Literature DB >> 26419598

Molecular diversity of spirooxindoles. Synthesis and biological activity.

Tetyana L Pavlovska1, Ruslan Gr Redkin2, Victoria V Lipson3,4, Dmytro V Atamanuk5.   

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.

Entities:  

Keywords:  Cycloadditions; DOS; Diversity-oriented synthesis; Highly functionalised molecules; Isatin; Multicomponent reactions (MCRs); Oxindoles; Spiroheterocyclic systems

Mesh：

Substances：

Year:  2015        PMID： 26419598     DOI： 10.1007/s11030-015-9629-8

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  117 in total

Review 1.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

Review 2.  Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis.

Authors:  Shu-Ming Li
Journal:  Nat Prod Rep       Date:  2009-11-19       Impact factor: 13.423

3.  Diastereo- and enantioselective [3 + 2] cycloaddition reaction of Morita-Baylis-Hillman carbonates of isatins with N-phenylmaleimide catalyzed by Me-DuPhos.

Authors:  Yan Wang; Li Liu; Tao Zhang; Neng-Jun Zhong; Dong Wang; Yong-Jun Chen
Journal:  J Org Chem       Date:  2012-04-10       Impact factor: 4.354

4.  Identification of the spiro(oxindole-3,3'-thiazolidine)-based derivatives as potential p53 activity modulators.

Authors:  Isabel Gomez-Monterrey; Alessia Bertamino; Amalia Porta; Alfonso Carotenuto; Simona Musella; Claudio Aquino; Ilaria Granata; Marina Sala; Diego Brancaccio; Delia Picone; Carmine Ercole; Paola Stiuso; Pietro Campiglia; Paolo Grieco; Pio Ianelli; Bruno Maresca; Ettore Novellino
Journal:  J Med Chem       Date:  2010-11-08       Impact factor: 7.446

5.  Luminescent bichromophoric spiroindolones--synthesis and electronic properties.

Authors:  Jan Schönhaber; Thomas J J Müller
Journal:  Org Biomol Chem       Date:  2011-07-28       Impact factor: 3.876

6.  Highly efficient hydrogen-bonding catalysis of the Diels-Alder reaction of 3-vinylindoles and methyleneindolinones provides carbazolespirooxindole skeletons.

Authors:  Bin Tan; Gloria Hernández-Torres; Carlos F Barbas
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

7.  2-(substituted phenyl)amino analogs of 1-methoxyspirobrassinol methyl ether: synthesis and anticancer activity.

Authors:  Peter Kutschy; Aneta Salayová; Zuzana Curillová; Tibor Kozár; Roman Mezencev; Ján Mojzis; Martina Pilátová; Eva Balentová; Pavel Pazdera; Marián Sabol; Michaela Zburová
Journal:  Bioorg Med Chem       Date:  2009-04-11       Impact factor: 3.641

8.  Versatile three-component procedure for combinatorial synthesis of 2-aminospiro[(3'H)-indol-3',4-(4H)-pyrans].

Authors:  Yuri M Litvinov; Valery Yu Mortikov; Anatoliy M Shestopalov
Journal:  J Comb Chem       Date:  2008-08-05

9.  Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences.

Authors:  Benito Alcaide; Pedro Almendros; Raquel Rodríguez-Acebes
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354

10.  Design and biological activities of L-163,191 (MK-0677): a potent, orally active growth hormone secretagogue.

Authors:  A A Patchett; R P Nargund; J R Tata; M H Chen; K J Barakat; D B Johnston; K Cheng; W W Chan; B Butler; G Hickey
Journal:  Proc Natl Acad Sci U S A       Date:  1995-07-18       Impact factor: 11.205
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  18 in total

1.  A synthesis of fused acenaphthopyrrolizines via the 1,3-dipolar cycloaddition reaction of azomethine ylides with acetylenic esters.

Authors:  Issa Yavari; Leila Baoosi; Mohammad R Halvagar
Journal:  Mol Divers       Date:  2017-01-13       Impact factor: 2.943

2.  A synthesis of functionalized dihydro-1Η-pyrrolizines and spiropyrrolizines via [2 + 3] cycloaddition reactions.

Authors:  Issa Yavari; Leila Baoosi; Mohammad R Halvagar
Journal:  Mol Divers       Date:  2017-02-12       Impact factor: 2.943

3.  Combined Scaffold Evaluation and Systems-Level Transcriptome-Based Analysis for Accelerated Lead Optimization Reveals Ribosomal Targeting Spirooxindole Cyclopropanes.

Authors:  Kevin X Rodriguez; Erin N Howe; Emily P Bacher; Miranda Burnette; Jennifer L Meloche; Jayda Meisel; Patricia Schnepp; Xuejuan Tan; Mayland Chang; Jeremiah Zartman; Siyuan Zhang; Brandon L Ashfeld
Journal:  ChemMedChem       Date:  2019-07-01       Impact factor: 3.466

4.  Synthesis, antioxidant activity and SAR study of novel spiro-isatin-based Schiff bases.

Authors:  Fatih Sonmez; Zuhal Gunesli; Belma Zengin Kurt; Isil Gazioglu; Davut Avci; Mustafa Kucukislamoglu
Journal:  Mol Divers       Date:  2019-01-05       Impact factor: 2.943

Review 5.  Recent Strategies in the Synthesis of Spiroindole and Spirooxindole Scaffolds.

Authors:  Shima Nasri; Mohammad Bayat; Faezeh Mirzaei
Journal:  Top Curr Chem (Cham)       Date:  2021-05-18

6.  Synthesis of functionalized dispiro[indoline-3,1[Formula: see text]-cyclopentane-3[Formula: see text],3[Formula: see text]-indolines] via cyclodimerization of 3-phenacylideneoxindolines with benzoylhydrazides and arylhydrazines.

Authors:  Ren-Yin Yang; Jing Sun; Gong Jin; Chao-Guo Yan
Journal:  Mol Divers       Date:  2017-10-20       Impact factor: 2.943

7.  A formal intermolecular [4 + 1] cycloaddition reaction of 3-chlorooxindole and o-quinone methides: a facile synthesis of spirocyclic oxindole scaffolds.

Authors:  Chao Lin; Qi Xing; Honglei Xie
Journal:  RSC Adv       Date:  2021-05-24       Impact factor: 4.036

8.  Preparation of GO/SiO2/PEA as a new solid base catalyst for the green synthesis of some spirooxindole derivatives.

Authors:  Mahla Toorbaf; Leila Moradi
Journal:  RSC Adv       Date:  2021-06-21       Impact factor: 3.361

9.  An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy.

Authors:  Alexei N Izmest'ev; Galina A Gazieva; Natalya V Sigay; Sergei A Serkov; Valentina A Karnoukhova; Vadim V Kachala; Alexander S Shashkov; Igor E Zanin; Angelina N Kravchenko; Nina N Makhova
Journal:  Beilstein J Org Chem       Date:  2016-10-24       Impact factor: 2.883

10.  A Facile One-Pot Construction of Succinimide-Fused Spiro[Pyrrolidine-2,3'-Oxindoles] via 1,3-Dipolar Cycloaddition Involving 3-Amino Oxindoles and Maleimides.

Authors:  Lunqiang Jin; Feng Liang
Journal:  Molecules       Date:  2018-03-05       Impact factor: 4.411
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