Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer

Gududuru, Veeresa; Hurh, Eunju; Dalton, James T.; Miller, Duane D.

doi:10.1016/j.bmcl.2004.08.029

Cited by 127 publications

(74 citation statements)

References 14 publications

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“…[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%

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: )mentioning

confidence: 99%

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

Moorkoth

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…经系统的结构优化, 2-(2,6-二卤代苯基)-3-(4,6-二甲基嘧啶-2-基)噻唑烷-4-酮化合物 1～4 较其它芳基取代具有更高的抗 HIV 活性(图 1) [6～10] . 目前大多数研究集中在 C-2 和 N-3 位的亲脂性芳基对 HIV-RT 的抑制活性的影响 [11] , 而脂肪族的亲水性基团, (6) [14,16,17] .…”

Section: 构类似物(图 1) 23-(二芳基)-13-噻唑烷-4-酮作为非核unclassified

“…活性测试表明化合物 8a, 8b, 9a, 按相同的方法, 分别以 12a 和 12c 为原料, 得到化合物 2-[2-(2,6-二氯苯基 )-4-氧代噻唑烷 -3-基 ] 乙酸 (14a) [16] 和 2-(4-氧代-2-苯基噻唑烷-3-基)乙酸(14c) [17] .…”

Section: 化合物 Hiv-rt 抑制活性评价unclassified

Synthesis and Anti-HIV-RT Activity of Novel Thiazolindin-4-one Derivatives Possessing Hydrophilic Groups

陈华¹,

黄长军²,

朱墨³

et al. 2014

Chin. J. Org. Chem.

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A series of thiazolidin-4-one derivatives possessing ester were synthesized under microwave irradiation, and then the corresponding products with hydrophilic groups, like carboxyl and hydroxyl groups, were obtained after hydrolysis reaction or reduction reaction. The compounds were evaluated for their human immunodeficiency virus (HIV) reverse transcriptases inhibitory activities in vitro HIV-RT kit assay (colorimetric method). The results showed that some of the compounds, such as 8a, 8b, 9a, 9b and 14c, could effectively inhibit RT activity. Among them, compounds 8a and 9a where ethyl group existed at 5-position on N-3 pyrimidine ring were the best ones with the IC 50 values of 3.02 and 3.06 μmol•L -1 , respectively. Structure activity relationship analysis of these analogues suggested that the introduction of hydrophilic groups had little effect on their anti-HIV-RT activity and the N-3 pyrimidine moiety on thiazolidin-4-one ring should be more favorable to the anti-HIV activity than the C-2 phenyl group.

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“…Furthermore 2-aryl-4-oxothiazolidin-3-yl amides have been reported to demonstrate antiproliferative activity in prostate cancer 18 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of new 5-methyl-N-(3-oxo-1-thia-4-azaspiro[4.5]-dec-4-yl)-3-phenyl-1H-indole-2-carboxamide derivatives

Güzel¹,

Terzioglu²,

Çapan³

et al. 2006

Arkivoc

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A series of new 5-methyl-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-3-phenyl-1H-indole-2-carboxamide derivatives (2 and 3) was synthesized and characterized by IR, 1 H-NMR, HSQC, HMBC, 13 C-NMR (APT), APCI mass spectral data and elemental analysis. All synthesized compounds were evaluated for in vitro antituberculosis activity against M.tuberculosis H37Rv.Compound 3c was found to provide the highest (90%) inhibition of mycobacterial growth in the primary screen conducted at 6.25 µg/mL. Compounds 2a, 2b, 3a, 3b and 3c chosen as prototypes were evaluated against the full panel of 55 human tumour cell lines in the National Cancer Institute's in vitro primary cytotoxicity assay. 2b showed the most favourable cytotoxic effects on ovarium cancer cell line IGROV1 (log 10 GI 50 value -7.31) and renal cancer cell line UO-31 (log 10 GI 50 value -7.56), whereas 3a showed favorable cytotoxicity on renal cancer cell line RXF-393 (log 10 GI 50 value -6.38).

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Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer

Cited by 127 publications

References 14 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

Synthesis and Anti-HIV-RT Activity of Novel Thiazolindin-4-one Derivatives Possessing Hydrophilic Groups

Synthesis and biological evaluation of new 5-methyl-N-(3-oxo-1-thia-4-azaspiro[4.5]-dec-4-yl)-3-phenyl-1H-indole-2-carboxamide derivatives

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