In vitro antiproliferative activity against human colon cancer cell lines of representative 4-thiazolidinones. Part I

Ottanà, Rosaria; Carotti, Stefania; Maccari, Rosanna; Landini, Ida; Chiricosta, Giuseppa; Caciagli, Barbara; Vigorita, Maria Gabriella; Mini, Enrico

doi:10.1016/j.bmcl.2005.05.093

Cited by 137 publications

(58 citation statements)

References 20 publications

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“…The reaction mixture was stirred at 30°C for 14 h and poured into crushed ice containing 5 N hydrochloric acid. The precipitated product was washed with cold water, dried and recrystallized from methanol to obtain 5′-acetamino-3-(3,4-dimethoxyphenyl)-2′-hydroxychalcone (14). Yield 70.20%.…”

Section: Methodsmentioning

confidence: 99%

“…mp 184°C. This product (14) was taken in a dry round bottom flask and added ethanol (200 mL) to make a suspension. To this was added 20% NaOH with stirring followed by the addition of 20% H 2 O 2 over a period of 30 min.…”

Section: Methodsmentioning

confidence: 99%

“…[8][9][10] Thiazolidinones are another class of heterocycle that are reported to possess anti-inflammatory, 11) anti-microbial, 12) anti-proliferative, 13,14) anti-viral, 15) anti-convulsant, 16,17) antifungal, 18) and anti-bacterial properties. 19) Recent reports indicate that these compounds possess anticancer properties.…”

Section: )mentioning

confidence: 99%

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Synthesis and Anti-cancer Activity of Novel Thiazolidinone Analogs of 6-Aminoflavone

Moorkoth

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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Novel heterocyclic analogs were synthesized by combining a flavone nucleus and thiazolidinone ring in an effort to potentiate the existing anti-cancer activity of flavone. The syntheses of 6-aminoflavone, 6-amino-3-methoxyflavone, 6-amino-3-methoxy-3′,4′-dimethxyflavone and their corresponding thiazolidinone analogs were performed. Fifteen novel analogs were synthesized and evaluated for their anti-cancer activity using cell-based assay techniques and in vivo testing. As expected, the analogs improved cytotoxicity and were shown to increase the life span of cancer-bearing mice. Cytotoxicity was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assays in HeLa, MDA-MB-435, and Vero cell lines. In vivo evaluation of anti-cancer activity performed in albino mice bearing Dalton's ascites carcinoma showed that the new analogs enhanced life span and prevented increases in body weight owing to tumor volumes. Moreover, cell-cycle analysis and Hoechst staining analysis proved the apoptotic potential of these analogs. Preliminary pharmacokinetic evaluation was carried out on the synthesized compounds to determine the lipophilicity and pK a . Lipophilicity was determined using high-performance liquid chromatography and the results showed a direct correlation between the observed anti-cancer activity and log P value, while pK a values indicated the ionizing range which is a prediction tool for solubility and permeability.Key words aminoflavone; thiazolidinone; anticancer; cytotoxicity; lipophilicity; in vivo activity Polyphenols such as flavonoids that contain chromone pharmacophore are known for their wide range of pharmacological activities. It is important to note that these compounds are non-toxic at concentrations that are normally consumed in a normal diet. A flavonoid-rich diet is also considered as a prophylactic treatment for cancer. Various clinical studies performed on flavonoids indicate that these molecules are potent chemotherapeutic agents against cancer. The anticancer activity of flavonoids is mainly by the inactivation of carcinogens, cell-cycle arrest, and by the induction of apoptosis.1) The approach to anticancer drug discovery is to develop cytotoxic agents that can differentiate cancer cells and normal cells. One way of synthesizing molecules with lesser toxicity would be to adopt the molecularly targeted therapeutics, which will provide sufficient selectivity to a receptor.2) The role of flavonoids in chemoprevention of cancer is well established. 3)Major highlight of flavonoids is that they act through multiple mechanisms such as angiogenesis inhibition, inactivation of carcinogen, 4-7) arresting the cell cycle and apoptosis induction. [8][9][10] Thiazolidinones are another class of heterocycle that are reported to possess anti-inflammatory, 11) anti-microbial, 12) anti-proliferative, 13,14) anti-viral, 15) anti-convulsant, 16,17) antifungal, 18) and anti-bacterial properties. 19) Recent reports indicate that these compounds possess anticancer properties. 20)Aminofla...

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis and Anti-cancer Activity of Novel Thiazolidinone Analogs of 6-Aminoflavone

Moorkoth

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The broad and potent activity of 4-thiazolidinones has established it as one of the biologically important scaffolds (2). 4-Thiazolidinone analogs possess a wide spectrum of biological activities, such as anti-inflammatory (3Á6), anticonvulsant (7), antibacterial (8Á10), antifungal (11), antihistaminic (12,13), FSH receptor agonist (14), anticancer (15), antiviral (16), and anthelmintic (17,18) activities.…”

Section: Introductionmentioning

confidence: 99%

Green route synthesis of 4-thiazolidinone analogs of isonicotinic acid hydrazide

Thomas

Sharma

Tupe

et al. 2011

Green Chemistry Letters and Reviews

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“…12 Recent studies on molecular modification of the latter (TBZs) revealed that, dismantling of the imidazole nucleus leading to the design of new 1,3-thiazolidin-4-one derivatives, maintained the molecular requirements for enzyme inhibition. 12 A literature search revealed that, 4-thiazolidinone derivatives may exhibit antibacterial 13-14 , antituberculosis, 15-17 antiviral 9,12,[18][19][20][21][22][23] and anticancer [24][25][26][27] properties. According to Andres et al 13 , 4-thiazolidinones may be considered as phosphate bioisosteres and therefore inhibit the bacterial enzyme MurB which is involved in the biosynthesis of peptidoglycan layer of the cell wall.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2-(benzoylamino)-4-(methylthio)butyryl]-4-alkyl/arylalkyl thiosemicarbazides

Tatar¹,

Küçükgüzel²,

Clercq³

et al. 2008

Arkivoc

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In vitro antiproliferative activity against human colon cancer cell lines of representative 4-thiazolidinones. Part I

Cited by 137 publications

References 20 publications

Synthesis and Anti-cancer Activity of Novel Thiazolidinone Analogs of 6-Aminoflavone

Synthesis and Anti-cancer Activity of Novel Thiazolidinone Analogs of 6-Aminoflavone

Green route synthesis of 4-thiazolidinone analogs of isonicotinic acid hydrazide

Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2-(benzoylamino)-4-(methylthio)butyryl]-4-alkyl/arylalkyl thiosemicarbazides

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