Arylidene indanone scaffold: medicinal chemistry and structure–activity relationship view

Menezes, José C. J. M. D. S.

doi:10.1039/c6ra28613e

Cited by 62 publications

(25 citation statements)

References 118 publications

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“…Arylidene rings are reported to confer stability to the molecule and its biological activity [22]. Many studies have assessed various other arylidene derivatives exhibiting antibacterial [23], antifungal [24], or anticancer [25, 26] activities.…”

Section: Discussionmentioning

confidence: 99%

Natural Hypoxia is Not a Limiting Factor in Evaluating the Novel Arylidene Derivative MLT-401 Against an In Vitro Colorectal Cancer Model

Bin-Jaliah¹

2018

Cell Physiol Biochem

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Background/Aims: Cancer cells in vivo develop resistance to many anti-tumor drugs. One known factor to influence such drug resistance is hypoxia, which is an important component of the tumor microenvironment. Standard cancer lines mostly do not exhibit a cellular hypoxic microenvironment and there is a paucity of information on the efficacy of lead molecules in both cellular- and environment-induced hypoxic conditions. Therefore, in the present study, we have evaluated the efficacy of the arylidene derivative MLT-401, a lead molecule showing activity against colorectal cancer model using the HCT 116 cell line and CCD-80-C control cells in normoxic and natural (marginal) hypoxic conditions, which is usually observed in high-altitude regions. Methods: The efficacy of MLT-401 on HCT 116 and CCD-80-C cells were tested in both normoxia and marginal hypoxia conditions. MTT assay was used to evaluate cell proliferation, Annexin V binding assay for apoptotic cell quantification and PI staining for cell cycle were done by flow cytometry. Induction of pro-apoptotic marker BAX and anti-apoptotic Bcl-2 were assessed by western blot. Bcl-2/BAX ratio was calculated based on protein expression by western blotting and bands were quantified by Image J software. Results: Analysis of cell proliferation showed an average 10-fold reduction in the inhibition of HCT 116 cells in hypoxic conditions with approximately 500 nM MLT-401, while there was no significant change noted in marginal hypoxic conditions. A proportionate increase in the number of apoptotic cells and large M4 fraction of 10.5% and 26.7% of HCT116 against 6.3% of control cells in cell cycle assessment with MLT-401 concentrations ranging from 250 to 500 nM respectively clearly demonstrated anti-cancer activity. A Bcl-2/BAX ratio of < 1 showed that the induction of apoptosis was the gross mechanism underlying the inhibition of HCT 116 cells by MLT-401. Conclusion: Collectively, these results show MLT-401 as an effective anti-colorectal cancer lead molecule irrespective of normoxia or natural hypoxia.

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Section: Discussionmentioning

confidence: 99%

Natural Hypoxia is Not a Limiting Factor in Evaluating the Novel Arylidene Derivative MLT-401 Against an In Vitro Colorectal Cancer Model

Bin-Jaliah¹

2018

Cell Physiol Biochem

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“…Wei and coworkers employed N ‐formylsaccharin in a carbonyl cyclization of ortho‐iodo‐tethered methylenecyclopropanes ( 10 ) to give the indanone derivatives ( 11 ) in 2019 (Scheme 7). [21] The indanone derivatives ( 11 ) play an important role in antibacterial, antispasmodic, cytotoxicity and antitumor activity in clinical trials [22,23] …”

Section: Carbonylation Productsmentioning

confidence: 99%

N‐Formylsaccharin as a CO Source: Applications and Recent Developments

et al. 2021

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This review describes the research progress of the N‐formylsaccharin as a newly efficient and environmentally friendly carbon monoxide (CO) surrogate in the carbonylation reactions including the synthesis of aldehydes, esters, ketones, acyl fluorides or other reactions. Besides, its advantages in term of inexpensive, ease of handling and stable on storage significantly enhance practicality of the approach in laboratory scale.

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“…Indanone derivatives and their analogues are important bioactive molecules, which are of great significance in antibacterial, antispasmodic and cytotoxic activities as well as antineoplastic activity . For example, Donepezil hydrochloride acting as an AChE (acetylcholinesterase) inhibitor has been used for the treatment of mild to moderate Alzheimer's disease .…”

Section: Figurementioning

confidence: 99%

Palladium‐Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho‐Iodo‐Tethered Methylenecyclopropanes (MCPs) Using N‐Formylsaccharin as CO Source

2019

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Arylidene indanone scaffold: medicinal chemistry and structure–activity relationship view

Abstract: Arylidene indanone (AI) scaffolds are considered as the rigid cousins of chalcones, incorporating the α,β-unsaturated ketone system of chalcones forming a cyclic 5 membered ring.

Cited by 62 publications

References 118 publications

Natural Hypoxia is Not a Limiting Factor in Evaluating the Novel Arylidene Derivative MLT-401 Against an In Vitro Colorectal Cancer Model

Natural Hypoxia is Not a Limiting Factor in Evaluating the Novel Arylidene Derivative MLT-401 Against an In Vitro Colorectal Cancer Model

N‐Formylsaccharin as a CO Source: Applications and Recent Developments

Palladium‐Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho‐Iodo‐Tethered Methylenecyclopropanes (MCPs) Using N‐Formylsaccharin as CO Source

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