Research Article
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Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives

Year 2019, Volume: 9 Issue: 2, 967 - 974, 01.06.2019
https://doi.org/10.21597/jist.480052

Abstract

The object of present study is to assess anticandidal activities of some new aryl (5-nitrobenzofuran-2-yl)keton and ketoxime compounds. Eight aryl (5-nitrobenzofuran-2-yl)ketones and ketoximes were synthesized. IR, 1H-NMR and HR-MS spectroscopic data, performed the structure elucidation of the synthesized compounds. Anticandidal activities of the all synthesized compounds were studied. Compound 2c bearing methoxy group on phenyl ring showed the highest activity with MIC value of 3.12 μg mL-1 against Candida albicans and Candida glabrata. None of the compounds activity results were equal to or better than that of the control compounds ketoconazole and fluconazole. However, compound 2c displayed a promising anticandidal activity.

Supporting Institution

Anadolu University Scientific Projects Fund

Project Number

1807S253

Thanks

Financial contribution of Anadolu University Scientific Projects Fund (Project No.: 1807S253) is gratefully acknowledged.

References

  • REFERENCES
  • Benedict K, Richardson M, Vallabhaneni S, Jackson BR, Chiller T, 2017. Emerging issues, challenges, and changing epidemiology of fungal disease outbreaks. The Lancet Infectious Diseases, 17 (12): e403-e11.
  • Borra RC, Lotufo MA, Gagioti SM, Barros Fde M, Andrade PM, 2009. A simple method to measure cell viability in proliferation and cytotoxicity assays. Brazilian Oral Research, 23 (3): 255-262.
  • de Souza Nunes JP, da Silva KA, da Silva GF, Quintao NL, Correa R, Cechinel-Filho V, et al, 2014. The antihypersensitive and antiinflammatory activities of a benzofuranone derivative in different experimental models in mice: the importance of the protein kinase C pathway. Anesthesia & Analgesia, 119 (4): 836-846.
  • Demirayak S, Yurttas L, Karaburun AC, Gundogdu-Karaburun N, Kayagil I, 2016. Synthesis and antiproliferative activity of 2-arylidene 6-(2-aryl-2-oxoethoxy)benzofuran-3-one derivatives. Letters in Drug Design & Discovery, 13 (6): 563-569.
  • Dimopoulos G, Koulenti D, Tabah A, Poulakou G, Vesin A, Arvaniti K, et al, 2015. Bloodstream infections in ICU with increased resistance: epidemiology and outcomes. Minerva Anestesiologica, 81 (4): 405-418.
  • Dos Santos Abrantes PM, McArthur CP, Africa CW, 2014. Multi-drug resistant oral Candida species isolated from HIV-positive patients in South Africa and Cameroon. Diagnostic Microbiology and Infectious Disease, 79 (2): 222-227.
  • Engler TA, LaTessa KO, Iyengar R, Chai W, Agrios K, 1996. Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues. Bioorganic & Medicinal Chemistry, 4 (10): 1755-1769.
  • Geronikaki A, Fesatidou M, Kartsev V, Macaev F, 2013. Synthesis and biological evaluation of potent antifungal agents. Current Topics in Medicinal Chemistry, 13 (21): 2684-2733.
  • Goncalves CJ, Lenoir AS, Padaratz P, Correa R, Niero R, Cechinel-Filho V, et al, 2012. Benzofuranones as potential antinociceptive agents: structure-activity relationships. European Journal of Medicinal Chemistry, 56: 120-126.
  • Grover C, Arora P, Manchanda V, 2012. Comparative evaluation of griseofulvin, terbinafine and fluconazole in the treatment of tinea capitis. International Journal of Dermatology, 51 (4): 455-458.
  • Healey KR, Zhao Y, Perez WB, Lockhart SR, Sobel JD, Farmakiotis D, et al, 2016. Prevalent mutator genotype identified in fungal pathogen Candida glabrata promotes multi-drug resistance. Nature Communications, 7: 11128.
  • Jiang X, Liu W, Zhang W, Jiang F, Gao Z, Zhuang H, et al, 2011. Synthesis and antimicrobial evaluation of new benzofuran derivatives. European Journal of Medicinal Chemistry, 46 (8): 3526-3530.
  • Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C, 2008. Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives. European Journal of Medicinal Chemistry, 43 (2): 300-308.
  • Mao ZW, Zheng X, Lin YP, Hu CY, Wang XL, Wan CP, et al, 2016. Design, synthesis and anticancer activity of novel hybrid compounds between benzofuran and N-aryl piperazine. Bioorganic & Medicinal Chemistry Letters, 26 (15): 3421-3424.
  • Miyazaki M, Horii T, Hata K, Watanabe NA, Nakamoto K, Tanaka K, et al, 2011. In vitro activity of E1210, a novel antifungal, against clinically important yeasts and molds. Antimicrobial Agents and Chemotherapy, 55 (10): 4652-4658.
  • Osman NM, Gomaa AA, Sayed NM, Abd el aziz AA, 2013. Microarray detection of fungal infection in pulmonary tuberculosis. Egyptian Journal of Chest Diseases and Tuberculosis, 62 (1): 151-157.
  • Palomino JC, Martin A, Camacho M, Guerra H, Swings J, Portaels F, 2002. Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. Antimicrobial Agents and Chemotherapy, 46 (8): 2720-2722.
  • Pestellini V, Giolitti A, Pasqui F, Abelli L, Cutrufo C, De Salvia G, et al, 1988. Synthesis and hypolipidemic activity of new substituted (benzofuran-2-yl)-phenyl-carbinols. European Journal of Medicinal Chemistry, 23 (2): 203-206.
  • Primožič I, Hrenar T, Baumann K, Krišto L, Križić I, Tomić S, 2014. Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations. Croatica Chemica Acta, 87 (2):153-160.
  • Rádl S, Hezký P, Konvička P, Krejčí I, 2000. Synthesis and analgesic activity of some substituted 1-benzofurans and 1-benzothiophenes. Collection of Czechoslovak Chemical Communications, 65 (7): 1093-1108.
  • Ravu RR, Chen YL, Jacob MR, Pan X, Agarwal AK, Khan SI, et al, 2013. Synthesis and antifungal activities of miltefosine analogs. Bioorganic & Medicinal Chemistry Letters, 23 (17): 4828-4831.
  • Rodriguez-Tudela JL, Arendrup MC, Barchiesi F, Bille J, Chryssanthou E, Cuenca-Estrella M, Dannaoui E, Denning DW, Donnelly JP, Dromer F, Fegeler W, 2008. EUCAST definitive document EDef 7.1: method for the determination of broth dilution MICs of antifungal agents for fermentative yeasts. Clinical Microbiology and Infection, 14 (4): 398-405.
  • Shemer A, Plotnik IB, Davidovici B, Grunwald MH, Magun R, Amichai B, 2013. Treatment of tinea capitis - griseofulvin versus fluconazole - a comparative study. Journal der Deutschen Dermatologischen Gesellschaft, 11 (8): 737-741.
  • Sipsas NV, Kontoyiannis DP, 2012. Invasive fungal infections in patients with cancer in the Intensive Care Unit. International Journal of Antimicrobial Agents, 39 (6): 464-471.
  • Telvekar VN, Belubbi A, Bairwa VK, Satardekar K, 2012. Novel N'-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents. Bioorganic & Medicinal Chemistry Letters, 22 (6): 2343-2346.
  • Valerio M, Vena A, Bouza E, Reiter N, Viale P, Hochreiter M, et al, 2015. How much European prescribing physicians know about invasive fungal infections management? BMC Infectious Diseases, 15: 80.
  • Vinh TK, Ahmadi M, Lopez Delgado PO, Fernandez Perez S, Walters HM, Smith HJ, Nicholls PJ, Simons C, 1999. 1-[(Benzofuran-2-yl)phenylmethyl]-triazoles and -tetrazoles - potent competitive inhibitors of aromatase. Bioorganic & Medicinal Chemistry Letters, 9 (14): 2105-2108.
  • Wallace SM, Shah VP, Epstein WL, Greenberg J, Riegelman S, 1977. Topically applied antifungal agents. Percutaneous penetration and prophylactic activity against Trichophyton mentagrophytes infection. Archives of Dermatology, 113 (11): 1539–1542.

Yeni Nitrobenzofuran Türevlerinin Sentezi ve Antifungal Etkileri

Year 2019, Volume: 9 Issue: 2, 967 - 974, 01.06.2019
https://doi.org/10.21597/jist.480052

Abstract

Bu çalışmada bazı yeni aril (5-nitrobenzofuran-2-il)keton ve ketoksim bileşiklerinin antikandidal etkinliklerinin değerlendirilmesi amaçlanmıştır. Sekiz aril (5-nitrobenzofuran-2-il)keton ve ketoksimi sentezlenmiştir. Sentezlenen bileşiklerin yapı aydınlatmaları IR, 1H-NMR ve HR-MS spektroskopik verileri ile gerçekleştirilmiştir. Bileşiklerin antikandidal etkinlikleri incelenmiştir. Fenil halkası üzerinde metoksi grubu taşıyan bileşik 2c, 3.12 μg mL-1 MİK değeri ile Candida albicans ve Candida glabrata’ya karşı en yüksek aktiviteyi göstermiştir. Hiçbir bileşik kontrol bileşikleri olan ketokonazol ve flukonazole eş ya da daha iyi aktivite sergileyememiştir. Ancak, bileşik 2c’nin aktivite sonuçları umut verici olarak değerlendirilmektedir.

Project Number

1807S253

References

  • REFERENCES
  • Benedict K, Richardson M, Vallabhaneni S, Jackson BR, Chiller T, 2017. Emerging issues, challenges, and changing epidemiology of fungal disease outbreaks. The Lancet Infectious Diseases, 17 (12): e403-e11.
  • Borra RC, Lotufo MA, Gagioti SM, Barros Fde M, Andrade PM, 2009. A simple method to measure cell viability in proliferation and cytotoxicity assays. Brazilian Oral Research, 23 (3): 255-262.
  • de Souza Nunes JP, da Silva KA, da Silva GF, Quintao NL, Correa R, Cechinel-Filho V, et al, 2014. The antihypersensitive and antiinflammatory activities of a benzofuranone derivative in different experimental models in mice: the importance of the protein kinase C pathway. Anesthesia & Analgesia, 119 (4): 836-846.
  • Demirayak S, Yurttas L, Karaburun AC, Gundogdu-Karaburun N, Kayagil I, 2016. Synthesis and antiproliferative activity of 2-arylidene 6-(2-aryl-2-oxoethoxy)benzofuran-3-one derivatives. Letters in Drug Design & Discovery, 13 (6): 563-569.
  • Dimopoulos G, Koulenti D, Tabah A, Poulakou G, Vesin A, Arvaniti K, et al, 2015. Bloodstream infections in ICU with increased resistance: epidemiology and outcomes. Minerva Anestesiologica, 81 (4): 405-418.
  • Dos Santos Abrantes PM, McArthur CP, Africa CW, 2014. Multi-drug resistant oral Candida species isolated from HIV-positive patients in South Africa and Cameroon. Diagnostic Microbiology and Infectious Disease, 79 (2): 222-227.
  • Engler TA, LaTessa KO, Iyengar R, Chai W, Agrios K, 1996. Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues. Bioorganic & Medicinal Chemistry, 4 (10): 1755-1769.
  • Geronikaki A, Fesatidou M, Kartsev V, Macaev F, 2013. Synthesis and biological evaluation of potent antifungal agents. Current Topics in Medicinal Chemistry, 13 (21): 2684-2733.
  • Goncalves CJ, Lenoir AS, Padaratz P, Correa R, Niero R, Cechinel-Filho V, et al, 2012. Benzofuranones as potential antinociceptive agents: structure-activity relationships. European Journal of Medicinal Chemistry, 56: 120-126.
  • Grover C, Arora P, Manchanda V, 2012. Comparative evaluation of griseofulvin, terbinafine and fluconazole in the treatment of tinea capitis. International Journal of Dermatology, 51 (4): 455-458.
  • Healey KR, Zhao Y, Perez WB, Lockhart SR, Sobel JD, Farmakiotis D, et al, 2016. Prevalent mutator genotype identified in fungal pathogen Candida glabrata promotes multi-drug resistance. Nature Communications, 7: 11128.
  • Jiang X, Liu W, Zhang W, Jiang F, Gao Z, Zhuang H, et al, 2011. Synthesis and antimicrobial evaluation of new benzofuran derivatives. European Journal of Medicinal Chemistry, 46 (8): 3526-3530.
  • Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C, 2008. Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives. European Journal of Medicinal Chemistry, 43 (2): 300-308.
  • Mao ZW, Zheng X, Lin YP, Hu CY, Wang XL, Wan CP, et al, 2016. Design, synthesis and anticancer activity of novel hybrid compounds between benzofuran and N-aryl piperazine. Bioorganic & Medicinal Chemistry Letters, 26 (15): 3421-3424.
  • Miyazaki M, Horii T, Hata K, Watanabe NA, Nakamoto K, Tanaka K, et al, 2011. In vitro activity of E1210, a novel antifungal, against clinically important yeasts and molds. Antimicrobial Agents and Chemotherapy, 55 (10): 4652-4658.
  • Osman NM, Gomaa AA, Sayed NM, Abd el aziz AA, 2013. Microarray detection of fungal infection in pulmonary tuberculosis. Egyptian Journal of Chest Diseases and Tuberculosis, 62 (1): 151-157.
  • Palomino JC, Martin A, Camacho M, Guerra H, Swings J, Portaels F, 2002. Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. Antimicrobial Agents and Chemotherapy, 46 (8): 2720-2722.
  • Pestellini V, Giolitti A, Pasqui F, Abelli L, Cutrufo C, De Salvia G, et al, 1988. Synthesis and hypolipidemic activity of new substituted (benzofuran-2-yl)-phenyl-carbinols. European Journal of Medicinal Chemistry, 23 (2): 203-206.
  • Primožič I, Hrenar T, Baumann K, Krišto L, Križić I, Tomić S, 2014. Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations. Croatica Chemica Acta, 87 (2):153-160.
  • Rádl S, Hezký P, Konvička P, Krejčí I, 2000. Synthesis and analgesic activity of some substituted 1-benzofurans and 1-benzothiophenes. Collection of Czechoslovak Chemical Communications, 65 (7): 1093-1108.
  • Ravu RR, Chen YL, Jacob MR, Pan X, Agarwal AK, Khan SI, et al, 2013. Synthesis and antifungal activities of miltefosine analogs. Bioorganic & Medicinal Chemistry Letters, 23 (17): 4828-4831.
  • Rodriguez-Tudela JL, Arendrup MC, Barchiesi F, Bille J, Chryssanthou E, Cuenca-Estrella M, Dannaoui E, Denning DW, Donnelly JP, Dromer F, Fegeler W, 2008. EUCAST definitive document EDef 7.1: method for the determination of broth dilution MICs of antifungal agents for fermentative yeasts. Clinical Microbiology and Infection, 14 (4): 398-405.
  • Shemer A, Plotnik IB, Davidovici B, Grunwald MH, Magun R, Amichai B, 2013. Treatment of tinea capitis - griseofulvin versus fluconazole - a comparative study. Journal der Deutschen Dermatologischen Gesellschaft, 11 (8): 737-741.
  • Sipsas NV, Kontoyiannis DP, 2012. Invasive fungal infections in patients with cancer in the Intensive Care Unit. International Journal of Antimicrobial Agents, 39 (6): 464-471.
  • Telvekar VN, Belubbi A, Bairwa VK, Satardekar K, 2012. Novel N'-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents. Bioorganic & Medicinal Chemistry Letters, 22 (6): 2343-2346.
  • Valerio M, Vena A, Bouza E, Reiter N, Viale P, Hochreiter M, et al, 2015. How much European prescribing physicians know about invasive fungal infections management? BMC Infectious Diseases, 15: 80.
  • Vinh TK, Ahmadi M, Lopez Delgado PO, Fernandez Perez S, Walters HM, Smith HJ, Nicholls PJ, Simons C, 1999. 1-[(Benzofuran-2-yl)phenylmethyl]-triazoles and -tetrazoles - potent competitive inhibitors of aromatase. Bioorganic & Medicinal Chemistry Letters, 9 (14): 2105-2108.
  • Wallace SM, Shah VP, Epstein WL, Greenberg J, Riegelman S, 1977. Topically applied antifungal agents. Percutaneous penetration and prophylactic activity against Trichophyton mentagrophytes infection. Archives of Dermatology, 113 (11): 1539–1542.
There are 29 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Kimya / Chemistry
Authors

Ahmet Çağrı Karaburun 0000-0002-2503-3824

Project Number 1807S253
Publication Date June 1, 2019
Submission Date November 7, 2018
Acceptance Date November 30, 2018
Published in Issue Year 2019 Volume: 9 Issue: 2

Cite

APA Karaburun, A. Ç. (2019). Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives. Journal of the Institute of Science and Technology, 9(2), 967-974. https://doi.org/10.21597/jist.480052
AMA Karaburun AÇ. Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives. J. Inst. Sci. and Tech. June 2019;9(2):967-974. doi:10.21597/jist.480052
Chicago Karaburun, Ahmet Çağrı. “Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives”. Journal of the Institute of Science and Technology 9, no. 2 (June 2019): 967-74. https://doi.org/10.21597/jist.480052.
EndNote Karaburun AÇ (June 1, 2019) Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives. Journal of the Institute of Science and Technology 9 2 967–974.
IEEE A. Ç. Karaburun, “Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives”, J. Inst. Sci. and Tech., vol. 9, no. 2, pp. 967–974, 2019, doi: 10.21597/jist.480052.
ISNAD Karaburun, Ahmet Çağrı. “Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives”. Journal of the Institute of Science and Technology 9/2 (June 2019), 967-974. https://doi.org/10.21597/jist.480052.
JAMA Karaburun AÇ. Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives. J. Inst. Sci. and Tech. 2019;9:967–974.
MLA Karaburun, Ahmet Çağrı. “Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives”. Journal of the Institute of Science and Technology, vol. 9, no. 2, 2019, pp. 967-74, doi:10.21597/jist.480052.
Vancouver Karaburun AÇ. Synthesis and Antifungal Activity of New Nitrobenzofuran Derivatives. J. Inst. Sci. and Tech. 2019;9(2):967-74.