Synthesis and Antiproliferative Activities of 1-Hydroxyindole-2-Carboxylates

被引：1

作者：

Park, Yeon Kyeong ^{[1
]}

Ryu, Yea Seong ^{[2
]}

Cho, Hyunsung ^{[1
]}

Chung, Ha Sook ^{[2
]}

Lee, Sang Hyup ^{[1
]}

机构：

[1] Duksung Womens Univ, Coll Pharm & Innovat Drug Ctr, Seoul 01369, South Korea

[2] Duksung Womens Univ, Coll Nat Sci, Seoul 01369, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2018年 / 39卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

Hydroxyindole; Conjugate nitrone; Stannous chloride; Antiproliferative activity; HCT116; MDA-Mb-231; A2058; cells; SUBSTITUTED N-HYDROXYINDOLES; 1-HYDROXYINDOLES; CONSTRUCTION;

D O I：

10.1002/bkcs.11418

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis and evaluation of antiproliferative activities of 1-hydroxyindole-2-carboxylates 1 were described. The toluene compounds 3 were treated with dimethyl oxalate and then, dimethylmethyleneammonium chloride to give intermediates 2. Compounds 2 were converted to desired compounds 1 by application of the reaction of 1-hydroxyindole formation using SnCl(2)2H(2)O and thiol (or alcohol). The measurements of antiproliferative activities of compounds 1a, 1b, and 1c against several cell lines revealed that compounds 1a and 1c showed strong antiproliferative activities in HCT116 and A2058 cancer cells and could serve as promising lead compounds for further development of anticancer agents.

引用

页码：512 / 515

页数：4

共 16 条

[1]

ACHESON RM, 1974, J CHEM SOC CHEM COMM, P671

[2]

CARMICHAEL J, 1987, CANCER RES, V47, P936

[3] Assessing the differential action on cancer cells of LDH-A inhibitors based on the N-hydroxyindole-2-carboxylate (NHI) and malonic (Mal) scaffolds [J].

Granchi, Carlotta ;

Calvaresi, Emilia C. ;

Tuccinardi, Tiziano ;

Paterni, Ilaria ;

Macchia, Marco ;

Martinelli, Adriano ;

Hergenrother, Paul J. ;

Minutolo, Filippo .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (38) :6588-6596

[4] Discovery of N-Hydroxyindole-Based Inhibitors of Human Lactate Dehydrogenase Isoform A (LDH-A) as Starvation Agents against Cancer Cells [J].

Granchi, Carlotta ;

Roy, Sarabindu ;

Giacomelli, Chiara ;

Macchia, Marco ;

Tuccinardi, Tiziano ;

Martinelli, Adriano ;

Lanza, Mario ;

Betti, Laura ;

Giannaccini, Gino ;

Lucacchini, Antonio ;

Funel, Nicola ;

Leon, Leticia G. ;

Giovannetti, Elisa ;

Peters, Godefridus J. ;

Palchaudhuri, Rahul ;

Calvaresi, Emilia C. ;

Hergenrother, Paul J. ;

Minutolo, Filippo .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) :1599-1612

[5] O-glycosides of N-hydroxyindoles [J].

Lavrenov, SN ;

Korolev, AM ;

Preobrazhenskaya, MN .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2001, 20 (10-11) :1881-1889

[6] New synthetic technology for the construction of N-hydroxyindoles and synthesis of nocathiacin I model systems [J].

Nicolaou, K. C. ;

Estrada, Anthony A. ;

Freestone, Graeme C. ;

Lee, Sang Hyup ;

Alvarez-Mico, Xavier .

TETRAHEDRON, 2007, 63 (27) :6088-6114

[7] Synthesis of highly substituted N-hydroxyindoles through 1,5-addition of carbon nucleophiles to in situ generated unsaturated nitrones [J].

Nicolaou, K. C. ;

Estrada, Anthony A. ;

Lee, Sang Hyup ;

Freestone, Graeme C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (32) :5364-5368

[8] Construction of substituted N-hydroxyindoles:: Synthesis of a nocathiacin I model system [J].

Nicolaou, KC ;

Lee, SH ;

Estrada, AA ;

Zak, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (24) :3736-3740

[9] Synthesis of New 1-Hydroxyindole-2-Carboxylates and Mechanistic Studies on Reaction Pathways [J].

Park, Yeon Kyeong ;

Lee, Sang Hyup .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (03) :1995-2002

[10] Synthesis of New Highly Substituted and Hindered 1-Hydroxyindole-2-carboxylates [J].

Park, Yeon Kyeong ;

Kim, Hyejin ;

Lee, Sang Hyup .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (01) :82-90

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