Literature DB >> 22405285

Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity.

Gangaru Bhaskar1, Yuvaraj Arun, Chandrasekar Balachandran, Chandrasekara Saikumar, Paramasivan T Perumal.   

Abstract

A series of novel spirooxindoles have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine or l-proline with the dipolarophile 1,4-naphthoquinone followed by spontaneous dehydrogenation. Synthesised compounds were evaluated for their antimicrobial activities against eight bacteria and three fungi. All the spirooxindole derivatives exhibited significant antibacterial activity against Staphylococcus aureus, S. aureus (MRSA), Enterobacter aerogens, Micrococcus luteus, Proteus vulgaris, Klebsiella pneumonia, Salmonella typhimurium, Salmonella paratyphi-B and anti-fungal activity against Malassesia pachydermatis, Candida albicans and Botyritis cinerea organisms. Among 23 compounds screened, 1'-acetyl-2,5'-dimethyl-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione was found to be more active against tested bacteria and fungi.
Copyright © 2012 Elsevier Masson SAS. All rights reserved.

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Year:  2012        PMID: 22405285     DOI: 10.1016/j.ejmech.2012.02.024

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN: 0223-5234            Impact factor:   6.514


  19 in total

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Review 2.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

3.  Construction of a spirooxindole amide library through nitrile hydrozirconation-acylation-cyclization cascade.

Authors:  Matthew G LaPorte; Sammi Tsegay; Ki Bum Hong; Chunliang Lu; Cheng Fang; Lirong Wang; Xiang-Qun Xie; Paul E Floreancig
Journal:  ACS Comb Sci       Date:  2013-06-26       Impact factor: 3.784

4.  Spirooxindole derivative SOID-8 induces apoptosis associated with inhibition of JAK2/STAT3 signaling in melanoma cells.

Authors:  Yan Tian; Sangkil Nam; Lucy Liu; Fumiko Yakushijin; Kenichi Yakushijin; Ralf Buettner; Wei Liang; Fan Yang; Yuelong Ma; David Horne; Richard Jove
Journal:  PLoS One       Date:  2012-11-16       Impact factor: 3.240

5.  Cu/TEMPO catalyzed dehydrogenative 1,3-dipolar cycloaddition in the synthesis of spirooxindoles as potential antidiabetic agents.

Authors:  Chitrala Teja; Spoorthy N Babu; Ayesha Noor; J Arul Daniel; S Asha Devi; Fazlur Rahman Nawaz Khan
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6.  Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.

Authors:  Perumal Prabhakaran; Perumal Rajakumar
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7.  The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids.

Authors:  Tatyana L Pavlovskaya; Fedor G Yaremenko; Victoria V Lipson; Svetlana V Shishkina; Oleg V Shishkin; Vladimir I Musatov; Alexander S Karpenko
Journal:  Beilstein J Org Chem       Date:  2014-01-09       Impact factor: 2.883

8.  Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol.

Authors:  Natarajan Arumugam; Abdulrahman I Almansour; Raju Suresh Kumar; Dhaifallah M Al-Thamili; Govindasami Periyasami; V S Periasamy; Jegan Athinarayanan; Ali A Alshatwi; S M Mahalingam; J Carlos Menéndez
Journal:  Chem Cent J       Date:  2018-09-01       Impact factor: 4.215

9.  Synthesis, Biological and In Silico Evaluation of Pure Nucleobase-Containing Spiro (Indane-Isoxazolidine) Derivatives as Potential Inhibitors of MDM2-p53 Interaction.

Authors:  Loredana Maiuolo; Vincenzo Algieri; Beatrice Russo; Matteo Antonio Tallarida; Monica Nardi; Maria Luisa Di Gioia; Zahra Merchant; Pedro Merino; Ignacio Delso; Antonio De Nino
Journal:  Molecules       Date:  2019-08-10       Impact factor: 4.411

10.  Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindoles via conjugate addition/Schmidt-type rearrangement of vinyl azides and (E)-alkenyloxindoles.

Authors:  Ziwei Zhong; Zhijie Xiao; Xiaohua Liu; Weidi Cao; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

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