Lefebvre, Quentin ;

Clayden, Jonathan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (46) :14602-14606

[5] The Chan-Evans-Lam N-Arylation of 2-Imidazolines [J].

Dar'in, Dmitry ;

Krasavin, Mikhail .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) :12514-12519

[6] Ring-Expansion Reactions in the Synthesis of Macrocycles and Medium-Sized Rings [J].

Donald, James R. ;

Unsworth, William P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (37) :8780-8799

[7] A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure [J].

Ha, Khanh ;

Monbaliu, Jean-Christophe M. ;

Williams, Byron C. ;

Pillai, Girinath G. ;

Ocampo, Charles E. ;

Zeller, Matthias ;

Stevens, Christian V. ;

Katritzky, Alan R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (40) :8055-8058

[8] Medium-Ring Nitrogen Heterocycles through Migratory Ring Expansion of Metalated Ureas [J].

Hall, Jessica E. ;

Matlock, Johnathan V. ;

Ward, John W. ;

Gray, Katharine V. ;

Clayden, Jonathan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11153-11157

[9] Consecutive Ring Expansion and Contraction for the Synthesis of 1-Aryl Tetrahydroisoquinolines and Tetrahydrobenzazepines from Readily Available Heterocyclic Precursors [J].

Hill, Jessica E. ;

Matlock, Johnathan V. ;

Lefebvre, Quentin ;

Cooper, Katie G. ;

Clayden, Jonathan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (20) :5788-5791

[10] Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII [J].

Kalinin, Stanislav ;

Kopylov, Stanislav ;

Tuccinardi, Tiziano ;

Sapegin, Alexander ;

Dar'in, Dmitry ;

Angeli, Andrea ;

Supuran, Claudiu T. ;

Krasavin, Mikhail .

ACS MEDICINAL CHEMISTRY LETTERS, 2017, 8 (10) :1105-1109

← 1 2 3 4 →