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Synthesis and Antimicrobial Evaluation of (Z)-5-((3-phenyl-1H-pyrazol-4- yl)methylene)-2-thioxothiazolidin-4-one Derivatives.
Med Chem. 2016; 12(8):751-759.MC

Abstract

BACKGROUND

An alarming increment in pathogenic resistance to existing anti-microbial agents is a serious problem and the treatment of these bacterial infections is becoming increasingly challenging. Therefore, there is an urgent need to develop novel antimicrobial agents.

OBJECTIVE

As a part of our ongoing studies toward the development of novel antibacterial agents, the synthesis and antibacterial activity of a series of (Z)-5-((3-phenyl-1H-pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one derivatives will be discussed in this study.

METHOD

(Z)-5-((3-phenyl-1H-pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one derivatives were designed, synthesized and evaluated for antibacterial activity. The structures were confirmed by IR, 1H NMR, 13C NMR and mass spectrometry. All of the synthesized compounds were evaluated in vitro using a 96-well microtiter plate and a serial dilution method to obtain their minimum inhibitory concentration (MIC) values against a variety of different strains, including multidrug-resistant clinical isolates.

RESULTS

The antibacterial test in-vitro showed that most compounds in series 7 and 9 exhibited significant inhibitory activities against anaerobic bacteria (Streptococcus mutans) strains with a MIC value of 1 µg/mL. Compounds 7c and 9c showed the most potent activity against MRSA (3167 and 3506) with a minimum inhibitory concentration (MIC) value of 1 µg/mL, which is equivalent to moxifloxacin and greater than gatifloxacin, oxacillin and norfloxacin. Additionally, compound 9c showed potent antibacterial activity against Bacillus subtilis (aerobic bacteria) with a MIC value of 2 µg/mL.

CONCLUSION

The work suggests that these type of rhodanine compounds had a better potent activity against MRSA compared with other perviously reported rhodanine derivatives, which might provide a valuable information for the development of new antibacterial agents against multidrug-resistant clinical isolates MRSA.

Authors+Show Affiliations

No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableKey Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education Yanbian University College of Pharmacy, Yanji, 133002, China. zhengcj@ybu.edu.cn.. piaohuri@aliyun.com.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27550428

Citation

Wei, Zhi-Yu, et al. "Synthesis and Antimicrobial Evaluation of (Z)-5-((3-phenyl-1H-pyrazol-4- Yl)methylene)-2-thioxothiazolidin-4-one Derivatives." Medicinal Chemistry (Shariqah (United Arab Emirates)), vol. 12, no. 8, 2016, pp. 751-759.
Wei ZY, Liu JC, Zhang W, et al. Synthesis and Antimicrobial Evaluation of (Z)-5-((3-phenyl-1H-pyrazol-4- yl)methylene)-2-thioxothiazolidin-4-one Derivatives. Med Chem. 2016;12(8):751-759.
Wei, Z. Y., Liu, J. C., Zhang, W., Li, Y. R., Li, C., Zheng, C. J., & Piao, H. R. (2016). Synthesis and Antimicrobial Evaluation of (Z)-5-((3-phenyl-1H-pyrazol-4- yl)methylene)-2-thioxothiazolidin-4-one Derivatives. Medicinal Chemistry (Shariqah (United Arab Emirates)), 12(8), 751-759.
Wei ZY, et al. Synthesis and Antimicrobial Evaluation of (Z)-5-((3-phenyl-1H-pyrazol-4- Yl)methylene)-2-thioxothiazolidin-4-one Derivatives. Med Chem. 2016;12(8):751-759. PubMed PMID: 27550428.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and Antimicrobial Evaluation of (Z)-5-((3-phenyl-1H-pyrazol-4- yl)methylene)-2-thioxothiazolidin-4-one Derivatives. AU - Wei,Zhi-Yu, AU - Liu,Jia-Chun, AU - Zhang,Wen, AU - Li,Ya-Ru, AU - Li,Chao, AU - Zheng,Chang-Ji, AU - Piao,Hu-Ri, PY - 2015/04/22/received PY - 2016/08/18/revised PY - 2016/08/18/accepted PY - 2016/8/24/pubmed PY - 2017/7/5/medline PY - 2016/8/24/entrez SP - 751 EP - 759 JF - Medicinal chemistry (Shariqah (United Arab Emirates)) JO - Med Chem VL - 12 IS - 8 N2 - BACKGROUND: An alarming increment in pathogenic resistance to existing anti-microbial agents is a serious problem and the treatment of these bacterial infections is becoming increasingly challenging. Therefore, there is an urgent need to develop novel antimicrobial agents. OBJECTIVE: As a part of our ongoing studies toward the development of novel antibacterial agents, the synthesis and antibacterial activity of a series of (Z)-5-((3-phenyl-1H-pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one derivatives will be discussed in this study. METHOD: (Z)-5-((3-phenyl-1H-pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one derivatives were designed, synthesized and evaluated for antibacterial activity. The structures were confirmed by IR, 1H NMR, 13C NMR and mass spectrometry. All of the synthesized compounds were evaluated in vitro using a 96-well microtiter plate and a serial dilution method to obtain their minimum inhibitory concentration (MIC) values against a variety of different strains, including multidrug-resistant clinical isolates. RESULTS: The antibacterial test in-vitro showed that most compounds in series 7 and 9 exhibited significant inhibitory activities against anaerobic bacteria (Streptococcus mutans) strains with a MIC value of 1 µg/mL. Compounds 7c and 9c showed the most potent activity against MRSA (3167 and 3506) with a minimum inhibitory concentration (MIC) value of 1 µg/mL, which is equivalent to moxifloxacin and greater than gatifloxacin, oxacillin and norfloxacin. Additionally, compound 9c showed potent antibacterial activity against Bacillus subtilis (aerobic bacteria) with a MIC value of 2 µg/mL. CONCLUSION: The work suggests that these type of rhodanine compounds had a better potent activity against MRSA compared with other perviously reported rhodanine derivatives, which might provide a valuable information for the development of new antibacterial agents against multidrug-resistant clinical isolates MRSA. SN - 1875-6638 UR - https://www.unboundmedicine.com/medline/citation/27550428/Synthesis_and_Antimicrobial_Evaluation_of__Z__5___3_phenyl_1H_pyrazol_4__yl_methylene__2_thioxothiazolidin_4_one_Derivatives_ L2 - http://www.eurekaselect.com/145002/article DB - PRIME DP - Unbound Medicine ER -