Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

Lobo, Gricela; Monasterios, Melina; Rodrígues, Juan; Gamboa, Neira; Capparelli, Mario V.; Martínez-Cuevas, Javier; Lein, Michael; Jung, Klaus; Abramjuk, Claudia; Charris, Jaime

doi:10.1016/j.ejmech.2015.04.023

Cited by 33 publications

(12 citation statements)

References 46 publications

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“…Among them, matrix metalloproteinases (MMPs), especially MMP-2 and MMP-9, play critical roles in the invasion and metastasis of malignant cells. 25,26 To probe the potential anti-invasive mechanisms of 4i, we determined the effect of 4i on the activity and protein expression of MMP-2 and MMP-9 in MDA-MB-231 cells. Firstly, gelatin zymography was carried out to examine the effect of 4i on the activity of MMP-2 and MMP-9.…”

Section: Effect Of 4i On the Activity And Protein Expression Of Mmp-2 And Mmp-9mentioning

confidence: 99%

Assessment of a bifendate derivative bearing a 6,7-dihydro-dibenzo[c,e]azepine scaffold as a potential anti-metastatic agent

et al. 2018

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Section: Effect Of 4i On the Activity And Protein Expression Of Mmp-2 And Mmp-9mentioning

confidence: 99%

Assessment of a bifendate derivative bearing a 6,7-dihydro-dibenzo[c,e]azepine scaffold as a potential anti-metastatic agent

et al. 2018

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“…In fact, indanones core structures are integral part of many natural products . Fused and spiro indanone structures are privileged motifs in drug discovery research due to their wide range of biological profiles such as antibacterial, antiviral, antialzheimer, anti‐tumor, anticancer, t‐RNA inhibitor, anti‐inflammatory activities etc (Figure ) . Moreover, indanone‐embedded heterocycles exhibit important photophysical property .…”

Section: Introductionmentioning

confidence: 99%

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

Das¹,

Dutta

2020

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Ninhydrin (1,2,3‐indanetrione hydrate) is a powerful electrophile having enormousapplications in organic and bio‐organic sciences. In the last few years, reactivity of various ninhydrin adducts have been exploited extensively for the development of diverse organic scaffolds. The present review focuses on the applications of readily accessible ninhydrin adducts as building block towards the synthesis of a variety of compounds including N‐inserted compounds, spiro‐heterocycles, medium ring compounds, polycyclic molecules, propellanes, cycloadducts, allylic anions, axially chiral molecules etc. Interestingly, some of the compounds have profound biological activities and a few display important photophysical properties. Most of the reactions described here are simple and carried out with easily available starting materials under green conditions.

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“…Hexahydroacridine‐1,8‐diones and indeno[1,2‐b]indole‐9,10‐diones constitutes a useful class of heterocyclic compounds which possess a large number of biologicalactivities . A number of strategies have been found in the literature for the synthesis of diversely substituted hexahydroacridine‐1,8‐diones and indeno[1,2‐b]indole‐9,10‐diones . But the reported methods have suffered from various limitations which include long reaction time, use of homogeneous corrosive acid catalysts that are non‐recyclable, tedious work‐up procedure, hazardous solvents, multistep synthesis, harsh reaction conditions and unsatisfactory yields.…”

Section: Introductionmentioning

confidence: 99%

Triflic Acid Functionalized Carbon@Silica Composite: Synthesis and Applications in Organic Synthesis; DFT Studies of Indeno[1,2‐b]indole

Sharma

et al. 2020

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Triflic acid functionalized carbon@silica composite (CStar@SiO2TfOH) was synthesized by the partial carbonization of starch in the presence of silica followed by the immobilization of triflic acid and its catalytic activity was explored for the three component synthesis of hexahydroacridine‐1,8‐diones and indeno[1,2‐b]indole‐9,10‐diones. CStar@SiO2‐TfOH was characterized using different techniques, such as Fourier‐Transform Infrared Spectroscopy (FTIR), Thermogravimetricanalysis (TGA), X‐ray Powder Diffraction (XRD), Energy Dispersive X‐ray (EDX), Scanning Electron Microscopy (SEM) and High Resolution Transmission Electron Microscopy (HR‐TEM) and was found to be recyclable upto five runs without any noticeable change. Further, the intermediate formed during the preparation of hexahydroacridine‐1,8‐dione has been isolated and its structure was confirmed by single crystal X‐ray crystallography which confirms the proposed mechanism. Also, to confirm the structure of 4b,9b‐dihydroxy‐5‐(4‐chlorophenyl)‐7,7‐dimethyl‐4b,5,7,8‐tetrahydroindeno[1,2‐b]indole‐9,10(6H,9bH)‐dione we have performed the DFT study and found that the 1H and 13C chemical shift values and IR wavenumbers predicted by B3LYP method were very close to the experimentally determined values.

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Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

Cited by 33 publications

References 46 publications

Assessment of a bifendate derivative bearing a 6,7-dihydro-dibenzo[c,e]azepine scaffold as a potential anti-metastatic agent

Assessment of a bifendate derivative bearing a 6,7-dihydro-dibenzo[c,e]azepine scaffold as a potential anti-metastatic agent

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

Triflic Acid Functionalized Carbon@Silica Composite: Synthesis and Applications in Organic Synthesis; DFT Studies of Indeno[1,2‐b]indole

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