Synthesis and biological evaluation of novel indoline-2,3-dione derivatives as antitumor agents

Li, Pengzhan; Tan, Yanmei; Liu, Guyue; Liu, Yang; Liu, Jianzhen; Yin, Yanzhen; Zhao, Guisen

doi:10.5582/ddt.2014.01012

Cited by 11 publications

(5 citation statements)

References 18 publications

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“…Indoline based nucleus has been reported to consist of various biological properties such as antimicrobial (Adel et al, 2000;Olgena and Ozkan, 2009;AbdelRahman et al, 2004;Sing and Luntha, 2009), anti-cancer (Sovic et al, 2014;Pengzhan et al, 2014;Xu et al, 2015;Jin et al, 2013), antidiabetic (Sato et al, 2014), antiinflammatory (Fur-man et al, 2014Rajanarendar et al, 2013), antitubulin (Chang et al, 2006). But indoline based target com-pounds have been poorly investigated their antidiabetic activity (Sato et al, 2014).…”

Section: Discussionmentioning

confidence: 99%

Synthesis, characterization and evaluation of antidiabetic activity of novel indoline derivatives

Manoharan¹,

Kulanthai²,

Gnanavel³

et al. 2017

Bangladesh J Pharmacol

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Series of indoline derivatives were synthesized using N-(4-aminophenyl)indoline-1-carbothiamide as a precursor. The confirmation of synthesized compounds was done by 1H-NMR, 13C-NMR, LC-MS (ESI) and FT-IR. In vitro antidiabetic activity of synthesized indoline derivatives were examined by standard α-amylase inhibition assay. The compounds 4a (IC50 = 52.1 µg/mL) and 4b (IC50 = 57.7 µg/mL) showed potent α-amylase inhibition activity. The compounds 3a (IC50 = 62.2 µg/mL) and 3b (IC50 = 60.7 µg/mL) showed moderate antidiabetic activity.Video Clip of Methodology:19 min 21 sec <a href="https://www.youtube.com/v/k5WdfpM-E8U">Full Screen</a> <a href="https://www.youtube.com/watch?v=k5WdfpM-E8U">Alternate</a>

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Section: Discussionmentioning

confidence: 99%

Synthesis, characterization and evaluation of antidiabetic activity of novel indoline derivatives

Manoharan¹,

Kulanthai²,

Gnanavel³

et al. 2017

Bangladesh J Pharmacol

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“…Additionally, they are considered as substantial compounds due to their widespread use as building blocks and as chiral support in asymmetric synthesis. [13] Likewise, many reports have been suggested that the indoline-based compounds have need further studies and investigations. [8,9] Subsequently, this review deals with the essential studies concerning to indoline-based heterocyclic scaffolds with focusing on their synthesis, reactions and their pharmacological activities.…”

Section: Cannabinoid Receptors Modulatorsmentioning

confidence: 99%

“…[24] Scheme 5 illustrates the mechanism of palladiumcatalyzed oxidative cascade cyclizations. The electrondeficient PdII complex coordinates to the o-allyl group of anilide (12) to generate intermediate (13) which undergoes amidopalladation to gives-alkylpalladium intermediate (14). Following intramolecular olefin insertion to obtain the product (15) by -hydride elimination.…”

Section: 1 1 Palladation-catalyzed C-n /C-c Bond Formationmentioning

confidence: 99%

Indoline-based heterocyclic scaffold: Synthetic methods, chemical reactions and biological prospect

Sharafeldin

2020

Egypt. J. Chem.

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Indolines are significant compounds because of their diversity of applications in synthetic organic chemistry, pharmaceutical, industrial chemistry as well as they are present in several biologically active compounds in both natural and synthetic origins. Recently,there are high expectations that they exhibit interesting applications in selective potentiate the activity of β-lactam antibiotics in MRSA as well as other pharmacological arena, such as anticancer, anti-inflammatory, antioxidant, anticoagulant agents, etc. Furthermore, they are considered as considerable compounds due to their widespread use as building blocks and as chiral support in asymmetric synthesis. As a result, a new trends for the indoline-based nucleus in medicinal chemistry studies require to be reviewed especially many reports have been suggested that the indoline-based compounds have a very high therapeutic value (in MRSA) and needs to be explored for further studies. So, this review deals with the main innovations regarding indoline-based heterocycle scaffold stressing on their synthesis, reactions and their pharmacological activities.

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“…Isatin and its derivatives are the natural heterocycles exhibiting a variety of biological activities [1] including antineoplastic [2,3], anticonvulsant [4], antiviral [5,6], and antibacterial [7] ones. Furthermore, structural features of the isatin molecule determine high reactivity of the endocyclic nitrogen atom and the 3-positioned carbonyl group leading to its widespread application in organic synthesis [8][9][10].…”

mentioning

confidence: 99%

Features of interaction of 1-hydroxymethylisatin with certain P-, S-, and C-electrophiles

et al. 2015

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Isatin and its derivatives are the natural heterocycles exhibiting a variety of biological activities [1] including antineoplastic [2,3], anticonvulsant [4], antiviral [5,6], and antibacterial [7] ones. Furthermore, structural features of the isatin molecule determine high reactivity of the endocyclic nitrogen atom and the 3-positioned carbonyl group leading to its widespread application in organic synthesis [8][9][10]. Thus, development of new approaches towards isatin functionalization is a promising research field. 1-Hydroxymethylisatin containing highly reactive hydroxyl group is among the promising substrates to do so [11].This work demonstrated the dual reactivity of 1hydroxymethylisatin I with respect to some C-, S-, and P-electrophiles. The reactions were carried out under the same conditions (benzene, 25°C) in the presence of equimolar amount of triethylamine. In particular, reaction of isatin I with chlorophosphinates II and III afforded new phosphinates IV and V with 57 and 81% yields, respectively, as the products of phosphorylation of the hydroxyl group. Their 1 H NMR spectra contained the doublets of the methylene proton signals in the range of 5.7-5.8 ppm with the coupling constants 3 J РН of 9.6-10.2 Hz. An unexpected result was obtained when attempting to introduce the allyl and tosyl groups into the molecule of I. In the both cases, 1-allylisatin VI and 1-tosylisatin VII were isolated as the only reaction product. The fact of Nsubstitution was confirmed by complete coincidence of the physical and chemical characteristics with those described previously in [12][13][14]. 1 H NMR spectra of the products contained no signals of methylene protons at 5.5 ppm (Scheme 1).

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Synthesis and biological evaluation of novel indoline-2,3-dione derivatives as antitumor agents

Cited by 11 publications

References 18 publications

Synthesis, characterization and evaluation of antidiabetic activity of novel indoline derivatives

Synthesis, characterization and evaluation of antidiabetic activity of novel indoline derivatives

Indoline-based heterocyclic scaffold: Synthetic methods, chemical reactions and biological prospect

Features of interaction of 1-hydroxymethylisatin with certain P-, S-, and C-electrophiles

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