Synthesis and Anticancer Activity Evaluation of Some Benzothiazole-Piperazine Derivatives

Gurdal, Enise Ece; Buclulgan, Ebru; Durmaz, İrem; Cetin-Atalay, Rengül; Yarım, Mine

doi:10.2174/1871520615666141216151101

Cited by 23 publications

(11 citation statements)

References 14 publications

(16 reference statements)

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“…Moreover, the benzothiazole core is a widespread scaffold that has been extensively studied [ 54 , 55 , 56 , 57 , 58 , 59 ] and many derivatives are found to be antimicrobial [ 49 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 ], anticancer [ 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 ], anti-Alzheimer’s [ 92 , 93 ], anti-inflammatory [ 94 , 95 , 96 ], anti-HIV [ 97 , 98 , 99 ] anticonvulsant [ 100 , 101 , 102 ], antioxidant [ 39 , 103 ], anti-tuberculosis [ 104 ...…”

Section: Benzazolesmentioning

confidence: 99%

Importance of Fluorine in Benzazole Compounds

2020

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Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of incorporating fluorine as a basic appendage in benzothiazole and benzimidazole skeletons. The chemistry and pharmacological activities of heterocycles containing fluorine during the past years are compiled and discussed.

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Section: Benzazolesmentioning

confidence: 99%

Importance of Fluorine in Benzazole Compounds

2020

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“…Compounds 1h and 1j were synthesized according to the procedure described by Gürdal et al (12) (Figure 1 …”

Section: Synthesis Of 1h and 1jmentioning

confidence: 99%

“…Among these compounds, aroyl substituted 1h and 1j were found to be active against HUH-7 (hepatocellular), MCF-7 (breast) and HCT-116 (colorectal) cancer cell lines. Although their direct mechanism of action has not been clarified yet, it was shown that these compounds cause apoptosis by cell cycle arrest at subG1 phase by Hoechst staining and Fluorescence Activated Cell Sorting (FACS) assays (12). Many studies focused on the evaluation of the genotoxicity of widely used anticancer agents in Turkey and around the world.…”

Section: Introductionmentioning

confidence: 99%

Piperazin halkası taşıyan benzotiyazol türevlerinin toksikolojik değerlendirilmesi

Charehsaz¹,

Gurdal²,

Helvacıoğlu³

et al. 2017

Marmara Pharmaceutical Journal

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Benzothiazole-piperazine derivatives prepared previously, 1h and 1j are potential anticancer agents. Since the mutagenic and genotoxic properties of anticancer drugs compose an essential issue to be researched, this study is focused on the analysis of the mutagenicity and genotoxicity of these molecules. The mutagenicity of 1h and 1j were determined by Ames test performed on Salmonella TA98 and TA100 strains. Sample 1j was mutagenic on TA98 bacterial strain. However, compound 1h was not mutagenic in bacterial strains TA98 and TA100 with and without S9 activation. The genotoxicity of 1h was evaluated by the chromosomal aberration assay on human lymphocytes. Compound 1h was also not genotoxic in human lymphocytes in vitro. All results revealed that, 1h was not mutagenic in the two Salmonella strains tested and was not genotoxic in chromosomal aberration assay. Therefore, results demonstrate that the described molecule is promising as a new anticancer drug without mutagenicity. Also, after performing Ames test with other recommended bacterial strains and in vivo experiments can be used safely for the development of new structures exhibiting anticancer activities.

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“…During phase I clinical trials in humans, positive responses were observed in pancreatic cancer, but a subsequent phase II clinical trials failed to show any objective responses [20]. Our previous work demonstrated that some Hoechst 33258 derivatives 1 have desirable antitumor activity and have better DNA minor groove binding ability [21], so further modifications may provide more effective.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Bis‐Benzothiazole Derivatives as DNA Minor Groove Binding Agents

Yang

Zhang

Wang

et al. 2017

Journal of Heterocyclic Chem

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A series of novel bis-benzothiazole derivatives with head-to-head orientation were designed, synthesized, and evaluated for their anti-proliferative activities on U937, HL60, and HeLa cells. A significant part of the targets exhibited considerable in vitro anticancer activity, and some of them were more potent than the reference 5-FU. Molecular modeling, fluorescence, and viscosimetry studies revealed that these compounds could bind into the minor groove of DNA. Amongst them, the most active compound 7 with IC 50 in a range of 6.76 to 8.67 μM against the tested three cell lines, which was 1.46-2.47 and 3.48-4.93 times more potent than 5-FU and Hoechst 33258, respectively, warrant further investigations.

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Synthesis and Anticancer Activity Evaluation of Some Benzothiazole-Piperazine Derivatives

Cited by 23 publications

References 14 publications

Importance of Fluorine in Benzazole Compounds

Importance of Fluorine in Benzazole Compounds

Piperazin halkası taşıyan benzotiyazol türevlerinin toksikolojik değerlendirilmesi

Design, Synthesis, and Evaluation of Bis‐Benzothiazole Derivatives as DNA Minor Groove Binding Agents

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