Design, synthesis and biological evaluation of novel pyrazolo-oxothiazolidine derivatives as antiproliferative agents against human lung cancer cell line A549

Yakaiah, S.; Kumar, P. S.; Rani, Preeti; Prasad, K. Durga; Aparna, P.

doi:10.1016/j.bmcl.2018.01.027

Cited by 21 publications

(9 citation statements)

References 15 publications

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“…Some groups are interested in the use of α , β -unsaturated ketones to access functionalized pyrazoline derivatives. For instance, Yakaiah and colleagues described the synthesis of pyrazolo-oxothiazolidine derivatives 99 with 80–93% yields through a three-component reaction of benzofuran-based chalcones 98 , thiosemicarbazide 23 , and dialkyl acetylenedicarboxylates 89 catalyzed by NaOH (20 mol%) in ethanol at 80 °C ( Scheme 5 ) [ 98 ]. The synthesized compounds were evaluated for their antiproliferative activity against the A549 Lung cancer cell line with IC 50 values ranging from 0.81 μg/mL to > 5 μg/mL.…”

Section: Multicomponent Synthesis Of Biologically Active Pyrazole Der...mentioning

confidence: 99%

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

2022

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Pyrazole and its derivatives are considered a privileged N-heterocycle with immense therapeutic potential. Over the last few decades, the pot, atom, and step economy (PASE) synthesis of pyrazole derivatives by multicomponent reactions (MCRs) has gained increasing popularity in pharmaceutical and medicinal chemistry. The present review summarizes the recent developments of multicomponent reactions for the synthesis of biologically active molecules containing the pyrazole moiety. Particularly, it covers the articles published from 2015 to date related to antibacterial, anticancer, antifungal, antioxidant, α-glucosidase and α-amylase inhibitory, anti-inflammatory, antimycobacterial, antimalarial, and miscellaneous activities of pyrazole derivatives obtained exclusively via an MCR. The reported analytical and activity data, plausible synthetic mechanisms, and molecular docking simulations are organized in concise tables, schemes, and figures to facilitate comparison and underscore the key points of this review. We hope that this review will be helpful in the quest for developing more biologically active molecules and marketed drugs containing the pyrazole moiety.

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Section: Multicomponent Synthesis Of Biologically Active Pyrazole Der...mentioning

confidence: 99%

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

2022

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“…In addition, various catalysts such as triethylamine, piperidine, KOH, H 2 SO 4 , acetic acid and NaOH were tested in ethanol at 80 °C, which sodium hydroxide (2 mol %) was selected as an effective catalyst and afforded maximum yield (Scheme 30). [55] Various 2-iminothiazoline-4-ones 79 were synthesized through the three-component reaction of amines 2, alkene acetylenedicarboxylate 1 and aryl/alkyl isothiocyanates 72 in C 2 H 5 OH under white LED (3w) at room temperature by Gao and co-workers in 2019. Worthy to mention that different para, meta and ortho-substituted isothiocyanatobenzenes having electron-withdrawing groups such as F, Cl, Br, CF 3 , NO 2 , CN and electron-donating groups such as C 2 H 5 , OCH 3 gave the expected products in good yields.…”

Section: Thiazolesmentioning

confidence: 99%

Section: Synthesis Of Five‐membered Rings With Two Heteroatom Includingmentioning

confidence: 99%

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

2022

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Dialkyl acetylenedicarboxylates (DAAD) are the class of acetylenic compounds that are broadly used in organic synthesis in a noticeable quantity. Their wide application has made them an important moiety in heterocyclic compounds and drug discovery programs. Dialkyl acetylenedicarboxylate is a di-ester in which the ester groups are conjugated with a carbon-carbon triple bond. As such, the molecule is very electrophilic, and is broadly used as a dienophile in various cycloaddition reactions, for example the Diels-Alder reaction. In addition, it is a strong Michael acceptor. Due the importance of dialkyl acetylenedicarboxylate in organic synthesis, we are trying to show the applications of this compound in the synthesis of different heterocycles using multicomponent reactions. In this review, we show recent advances (2016)(2017)(2018)(2019)(2020)(2021)(2022) for the synthesis of various heterocycles that have different ring sizes (five, six and seven membered, Spiro and fused heterocycles), using DAAD via multicomponent reactions.

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“…Thus, a mixture of (tetrahydro-carbazol-1'-ylidene)-propanedinitriles type 146, ninhydrin (150) and o-phenylenediamines 111 were subjected to reflux in methanol as the solvent and catalytic amount of TEA to afford the target products 151 in 67-90% yield (Scheme 73). The obtained compounds were studied for colorectal cancer activity, as well as, free radical scavenging in vitro via MTT and DPPH assays, respectively.…”

Section: Carbazole (Benzo[b]indole)-substituted Heterocyclic Derivativesmentioning

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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Design, synthesis and biological evaluation of novel pyrazolo-oxothiazolidine derivatives as antiproliferative agents against human lung cancer cell line A549

Cited by 21 publications

References 15 publications

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

Synthesis of Biologically Active Molecules through Multicomponent Reactions

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