Literature DB >> 28816439

1,3-Dipolar Cycloaddition Reactions for the Synthesis of Novel Oxindole Derivatives and Their Cytotoxic Properties.

Prakash R Mali1,2, Prashishkumar K Shirsat1,2, Navnath Khomane1,2, Lakshama Nayak1, Jagadeesh Babu Nanubolu3, H M Meshram1.   

Abstract

The multicomponent reaction between isatin, amino acid, but-2-ynedioates, and phenacyl bromide has been developed using microwave irradiation under catalyst and base-free conditions in aqueous medium. This synthetic protocol is useful for the synthesis of various functionalized spirooxindole derivatives. This MCR exhibits a broad substrate scope with excellent yields and shorter reaction time. Additionally the synthesized spirooxindole derivatives were evaluated for their anticancer activity against three human cancer cell lines: MCF-7 (breast), A549 (lung), and HeLa cervical. Most of the compounds showed moderate to potent cytotoxic activity against the tested cell lines.

Entities:  

Keywords:  1,3-dipolar cycloaddition; N-substituted oxindole derivatives; amino acid; aqueous medium; but-2-ynedioates; cytotoxic properties; microwave assisted

Mesh:

Substances:

Year:  2017        PMID: 28816439     DOI: 10.1021/acscombsci.7b00044

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN: 2156-8944            Impact factor:   3.784


  5 in total

Review 1.  Isatin and its derivatives: a survey of recent syntheses, reactions, and applications.

Authors:  Rita Kakkar
Journal:  Medchemcomm       Date:  2019-01-15       Impact factor: 3.597

2.  Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells.

Authors:  Selvaraj Shyamsivappan; Raju Vivek; Arjunan Saravanan; Thangaraj Arasakumar; Gopalan Subashini; Thangaraj Suresh; Ramasamy Shankar; Palathurai Subramaniam Mohan
Journal:  Medchemcomm       Date:  2019-01-22       Impact factor: 3.597

Review 3.  Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects.

Authors:  Shivani Gulati; Stephy Elza John; Nagula Shankaraiah
Journal:  Beilstein J Org Chem       Date:  2021-04-19       Impact factor: 2.883

4.  A one-pot, multicomponent reaction for the synthesis of novel 2-alkyl substituted 4-aminoimidazo[1,2-a][1,3,5]triazines.

Authors:  Felicia Phei Lin Lim; Lin Yuing Tan; Edward R T Tiekink; Anton V Dolzhenko
Journal:  RSC Adv       Date:  2018-06-12       Impact factor: 3.361

5.  Covalent organic functionalization of graphene nanosheets and reduced graphene oxide via 1,3-dipolar cycloaddition of azomethine ylide.

Authors:  Luca Basta; Aldo Moscardini; Filippo Fabbri; Luca Bellucci; Valentina Tozzini; Silvia Rubini; Andrea Griesi; Mauro Gemmi; Stefan Heun; Stefano Veronesi
Journal:  Nanoscale Adv       Date:  2021-08-30
  5 in total

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