(3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters

Meryem Pir; Fatma Budak

doi:10.29130/dubited.944684

TR EN

(3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters

Abstract

We intended to quantify the antibacterial and antifungal activity results of 4,5-dihydroisoxazole dimethanol compound (1a) against several bacteria and fungi and also calculate some structural parameters (theoretical descriptors) of compound (1a) with this work. Microdilution broth procedures were studied using microdilution wells for the minimal inhibitory concentrations (MICs) test. Compound (1a) exhibited fair activities against all the bacteria and fungi. Compound (1a) has been a good result (MIC = 50 µg/ml) against particularly P. aeruginosa. The structure of compound (1a) was drawn, and geometrical optimization was done using the Ab initio (RHF/3-21G) level.

Keywords

Antimicrobial activity, Dihydroisoxazole dimethanol compound, MIC

Supporting Institution

Kocaeli University BAP

Project Number

Project No:2019/009HD

Thanks

This study is based on the Project No:2019/009HD supported by Kocaeli University, BAP.

References

[1] M. Serpi, Z. Özdemir, Y. Salman, “Investigation of the antibacterial effects of some plant extracts on Propionibacterium acnes,” KSU Journal of Agriculture and Nature, vol. 15, no. 1, pp. 7-12, 2012.
[2] E. S. Bireller, A. B. Dinç, E. Şahin, A. Ergen, B. Çakmakoğlu, “Inverstigation of rational use of antibiotics on parents,” Experimed, vol. 6, no. 12, pp. 33-44, 2016.
[3] D. L. Kiska, P. H. Gilligan, Pseudomonas. Manual of Clinical Microbiology, 7th ed., Washington, DC, USA: ASM Press., 1999, pp. 517-525.
[4] A. U. Akbal, A. Y. Çoban, B. Durupınar, “New antibacterials,” Türk Mikrobiyoloji Cemiyeti Dergisi, vol. 48, no. 2, pp. 87-99, 2018.
[5] K. Lewis, “New approaches to antimicrobial discovery,” Biochemical Pharmacology, vol. 134, pp. 87-98, 2017.
[6] H. Krauss, A. Weber, M. Appel, Zoonoses. Infectious Diseases Transmissible from Animals to Humans, 3rd ed., vol. 194, Washington DC, USA: ASM Press, 2003, p. 456.
[7] A. Waness, “Revisiting methicillin-resistant Staphylococcus aureus infections,” Journal of Global Infectious Diseases, vol. 2, no. 1, pp. 49-56, 2010.
[8] A. E. Villaruz, J. B. Wardenburg, B. A. Khan, A. R. Whitney, D. E. Sturdevant, D. J. Gardner, F. R. DeLeo, M. Otto, “A point mutation in the agr locus rather than expression of the panton-valentine Leukocidin caused previously reported phenotypes in Staphylococcus aureus pneumonia and gene regulation,” The Journal of Infectious Diseases, vol. 200, no. 5, pp. 724-734, 2009.
[9] M. C. Enright, D. A. Robinson, G. Randle, E. J. Feil, H. Grundmann, B. G. Spratt, “The evolutionary history of methicillin-resistant Staphylococcus aureus (MRSA),” Proceedings of the National Academy of Sciences, vol. 99, no. 11, pp. 7687-7692, 2002.
[10] G. Cornaglia, G. M. Rossolini, “Forthcoming therapeutic perspectives for infections due to multidrug-resistant Gram-positive pathogens,” Clinical Microbiology and Infection, vol. 15, pp. 218-223, 2009.

[11] U. Kayiş, “Antimicrobial Resistance Mechanisms,” ASD., vol. 5, no. 1, pp. 1-12, 2019.
[12] A. Martinez, S. J. Kolvek, C. L. T. Yip, J. Hopke, K. A. Brown, I. A. Macneil, M. S. Osburne, “Genetically modified bacterial strains and novel bacterial artificial chromosome shuttle vectors for constructing environmental libraries and detecting heterologous natural products in multiple expression hosts,” Applied and Environmental Microbiology, vol. 70, no. 4, pp. 2452-2463, 2004.
[13] A. Jabbour, M. Srebnik, B. Zaks, V. Dembitsky, D. Steinberg, “Evaluation of oxazaborolidine activity on Streptococcus mutans biofilm formation,” International Journal of Antimicrobial Agents, vol. 26, pp. 491-496, 2005.
[14] E. J. C. Goldstein, D. M. Citron, K. L. Tyrrell, C. V. Merriam, “Comparative In Vitro Activities of GSK2251052, a Novel Boron-Containing Leucyl-tRNA Synthetase Inhibitor, against 916 Anaerobic Organisms,” Antimicrobial Agents and Chemotherapy, vol. 57, no. 5, pp. 2401-2404, 2013.
[15] D. Song, F. Bi, N. Zhang, Y. Qin, X. Liu, Y. Teng, S. Ma, “Design, synthesis of novel 4,5-dihydroisoxazole-containing benzamide derivatives as highly potent FtsZ inhibitors capable of killing a variety of MDR Staphylococcus aureus,” Bioorganic & Medicinal Chemistry, vol. 28, no. 115729, pp. 1-16, 2020.
[16] A. D. B. Gabriela, A. P. Aguiar, C. E. Martins, R. N. J. Maria, “Synthesis of 3-furanyl-4,5-dihydroisoxazole derivatives via cycloaddition and their antibacterial evaluation,” Letters in Drug Design Discovery, vol. 16, no. 3, pp. 364-369, 2019.
[17] J. Sowdari, S. Thata, Y. Gudi, P. Venkatapuram, P. Adiviredd, “Synthesis of amide-linked benzazolyl isoxazoles adoptinggreen methods and evaluation as antimicrobials,” Journal of Heterocyclic Chemistry, vol. 57, pp. 1882-1892, 2020.
[18] M. Pir, H. Agirbas, F. Budak, O. Sahin, “Synthesis, characterization, antimicrobial activity and QSAR studies of some new 6-substituted phenyl 3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino[5,6-d]isoxazoles,” Heteroatom Chemistry, vol. 28, no. 2, e21363, 2017.
[19] N. S. Hosmane, Boron science. New technologies and applications, 1st ed., US: CRC Press, 2012, pp. 45-50.
[20] B. T. Cho, “Recent advances in the synthetic applications of the oxazaborolidine-mediated asymmetric reduction,” Tetrahedron, vol. 62, no. 33, pp. 7621-7643, 2006.
[21] Y. K. Zhang, J. J. Plattner, T. Akama, S. J. Baker, V. S. Hernandez, V. Sanders, Y. Freund, R. Kimura, W. Bu, K. M. Hold, X. S. Lu, “Design and synthesis of boron-containing PDE4 inhibitors using soft-drug strategy for potential dermatologic anti-inflammatory application,” Bioorganic & Medicinal Chemistry Letters, vol. 20, no. 7, pp. 2270-2274, 2010.
[22] R. L. Papke, G. Zheng, N. A. Horenstein, L. P. Dwoskin, P. A. Crooks, “The characterization of a novel rigid nicotine analog with α7-selective nAChR agonist activity and modulation of agonist properties by boron inclusion,” Bioorganic & Medicinal Chemistry Letters, vol. 15, no. 17, pp. 3874-3880, 2005.
[23] K. Barral, S. Priet, C. D. Michelis, J. Sire, J. Neyts, J. Balzarini, B. Canard, K. Alvarez, “Synthesis and antiviral activity of boranophosphonate isosteres of AZT and d4T monophosphates,” Europen Journal of Medicinal Chemistry, vol. 45, no. 2, pp. 849-856, 2010.
[24] R. Trivedi, E. R. Reddy, C. K. Kumar, B. Sridhar, K. P. Kumar, M S. Rao, “Efficient synthesis, structural characterization and antimicrobial activity of chiral aryl boronate esters of 1,2-O-isopropylidene-α-D-xylofuranose,” Bioorganic & Medicinal Chemistry Letters, vol. 21, pp. 3890-3893, 2011.
[25] Y. K. Zhang, J. J. Plattner, Y. R. Freund, E. E. Easom, Y. Zhou, J. Gut, P. J. Rosenthal, D. Waterson, F. J. Gamo, I. A. Barturen, M. Ge, Z. Li, L. Li, Y. Jian, H. Cui, H. Wang, J. Yang, “Synthesis and structure-activity relationships of novel benzoxaboroles as a new class of antimalarial agents,” Bioorganic & Medicinal Chemistry Letters, vol. 21, pp. 644-651, 2011.
[26] S. Song, P. Gaoa, L. Sun, D. Kang, J. Kongsted, V. Poongavanam, P. Zhan, X. Liu, “Recent developments in the medicinal chemistry of single boron atom-containing compounds,” Acta Pharmaceutica Sinica B, 2021;10.1016/j.apsb.2021.01.010.
[27] I. R. V. Valdez, M. N. Rosalez, J. M. Q. Santiago, D. F. G. Eunice, A. S. U. Marvin, “Docking simulations exhibit Bortezomib and other boron-containing peptidomimetics as potential inhibitors of SARS-CoV-2 Main Protease,” Current Chemical Biology, vol. 14, pp. 279-288, 2020.
[28] Y. S. Kara, “Nitril oksit ve amidoksim kullanılarak yeni hetero halkalı bileşiklerin sentezi,” Doktora tezi, Kimya Bölümü, Kocaeli Üniversitesi, Kocaeli, Türkiye, 2009.
[29] CLSI. Methods for diluation antimicrobial susceptibility tests for bacteria that grow aerobically: Approved Standard, M-7, A-7, Wayne: PA, USA, Clinical Laboratory Standards Institute, 2006.
[30] CLSI. Performance standards for antimicrobial susceptibility testing. Fifteenth Informational Supplement, CLSI-M110-S15, CLSI, Wayne: PA, USA, Clinical Laboratory Standards Institute, 2005.
[31] CLSI. Reference method for broth dilution antifungal susceptibility testing of yeast: Approved Standard, M27 A2, 2nd ed. CLSI, Wayne: PA, USA, Clinical Laboratory Standards Institute, 2002.
[32] HyperChem for Windows, Computer Program, 7.2 version, Georgia, (USA): Hypercube, Inc., Gainesville, FL, 2002.
[33] H. M. Patel, M. N. Noolvi, P. Sharma, V. Jaiswal, S. Bansal, S. Lohan, S. S. Kumar, V. Abbot, S. Dhiman, V. Bhardwaj, “Quantitative structure-activity relationship (QSAR) studies as strategic approach in drug discovery,” Medicinal Chemistry Research, vol. 23, pp. 4991-5007, 2014.
[34] C. Huang, M. J. Embrechts, N. Sukumar, C. M. Breneman, “Data fusion and auto-fusion for quantitative structure-activity relationship (QSAR). Artificial neural networks-ICANN,” 17th International Conference, 2007, pp. 9-13.
[35] S. Özden, R. Ertan, E. Akı-Şener, İ. Yalçın, D. Nebioğlu, E. Büyükbingöl, H. Göker, İ. Yıldız, T. G. Altuntaş-Dinlenç, M. Tunçbilek, G. Ayhan-Kılçıgil, S. Ölgen, S. Süzen, Ö. Temiz-Arpacı, C. Kuş, O. Bozdağ-Dündar, B. Tekiner-Gülbaş, Z. Ateş-Alagöz, Farmasötik Kimya Pratikleri 1-2, 1. baskı, Ankara, Türkiye: Ankara Üniversitesi Basımevi, 2004, böl. 4, ss. 63-95.

Details

Primary Language

English

Subjects

Engineering

Journal Section

Research Article

Authors

Meryem Pir ^*
0000-0003-4305-8838
Türkiye

Fatma Budak
0000-0001-8439-3881
Türkiye

Publication Date

April 30, 2022

Submission Date

May 29, 2021

Acceptance Date

October 31, 2021

Published in Issue

Year 2022 Volume: 10 Number: 2

DOI

https://doi.org/10.29130/dubited.944684

IZ

https://izlik.org/JA49WM29ST

APA

Pir, M., & Budak, F. (2022). (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters. Duzce University Journal of Science and Technology, 10(2), 815-822. https://doi.org/10.29130/dubited.944684

AMA

1.Pir M, Budak F. (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters. DUBİTED. 2022;10(2):815-822. doi:10.29130/dubited.944684

Chicago

Pir, Meryem, and Fatma Budak. 2022. “(3-(4-Chlorophenyl)-4,5-Dihydroisoxazole-4,5-Diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters”. Duzce University Journal of Science and Technology 10 (2): 815-22. https://doi.org/10.29130/dubited.944684.

EndNote

Pir M, Budak F (April 1, 2022) (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters. Duzce University Journal of Science and Technology 10 2 815–822.

IEEE

[1]M. Pir and F. Budak, “(3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters”, DUBİTED, vol. 10, no. 2, pp. 815–822, Apr. 2022, doi: 10.29130/dubited.944684.

ISNAD

Pir, Meryem - Budak, Fatma. “(3-(4-Chlorophenyl)-4,5-Dihydroisoxazole-4,5-Diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters”. Duzce University Journal of Science and Technology 10/2 (April 1, 2022): 815-822. https://doi.org/10.29130/dubited.944684.

JAMA

1.Pir M, Budak F. (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters. DUBİTED. 2022;10:815–822.

MLA

Pir, Meryem, and Fatma Budak. “(3-(4-Chlorophenyl)-4,5-Dihydroisoxazole-4,5-Diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters”. Duzce University Journal of Science and Technology, vol. 10, no. 2, Apr. 2022, pp. 815-22, doi:10.29130/dubited.944684.

Vancouver

1.Meryem Pir, Fatma Budak. (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters. DUBİTED. 2022 Apr. 1;10(2):815-22. doi:10.29130/dubited.944684

Cited By

Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds

International Journal of Chemistry and Technology

https://doi.org/10.32571/ijct.1109476

(3-(4-klorofenil)-4,5-dihidroizoksazol-4,5-diil)dimetanol Bileşiği: Antibakteriyel Aktivite, Antifungal Aktivite ve Hesaplanmış Yapısal Parametreler

Abstract

Keywords

Project Number

(3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol Compound: Antibacterial Activity, Antifungal Activity and Calculated Structural Parameters

Abstract

Keywords

Supporting Institution

Project Number

Thanks

References

Details

Primary Language

Subjects

Journal Section

Authors

Publication Date

Submission Date

Acceptance Date

Published in Issue

DOI

IZ

Cite

Cited By

Determination of in vitro antifungal activity of dihydroisoxazole dimethanol compound against dermatophytes obtained from clinical isolates and design of some new dihydroisoxazole dimethanol compounds