4-Thiazolidinone derivatives: synthesis, antimicrobial, anticancer evaluation and QSAR studies

Deep, Aakash; Narasimhan, B.; Lim, Siong Meng; Ramasamy, Kalavathy; Mishra, Rakesh K.; Mani, Vasudevan

doi:10.1039/c6ra23006g

Cited by 44 publications

(33 citation statements)

References 21 publications

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“…The formed precipitate was filtered off, dried and recrystallized from appropriate solvent to give target compounds. In case of no precipitate formed upon cooling, the solution was added to water and neutralized using Na 2 CO 3 solution, the formed precipitate was filtered, dried and recrystallized to obtain the expected thiazolidinone products (13)(14)(15)(16)(17)(18)(19)(20), respectively.…”

Section: General Procedures For the Synthesis Of 2-substituted-3-(quimentioning

confidence: 99%

“…It has been reported that these derivatives possesses anti-tuberculosis [6,7], Antiplasmodial [4], Antibacterial [5], antihistamine [6], anticancer [11][12][13][14], anti-hypertensive [9], antifungal [10], antimalarial [11], anti-HIV [12] and antioxidant activities [13]. On the other hand, thiazole and thiazolidinone derivatives are known to exhibit diverse biological activities [14][15][16], they have anti-inflammatory [20,21], anticancer, antimicrobial [19], anti-tuberculosis [20] and antioxidant activity [21]. Inflammation is a fundamental physiological process that is ATEF M. AMER et al…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

et al. 2018

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not only essential for survival but also at the same time is one of the major causes of human mortality [25,26]. It's known that, non-steroidal anti-inflammatory drugs (NSAIDs) are used to treat a wide variety of illnesses and diseases, such as inflammation [24], cancers [25] and the peripheral and central nervous system diseases [26]. The anti-inflammatory effect of NSAIDs arises from their ability to inhibit both COX-1 and COX-2 isoforms of cyclooxygenase (COX) enzyme [27]. Literature survey revealed that some of the synthesized derivatives having quinoline ring or bearing thiazole ring have significant antiinflammatory and analgesic activity [31-33, 20, 21]. In the light of above mentioned facts and our interest in designing new biologically active molecules, our efforts were directed towards I N this paper we report the synthesis of some quinoline based thiazolidinone derivatives (13-22) in a three-step process. Condensation of 2-hydrazinylquinoline 2 with different aromatic aldehydes gave the corresponding Schiff bases 3-10 which in turn were reacted with thioglycolic acid to furnish the corresponding thiazolidinone derivatives 13-20. Reaction of compound 2 with isatin or methyl isatin gave 1-sustituted-3-(2-(quinolin-2-yl)hydrazono) indolin-2-ones 11 and 12, which were converted to 1-substituted 3'-(quinolin-2-ylamino) spiro[indoline-3,2'-thiazolidine]-2,4'-dione 21 and 22 by cyclocondensation with thioglycolic acid. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1 H NMR and MS. Furthermore, all new thiazolidinone derivatives were evaluated for their anti-inflammatory and analgesic activity. The Study results revealed that the highest anti-inflammatory potency was gained by 6 derivatives according to the following order 22 > 17 >13 > 14 > 21 > 15, showing a good edema inhibition compared to the reference drug indomethacin. Compound 22 carrying indole ring system inhibited the edema volume significantly at the 1 st h post administration, and the activity was enhanced up to the 4 th h giving a promising edema volume inhibition compared to that produced by indomethacin. The longest duration of analgesic action up to 90 min post compounds administration was obtained by the compounds 13, 17 and 22, they exhibited potent analgesia compared to that obtained by aspirin.

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Section: General Procedures For the Synthesis Of 2-substituted-3-(quimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

et al. 2018

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“…[30] As various studies have revealed that some of the antimicrobial compounds having toxicity on bacteria display cytotoxic activity against cancer cells, [27][28][29] we evaluated the effect of the distance between the pyridinium nitrogen and the phenyl ring on the cytotoxic activity. [30] As various studies have revealed that some of the antimicrobial compounds having toxicity on bacteria display cytotoxic activity against cancer cells, [27][28][29] we evaluated the effect of the distance between the pyridinium nitrogen and the phenyl ring on the cytotoxic activity.…”

Section: Biological Evaluationmentioning

confidence: 99%

“…[4] Autophagy is a physiological process that maintains cellular homeostasis by degrading and recycling organelles and proteins. [27][28][29] In our previous studies, oxime ether and hydrazone derivatives with quaternary pyridinium core were found to have remarkable antimicrobial and antileishmanial activities. On the contrary, autophagy may increase stress tolerance and survival in cancer cells under adverse conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of pyridinium‐hydrazone derivatives as potential antitumoral agents

et al. 2018

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The hydrazones of 4-hydrazinylpyridinium bearing alkylphenyl groups on pyridinium nitrogen were synthesized and evaluated for their cytotoxic activity against MCF-7, PC3, U2OS, and HEK293 cell lines by Wst1 cell proliferation assay. Cytotoxic activity results indicated that d derivatives having butylene chain; 4 and 5 series having naphthalene and anthracene ring systems showed high cytotoxic activity (IC = 3.27-8.54 μm) on cancer cells. 3d (4-(2-(4-hydroxybenzylidene)hydrazinyl)-1-(4-phenylbutyl)pyridinium bromide) was the most cytotoxic compound with IC value of 3.27 μm against MCF-7. The most active derivatives (1d, 2d, 3d, 4, and 5 series) were selected to investigate for the effects on autophagy by analyzing the expression of autophagy marker proteins. The conversion of LC3-I to its lipidated form LC3-II is essential for autophagy and related to autophagosomes. According to our results, all tested compounds except for 3d induced lipidated form LC3-II accumulation. Then, the effects of the compounds on p62 protein level were also analyzed by the immunoblotting as the autophagy inhibition results in accumulation of p62. Further molecular mechanistic studies including morphological analysis and live-death assays indicated that all tested compounds (1d, 2d, 3d, 4, and 5 series) are potent antitumoral molecules and all except for 3d have potential to inhibit autophagic flux.

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“…Anticancer screening results indicated that compound 24 (IC50 = 15.18 µM) was the most active anticancer agent and was more potent than the standard drug, carboplatin (IC50 > 100 µM). Antimicrobial activity results indicated that 25 was the most active antimicrobial agent (pMICec = 2.14 µM) and may serve as an important lead for the discovery of novel antimicrobial agents 20 . …”

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confidence: 99%

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2017

Hygeia.J.D.Med

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4-Thiazolidinone derivatives: synthesis, antimicrobial, anticancer evaluation and QSAR studies

Abstract: A series of novel 4-thiazolidinone derivatives (1–18) was synthesized evaluated for its antimicrobial and anticancer potential.

Cited by 44 publications

References 21 publications

Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

Synthesis and evaluation of pyridinium‐hydrazone derivatives as potential antitumoral agents

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