Expedient Access to 2-Benzazepines by Palladium-Catalyzed C-H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold

被引：12

作者：

Virelli, Matteo ^{[1
]}

Moroni, Elisabetta ^{[2
]}

Colombo, Giorgio ^{[1
,3
]}

Fiengo, Lorenzo ^{[4
]}

Porta, Alessio ^{[1
]}

Ackermann, Lutz ^{[1
,5
]}

Zanoni, Giuseppe ^{[1
]}

机构：

[1] Univ Pavia, Dept Chem, Viale Taramelli 10, I-27100 Pavia, Italy

[2] IRCCS MultiMed, Via Fantoli 16-15, I-20138 Milan, Italy

[3] CNR, Ist Chim Riconoscimento Mol, Via Mario Bianco 9, I-20131 Milan, Italy

[4] Univ Salerno, Dept Pharm, Via Giovanni Paolo II 132, I-84084 Fisciano, Italy

[5] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 62期

关键词：

benzazepines; C-H activation; docking analysis; Hsp90; inhibitors; DIRECT ARYLATION; ANTILEUKEMIC ACTIVITY; TERMINAL INHIBITORS; BOND ACTIVATION; FUNCTIONALIZATION; DISCOVERY; CANCER; 1,2,3-TRIAZOLES; HETEROCYCLES; DERIVATIVES;

D O I：

10.1002/chem.201804244

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bioactive 2-benzazepines were accessed in an atom- and step-economical manner through a versatile palladium-catalyzed C-H activation strategy. The C-H arylation required low catalyst loading and a mild base, which was reflected by a broad scope and high functional-group tolerance. The benzotriazolodiazepinones were identified as new heat shock protein 90 (Hsp90) inhibiting lead compounds, with considerable potential for anti-cancer applications.

引用

页码：16516 / 16520

页数：5

共 62 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Born, Robert .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :741-748

[3] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].

Ackermann, Lutz ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629

[4] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[5] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[6] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].

Ackermann, Lutz ;

Althammer, Andreas ;

Fenner, Sabine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204

[7] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[8] VYNYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .23. SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF BIS[[(CARBAMOYL)OXY]METHYL]-SUBSTITUTED PYRROLO[I,1-A]ISOQUINOLINES, PYRROLO[1,2-A]QUINOLINES, PYRROLO[2,1-A]ISOBENZAZEPINES, AND PYRROLO[1,2-A]BENZAZEPINES [J].

ANDERSON, WK ;

HEIDER, AR ;

RAJU, N ;

YUCHT, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2097-2102

[9]

[Anonymous], 2009, ANGEW CHEM-GER EDIT

[10]

[Anonymous], 2007, ANGEW CHEM-GER EDIT

← 1 2 3 4 5 6 7 →