Synthesis of 3,3-disubstituted oxindoles from N-arylacrylamides and unactivated alkyl bromides via nickel-catalyzed cascade cyclization and their inhibitory effect on NO release

被引：2

作者：

Lv, Jiaxing ^{[1
]}

Ma, Mingyu ^{[1
]}

Geng, Zhiyuan ^{[1
]}

Huang, Yuru ^{[1
]}

Wei, Hanyu ^{[1
]}

Yang, Runzhe ^{[1
]}

Fang, Xianhe ^{[1
]}

Bi, Yi ^{[1
]}

机构：

[1] Yantai Univ, Sch Pharm, Yantai 264005, Shandong, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2024年 / 48卷 / 43期

基金：

中国国家自然科学基金;

关键词：

MAMMALIAN-CELL CYCLE; NITRIC-OXIDE; ASPERGILLUS-FUMIGATUS; ALKALOIDS; POTENT; DESIGN;

D O I：

10.1039/d4nj03615h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ni-catalyzed cascade cyclization of N-acrylamides and unactivated alkyl bromides to synthesize 3,3-disubstituted oxindoles was reported. Up to 22 different oxindole derivatives were synthesized by this method and all the synthesized molecules were tested for inhibitory activity of nitric oxide release. The results show that 3,3-disubstituted oxindole is a potential scaffold to design new nitric oxide release inhibition drugs.

引用

页码：18356 / 18359

页数：4

共 30 条

[1] Design of Chemically Stable, Potent, and Efficacious MDM2 Inhibitors That Exploit the Retro-Mannich Ring-Opening-Cyclization Reaction Mechanism in Spiro-oxindoles [J].

Aguilar, Angelo ;

Sun, Wei ;

Liu, Liu ;

Lu, Jianfeng ;

McEachern, Donna ;

Bernard, Denzil ;

Deschamps, Jeffrey R. ;

Wang, Shaomeng .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (24) :10486-10498

[2] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].

Biswas, Soumik ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197

[3]

Chen HY, 2023, Sheng Yen Series Chi, P63

[4] Synthesis and Antitumor Effect in Vitro and in Vivo of Substituted 1,3-Dihydroindole-2-ones [J].

Christensen, Mette K. ;

Erichsen, Kamille D. ;

Trojel-Hansen, Christina ;

Tjornelund, Jette ;

Nielsen, Soren J. ;

Frydenvang, Karla ;

Johansen, Tommy N. ;

Nielsen, Birgitte ;

Schested, Maxwell ;

Jensen, Peter B. ;

Ikaunieks, Martins ;

Zaichenko, Andrei ;

Loza, Einars ;

Kalvinsh, Ivars ;

Bjorkling, Fredrik .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :7140-7145

[5] NITRIC-OXIDE MEDIATES CYTOKINE-INDUCED INHIBITION OF INSULIN-SECRETION BY HUMAN ISLETS OF LANGERHANS [J].

CORBETT, JA ;

SWEETLAND, MA ;

WANG, JL ;

LANCASTER, JR ;

MCDANIEL, ML .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (05) :1731-1735

[6] Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (08) :832-835

[7] Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1997, 53 (01) :59-72

[8] Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1996, 52 (39) :12651-12666

[9] NITRIC-OXIDE MEDIATES GLUTAMATE NEUROTOXICITY IN PRIMARY CORTICAL CULTURES [J].

DAWSON, VL ;

DAWSON, TM ;

LONDON, ED ;

BREDT, DS ;

SNYDER, SH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (14) :6368-6371

[10] Structure-based design of potent non-peptide MDM2 inhibitors [J].

Ding, K ;

Lu, Y ;

Nikolovska-Coleska, Z ;

Qiu, S ;

Ding, YS ;

Gao, W ;

Stuckey, J ;

Krajewski, K ;

Roller, PP ;

Tomita, Y ;

Parrish, DA ;

Deschamps, JR ;

Wang, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10130-10131

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