N-Phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents

Matesic, Lidia; Locke, Julie M.; Bremner, John B.; Pyne, Stephen G.; Skropeta, Danielle; Ranson, Marie; Vine, Kara L.

doi:10.1016/j.bmc.2007.12.026

Cited by 73 publications

(60 citation statements)

References 16 publications

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“…Isatin (indoline-2,3-dione) has provoked tremendous interest due to its numerous biological and pharmacological activities. The growing importance of substituted isatins in the field of medicinal chemistry as potential chemotherapeutic agents and their implications for prodrug design have been reported (Matesic et al, 2008;Wang et al, 2008;Lane et al, 2001;Patyna et al, 2006). As a continuation of our research devoted to the development of isatin derivatives (Qachchachi et al, 2014a,b), we report herein on the synthesis and crystal structure of a new indoline-2,3-dione derivative.…”

Section: Structure Descriptionmentioning

confidence: 85%

1-[(2E)-3-Phenylprop-2-en-1-yl]-1H-indole-2,3-dione

Qachchachi¹,

Rodi²,

Haoudi³

et al. 2016

IUCr Data

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In the title compound, C 17 H 13 NO 2 , the indole ring is essentially planar (r.m.s. deviation = 0.027 Å ) and is oriented at an angle of 69.33 (7) with respect to the phenyl ring. In the crystal, C-HÁ Á ÁO hydrogen bonds link the molecules, forming zigzag chains propagating along the a-axis direction. Within the chains there are -stacking interactions [centroid-centroid distances = 3.7163 (8) and 3.7162 (8) Å ] involving isatin groups of neighbouring molecules.

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Section: Structure Descriptionmentioning

confidence: 85%

1-[(2E)-3-Phenylprop-2-en-1-yl]-1H-indole-2,3-dione

Qachchachi¹,

Rodi²,

Haoudi³

et al. 2016

IUCr Data

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“…[51]. All five N-phenethyl derivatives (8a-e) exhibited low to sub-micromolar cytotoxic activity against a panel of human leukemic, lymphoma and carcinoma cell lines where introduction of a hydrophobic bromo substituent in the meta (8b) or para (8c) position yielded the most active compounds [51]. Interestingly, the corresponding phenacyl derivatives (not shown) were at least 3-5 times less active against the U937 cells [51].…”

Section: N-alkyl Substituted Isatin Derivativesmentioning

confidence: 98%

“…This effect was further enhanced by at least a factor of two when the incubation time was increased from 24 h to 72 h, making this class of compounds >10 times more active than the conventional chemotherapeutic agents 5-fluorouracil (5-FU), paclitaxel and vinblastine against U937 cells [50]. [51]. All five N-phenethyl derivatives (8a-e) exhibited low to sub-micromolar cytotoxic activity against a panel of human leukemic, lymphoma and carcinoma cell lines where introduction of a hydrophobic bromo substituent in the meta (8b) or para (8c) position yielded the most active compounds [51].…”

Section: N-alkyl Substituted Isatin Derivativesmentioning

confidence: 99%

“…All five N-phenethyl derivatives (8a-e) exhibited low to sub-micromolar cytotoxic activity against a panel of human leukemic, lymphoma and carcinoma cell lines where introduction of a hydrophobic bromo substituent in the meta (8b) or para (8c) position yielded the most active compounds [51]. Interestingly, the corresponding phenacyl derivatives (not shown) were at least 3-5 times less active against the U937 cells [51]. Related N-phenylacetamide derivatives (9a-e) prepared by Modi et al [52] were also active against a MCF-7 human mammary adenocarcinoma cell line with after a 48 h incubation, with the most active compound, 4-bromo-1-diethylaminomethyl-1H-indole-2,3-dione (IC 50 11.68 µM; MDA-MB-468), displaying 10-15 fold greater selectivity for cancer over non-cancer cells.…”

Section: N-alkyl Substituted Isatin Derivativesmentioning

confidence: 99%

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Recent Highlights in the Development of Isatin-Based Anticancer Agents

Vine¹,

Matesic²,

Locke³

et al. 2013

Advances in Anticancer Agents in Medicinal Chemistry

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Isatin (1H-indole-2,3-dione) and its derivatives are responsible for a broad spectrum of biological activities. Among these the cytotoxic and antineoplastic properties have been the most widely reported. The synthetic versatility of the isatin, due to its privileged scaffold, has led to the generation of a large number of structurally diverse derivatives which include analogues derived from either mono-, di-, and trisubstitution of the aryl ring A, and/or those obtained by derivatisation of the isatin nitrogen and C2/C3 carbonyl moieties. These compounds inhibit cancer cell proliferation and tumour growth via interaction with a variety of intracellular targets such as DNA, telomerase, tubulin, P-glycoprotein, protein kinases and phosphatases. Herein we review recent highlights in the development of isatin-based compounds as anticancer agents with a particular focus on the cytotoxicity and structure activity relationships. Abstract:Isatin (1H-indole-2,3-dione) and its derivatives are responsible for a broad spectrum of biological activities. Among these the cytotoxic and antineoplastic properties have been the most widely reported. The synthetic versatility of the isatin, due to its privileged scaffold, has led to the generation of a large number of structurally diverse derivatives which include analogues derived from either mono-, di-, and tri-substitution of the aryl ring A, and/or those obtained by derivatisation of the isatin nitrogen and C2/C3 carbonyl moieties. These compounds inhibit cancer cell proliferation and tumour growth via interaction with a variety of intracellular targets such as DNA, telomerase, tubulin, Pglycoprotein, protein kinases and phosphatases. Herein we review recent highlights in the development of isatin-based compounds as anticancer agents with a particular focus on the cytotoxicity and structure activity relationships.

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“…N-Substituted isatins 2 especially are reported to show a wide range of biological activities such as antibacterial, 3 anti-fungal 4,5 antiviral 6 and anti-HIV, 7,8 antileukemia. 9 These compounds were also reported to have effects on central nervous system. 10,11 The chemistry of oxazolidinone and its derivatives has received considerable attention owing to their synthetic and biological importance.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new oxindole derivatives containing oxazolidin-2-one

Essassi¹,

Alsubari²,

Bouhfid³

2009

Arkivoc

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The reactions of bis(2-chloroethyl)amine in presence of potassium carbonate with substituted isatins afforded the corresponding 1-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl)indoline-2,3-diones, which are used as starting materials for the preparation of new heterocyclic systems containing quinoxaline, oxazolidine, benzimidazoquinazoline and oxindole nuclei. The structures of the products were established by NMR spectroscopy, mass spectra and X-ray diffraction analysis.

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N-Phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents

Cited by 73 publications

References 16 publications

1-[(2E)-3-Phenylprop-2-en-1-yl]-1H-indole-2,3-dione

1-[(2E)-3-Phenylprop-2-en-1-yl]-1H-indole-2,3-dione

Recent Highlights in the Development of Isatin-Based Anticancer Agents

Synthesis of new oxindole derivatives containing oxazolidin-2-one

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