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Volumn 20, Issue 5, 2015, Pages 8666-8686

Synthesis, antiproliferative and antifungal activities of 1,2,3-Triazole-substituted carnosic acid and carnosol derivatives

Author keywords

Antifungal; Antiproliferative; Carnosic Acid; Carnosol; Click Chemistry

Indexed keywords

ABIETANE DERIVATIVE; ANTIFUNGAL AGENT; CARNOSIC ACID; CARNOSOL; PLANT EXTRACT; TRIAZOLE DERIVATIVE;

EID: 84948134503     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules20058666     Document Type: Article
Times cited : (33)

References (30)
  • 1
    • 84905158330 scopus 로고    scopus 로고
    • The value of nature's natural product library for the discovery of new chemical entities: The discovery of ingenol mebutate
    • Ogbourne, S.M.; Parsons, P.G. The value of nature's natural product library for the discovery of new chemical entities: The discovery of ingenol mebutate. Fitoterapia 2014, 98, 36-44.
    • (2014) Fitoterapia , vol.98 , pp. 36-44
    • Ogbourne, S.M.1    Parsons, P.G.2
  • 3
    • 84908043657 scopus 로고    scopus 로고
    • Synthetic derivatives of aromatic abietane diterpenoids and their biological activities
    • González, M.A. Synthetic derivatives of aromatic abietane diterpenoids and their biological activities. Eur. J. Med. Chem. 2014, 87, 834-842.
    • (2014) Eur. J. Med. Chem , vol.87 , pp. 834-842
    • González, M.A.1
  • 4
    • 84917727174 scopus 로고    scopus 로고
    • Multiple pro-Apoptotic targets of abietane diterpenoids from Salvia species
    • Akaberi, M.; Mehri, S.; Iranshahi, M. Multiple pro-Apoptotic targets of abietane diterpenoids from Salvia species. Fitoterapia 2015, 100, 118-132.
    • (2015) Fitoterapia , vol.100 , pp. 118-132
    • Akaberi, M.1    Mehri, S.2    Iranshahi, M.3
  • 5
    • 28444448319 scopus 로고    scopus 로고
    • Fast high performance liquid chromatography and ultraviolet-visible quantification of principal phenolic antioxidants in fresh rosemary
    • Troncoso, N.; Sierra, H.; Carvajal, L.; Delpiano, P.; Günther, G. Fast high performance liquid chromatography and ultraviolet-visible quantification of principal phenolic antioxidants in fresh rosemary. J. Chromatogr. A 2005, 1100, 20-25.
    • (2005) J. Chromatogr. A , vol.1100 , pp. 20-25
    • Troncoso, N.1    Sierra, H.2    Carvajal, L.3    Delpiano, P.4    Günther, G.5
  • 7
    • 9244231265 scopus 로고    scopus 로고
    • Antibacterial and resistance modifying activity of Rosmarinus officinalis
    • Oluwatuyi M.; Kaatz, G.W.; Gibbons, S. Antibacterial and resistance modifying activity of Rosmarinus officinalis. Phytochemistry 2004, 65, 3249-3254.
    • (2004) Phytochemistry , vol.65 , pp. 3249-3254
    • Oluwatuyi, M.1    Kaatz, G.W.2    Gibbons, S.3
  • 9
    • 84921454591 scopus 로고    scopus 로고
    • HPLC-SPE-NMR characterization of major metabolites in Salvia fruticosa Mill Extract with antifungal potential: Relevance of carnosic acid, carnosol, and hispidulin
    • Exarchou, V.; Kanetis, L.; Charalambous, Z.; Apers, S.; Pieters, L.; Gekas, V.; Goulas, V. HPLC-SPE-NMR characterization of major metabolites in Salvia fruticosa Mill. Extract with antifungal potential: Relevance of carnosic acid, carnosol, and hispidulin. J. Agric. Food Chem. 2015, 63, 457-463.
    • (2015) J. Agric. Food Chem , vol.63 , pp. 457-463
    • Exarchou, V.1    Kanetis, L.2    Charalambous, Z.3    Apers, S.4    Pieters, L.5    Gekas, V.6    Goulas, V.7
  • 11
    • 79953171483 scopus 로고    scopus 로고
    • A promising anti-cancer and anti-inflammatory agent
    • Johnson, J.J. Carnosol: A promising anti-cancer and anti-inflammatory agent. Cancer Lett. 2011, 305, 1-7.
    • (2011) Cancer Lett , vol.305 , pp. 1-7
    • Johnson, J.J.1    Carnosol2
  • 14
    • 84893137519 scopus 로고    scopus 로고
    • Gastroprotective mechanisms of action of semisynthetic carnosic acid derivatives in human cells
    • Theoduloz, C.; Pertino, M.W.; Schmeda-Hirschmann, G. Gastroprotective mechanisms of action of semisynthetic carnosic acid derivatives in human cells. Molecules 2014, 19, 581-594.
    • (2014) Molecules , vol.19 , pp. 581-594
    • Theoduloz, C.1    Pertino, M.W.2    Schmeda-Hirschmann, G.3
  • 15
    • 43449108552 scopus 로고    scopus 로고
    • Efficient construction of terapeutics bioconjugates biomaterials and bioactive surfaces using azide-Alkyne click chemistry
    • Lutz, J.; Zoya, Z. Efficient construction of terapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-Alkyne "click" chemistry. Adv. Drug Deliver Rev. 2008, 60, 958-979.
    • (2008) Adv. Drug Deliver Rev , vol.60 , pp. 958-979
    • Lutz, J.1    Zoya, Z.2
  • 16
    • 0030056717 scopus 로고    scopus 로고
    • Identification and characterization of human metabolites of CAI [5-Amino-1-1(4′-chlorobenzoyl-3, 5-dichlorobenzyl)-1, 2, 3-Triazole-4-carboxamide
    • Soltis, M.J.; Yeh, H.J.; Cole, K.A.; Whittaker, N.; Wersto, R.P.; Kohn, E.C. Identification and characterization of human metabolites of CAI [5-Amino-1-1(4′-chlorobenzoyl-3, 5-dichlorobenzyl)-1, 2, 3-Triazole-4-carboxamide). Drug Metab. Dispos. 1996, 24, 799-806.
    • (1996) Drug Metab. Dispos , vol.24 , pp. 799-806
    • Soltis, M.J.1    Yeh, H.J.2    Cole, K.A.3    Whittaker, N.4    Wersto, R.P.5    Kohn, E.C.6
  • 17
    • 42949170958 scopus 로고    scopus 로고
    • Phase III randomized, double-blind study of maintenance CAI or placebo in patients with advanced non-small cell lung cancer (NSCLC) after completion of initial therapy (NCCTG 97-24-51
    • Johnson, E.A.; Marks, R.S.; Mandrekar, S.J.; Hillman, S.L.; Hauge, M.D.; Bauman, M.D.; Wos, E.J.; Moore, D.F.; Kugler, J.W.; Windschitl, H.E.; et al. Phase III randomized, double-blind study of maintenance CAI or placebo in patients with advanced non-small cell lung cancer (NSCLC) after completion of initial therapy (NCCTG 97-24-51). Lung Cancer 2008, 60, 200-207.
    • (2008) Lung Cancer , vol.60 , pp. 200-207
    • Johnson, E.A.1    Marks, R.S.2    Mandrekar, S.J.3    Hillman, S.L.4    Hauge, M.D.5    Bauman, M.D.6    Wos, E.J.7    Moore, D.F.8    Kugler, J.W.9    Windschitl, H.E.10
  • 18
    • 77951103833 scopus 로고    scopus 로고
    • N-((1-Benzyl-1H-1, 2, 3-Triazol-4-yl)methyl)arylamide as a new scaffold that provides rapid access to antimicrotubule agents: Synthesis and evaluation of antiproliferative activity against select cancer cell lines
    • Stefely, J.A.; Palchaudhuri, R.; Miller, P.A.; Peterson, R.J.; Moraski, G.C.; Hergenrother, P.J.; Miller, M.J. N-((1-Benzyl-1H-1, 2, 3-Triazol-4-yl)methyl)arylamide as a new scaffold that provides rapid access to antimicrotubule agents: Synthesis and evaluation of antiproliferative activity against select cancer cell lines. J. Med. Chem. 2010, 53, 3389-3395.
    • (2010) J. Med. Chem , vol.53 , pp. 3389-3395
    • Stefely, J.A.1    Palchaudhuri, R.2    Miller, P.A.3    Peterson, R.J.4    Moraski, G.C.5    Hergenrother, P.J.6    Miller, M.J.7
  • 19
    • 84872683595 scopus 로고    scopus 로고
    • Design and synthesis of novel 1, 2, 3-Triazole-dithiocarbamate hybrids as potential anticancer agents
    • Duan, Y.C.; Ma, Y.C.; Zhang, E.; Shi, X.J.; Wang, M.M.; Ye, X.W.; Liu, H.M. Design and synthesis of novel 1, 2, 3-Triazole-dithiocarbamate hybrids as potential anticancer agents. Eur. J. Med. Chem. 2013, 62, 11-19.
    • (2013) Eur. J. Med. Chem , vol.62 , pp. 11-19
    • Duan, Y.C.1    Ma, Y.C.2    Zhang, E.3    Shi, X.J.4    Wang, M.M.5    Ye, X.W.6    Liu, H.M.7
  • 20
    • 84882556503 scopus 로고    scopus 로고
    • Design synthesis and biological evaluation of novel mansonone e derivatives prepared via CuAAC click chemistry as topoisomerase II inhibitors
    • Huang, Z.H.; Zhuo, S.T.; Li, C.Y.; Xie, H.T.; Li, D.; Tan, J.H.; Ou, T.M.; Huang, Z.H.; Gu, L.Q.; Huang, S.L. Design, synthesis and biological evaluation of novel mansonone E derivatives prepared via CuAAC click chemistry as topoisomerase II inhibitors. Eur. J. Med. Chem. 2013, 68, 58-71.
    • (2013) Eur. J. Med. Chem , vol.68 , pp. 58-71
    • Huang, Z.H.1    Zhuo, S.T.2    Li, C.Y.3    Xie, H.T.4    Li, D.5    Tan, J.H.6    Ou, T.M.7    Huang, Z.H.8    Gu, L.Q.9    Huang, S.L.10
  • 21
    • 84878343968 scopus 로고    scopus 로고
    • Dimeric labdane diterpenes: Synthesis and antiproliferative effects
    • Pertino, M.W.; Theoduloz, C.; Bastías, M.; Schmeda-Hirschmann, G. Dimeric labdane diterpenes: synthesis and antiproliferative effects. Molecules 2013, 18, 5936-5953.
    • (2013) Molecules , vol.18 , pp. 5936-5953
    • Pertino, M.W.1    Theoduloz, C.2    Bastías, M.3    Schmeda-Hirschmann, G.4
  • 22
    • 84880781906 scopus 로고    scopus 로고
    • 1, 2, 3-Triazole-substituted oleanolic acid derivatives: Synthesis and antiproliferative activity
    • Pertino, M.W.; Lopez, C.; Theoduloz, C.; Schmeda-Hirschmann, G. 1, 2, 3-Triazole-substituted oleanolic acid derivatives: Synthesis and antiproliferative activity. Molecules 2013, 18, 7661-7674.
    • (2013) Molecules , vol.18 , pp. 7661-7674
    • Pertino, M.W.1    Lopez, C.2    Theoduloz, C.3    Schmeda-Hirschmann, G.4
  • 23
    • 84894620086 scopus 로고    scopus 로고
    • Synthesis and antiproliferative activity of some novel triazole derivatives from dehydroabietic acid
    • Pertino, M.W.; Verdugo, V.; Theoduloz, C.; Schmeda-Hirschmann, G. Synthesis and antiproliferative activity of some novel triazole derivatives from dehydroabietic acid. Molecules 2014, 19, 2523-2535.
    • (2014) Molecules , vol.19 , pp. 2523-2535
    • Pertino, M.W.1    Verdugo, V.2    Theoduloz, C.3    Schmeda-Hirschmann, G.4
  • 25
    • 77956182470 scopus 로고    scopus 로고
    • Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase
    • Yu, S.; Chai, X.; Hu, H.; Yan, Y.; Guan, Z.; Zou, Y.; Sun, Q.; Wu, Q. Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase. Eur. J. Med. Chem. 2010, 45, 4435-4445.
    • (2010) Eur. J. Med. Chem , vol.45 , pp. 4435-4445
    • Yu, S.1    Chai, X.2    Hu, H.3    Yan, Y.4    Guan, Z.5    Zou, Y.6    Sun, Q.7    Wu, Q.8
  • 26
    • 84859445044 scopus 로고    scopus 로고
    • New triazole derivatives as antifungal agents: Synthesis via click reaction, in vitro evaluation and molecular docking studies
    • Zou, Y.; Zhao, Q.; Liao, J.; Hu, H.; Yu, S.; Chai, X.; Xu, M.; Wu, Q. New triazole derivatives as antifungal agents: Synthesis via click reaction, in vitro evaluation and molecular docking studies. Bioorg. Med. Chem. Lett. 2012, 22, 2959-2962.
    • (2012) Bioorg. Med. Chem. Lett , vol.22 , pp. 2959-2962
    • Zou, Y.1    Zhao, Q.2    Liao, J.3    Hu, H.4    Yu, S.5    Chai, X.6    Xu, M.7    Wu, Q.8
  • 27
    • 84868603721 scopus 로고    scopus 로고
    • Click chemistry inspired structural modification of azole antifungal agents to synthesize novel drug like molecules
    • Pericherla, K.; Khedar, P.; Khungar, B.; Kumar, A. Click chemistry inspired structural modification of azole antifungal agents to synthesize novel "drug like" molecules. Tetrahedron Lett. 2012, 53, 6761-6764.
    • (2012) Tetrahedron Lett , vol.53 , pp. 6761-6764
    • Pericherla, K.1    Khedar, P.2    Khungar, B.3    Kumar, A.4
  • 28
  • 29
    • 84878284551 scopus 로고    scopus 로고
    • approved standard-3rd ed., CLSI Document M27-A3; CLSI: Wayne, PA, USA Clinical and Laboratory Standards Institute
    • Clinical and Laboratory Standards Institute. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; approved standard-3rd ed., CLSI Document M27-A3; CLSI: Wayne, PA, USA, 2008; Volume 28, pp. 1-25.
    • (2008) Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts , vol.28 , pp. 1-25
  • 30
    • 84983667190 scopus 로고    scopus 로고
    • OriginLab: Northampton, MA, USA
    • OriginPro 8.1; OriginLab: Northampton, MA, USA, 2012.
    • (2012) OriginPro 8.1


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