Novel quinolone substituted thiazolidin-4-ones as anti-inflammatory, anticancer agents: Design, synthesis and biological screening

Kumar, Sunita; Jaiswal, Varun; Lohan, Sandeep; Bansal, Sumit; Chaudhary, Anurag; Tiwari, Amit K.; Alex, Angel Treasa; Joesph, Alex

doi:10.1016/j.ejmech.2013.03.011

Cited by 73 publications

(32 citation statements)

References 42 publications

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“…Moreover, the combination of two pharmacophores in a single molecule is a well established hypothesis for synthesis of more active drugs with dual activity (23). Also, single molecule acting on multiple targets is better drug candidate compared to drug combinations, as administration of single drug will have more predictable pharmacokinetic and pharmacodynamic properties and improved patient compliance (23). Thus, a series of novel 5-alkyl/aryl thiadiazole substituted thiazolidine-4-ones were synthesized and evaluated for their antioxidant and anticancer activity.…”

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confidence: 99%

Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones

Joseph¹,

Shah²,

Kumar³

et al. 2013

Acta Pharmaceutica

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Reactive oxygen species (ROS) induced oxidative stress is believed to be a primary causative factor of various inflammatory diseases. ROS has been linked with cancer, coronary heart disease, and neurodegenerative diseases, and their presence in the body causes damage to the DNA of cells. Antioxidants exert their effects by scavenging or preventing the generation of ROS, which can protect the formation of free radicals and retard the progress of many chronic diseases, including cancer, inflammation, and car- A series of novel 5-alkyl/aryl thiadiazole substituted thiazolidin-4-ones were synthesized by a two-step process. In the first step, 5-alkyl/aryl substituted 2-aminothiadiazoles were synthesized, which on reaction with substituted aromatic aldehydes and thioglycolic acid in the presence of dicyclohexylcarbodiimide afforded thiazolidin-4-ones. All the compounds were synthesized in fairly good yields and their structures were confirmed by spectral and physical data. The title compounds were screened for in vitro anti-proliferative activity on human breast adenocarcinoma cells (MCF-7) by MTT assay. Most of the derivatives showed an IC 50 less than 150 µmol L -1 . Among the compounds tested, 2-(2-nitrophenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-thiazolidin-4-one (3f), 2-(3-fluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2--yl)-thiazolidin-4-one (3b), and 2-(4-chlorophenyl)-3--(5-methyl-1,3,4-thiadiazol-2-yl)-thiazolidin-4-one (3c) were found to be the most active derivatives with IC 50 values of 46.34, 66.84, and 60.71 µmol L -1 , respectively. Antioxidant studies of all the synthesized compounds were carried out by diphenylpicrylhydrazyl (DPPH) assay. Among the compounds tested, 2-phenyl-3-(5-styryl--1,3,4-thiadiazol-2-yl)-thiazolidin-4-one (3s) elicited superior antioxidant activity with IC 50 of 161.93 µmol L -1 .

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confidence: 99%

Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones

Joseph¹,

Shah²,

Kumar³

et al. 2013

Acta Pharmaceutica

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“…Isocyanide insertion of tert -butyl isocyanide on complex 15 produces Pd(II) species 16 A convenient one-pot method to synthesize 4(3 H )-quinazolinones has been developed [23] . The aminocarbonylation of bromobenzene 8 using substituted amines 19 in the presence of Pd(OAc) 2 and Mo(CO) 6 [24] . Results for the reaction of o -aminobenzamides 22 with several benzyl alcohols 23 using Pd(OAc) 2 (5 mol%) and sodium (diphenylphosphino)benzene-3-sulfonate (TPPMS; 10 mol%) in water for 16 h under air in a sealed tube are summarized in Scheme 11 .…”

Section: -Substituted Quinazolinonesmentioning

confidence: 99%

“…A few examples of transition metal-catalyzed routes to form 4(3 H )-quinazolinones have been reported, including the use of PdCl 2 -(PPh 3 ) 2 and SnCl 2 catalysis [15] . 4(3 H )-quinazolinones have also been synthesized using dicobalt octacarbonyl ruthenium, platinum complexes, or titanium catalysts [16] .…”

Section: Introductionmentioning

confidence: 99%

“…In particular, heterocyclic structures form the basis of many pharmaceutical, agrochemical, and veterinary products. Quinazoline ( 1 ) and related 4(3 H )-quinazolinone ( 2 in Scheme 1 ) are classes of fused heterocycles that are of considerable interest because of the diverse range of biological properties of their derivatives, including anticancer [1] , diuretic, antiinflammatory [2] , anticonvulsionary, lung antifibrotic [3] , antimicrobial [4] , antimalarial [5] , antiepileptic [6] , and antihypertensive [7] activities.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of quinazolines and quinazolinones via palladium-mediated approach

Abdou

AlNeyadi

2015

Heterocyclic Communications

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“…Many effects have been found, including anti-inflammatory and analgesic [15], antitubercular [16], antimicrobial and antifungal [17], antiviral, especially as anti-HIV agents [18], anticancer, antioxidants [19], anticonvulsants [20] and antidiabetic activity [21]. In the present study, some new derivatives of ibuprofen that contain thiazolidine-4-one scaffolds were synthesized in order to obtain compounds with double effect-antioxidant and anti-inflammatory properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

et al. 2014

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New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, 1 H-NMR, 13 C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a-l through cyclization to the corresponding thiazolidine-4-ones 4a-n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.

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Novel quinolone substituted thiazolidin-4-ones as anti-inflammatory, anticancer agents: Design, synthesis and biological screening

Cited by 73 publications

References 42 publications

Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones

Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones

Synthesis of quinazolines and quinazolinones via palladium-mediated approach

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

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