Synthesis and bio-evaluation of indole-chalcone based benzopyrans as promising antiligase and antiproliferative agents

Gupta, Sandeep; Maurya, Pooja; Upadhyay, Akanksha; Kushwaha, Pragati; Krishna, Shagun; Siddiqi, Mohammad Imran; Sashidhara, Koneni V.; Banerjee, Dibyendu

doi:10.1016/j.ejmech.2017.11.015

Cited by 45 publications

(11 citation statements)

References 48 publications

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“…Meanwhile, compound 99 potently inhibited CYP1B1 with an IC50 (∼0.2 μM) in Sacchrosomes™ and CYP1B1-expressing live human cells [24]. While compound 100 possessed both anti ligase (inhibit human DNA Ligase I) and antiproliferative activity (enhanced cytotoxicity against colon cancer (DLD-1 at IC 50 4.6µM)) [25] (Fig. 6).…”

Section: Anti-cancer Activitiesmentioning

confidence: 98%

“…Chalcones are multifunctional molecules that possess promising pharmacological activities. Chalcones have been found useful as anticancer [23][24][25], antioxidant [26][27][28][29], antiinflammatory [30][31][32], anti-microbial [23,[33][34][35][36], anti-tubercular [34,37,38], antileishmanial [39], antimalarial [40][41][42], anthelmintic [27], osteogenic activity [43]. This review article focuses on recent applications of Claisen-Schmidt condensation reaction employed in the synthesis of chalcone, its transformation to heterocyclic compounds and pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

Ovonramwen

Owolabi

Oviawe

2019

AJOCS

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Chalcones are useful intermediates in the synthesis of heterocyclic compound and the unique reagents in organic synthesis. The usual approach to obtain chalcones is through Claisen-Schmidt condensation. Several novel heterocyclic chalcone analogs have emerged. Chalcones are multifunctional molecules that possess promising pharmacological activities. Chalcones are known for anti-cancer, antioxidant, anti-inflammatory, anti-microbial, anti-tubercular, antileishmanial, antimalarial, anthelmintic, osteogenic activities. This review article focuses on recent applications of Claisen-Schmidt condensation reaction employed in the synthesis of chalcone, its transformation to heterocyclic compounds and pharmacological activities.

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Section: Anti-cancer Activitiesmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

Ovonramwen

Owolabi

Oviawe

2019

AJOCS

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“…The synthetic molecules 145 were tested for their antiligase and antiproliferative activities in cancer cells. A detailed study of the most active compound 145a (R = H, R 1 = tBu, R 2 = C 4 H 3 S) was carried out in order to verify the mode of action and cytotoxicity in in vitro and 3D tumor models [159].…”

Section: Indole-based Anticancer Heterocyclic Systemsmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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“…DNA ligases play a crucial role in causing cancer. Gupta et al reported the inhibition DNA ligases resulting in DNA nick-sealing activity followed by the antiproliferative activity of the indole-chalcone based benzopyran chalcones (33) on cancer cells [34].…”

Section: Anticancer Chalconesmentioning

confidence: 99%

Biological Role of Chalcones in Medicinal Chemistry

Tekale¹,

Mashele²,

Pooe³

et al. 2020

Vector-Borne Diseases - Recent Developments in Epidemiology and Control

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Chalcones are promising synthons and bioactive scaffolds of great medicinal interest due to their numerous pharmacological and biological activities. They are well recognized to possess antimicrobial, anticancer, antitubercular, antioxidant, anti-inflammatory, antileishmanial, and other significant biological activities. This chapter highlights recent updates and applications of chalcones as biologically, pharmacologically, and medicinally important entities.

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Synthesis and bio-evaluation of indole-chalcone based benzopyrans as promising antiligase and antiproliferative agents

Cited by 45 publications

References 48 publications

Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Biological Role of Chalcones in Medicinal Chemistry

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