Synthesis of 3-Amino-2-carboxamide Tetrahydropyrrolo[2,3-b]quinolines

被引：7

作者：

Pilkington, Lisa I. ^{[1
]}

Haverkate, Natalie A. ^{[1
]}

Van Rensburg, Michelle ^{[1
]}

Reynisson, Johannes ^{[1
]}

Leung, Euphemia ^{[2
,3
]}

Barker, David ^{[1
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Private Bag 92019, Auckland 1142, New Zealand

[2] Univ Auckland, Auckland Canc Soc Res Ctr, Private Bag 92019, Auckland 1142, New Zealand

[3] Univ Auckland, Dept Mol Med & Pathol, Private Bag 92019, Auckland 1142, New Zealand

来源：

SYNLETT | 2016年 / 27卷 / 20期

关键词：

pyrrolo[2,3-b]quinolines; Thorpe-Ziegler; pyrrolo[2,3-b]pyridines; thieno[2,3-b]pyridines; heterocycles; DERIVATIVES; INHIBITORS; IDENTIFICATION; CYTOTOXICITY; CELLS;

D O I：

10.1055/s-0036-1588619

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This article communicates the first synthesis of 3-amino-2-carboxamide pyrrolo[2,3-b]quinolines and fused-ring pyrrolopyridines in an efficient synthesis via a Thorpe-Ziegler transformation. The reported synthetic route allows for a wide range of nitrogen analogues of thienopyridines - compounds which have potent bioactivities but poor aqueous solubility.

引用

页码：2811 / 2814

页数：4

共 16 条

[1]

Arabshahi H. J., 2015, J MED CHEM COMMUN, V6, P1987

[2] The development of thieno[2,3-b]pyridine analogues as anticancer agents applying in silico methods [J].

Arabshahi, Homayon J. ;

Leung, Euphemia ;

Barker, David ;

Reynisson, Johannes .

MEDCHEMCOMM, 2014, 5 (02) :186-191

[3] SYNTHESIS AND NEUROTROPIC ACTIVITY OF NEW PYRIMIDO[4′,5′:4,5]THIENO[2,3-b]QUINOLINE DERIVATIVES [J].

Dabaeva, V. V. ;

Bagdasaryan, M. R. ;

Noravyan, A. S. ;

Dzhagatspanyan, I. A. ;

Nazaryan, I. M. ;

Akopyan, A. G. .

PHARMACEUTICAL CHEMISTRY JOURNAL, 2015, 49 (09) :587-591

[4]

Daghish M., 2006, [No title captured], Patent No. [WO 2006100095, 2006100095]

[5] Pharmacophore modelling and virtual screening for identification of new aurora-a kinase inhibitors [J].

Deng, Xiao-Qiang ;

Wang, Hui-Yuan ;

Zhao, Ying-Lan ;

Xiang, Ming-Li ;

Jiang, Pei-Du ;

Cao, Zhi-Xing ;

Zheng, Yu-Zhu ;

Luo, Shi-Dong ;

Yu, Luo-Ting ;

Wei, Yu-Quan ;

Yang, Sheng-Yong .

CHEMICAL BIOLOGY & DRUG DESIGN, 2008, 71 (06) :533-539

[6]

Dyke H. J., 2009, [No title captured], Patent No. [WO 2009151589, 2009151589]

[7] The effect of PLC-γ2 inhibitors on the growth of human tumour cells [J].

Feng, Linda ;

Reynisdottir, Inga ;

Reynisson, Johannes .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 :463-469

[8] Synthesis and cytotoxicity of thieno[2,3-b]pyridine and furo[2,3-b]pyridine derivatives [J].

Hung, Joy M. ;

Arabshahi, Homayon J. ;

Leung, Euphemia ;

Reynisson, Johannes ;

Barker, David .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 86 :420-437

[9] Synthesis and cytotoxicity of thieno[2,3-b]quinoline-2-carboxamide and cycloalkyl[b]thieno[3,2-e]pyridine-2-carboxamide derivatives [J].

Leung, Euphemia ;

Pilkington, Lisa I. ;

van Rensburg, Michelle ;

Jeon, Chae Yeon ;

Song, Mirae ;

Arabshahi, Homayon J. ;

De Zoysa, Gayan Heruka ;

Sarojini, Vijayalekshmi ;

Denny, William A. ;

Reynisson, Johannes ;

Barker, David .

BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (05) :1142-1154

[10] The effect of a thieno[2,3-b] pyridine PLC-γ inhibitor on the proliferation, morphology, migration and cell cycle of breast cancer cells [J].

Leung, Euphemia ;

Hung, Joy M. ;

Barker, David ;

Reynisson, Johannes .

MEDCHEMCOMM, 2014, 5 (01) :99-106

← 1 2 →