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3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs
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    3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs
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    Laboratory of Structure and Interactions of Biologically Active Molecules, Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic, Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic, Department of Pharmacology and Toxicology, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic, and Research Centre LN00B125, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2001, 44, 17, 2701–2706
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    https://doi.org/10.1021/jm010155x
    Published July 21, 2001
    Copyright © 2001 American Chemical Society

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    3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (−)incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34 μg/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 μg/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

    Copyright © 2001 American Chemical Society

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     Dedicated to Professor Karel Waisser on the occasion of his 65th birthday.

    *

     To whom correspondence should be addressed. Phone:  +420-49-5067277. Fax:  +420-49-5210002. E-mail:  [email protected].

     Laboratory of Structure and Interactions of Biologically Active Molecules, Charles University.

    §

     Department of Biological and Medical Sciences, Charles University.

     Department of Pharmacology and Toxicology, Charles University.

     Research Centre LN00B125.

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    3. Aidang Lu, Jinjin Wang, Tengjiao Liu, Jian Han, Yinhui Li, Min Su, Jianxin Chen, Hui Zhang, Lizhong Wang, and Qingmin Wang . Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents. Journal of Agricultural and Food Chemistry 2014, 62 (35) , 8799-8807. https://doi.org/10.1021/jf503060k
    4. Maddi Sridhar Reddy, Nuligonda Thirupathi, Madala Hari Babu, and Surendra Puri . Synthesis of Substituted 3-Iodocoumarins and 3-Iodobutenolides via Electrophilic Iodocyclization of Ethoxyalkyne Diols. The Journal of Organic Chemistry 2013, 78 (12) , 5878-5888. https://doi.org/10.1021/jo400499r
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    6. Teresa Olejniczak, Filip Boratyński, and Agata Białońska . Fungistatic Activity of Bicyclo[4.3.0]-γ-lactones. Journal of Agricultural and Food Chemistry 2011, 59 (11) , 6071-6081. https://doi.org/10.1021/jf105019u
    7. Nicholas A. Magnus, Silvio Campagna, Pat N. Confalone, Scott Savage, David J. Meloni, Robert E. Waltermire, Robert G. Wethman and Mathew Yates. Quaternary Chiral Center via Diastereoselective Enolate Amination Enables the Synthesis of an Anti-inflammatory Agent. Organic Process Research & Development 2010, 14 (1) , 159-167. https://doi.org/10.1021/op900255k
    8. Giuseppe La Regina, Felicia Diodata D’Auria, Andrea Tafi, Francesco Piscitelli, Stefania Olla, Fabiana Caporuscio, Lucia Nencioni, Roberto Cirilli, Francesco La Torre, Nadja Rodrigues De Melo, Steven L. Kelly, David C. Lamb, Marino Artico, Maurizio Botta, Anna Teresa Palamara and Romano Silvestri. 1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity against Candida albicans and Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies. Journal of Medicinal Chemistry 2008, 51 (13) , 3841-3855. https://doi.org/10.1021/jm800009r
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    10. B. Haridevamuthu, S. Madesh, Ankit Kumar Bharti, L.S. Dhivya, Rajakrishnan Rajagopal, Ahmed Alfarhan, Kathiravan Muthu Kumaradoss, Jesu Arockiaraj. Protective effect of a novel furan hybrid chalcone against bisphenol A-induced craniofacial developmental toxicity in zebrafish embryos. Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology 2025, 288 , 110072. https://doi.org/10.1016/j.cbpc.2024.110072
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    12. G. Logeshwari, R. RajaRajeshwari, E. Dhineshkumar, M. Seenivasan, H. Manikandan. Synthesis, spectral and antimicrobial studies of some 3-Arylideneamino-1,2,3-triarylpropan-1-ones. Materials Today: Proceedings 2022, 51 , 2207-2217. https://doi.org/10.1016/j.matpr.2021.11.331
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    14. G. M. Talybov. Isomerization of Propargyl Ethers of 2-Hydroxyoxiranes to Furan Derivatives on Silver Catalysts. Russian Journal of General Chemistry 2021, 91 (6) , 1153-1156. https://doi.org/10.1134/S107036322106027X
    15. Patricia Mowery, Madison M. Filkorn, Brianna Hurysz, Deborah O. Kwansare, Megan M. Lafferty, Marissa A. McFadden, Namita D. Neerukonda, Roslyn R. Patel, Kelsey Pierce, Kaitlynn A. Sockett, Nathanyal J. Truax, Nathan R. Webster, Erin T. Pelkey. Discovery of an indole-substituted furanone with tubulin polymerization inhibition activity. Bioorganic & Medicinal Chemistry Letters 2021, 41 , 127991. https://doi.org/10.1016/j.bmcl.2021.127991
    16. Kai Yang, Jian-Qiong Yang, Shi-He Luo, Wen-Jie Mei, Jian-Yun Lin, Jia-Qi Zhan, Zhao-Yang Wang. Synthesis of N-2(5H)-furanonyl sulfonyl hydrazone derivatives and their biological evaluation in vitro and in vivo activity against MCF-7 breast cancer cells. Bioorganic Chemistry 2021, 107 , 104518. https://doi.org/10.1016/j.bioorg.2020.104518
    17. Chengsheng Chen, Jean-Marc Lawrence, Mark W. Peczuh. Amino [13]-macrodilactones: Synthesis, derivatization, and structural motifs. Tetrahedron Letters 2020, 61 (48) , 152579. https://doi.org/10.1016/j.tetlet.2020.152579
    18. Chengsheng Chen, Cristin Bosko, Catherine P. McGeough, Ryan McLean, Angela M. Zaino, M. Kyle Hadden, Mark W. Peczuh. Exploring the physicochemical and antiproliferative properties of biaryl-linked [13]-macrodilactones. Bioorganic & Medicinal Chemistry 2020, 28 (20) , 115671. https://doi.org/10.1016/j.bmc.2020.115671
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    20. Hossein Shahbazi-Alavi, Sheida Khojasteh-Khosro, Javad Safaei-Ghomi, Seyed Hadi Nazemzadeh. Sonosynthesis of furan-2(5H)-ones using nanosilica-tethered polyhedral oligomeric silsesquioxanes. Journal of the Iranian Chemical Society 2019, 16 (11) , 2433-2440. https://doi.org/10.1007/s13738-019-01711-5
    21. H. Ozpinar, N. Ozpinar, N. Eruygur. Effect of Viscum album L. ssp. austriacum (WİESP.) Vollman on metronidazole resistant and sensitive strains of Trichomonas vaginalis. South African Journal of Botany 2019, 125 , 81-85. https://doi.org/10.1016/j.sajb.2019.07.008
    22. Asif Husain, Shah Alam Khan, Farah Iram, Md Azhar Iqbal, Mohammad Asif. Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore. European Journal of Medicinal Chemistry 2019, 171 , 66-92. https://doi.org/10.1016/j.ejmech.2019.03.021
    23. Rajesh Kumar Sharma, Diksha Katiyar. Recent Advances in the Development of Coumarin Derivatives as Antifungal Agents. 2019, 235-263. https://doi.org/10.1007/978-981-13-9435-5_10
    24. Osman Asheri, Sayyed Mostafa Habibi-Khorassani, Mehdi Shahraki. A Study on the Kinetics and Mechanism of the One-Pot Formation of 3,4,5-Substituted Furan-2(5 H )-Ones in the Presence of Lactic Acid: Effect of Different Substituents. Progress in Reaction Kinetics and Mechanism 2018, 43 (3-4) , 286-299. https://doi.org/10.3184/146867818X15319903829218
    25. M. Musawwer Khan, Sarfaraz Khan, Saigal, Subash C. Sahoo. Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst. ChemistrySelect 2018, 3 (5) , 1371-1380. https://doi.org/10.1002/slct.201702933
    26. Nirav R. Patel, Dushyant V. Patel. Synthesis and Biological Activities of Vicinal Diaryl Furans. 2018, 221-244. https://doi.org/10.1016/B978-0-08-102237-5.00007-9
    27. P. Horký, M. Voráčová, K. Konečná, D. Sedlák, P. Bartůněk, J. Vacek, J. Kuneš, M. Pour. Nontoxic combretafuranone analogues with high in vitro antibacterial activity. European Journal of Medicinal Chemistry 2018, 143 , 843-853. https://doi.org/10.1016/j.ejmech.2017.11.078
    28. Bubun Banerjee. Recent developments on nano-ZnO catalyzed synthesis of bioactive heterocycles. Journal of Nanostructure in Chemistry 2017, 7 (4) , 389-413. https://doi.org/10.1007/s40097-017-0247-0
    29. Javad Safaei-Ghomi, Alireza Hatami, Hossein Shahbazi-Alavi. A Highly Flexible Green Synthesis of 3,4,5-Substituted Furan-2(5 H )-ones Using Nano-CdZr 4 (PO 4 ) 6 as Catalyst under Microwave Irradiation. Polycyclic Aromatic Compounds 2017, 37 (5) , 407-414. https://doi.org/10.1080/10406638.2015.1129975
    30. Kelli M. Rutledge, Trevor A. Hamlin, Donna M. Baldisseri, F. Matthias Bickelhaupt, Mark W. Peczuh. Macrocycles All Aflutter: Substitution at an Allylic Center Reveals the Conformational Dynamics of [13]‐Macrodilactones. Chemistry – An Asian Journal 2017, 12 (19) , 2623-2633. https://doi.org/10.1002/asia.201700997
    31. Madasamy Kumar, Vediappen Padmini, Nattamai Bhuvanesh. Stereo-selective green protocol for the synthesis of highly substituted 1-phenyl-tetrahydro indeno [1, 2-b]pyrroles. Research on Chemical Intermediates 2017, 43 (8) , 4517-4530. https://doi.org/10.1007/s11164-017-2893-8
    32. Alexander K. Osipov, Alexander A. Anis'kov, Vyacheslav S. Grinev, Alevtina Yu. Yegorova. Study of E/Z isomerization of (arylamino)methylidenefuran‐2( 3H )‐ones by 1 H, 13 C, 15 N spectroscopy and DFT calculations in different solvents. Magnetic Resonance in Chemistry 2017, 55 (8) , 730-737. https://doi.org/10.1002/mrc.4583
    33. A. K. Osipov, A. A. Anis’kov, A. Yu. Yegorova. Synthesis and configuration of (arylamino)methylidene-3H-furan-2-ones. Russian Journal of Organic Chemistry 2017, 53 (2) , 210-214. https://doi.org/10.1134/S1070428017020117
    34. Jothi L. Nallasivam, Rodney A. Fernandes. A Concise Synthesis of (−)-Incrustoporin and its Analogues by Pd-catalyzed Suzuki-Miyaura Coupling from γ -Vinyl- γ -butyrolactone. ChemistrySelect 2016, 1 (16) , 5137-5140. https://doi.org/10.1002/slct.201601379
    35. Mehrnoosh Kangani, Malek-Taher Maghsoodlou, Nourallah Hazeri. Vitamin B12: An efficient type catalyst for the one-pot synthesis of 3,4,5-trisubstituted furan-2(5 H )-ones and N -aryl-3-aminodihydropyrrol-2-one-4-carboxylates. Chinese Chemical Letters 2016, 27 (1) , 66-70. https://doi.org/10.1016/j.cclet.2015.07.025
    36. Aarti Singh, Sarvesh Kumar Paliwal, Mukta Sharma, Anupama Mittal, Swapnil Sharma, Jai Prakash Sharma. In silico and in vitro screening to identify structurally diverse non-azole CYP51 inhibitors as potent antifungal agent. Journal of Molecular Graphics and Modelling 2016, 63 , 1-7. https://doi.org/10.1016/j.jmgm.2015.10.014
    37. Fei-Hu Cui, Shi-Xia Su, Yan-li Xu, Ying Liang, Heng-shan Wang, Ying-Ming Pan. Capture of CO 2 in air for 4,5-disubstituted furan-2(5H)-ones. Organic Chemistry Frontiers 2016, 3 (10) , 1304-1308. https://doi.org/10.1039/C6QO00328A
    38. Daniel Zárate-Zárate, Raúl Aguilar, R. Israel Hernández-Benitez, Ehecatl M. Labarrios, Francisco Delgado, Joaquín Tamariz. Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products. Tetrahedron 2015, 71 (38) , 6961-6978. https://doi.org/10.1016/j.tet.2015.07.010
    39. Ondřej Krenk, Jiří Kratochvíl, Marcel Špulák, Vladimír Buchta, Jiří Kuneš, Lucie Nováková, Mukund Ghavre, Milan Pour. Methodology for Synthesis of Enantiopure 3,5‐Disubstituted Pyrrol‐2‐ones. European Journal of Organic Chemistry 2015, 2015 (24) , 5414-5423. https://doi.org/10.1002/ejoc.201500620
    40. Jothi L. Nallasivam, Rodney A. Fernandes. Development of Unimolecular Tetrakis(piperidin‐4‐ol) as a Ligand for Suzuki–Miyaura Cross‐Coupling Reactions: Synthesis of Incrustoporin and Preclamol. European Journal of Organic Chemistry 2015, 2015 (16) , 3558-3567. https://doi.org/10.1002/ejoc.201500353
    41. Supasorn Phae-nok, Chutima Kuhakarn, Manat Pohmakotr, Vichai Reutrakul, Darunee Soorukram. Convenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoin. Organic & Biomolecular Chemistry 2015, 13 (45) , 11087-11095. https://doi.org/10.1039/C5OB01574J
    42. Guopeng Shen, Xin Jia, Sijia Ma, Tiantian Wang, Bin Du, Zhenzhong Zhang. RESOLUTION OF RACEMIC γ-SUBSTITUTED BUTENOLIDE DERIVATIVES USING A POLYSACCHARIDE TYPE STATIONARY PHASE BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY. Journal of Liquid Chromatography & Related Technologies 2014, 37 (6) , 841-849. https://doi.org/10.1080/10826076.2012.758147
    43. Minoo Dabiri, Peyman Salehi, Mahboubeh Bahramnejad, Majid Koohshari, Atousa Aliahmadi. One‐Pot Synthesis of (1,2,3‐Triazolyl)methyl 3,4‐Dihydro‐2‐oxo‐1 H ‐pyrimidine‐5‐carboxylates as Potentially Active Antimicrobial Agents. Helvetica Chimica Acta 2014, 97 (3) , 375-383. https://doi.org/10.1002/hlca.201300198
    44. Rodney A. Fernandes, Pradnya H. Patil, Asim K. Chowdhury. Ring‐Closing Metathesis Enabled Efficient Synthesis of γ ‐Butenolide Antifungal Agent (−)‐Incrustoporin and its Analogues. Asian Journal of Organic Chemistry 2014, 3 (1) , 58-62. https://doi.org/10.1002/ajoc.201300216
    45. Sunil U. Tekale, Sushma S. Kauthale, Vijay P. Pagore, Vivekanand B. Jadhav, Rajendra P. Pawar. ZnO nanoparticle-catalyzed efficient one-pot three-component synthesis of 3,4,5-trisubstituted furan-2(5H)-ones. Journal of the Iranian Chemical Society 2013, 10 (6) , 1271-1277. https://doi.org/10.1007/s13738-013-0266-9
    46. Vijai K. Rai, Priya Tiku, Anil Kumar. Efficient Ce(III)-Catalyzed cis -Selective Synthetic Approach to γ -Lactones in Aqueous Media. Synthetic Communications 2012, 42 (10) , 1489-1499. https://doi.org/10.1080/00397911.2010.540923
    47. Jun-Tae Mo, Hoon Hwang, Phil-Ho Lee. Palladium-Catalyzed Cross-Coupling Reaction and Gold-Catalyzed Cyclization for Preparation of Ethyl 2-Aryl 2,3-Alkadienoates and α-Aryl γ-Butenolides. Bulletin of the Korean Chemical Society 2011, 32 (spc8) , 2911-2915. https://doi.org/10.5012/bkcs.2011.32.8.2911
    48. Hanumant B. Borate, Sangmeshwer P. Sawargave, Subhash P. Chavan, Mohan A. Chandavarkar, Ramki Iyer, Amit Tawte, Deepali Rao, Jaydeep V. Deore, Ananada S. Kudale, Pankaj S. Mahajan, Gopinath S. Kangire. Novel hybrids of fluconazole and furanones: Design, synthesis and antifungal activity. Bioorganic & Medicinal Chemistry Letters 2011, 21 (16) , 4873-4878. https://doi.org/10.1016/j.bmcl.2011.06.022
    49. Yong Lei, Zhi‐Qiang Wang, Ye‐Xiang Xie, Shang‐Ci Yu, Bo‐Xiao Tang, Jin‐Heng Li. Base‐Mediated Tandem Reaction Consisting of an Acyl Shift Strategy Leading to 4,5‐Disubstiuted Furan‐2(5 H )‐ones. Advanced Synthesis & Catalysis 2011, 353 (1) , 31-35. https://doi.org/10.1002/adsc.201000762
    50. Radan Schiller, Lucie Tichotová, Jan Pavlík, Vladimír Buchta, Bohuslav Melichar, Ivan Votruba, Jiří Kuneš, Marcel Špulák, Milan Pour. 3,5-Disubstituted pyranone analogues of highly antifungally active furanones: Conversion of biological effect from antifungal to cytostatic. Bioorganic & Medicinal Chemistry Letters 2010, 20 (24) , 7358-7360. https://doi.org/10.1016/j.bmcl.2010.10.052
    51. Pradeep Mathur, Raj Kumar Joshi, Badrinath Jha, Amrendra K. Singh, Shaikh M. Mobin. Towards the catalytic formation of α,β-vinylesters and alkoxy substituted γ-lactones. Journal of Organometallic Chemistry 2010, 695 (24) , 2687-2694. https://doi.org/10.1016/j.jorganchem.2010.08.036
    52. Petr Šenel, Lucie Tichotová, Ivan Votruba, Vladimír Buchta, Marcel Špulák, Jiří Kuneš, Milan Nobilis, Ondřej Krenk, Milan Pour. Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives. Bioorganic & Medicinal Chemistry 2010, 18 (5) , 1988-2000. https://doi.org/10.1016/j.bmc.2010.01.030
    53. Vojtěch Balšánek, Lucie Tichotová, Jiří Kuneš, Marcel Špulák, Milan Pour, Ivan Votruba, Vladimír Buchta. Cytostatic tetrazole–butenolide conjugates: linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances. Collection of Czechoslovak Chemical Communications 2009, 74 (7-8) , 1161-1178. https://doi.org/10.1135/cccc2009040
    54. Karel Pomeisl, Jan Čejka, Jaroslav Kvíčala, Oldřich Paleta. Synthesis of 3‐Fluorofuran‐2(5 H )‐ones Based on Z / E Photoisomerisation and Cyclisation of 2‐Fluoro‐4‐hydroxybut‐2‐enoates. European Journal of Organic Chemistry 2007, 2007 (35) , 5917-5925. https://doi.org/10.1002/ejoc.200700439
    55. Milan Nobilis, Milan Pour, Petr Šenel, Jan Pavlík, Jiří Kuneš, Marie Vopršalová, Lenka Kolářová, Michal Holčapek. Metabolic profiling of a potential antifungal drug, 3-(4-bromophenyl)-5-acetoxymethyl-2,5-dihydrofuran-2-one, in mouse urine using high-performance liquid chromatography with UV photodiode-array and mass spectrometric detection. Journal of Chromatography B 2007, 853 (1-2) , 10-19. https://doi.org/10.1016/j.jchromb.2007.02.045
    56. Ivan Šnajdr, Jan Pavlík, Radan Schiller, Jiří Kuneš, Milan Pour. Pentenolide Analogues of Antifungal Butenolides: Strategies Towards 3,6-Disubstituted Pyranones and Unexpected Loss of Biological Effect. Collection of Czechoslovak Chemical Communications 2007, 72 (11) , 1472-1498. https://doi.org/10.1135/cccc20071472
    57. L. A. Vale-Silva, V. Buchta, E. Valentová. Effect of subinhibitory concentration of some established and experimental antifungal compounds on the germ tube formation inCandida albicans. Folia Microbiologica 2007, 52 (1) , 39-43. https://doi.org/10.1007/BF02932136
    58. Young Seob Song, Yun-Jeong Lee, Bum Tae Kim, Jung-Nyoung Heo. An efficient procedure for the synthesis of 3-aryl-4-methoxy-2(5H)-furanones by using the microwave-promoted Suzuki–Miyaura coupling reactions. Tetrahedron Letters 2006, 47 (42) , 7427-7430. https://doi.org/10.1016/j.tetlet.2006.08.052
    59. Kamal M. Dawood, Ahmad M. Farag, Hatem A. Abdel‐Aziz. A Convenient Access to Functionalized Pyrazole, Pyrazolyl‐Azole, and Pyrazolo[3,4‐d]Pyridazine Derivatives. Journal of the Chinese Chemical Society 2006, 53 (4) , 873-880. https://doi.org/10.1002/jccs.200600116
    60. Luís A. Vale-Silva, Vladimír Buchta, Doris Vokurková, Milan Pour. Investigation of the mechanism of action of 3-(4-bromophenyl)-5-acyloxymethyl-2,5-dihydrofuran-2-one against Candida albicans by flow cytometry. Bioorganic & Medicinal Chemistry Letters 2006, 16 (9) , 2492-2495. https://doi.org/10.1016/j.bmcl.2006.01.094
    61. Poongavanam Vasanthanathan, Manickavasagam Lakshmi, Marianesan Arockia Babu, Arun Kumar Gupta, Sathish Gopalrao Kaskhedikar. QSAR Study of 3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones as Antifungal Agents: The Dominant Role of Electronic Parameter. Chemical and Pharmaceutical Bulletin 2006, 54 (4) , 583-587. https://doi.org/10.1248/cpb.54.583
    62. O.A. Rakitin. Vinyl and Aryl Chalcogenides: Sulfur-, Selenium-, and Tellurium-based Functional Groups. 2005, 659-707. https://doi.org/10.1016/B0-08-044655-8/00036-2
    63. Ahmad M. Farag, Kamal M. Dawood, Hatem A. Abdel-Aziz. Synthesis of some new pyridazine, 1,2,4-triazine and 1,3,4-thiadiazole derivatives. Journal of Chemical Research 2004, 2004 (12) , 808-810. https://doi.org/10.3184/0308234043431357
    64. Vladimír Buchta, Milan Pour, Petra Kubanová, Luis Silva, Ivan Votruba, Marie Vopršálová, Radan Schiller, Helena Fáková, Marcel Špulák. In Vitro Activities of 3-(Halogenated Phenyl)-5-Acyloxymethyl- 2,5-Dihydrofuran-2-ones against Common and Emerging Yeasts and Molds. Antimicrobial Agents and Chemotherapy 2004, 48 (3) , 873-878. https://doi.org/10.1128/AAC.48.3.873-878.2004
    65. Milan Pour, Marcel Špulák, Vojtěch Balšánek, Jiřı́ Kuneš, Petra Kubanová, Vladimı́r Buchta. Synthesis and structure–antifungal activity Relationships of 3-Aryl-5-alkyl-2,5-dihydrofuran-2-ones and Their Carbanalogues: further refinement of tentative pharmacophore group. Bioorganic & Medicinal Chemistry 2003, 11 (13) , 2843-2866. https://doi.org/10.1016/S0968-0896(03)00220-7
    66. K. Waisser, L. Kubicová, V. Buchta, P. Kubanová, K. Bajerová, L. Jirásková, O. Bednařík, O. Bureš, P. Holý. In vitro antifungal activity of 3-phenyl-2H-benzoxazine-2,4(3H)-diones. Folia Microbiologica 2002, 47 (5) , 488-492. https://doi.org/10.1007/BF02818786
    67. Jaques FGM Meis, Elisabeth J Ruijgrok. Pharmacological agents in development for invasive aspergillosis. Expert Opinion on Emerging Drugs 2002, 7 (1) , 33-45. https://doi.org/10.1517/14728214.7.1.33
    68. Milan Pour, Marcel Spulak, Vladimir Buchta, Petra Kubanova, Marie Voprsalova, Vladimir Wsol, Helena Fakova, Petr Koudelka, Hana Pourova, Radan Schiller. ChemInform Abstract: 3‐Phenyl‐5‐acyloxymethyl‐2H,5H‐furan‐2‐ones: Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs.. ChemInform 2001, 32 (49) https://doi.org/10.1002/chin.200149079
    69. Jiří Kuneš, Vojtěch Balšánek, Milan Pour, Vladimír Buchta. Synthesis and Antifungal Activity Evaluation of 3-Hetaryl-2,5-dihydrofuran-2-ones. An Unusual Fragmentation of the Oxazole Ring via 2,3-Selenoxide Shift. Collection of Czechoslovak Chemical Communications 2001, 66 (12) , 1809-1830. https://doi.org/10.1135/cccc20011809

    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2001, 44, 17, 2701–2706
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm010155x
    Published July 21, 2001
    Copyright © 2001 American Chemical Society

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