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螺环氧化吲哚的分子多样性。合成与生物活性。

Molecular diversity of spirooxindoles. Synthesis and biological activity.

作者信息

Pavlovska Tetyana L, Redkin Ruslan Gr, Lipson Victoria V, Atamanuk Dmytro V

机构信息

State Scientific Institution, "Institute for Single Crystals" of National Academy of Sciences of Ukraine, Lenina Pr., 60, Kharkov, 61002, Ukraine.

National University of Pharmacy, Pushkinska Str., 53, Kharkov, 61002, Ukraine.

出版信息

Mol Divers. 2016 Feb;20(1):299-344. doi: 10.1007/s11030-015-9629-8. Epub 2015 Sep 29.

DOI:10.1007/s11030-015-9629-8
PMID:26419598
Abstract

Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.

摘要

螺环氧化吲哚是具有广泛生物活性和药物研发应用的重要合成目标物。本综述聚焦于基于过去十年的报道及早期研究工作中对螺环氧化吲哚对映选择性合成的各种策略。本综述中的螺环氧化吲哚被分为三个结构类别，然后根据生成螺环的方法类型进一步分类。

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Mol Divers. 2015 May;19(2):251-61. doi: 10.1007/s11030-015-9574-6. Epub 2015 Mar 8.
2
Enantioselective Synthesis of Spiro[cyclohexane-1,3'-indolin]-2'-ones Containing Multiple Stereocenters via Organocatalytic Michael/Aldol Cascade Reactions.通过有机催化的迈克尔/羟醛串联反应对含多个立体中心的螺[环己烷-1,3'-吲哚啉]-2'-酮进行对映选择性合成。
Tetrahedron Lett. 2013 May 8;54(19):2311-2314. doi: 10.1016/j.tetlet.2013.02.030.
3
针对一系列螺环氧化吲哚衍生物对结肠癌细胞系HCT - 116的抗癌活性的定量构效关系及药物代谢动力学预测研究。
Heliyon. 2024 Aug 8;10(16):e35897. doi: 10.1016/j.heliyon.2024.e35897. eCollection 2024 Aug 30.
4
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Heliyon. 2024 Apr 4;10(8):e29277. doi: 10.1016/j.heliyon.2024.e29277. eCollection 2024 Apr 30.
5
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ACS Omega. 2023 Sep 14;8(38):35283-35294. doi: 10.1021/acsomega.3c05020. eCollection 2023 Sep 26.
8
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RSC Adv. 2023 Mar 1;13(11):7063-7075. doi: 10.1039/d3ra00017f.
9
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Beilstein J Org Chem. 2022 Nov 10;18:1532-1538. doi: 10.3762/bjoc.18.162. eCollection 2022.
10
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Int J Mol Sci. 2022 Nov 10;23(22):13820. doi: 10.3390/ijms232213820.
Amino acid derived phosphine-catalyzed enantioselective 1,4-dipolar spiroannulation of cyclobutenones and isatylidenemalononitrile.氨基酸衍生的膦催化环丁烯酮与异亚丙基丙二腈的对映选择性1,4-偶极螺环化反应。
Chemistry. 2015 Mar 9;21(11):4224-8. doi: 10.1002/chem.201406475. Epub 2015 Jan 28.
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7
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8
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Angew Chem Int Ed Engl. 2013 May 10;52(20):5360-3. doi: 10.1002/anie.201301017. Epub 2013 Apr 16.
9
Synthesis of novel spirooxindolo-pyrrolidines, pyrrolizidines, and pyrrolothiazoles via a regioselective three-component [3+2] cycloaddition and their preliminary antimicrobial evaluation.通过区域选择性的三组分[3+2]环加成反应合成新型螺环氧化吲哚-吡咯烷、吡咯里西啶和吡咯并噻唑及其初步抗菌评价。
Mol Divers. 2013 May;17(2):271-83. doi: 10.1007/s11030-013-9432-3. Epub 2013 Mar 7.
10
Catalytic asymmetric Michael addition/cyclization of isothiocyanato oxindoles: highly efficient and versatile approach for the synthesis of 3,2'-pyrrolidinyl mono- and bi-spirooxindole frameworks.异硫氰酸酯氧化吲哚的催化不对称迈克尔加成/环化反应：合成3,2'-吡咯烷基单螺和双螺氧化吲哚骨架的高效通用方法
Chemistry. 2013 Jan 21;19(4):1184-8. doi: 10.1002/chem.201204114. Epub 2012 Dec 18.