Synthesis and Biological Evaluation of Pyrazoline Derivatives Bearing an Indole Moiety as New Antimicrobial Agents

Özdemir, Ahmet; Altıntop, Mehlika Dilek; Kaplancıklı, Zafer Asım; Turan-Zitouni, Gülhan; Karaca, Hülya; Tunalı, Yağmur

doi:10.1002/ardp.201200479

Cited by 26 publications

(13 citation statements)

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“…Prompted by the aforementioned findings and in the continuation of our ongoing research in the field of design, synthesis, and biological evaluation of pyrazoline derivatives [30][31][32][33][34][35], herein we described the synthesis and evaluation of a new series of heteroaryl substituted pyrazolines as potential anticancer agents against AsPC-1 human pancreatic adenocarcinoma and two glioblastoma cell lines, U87 and U251 cell lines. Furthermore, tumor selectivity test on blood cells (PBMC and Jurkat cells) and the apoptotic, necrotic, and DNA-cleavage analysis against U251 cells were carried out using the most effective compound.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

et al. 2015

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New pyrazoline derivatives were synthesized and evaluated for their cytotoxic effects on AsPC-1 human pancreatic adenocarcinoma, U87 and U251 human glioblastoma cell lines. 1-[((5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetyl]-3-(2-thienyl)-5-(4-chlorophenyl)-2-pyrazoline (11) was found to be the most effective anticancer agent against AsPC-1 and U251 cell lines, with IC50 values of 16.8 µM and 11.9 µM, respectively. Tumor selectivity of compound 11 was clearly seen between Jurkat human leukemic T-cell line and human peripheral blood mononuclear cells (PBMC). Due to its promising anticancer activity, compound 11 was chosen for apoptosis/necrosis evaluation and DNA-cleavage analysis in U251 cells. Compound 11-treated U251 cells exhibited apoptotic phenotype at low concentration (1.5 µM). DNA-cleaving efficiency of this ligand was more significant than cisplatin and was clearly enhanced by Fe(II)-H2O2-ascorbic acid systems. This result pointed out the relationship between the DNA cleavage and the cell death.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

et al. 2015

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“…A fim de lidar com este grave problema, que é considerado uma conseqüência do uso generalizado desses agentes, o desenvolvimento de novas drogas antimicrobianas ganhou grande importância. 6 Frente à busca de novas drogas que sejam efetivas contra esta bactéria, um enfoque importante nas pesquisas terapêuticas é a triagem de compostos químicos por testes biológicos. Assim, as estruturas químicas com melhor atividade serão selecionadas para a realização de testes mais específicos.…”

Section: Novos Compostos Sintetizados Estão Sendo Utilizados Em Pesquunclassified

Efeitos antimicrobianos in vitro do composto pirazol frente a Klebsiella pneumoniae

Jorge

Oliveira²,

Frade³

et al. 2013

BBR - Biochem. Biotechnol.

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. O aumento significativo na resistência aos agentes antimicrobianos tornou-se uma grande preocupação para a saúde pública. A alta prevalência de multidrogas resistentes aos patógenos levou ao fracasso de tratamentos atuais e mortes de pacientes imunocomprometidos. A fim de lidar com este grave problema, que é considerado uma conseqüência do uso generalizado desses agentes, o desenvolvimento de novas drogas antimicrobianas ganhou grande importância. RESUMO Novos compostos sintetizados estão sendo utilizados em pesquisas com 6Frente à busca de novas drogas que sejam efetivas contra esta bactéria, um enfoque importante nas pesquisas terapêuticas é a triagem de compostos químicos por testes biológicos. Assim, as estruturas químicas com melhor atividade serão selecionadas para a realização de testes mais específicos. Este estudo teve como objetivo avaliar a atividade antimicrobiana do pirazol, um composto aromático pentagonal, frente à bactéria K. penumoniae. 7; 8 MATERIAL E MÉTODOSFoi utilizada a bactéria K. pneumoniae ATCC 43816, proveniente do Laboratório de Imunofarmacologia -ICB/UFMG. Frente a esta bactéria, foi testado o composto aromático pirazol, cedidos pelo Professor Rafael César Russo Chagas, originários de uma quimioteca do Laboratório de Química Analítica. Esses compostos foram testados através do método de microdiluição em caldo para determinação da concentração inibitória mínima (CIM) frente à K. pneumoniae.Os testes foram realizados em dois momentos, um imediatamente após diluição dos compostos e outro após 24h de armazenamento em

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“…has been found with broad spectrum of antimicrobial activity [5]. Many indole scaffold antimicrobial agents have been well investigated [7]-[9].…”

Section: Introductionmentioning

confidence: 99%

“…Several chemical structures have been found effective on killing or inhibiting the microbial growth which including indole [5] and azole derivatives [6]. Some indole derivatives Manuscript received February 18, 2017; revised May 7, 2017.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Imidazole and Indole Hybrid Molecules and Antifungal Activity against Rice Blast

Sumiya¹,

Ishigaki²,

Oh³

2017

IJCEA

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Abstract-Azole and indole are parent substances of many natural and synthetic compounds with significant biological activity. However, the biological activity of the indole and azole conjugates are lack of investigation. In the present work, a series of hybrid molecules with imidazole and indole moiety were designed by using camalexin as a molecular scaffold. Compounds with different length of the carboxylic acid (4a-4f) were prepared. The antifungal activity of this synthetic series together with the ethyl esters analogues (3a-3f) against Magnaporthe oryzae were determined by using agar cup plate assay. Data obtained from the structure-activity relationship studies indicated that the ester analogues displayed antifungal activity against Magnaporthe oryzae while the carboxylic acid derivatives did not. This result indicated that the carboxylic acid ethyl ester moiety is important to antifungal activity. Among all the synthesized compounds, we found that, at a concentration of 100 M, compound 3c displays the most potent inhibition activity with 38.8±2.5% on the inhibition of the diameter of the mycelial mat of Magnaporthe oryzae while the positive control of propiconazole (10 M) was found 39.3±2.9%.Index Terms-Antifungal activity, imidazole, indole, rice blast. I. INTRODUCTIONThere are tremendous needs to control pathogenic microbes for health care and in agricultural industry. The chemicals that either kill or display inhibitory activity on microbial growth are currently the major solutions for pathogenic microbe control [1].Rice blast disease (RBD) which is caused by the pathogenic fungi of M. oryzae, is a leading constraint in world rice production [2]. The high incidence of plant mortality and the lack of effective control methods cause billions of dollars in losses worldwide each year. Hence, great efforts and various management strategies have been made to control the RBD [3] inimize the severity of RBD [4].Some fungicides are targeting membranes functions due to the cell order and integrity of microbial membrane are significantly important. Chemicals that directly or indirectly target membranes functions or their components synthesis are quite effective to cause the lethality of the microbes thereby controlling the microbial disease.Several chemical structures have been found effective on killing or inhibiting the microbial growth which including indole [5] and azole derivatives [6]. Some indole derivatives Manuscript received February 18, 2017; revised May 7, 2017. The authors were with the Department of Biotechnology, Akita Prefectural University, 241-438, Shimoshinjo Nakano Akita-Shi, Akita 010-0195 Japan (e-mail: K.O. e-mail: jmwang@akita-pu.ac.jp).has been found with broad spectrum of antimicrobial activity [5]. Many indole scaffold antimicrobial agents have been well investigated [7]-[9]. On the other hand, azole derivatives are also well known antimicrobial agents [6]. The action mechanism of azoles is believed that they targeting the P450 enzymes involved in the biosynthesis of sterol [10]. It is...

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Synthesis and Biological Evaluation of Pyrazoline Derivatives Bearing an Indole Moiety as New Antimicrobial Agents

Cited by 26 publications

References 33 publications

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

Efeitos antimicrobianos in vitro do composto pirazol frente a Klebsiella pneumoniae

Synthesis of Imidazole and Indole Hybrid Molecules and Antifungal Activity against Rice Blast

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