Literature DB >> 30996856

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

Rita Kakkar1.   

Abstract

Isatin (1H-indole-2,3-dione) and its derivatives represent an important class of heterocyclic compounds that can be used as precursors for drug synthesis. Since its discovery, a lot of research work has been done regarding the synthesis, chemical properties, and biological and industrial applications of isatin. In this review, we have reported several novel methods for the synthesis of N-, C2-, and C3-substituted and spiro derivatives of isatin. The isatin moiety also shows important chemical reactions such as oxidation, ring expansion, Friedel-Crafts reaction and aldol condensation. These reactions, in turn, produce several biologically viable compounds like 2-oxindoles, tryptanthrin, indirubins, and many more. We have also summarized some recently reported biological activities exhibited by isatin derivatives, like anti-cancer, anti-bacterial, anti-diabetic and others. Special attention has been paid to their anti-cancer activity, and various anti-cancer targets such as histone deacetylase, carbonic anhydrase, tyrosine kinase, and tubulin have been discussed in detail. Other applications of isatin derivatives, such as in the dye industry and in corrosion prevention, have also been discussed.

Entities:  

Year:  2019        PMID: 30996856      PMCID: PMC6438150          DOI: 10.1039/c8md00585k

Source DB:  PubMed          Journal:  Medchemcomm        ISSN: 2040-2503            Impact factor:   3.597


  74 in total

1.  Discovery of zoniporide: a potent and selective sodium-hydrogen exchanger type 1 (NHE-1) inhibitor with high aqueous solubility.

Authors:  A Guzman-Perez; R T Wester; M C Allen; J A Brown; A R Buchholz; E R Cook; W W Day; E S Hamanaka; S P Kennedy; D R Knight; P J Kowalczyk; R B Marala; C J Mularski; W A Novomisle; R B Ruggeri; W R Tracey; R J Hill
Journal:  Bioorg Med Chem Lett       Date:  2001-03-26       Impact factor: 2.823

Review 2.  Epilepsy: A Spectrum Disorder.

Authors:  Joseph I Sirven
Journal:  Cold Spring Harb Perspect Med       Date:  2015-09-01       Impact factor: 6.915

3.  An investigation into the cytotoxicity and mode of action of some novel N-alkyl-substituted isatins.

Authors:  Kara L Vine; Julie M Locke; Marie Ranson; Stephen G Pyne; John B Bremner
Journal:  J Med Chem       Date:  2007-09-21       Impact factor: 7.446

4.  Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino) benzenesulfonamides: Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies.

Authors:  Wagdy M Eldehna; Mahmoud F Abo-Ashour; Alessio Nocentini; Paola Gratteri; Ibrahim H Eissa; Mohamed Fares; Omnia E Ismael; Hazem A Ghabbour; Mahmoud M Elaasser; Hatem A Abdel-Aziz; Claudiu T Supuran
Journal:  Eur J Med Chem       Date:  2017-08-01       Impact factor: 6.514

5.  Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII.

Authors:  Hany S Ibrahim; Sahar M Abou-Seri; Muhammet Tanc; Mahmoud M Elaasser; Hatem A Abdel-Aziz; Claudiu T Supuran
Journal:  Eur J Med Chem       Date:  2015-09-16       Impact factor: 6.514

6.  Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII.

Authors:  Wagdy M Eldehna; Mohamed Fares; Mariangela Ceruso; Hazem A Ghabbour; Sahar M Abou-Seri; Hatem A Abdel-Aziz; Dalal A Abou El Ella; Claudiu T Supuran
Journal:  Eur J Med Chem       Date:  2016-01-20       Impact factor: 6.514

7.  Isatin thiazoline hybrids as dual inhibitors of HIV-1 reverse transcriptase.

Authors:  Rita Meleddu; Simona Distinto; Angela Corona; Enzo Tramontano; Giulia Bianco; Claudia Melis; Filippo Cottiglia; Elias Maccioni
Journal:  J Enzyme Inhib Med Chem       Date:  2016-10-21       Impact factor: 5.051

8.  Azide-Alkyne Cycloaddition En Route to 1H-1,2,3-Triazole-Tethered Isatin-Ferrocene, Ferrocenylmethoxy-Isatin, and Isatin-Ferrocenylchalcone Conjugates: Synthesis and Antiproliferative Evaluation.

Authors:  Amandeep Singh; Sourav Taru Saha; Shanen Perumal; Mandeep Kaur; Vipan Kumar
Journal:  ACS Omega       Date:  2018-01-30

9.  α-Glucosidase inhibitors and their use in clinical practice.

Authors:  Giuseppe Derosa; Pamela Maffioli
Journal:  Arch Med Sci       Date:  2012-11-07       Impact factor: 3.318

10.  Ribonuclease H/DNA Polymerase HIV-1 Reverse Transcriptase Dual Inhibitor: Mechanistic Studies on the Allosteric Mode of Action of Isatin-Based Compound RMNC6.

Authors:  Angela Corona; Rita Meleddu; Francesca Esposito; Simona Distinto; Giulia Bianco; Takashi Masaoka; Elias Maccioni; Luis Menéndez-Arias; Stefano Alcaro; Stuart F J Le Grice; Enzo Tramontano
Journal:  PLoS One       Date:  2016-01-22       Impact factor: 3.240

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  25 in total

Review 1.  Evolution of 3-(4-hydroxyphenyl)indoline-2-one as a scaffold for potent and selective anticancer activity.

Authors:  Matthew W Boudreau; Paul J Hergenrother
Journal:  RSC Med Chem       Date:  2022-05-09

2.  N-1,2,3-Triazole-isatin derivatives: anti-proliferation effects and target identification in solid tumour cell lines.

Authors:  Natalia Busto; Joana Leitão-Castro; Alfonso T García-Sosa; Francisco Cadete; Carolina S Marques; Renata Freitas; Anthony J Burke
Journal:  RSC Med Chem       Date:  2022-06-10

3.  Tackling Microbial Resistance with Isatin-Decorated Thiazole Derivatives: Design, Synthesis, and in vitro Evaluation of Antimicrobial and Antibiofilm Activity.

Authors:  Refaie M Kassab; Sami A Al-Hussain; Nooran S Elleboudy; Amgad Albohy; Magdi E A Zaki; Khaled A M Abouzid; Zeinab A Muhammad
Journal:  Drug Des Devel Ther       Date:  2022-08-25       Impact factor: 4.319

4.  Design, Synthesis, Anticancer Evaluation, Enzymatic Assays, and a Molecular Modeling Study of Novel Pyrazole-Indole Hybrids.

Authors:  Ashraf S Hassan; Gaber O Moustafa; Hanem M Awad; Eman S Nossier; Mohamed F Mady
Journal:  ACS Omega       Date:  2021-04-29

5.  (3Z)-5-Chloro-3-(Hydroxyimino)indolin-2-one attenuates hyperglycemia, increased hepatic glycogen content and hepatic damage induced by malathion acute exposure in rats.

Authors:  Edina da Luz Abreu; Anne Suély Pinto Savall; Allyson Ardais Boneberg; Bianca Barreto Martins; Vanessa Carratú Gervini; Tuane Bazanella Sampaio; André Ricardo Fajardo; Natália Paroul; Daniel Henrique Roos; Simone Pinton
Journal:  Nutr Metab (Lond)       Date:  2019-09-05       Impact factor: 4.169

6.  Design, synthesis, in silico studies and in vitro evaluation of isatin-pyridine oximes hybrids as novel acetylcholinesterase reactivators.

Authors:  Daniel A S Kitagawa; Rafael B Rodrigues; Thiago N Silva; Wellington V Dos Santos; Vinicius C V da Rocha; Joyce S F D de Almeida; Leandro B Bernardo; Taynara Carvalho-Silva; Cintia N Ferreira; Angelo A T da Silva; Alessandro B C Simas; Eugenie Nepovimova; Kamil Kuča; Tanos C C França; Samir F de A Cavalcante
Journal:  J Enzyme Inhib Med Chem       Date:  2021-12       Impact factor: 5.051

7.  N-alkylisatin-based microtubule destabilizers bind to the colchicine site on tubulin and retain efficacy in drug resistant acute lymphoblastic leukemia cell lines with less in vitro neurotoxicity.

Authors:  Bryce Keenan; Rocio K Finol-Urdaneta; Ashleigh Hope; John B Bremner; Maria Kavallaris; Daniel Lucena-Agell; María Ángela Oliva; Jose Fernando Díaz; Kara L Vine
Journal:  Cancer Cell Int       Date:  2020-05-15       Impact factor: 5.722

8.  Streptavidin-Hosted Organocatalytic Aldol Addition.

Authors:  Nicolò Santi; Louis C Morrill; Louis Y P Luk
Journal:  Molecules       Date:  2020-05-25       Impact factor: 4.411

Review 9.  Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview.

Authors:  Dimitris Matiadis; Marina Sagnou
Journal:  Int J Mol Sci       Date:  2020-07-31       Impact factor: 5.923

10.  Antitumor properties of certain spirooxindoles towards hepatocellular carcinoma endowed with antioxidant activity.

Authors:  Sara T Al-Rashood; Ahmed R Hamed; Ghada S Hassan; Hamad M Alkahtani; Abdulrahman A Almehizia; Amal Alharbi; Mohammad M Al-Sanea; Wagdy M Eldehna
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

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