Recent advances in antifungal fluconazole

Chinese Journal of Antibiotics

Volumn 37, Issue 1, 2012, Pages 8-15

  Kun, Wan ^a   Zhang, Yi Yi ^a   Zhou, Cheng He ^a   Zhou, Xiang Dong ^b   Geng, Rong Xia ^a   Ji, Qing Gang ^a  

^a SOUTHWEST UNIVERSITY   (China)

^b THIRD MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Antifungal; Antitumor; Fluconazole; Supermolecule; Synthesis

Indexed keywords

FLUCONAZOLE;

ARTICLE; DRUG SAFETY; DRUG STRUCTURE; SUPRAMOLECULAR CHEMISTRY;

EID: 84865135008     PISSN: 10018689     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (47)

1. Vensel Hilley T D. Fluconazole: a valuable fungitatic[J]. Antibiot Rev, 2002, 9 (5): 181-183.
2. Lebouvier N, Pagniez F, Duflos M, et al. Synthesis and antifungal activities of new fluconazole analogues with azaheterocycle moiety[J]. Bioorg Med Chem Lett, 2007, 17 (13): 3686-3689.
3. Aher N G, Pore V S, Mishra N N, et al. Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues[J]. Bioorg Med Chem Lett, 2009, 19 (3): 759-763.
4. Richardson K. Antifungal 1,3-bis-triazolyl-2-propanol derivative: US, 4404216[P]. 1983-09-13.
5. Chinese source, 2006, 23 (1): 35-37.
6. Palomo C A. Process for preparing biologically active derivatives of 1,2,4-triazol and intermediaries useful in this process: EP 00967210A1[P]. 1999-12-29.
7. Murthy K, Weeeratunga G, Norris D J. Methods for the manufacture of fluconazole: US, 5508423 A[P]. 1996-04-16.
8. Chinese source 2002, 12 (6):344-346.
9. Giraud F, Guillon R, Logé C, et al. Synthesis and structureactivity relationships of 2-phenyl-1-[(pyridinyl and piperidinylmethyl)amino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents[J]. Bioorg Med Chem Lett, 2009, 19 (2): 301-304.
10. Aher N G, Pore V S, Mishra N N, et al. Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues[J]. Bioorg Med Chem Lett, 2009, 19 (3): 759-763.
11. Yu G P, Xu L Z, Yi X, et al. Synthesis and fungicidal evaluation of 2-arylphenylether-3-(1H-1,2,4-triazol- 1-yl) propan-2-ol derivatives[J]. J Agric Food Chem, 2009, 57(11): 4854-4860.
12. Chinese source, 2007, 32 (17): 583-583.
13. Yu S C, Chai X Y, Hu H G, Yan Y Z, Guan Z J, Zou Y, Sun Q Y, Wu Q Y. Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14a-demethylase[J]. Eur J Med Chem, 2010, 45(10): 4435-4445.
14. Hecker S J, Erion M D. Prodrugs of phosphates and phosphonates[J]. J Med Chem, 2008, 51 (8): 2328-2345.
15. Bentley A, Butters M, Green S P, et al. The discovery and process development of a commercial route to the water soluble prodrug, fosfluconazole[J]. Organ Prog Res Develop, 2002, 6 (2): 109-112.
16. Sobue S, Tan K, Haug-Pihale G. The effects of hepatic impairment on the pharmacokinetics of fosfluconazole and fluconazole following a single intravenous bolus injection of fosfluconazole[J]. Br J Clin Pharmocol, 2005, 59 (2): 160-166.
17. Sobue S, Tan K, Layton G, et al. The effects of renal impairment on the pharmacokinetics and safety of fosfluconazole and fluconazole following a single intravenous bolus injection of fosfluconazole[J]. Br J Clin Pharmocol, 2004, 57 (6): 773-784.
18. Nam N H, Sardari S, Selecky M, et al. Carboxylic acid and phosphate ester derivatives of fluconazole: synthesis and antifungal activities[J]. Bioog Med Chem, 2004, 12 (23): 6255-6269.
19. Mora S J, Cormick M P, Milanesio M E, et al. The photodynamic activity of a novel porphyrin derivative bearing a fluconazole structure in different media and against Candida albicans[J]. Dyes Pig, 2010, 87(3): 234-240.
20. Cormick M P, Rovera M, Durantini E N. Synthesis, spectroscopic properties and photodynamic activity of a novel Zn (II) phthalocyanine substituted by fluconazole groups[J]. J Photochem Photobiol A: Chem, 2008, 194 (2,3): 220-229.
21. Emami S, Foroumadi A, Falahati M, et al. 2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents[J]. Bioorg Med Chem Lett, 2008, 18 (1): 141-146.
22. Francavilla C, Low E, Nair S, et al. Quaternary ammonium N,N-dichloroamines as topical antimicrobial agents[J]. Bioorg Med Chem Lett, 2009, 19 (10): 2731-2734.
23. Luo Y, Lu Y H, Gan L L, et al. Synthesis, antibacterial and antifungal activities of novel 1,2,4- triazolium derivatives[J]. Arch Pharm, 2009, 342 (7): 386-393.
24. Zhang F F, Gan L L, Zhou C H. Synthesis, antibacterial and antifungal activities of some carbazole derivative[J]. Bioorg Med Chem Lett, 2010, 20 (6): 1881-1884.
25. Wan K, Zhou C H. Synthesis of novel halobenzyloxy and alkoxy 1,2,4-triazoles and evaluation for their antifungal and antibacterial activities[J]. Bull Korean Chem Soc, 2010, 31 (7): 2003-2010.
26. Wang X L, Wan K, Zhou C H. Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities[J]. Eur J Med Chem, 2010, 45 (10): 4631-4639.
27. Wei J J, Jin L, Wan K, et al. Synthesis of novel D-glucosederived benzyl and alkyl 1,2,3-triazoles as potential antifungal and antibacterial agents[J]. Bull Korean Chem Soc, 2011, 32 (1): 229-238.
28. Chinese source, 2011, 41 (3): 451-460.
29. Fang B, Zhou C H, Rao X C. Synthesis and biological activities of novel amine-derived bis-azoles as potential antibacterial and antifungal agents[J]. Eur J Med Chem, 2010, 45 (9): 4388-4398.
30. Shi Y, Zhou C H. Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents[J]. Bioorg Med Chem Lett, 2011, 21 (3): 956-960.
31. Zhang Y Y, Mi J L, Zhou C H, et al. Synthesis of novel fluconazoliums and their evaluation for antibacterial and antifungal activities[J]. Eur J Med Chem, 2011, 46(9): 4391-4402.
32. Molina J, Brener Z, Romanha A J, et al. In vivo activity of the bis-triazole D0870 against drug-susceptible and drugresistant strains of the protozoan parasite Trypanosoma cruzi[J]. J Antimicrob Chemother, 2000, 46 (1): 137-140.
33. Schell W A., Almeida G M D D, Dodge R K, et al. In vitro and in vivo efficacy of the triazole TAK-187 against Cryptococcus neoformans[J]. Antimicrob Agents Chemother, 1998, 42 (10): 2630-2632.
34. Zhou C H, Gan L L, Zhang Y Y, et al. Researches in supermolecules as chemical drugs[J]. Sci China Ser B-Chem, 2009, 52 (4): 415-458.
35. Chinese source, 2009, 39 (3): 208-252.
36. Zhang L, Ling Y, Du M. Synthesis, crystal structures and in vitro antifungal activities of two silver(I) coordination polymers with fluconazole[J]. Inorg Chimi Acta, 2007, 360 (10): 3182-3188.
37. Gaccioli F, Franchi-Gazzola R, Lanfranchi M, et al. Synthesis, solution equilibria and antiproliferative activity of copper(II) aminomethyltriazole and aminomethylthioxotriazoline complexes[J]. J Inorg Biochem, 2005, 99 (8): 1573-1584.
38. Upadhyay S K, Kumar G. NMR and molecular modelling studies on the interaction of fluconazole with betacyclodextrin[J]. Chem Cent J, 2009, 3 (9): 1-9.
39. Al-Marzouqi A H, Elwya H M, Shehadib I, et al. Physicochemical properties of antifungal drug-cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques[J]. J Pharm Biomed Anal, 2009, 49 (2): 227-233.
40. Zhao S S, Du Q, Cao DY. Preparation of liposomal fluconazole gel and in vitro transdermal delivery[J]. J Chin Pharma Sci, 2007, 16 (2): 116-118.
41. Barchiesi F, Schimizzi A M, Caselli F, et al. Interactions between triazoles and amphotericin B against Cryptococcus neoformans[J]. Antimicrob Agents Chemother, 2000, 44 (9): (???20?)
42. Karatza A A, Dimitriou G, Marangos M, et al. Successful resolution of cardiac mycetomas by combined liposomal amphotericin B with fluconazole treatment in premature neonates[J]. Eur J Pediatr, 2008, 167 (9): 1021-1023.
43. Mosquera J, Sharp A, Moore C B, et al. In vitro interaction of terbinafine with itraconazole, fluconazole, amphotericin B and 5-flucytosine against Aspergillus spp.[J]. J Antimicrob Chemoter, 2002, 50 (2): 189-194.
44. Schwarz P, Dromer F, Lortholary O, et al. In vitro interaction of flucytosine with conventional and new antifungals against Cryptococcus neoformans clinical isolates[J]. Antimicrob Agents Chemother, 2003, 47 (10): 3361-3364.
45. Roling E E, Klepser M E, Wasson A, et al. Antifungal activities of fluconazole, caspofungin (MK0991), and anidulafungin (LY 303366) alone and in combination against Candida spp. and Crytococcus neoformans via time-kill methods[J]. Diagn Micr Infect Dis, 2002, 43 (1): 13-17.
46. Karlowsky J A, Hoban D J, Zhanel G G., et al. In vitro interactions of anidulafungin with azole antifungals, amphotericin B and 5-fluorocytosine against Candida species[J]. Int J Antimicrob Agents, 2006, 27 (2): 174-177.
47. Serena C, Mariné M, Pastor F J, et al. In vitro interaction of micafungin with conventional and new antifungals against clinical isolates of Trichosporon, Sporobolomyces and Rhodotorula[J]. J Antimicrob Chemoter, 2005, 55 (6): 1020-1023.