Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents

European Journal of Medicinal Chemistry

Volumn 108, Issue , 2016, Pages 166-176

  Ji, Qinggang ^a   Ge, Zhiqiang ^a   Ge, Zhixing ^a   Chen, Kaizhi ^a   Wu, Hualong ^a   Liu, Xiaofei ^a   Huang, Yanrong ^a   Yuan, Lvjiang ^a   Yang, Xiaolan ^b   Liao, Fei ^b  

^a SOUTHWEST UNIVERSITY   (China)

^b CHONGQING MEDICAL UNIVERSITY   (China)

Author keywords

Antifungal agents; Chitin synthase inhibitor; Coumarin; Phosphoramidate

Indexed keywords

4 HYDROXYCOUMARIN; 4 HYDROXYCOUMARIN DERIVATIVE; 4 [(2 HYDROXYETHYL)(METHYL)AMINO] 6 METHYLCOUMARIN; 4 [(2 HYDROXYETHYL)(METHYL)AMINO] 7 METHYLCOUMARIN; 4 [(2 HYDROXYETHYL)(METHYL)AMINO] 8 METHYLCOUMARIN; 4 [(2 HYDROXYETHYL)(METHYL)AMINO]COUMARIN; 6 METHYL 4 HYDROXYCOUMARIN; 6 TERT BUTY 4 HYDROXYCOUMARIN; 7 METHYL 4 HYDROXYCOUMARIN; 8 METHYL 4 HYDROXYCOUMARIN; ANTIFUNGAL AGENT; CHITIN SYNTHASE; COUMARIN; FLUCONAZOLE; GLYCOSYLTRANSFERASE INHIBITOR; METHYL 2 [2 [METHYL(2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]PROPANOATE; METHYL 2 [[2 [METHYL(2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]ACETATE; METHYL 2 [[2 [METHYL(6 METHYL 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]ACETATE; METHYL 2 [[2 [METHYL(6 METHYL 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]PROPANOATE; METHYL 2 [[2 [METHYL(6 TERT BUTY 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)ACETATE; METHYL 2 [[2 [METHYL(6 TERT BUTY 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]PROPANOATE; METHYL 2 [[2 [METHYL(7 METHYL 2 OXO 2H CHROMENA 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]PROPANOATE; METHYL 2 [[2 [METHYL(8 METHYL 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]ACETATE; METHYL 2 [[2 [METHYL(8 METHYL 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]PROPANOATE; METHYL 3 METHYL 2 [[2 (METHYL(8 METHYL 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]BUTANOATE; METHYL 3 METHYL 2 [[2 [METHYL(2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]BUTANOATE; METHYL 3 METHYL 2 [[2 [METHYL(6 TERT BUTY 2 OXO 2H CHROMEN 4 YL)AMINO]ETHOXY](PHENOXY)PHOSPHORYLAMINO]BUTANOATE; PHOSPHORAMIDIC ACID DERIVATIVE; POLYOXIN B; UNCLASSIFIED DRUG; UNINDEXED DRUG; AMIDE; COUMARIN DERIVATIVE; ENZYME INHIBITOR; PHOSPHORAMIDIC ACID; PHOSPHORIC ACID;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; BIOLOGICAL ACTIVITY; CANDIDA TROPICALIS; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IC50; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; ANTAGONISTS AND INHIBITORS; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CHEMISTRY; CRYPTOCOCCUS NEOFORMANS; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; METABOLISM; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMIDES; ANTIFUNGAL AGENTS; ASPERGILLUS FLAVUS; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDA TROPICALIS; CHITIN SYNTHASE; COUMARINS; CRYPTOCOCCUS NEOFORMANS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MICROBIAL SENSITIVITY TESTS; PHOSPHORIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84948427792     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.11.027     Document Type: Article

References (43)

1. MA Pfaller, D.J. Diekem, Epidemiology of invasive candidiasis: a persistent public health problem, Clin. Microbiol. Rev. 20 (2007) 133-163.
2. S. Seyedmousavi, P.E. Verweij, J.W. Mouton, Isavuconazole, a broad-spectrum triazole for the treatment of systemic fungal diseases, Expert Rev. Anti Infect. Ther. 13 (2015) 9-27.
3. M.K. Kathiravan, A.B. Salake, A.S. Chothe, P.B. Dudhe, R.P. Watode, M.S. Mukta, S. Gadhwe, The biology and chemistry of antifungal agents: a review, Bioorg Med. Chem. 20 (2012) 5678-5698.
4. D.S. Perlin, Resistance to echinocandin-class antifungal drugs, Drug Resist Update 10 (2007) 121-130.
5. LA. Walker, N.A.R. Gow, CA. Munro, Fungal echinocandin resistance, Fungal Genet. Biol. 47 (2010) 117-126.
6. P.E. Verweij, E. Snelders, G.H. Kema, E. Mellado, W.J.G. Melchers, Azole resistance in Aspergillus fumigatus: a side-effect of environmental fungicide use ? Lancet Infect. Dis. 9 (2009) 789-795.
7. RJ. Scheffler, S. Colmer, H. Tynan, A.L. Demain, V.P. Gullo, Antimicrobials, drug discovery, and genome mining, Microbiol. Biotechnol. 97 (2013) 969-978.
8. W.Z. Jiang, S. Cossey, J. Rosenberg, G. Oyler, B. Olson, D. Weeks, A rapid live-cell ELISA for characterizing antibodies against cell surface antigens of Chla-mydomonas reinhardtii and its use in isolating algae from natural environments with related cell wall components, BMC Plant Biol. 14 (2014) 244.
9. A.R. Yeagera, N.S. Finney, Second-generation dimeric inhibitors of chitin synthase, Bioorg Med. Chem. 12 (2004) 6451-6460.
10. H. Magellan, M. Boccara, T. Drujon, M.C. Soulie, C. Guillou, J. Dubois, H.F. Becker, Discovery of two new inhibitors of Botrytis cinerea chitin synthase by a chemical library screening, Bioorg Med. Chem. 21 (2013) 4997-5003.
11. V. Aimanianda, J.P. Latge, Problems and hopes in the development of drugs targeting the fungal cell wall, Expert Rev. Anti Infect. Ther. 8 (2010) 359-364.
12. P.M. Chaudhary, S.G. Tupe, M.V. Deshpande, Chitin synthase inhibitors as antifungal agents, Mini-rev Med. Chem. 13 (2013) 222-236.
13. M.D. Lenardon, CA. Munr, N.A.R. Gow, Chitin synthesis and fungal pathogenesis, Curr. Opin. Microbiol. 13 (2010) 416-423.
14. K.E. Jackson, P.K. Pogula, S.E. Patterson, Polyoxin and nikkomycin analogs: recent design and synthesis of novel peptidyl nucleosides, Heterocycl. Commun. 19 (2013) 375-386.
15. X.M. Peng, G.L.V. Damu, C.H. Zhou, Current developments of coumarin compounds in medicinal chemistry, Curr. Pharm. Des. 19 (2013) 3884-3930.
16. N. Renuka, K.A. Kumar, Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents, Bioorg Med. Chem. Lett. 23 (2013) 6406-6409.
17. A. Gomez-Outes, M.L. Suarez-Gea, G. Calvo-Rojas, R. Lecumberri, E. Rocha, C. Pozo-Hernandez, A.I. Terleira-Fernandez, E. Vargas-Castrillon, Discovery of anticoagulant drugs: a historical perspective, Curr. Drug Discov. Technol. 9 (2012) 83-104.
18. I. Mitra, A. Saha, K. Roy, Quantification of contributions of different molecular fragments for antioxidant activity of coumarin derivatives based on QSAR analyses, Can. J. Chem. 91 (2013) 428-441.
19. Y. Bansal, P. Sethi, G. Bansal, Coumarin: a potential nucleus for antiinflammatory molecules, Med. Chem. Res. 22 (2013) 3049-3060.
20. R.S. Keri, K.M. Hosamani, R.V. Shingalapur, M.H. Hugar, Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety, Eur. J. Med. Chem. 45 (2010) 2597-2605.
21. L.D. Via, O. Gia, S.M. Magno, L Santana, M. Teijeira, E. Uriarte, New tetracyclic analogues of photochemotherapeutic drugs 5-MOP and 8-MOP: synthesis, DNA interaction, and antiproliferative activity, J. Med. Chem. 42 (1999) 4405-4413.
22. C. Spino, M. Dodier, S. Sotheeswaran, Anti-HIV coumarins from calophyllum seed oil, Bioorg Med. Chem. Lett. 8 (1998) 3475-3478.
23. J.R. Hwu, R. Singha, S.C. Hong, Y.H. Chang, A.R. Das, I. Vliegen, E.D. Clercq, J. Neyts, Synthesis of new benzimidazoleecoumarin conjugates as anti-hepatitis C virus agents, Antivir. Res. 77 (2008) 157-162.
24. R. Kumar, A. Saha, D. Saha, A new antifungal coumarin from Clausena excavata, Fitoterapia 83 (2012) 230-233.
25. S.U. Rehman, Z.H. Chohan, F. Gulnaz, C.T. Supuran, In-vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes, J. Enzym. Inhib. Med. Ch 20 (2005) 333-340.
26. M. Mladenovic, N. Vukovic, N. Niciforovic, S. Sukdolak, S. Solujic, Synthesis and molecular descriptor characterization of novel 4-Hydroxy-chromene-2-one derivatives as antimicrobial agents, Molecules 14 (2009) 1495-1512.
27. C. Subramanyam, K.V. Ramana, S. Rasheed, S. Adam, C.N. Raju, Synthesis and biological activity of novel diphenyl N-substituted carbamimidoylphos-phoramidate derivatives, Phosphorus, Sulfur, Silicon 188 (2013) 1228-1235.
28. X.L. Chen, J.W. Yuan, S.R. Zhang, L.B. Qu, Y.F. Zhao, Synthesis of the novel phosphoramidate derivatives of chrysin, Phosphorus, Sulfur, Silicon 185 (2010) 274-278.
29. Z.W. Wang, C.C. Guo, W.Z. Xie, C.Z. Liu, C.G. Xiao, Z. Tan, Novel phosphor-amidates with porphine and nitrogenous drug: one-pot synthesis and orientation to cancer cells, Eur. J. Med. Chem. 45 (2010) 890-895.
30. B.S. Ross, P.G. Reddy, H.R. Zhang, S. Rachakonda, M.J. Sofia, Synthesis of dia-stereomerically pure nucleotide phosphoramidates, J. Org. Chem. 76 (2011) 8311-8319.
31. A. Cho, LJ. Zhang, J. Xu, R. Lee, T. Butler, S. Metobo, V. Aktoudianakis, W. Lew, H. Ye, M. Clarke, E. Doerffler, D. Byun, T. Wang, D. Babusis, A.C. Carey, P. German, D. Sauer, W.D. Zhong, S. Rossi, M. Fenaux, J.G. McHutchison, J. Perry, J. Feng, A.S. Ray, CU. Kim, Discovery of the first c-nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients, J. Med. Chem. 57 (2014) 1812-1825.
32. J.H. Cho, L. Bondana, MA Detorio, C. Montero, LC. Bassit, F. Amblard, S.J. Coats, R.F. Schinazi, Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs, Bioorg Med. Chem. 22 (2014) 6665-6671.
33. B.S. Kumar, M.V.N. Reddy, G.C.S. Reddy, A.B. Krishna, CS. Reddy, Synthesis and antimicrobial activity of 2,10-dichloro-6-substituted amino acid ester-12H-dibenzo[d,g][1,3,2]dioxaphosphocin-6-oxides, Bulg. Chem. Commun. 41 (2009) 422-426.
34. M.D. Disney, T. Matray, S.M. Gryaznov, D.H. Turner, Binding enhancement by tertiary interactions and suicide inhibition of a Candida albicans group I intron by phosphoramidate and 2¢-O-methyl hexanucleotides, Biochemistry 40 (2001) 6520-6526.
35. D.R. Buckle, B.C.C. Cantello, H. Smith, B.A. Spicer, Antiallergic activity of 4-Hydroxy-3-nitrocoumarins, J. Med. Chem. 18 (1975) 391-394.
36. M.L.N. Rao, A. Kumar, Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents, Tetrahedron 70 (2014) 6995-7005.
37. Y.Z. Dong, K. Nakagawa-Goto, C.Y. Lai, S.L Morris-Natschke, K.F. Bastow, K.H. Lee, Antitumor agents 281. Design, synthesis, and biological activity of substituted 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one analogs (ATBO) as potent in vitro anticancer agents, Bioorg Med. Chem. Lett. 21 (2011) 546-549.
38. CM. Ma, R.H. Cao, B.X. Shi, S.X. Li, Z.Y. Chen, W. Yi, W.L Peng, Z.H. Ren, H.C. Song, Synthesis and cytotoxic evaluation of N2-benzylated quaternary b-carboline amino acid ester conjugates, Eur. J. Med. Chem. 45 (2010) 1515-1523.
39. M. Slusarczyk, M.H. Lopez, J. Balzarini, M. Mason, W.G. Jiang, S. Blagden, E. Thompson, E. Ghazaly, C McGuigan, Application of ProTide technology to gemcitabine: a successful approach to overcome the key cancer resistance mechanisms leads to a new agent (NUC-1031) in clinical development, J. Med. Chem. 57 (2014) 1531-1542.
40. HA Lucero, M.J. Kuranda, D.A. Bulik, A. Nonradioactive, High throughput assay for chitin synthase activity, Anal. Biochem. 305 (2002) 97-105.
41. X. Zhang, K.Y. Zhu, Biochemical characterization of chitin synthase activity and inhibition in the African malaria mosquito, Anopheles gambiae, J. Insect. Sci. 20 (2013) 158-166.
42. Q.G. Ji, D. Yang, X. Wang, CY. Chen, Q. Deng, Z.Q. Ge, LJ. Yuan, X.L. Yang, F. Liao, Design, synthesis and evaluation of novel quinazoline-2,4-dione de rivatives as chitin synthase inhibitors and antifungal agents, Bioorg Med. Chem. 22 (2014) 3405-3413.
43. NCCLS (National Committee for Clinical Laboratory Standards), Performance Standards for Antimicrobial Susceptibility Testing: Twelfth Informational Supplement, 2002, 1-56238-454-6 M100-S12(M7).