메뉴 건너뛰기




Volumn 19, Issue 11, 2014, Pages 18676-18689

Design and synthesis of isosteviol triazole conjugates for cancer therapy

Author keywords

Anticancer activity; Click chemistry; Isosteviol; Triazole conjugates

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOTOXIN; ISOSTEVIOL; KAURANE DERIVATIVE; TRIAZOLE DERIVATIVE;

EID: 84912058912     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules191118676     Document Type: Article
Times cited : (34)

References (35)
  • 1
    • 42949160050 scopus 로고    scopus 로고
    • Natural products as leads to potential drugs: An old process or the new hope for drug discovery?
    • Newman, D.J. Natural products as leads to potential drugs: An old process or the new hope for drug discovery? J. Med. Chem. 2008, 51, 2589-2599
    • (2008) J. Med. Chem. , vol.51 , pp. 2589-2599
    • Newman, D.J.1
  • 2
    • 67650675111 scopus 로고    scopus 로고
    • Impact of natural products on developing new anti-cancer agents
    • Cragg, G.M.; Grothaus, P.G.; Newman, D.J. Impact of natural products on developing new anti-cancer agents. Chem. Rev. 2009, 109, 3012-3043
    • (2009) Chem. Rev. , vol.109 , pp. 3012-3043
    • Cragg, G.M.1    Grothaus, P.G.2    Newman, D.J.3
  • 3
    • 84858308226 scopus 로고    scopus 로고
    • Natural products as sources of new drugs over the 30 years from 1981 to 2010
    • Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 2012, 75, 311-335
    • (2012) J. Nat. Prod. , vol.75 , pp. 311-335
    • Newman, D.J.1    Cragg, G.M.2
  • 4
    • 0034748170 scopus 로고    scopus 로고
    • The antihypertensive effects of stevioside derivative isosteviol in spontaneously hypertensive rats
    • Liu, J.C.; Kao, P.F.; Hsieh, M.H.; Chen, Y.J.; Chan, P. The antihypertensive effects of stevioside derivative isosteviol in spontaneously hypertensive rats. Acta Cardiol. Sin. 2001, 17, 133-140
    • (2001) Acta Cardiol. Sin. , vol.17 , pp. 133-140
    • Liu, J.C.1    Kao, P.F.2    Hsieh, M.H.3    Chen, Y.J.4    Chan, P.5
  • 5
    • 1542284229 scopus 로고    scopus 로고
    • Isosteviol as a potassium channel opener to lower intracellular calcium concentrations in cultured aortic smooth muscle cells
    • Wong, K.L.; Yang, H.Y.; Chan, P.; Cheng, T.H.; Liu, J.C.; Hsu, F.L.; Liu, I.M.; Cheng, Y.W.; Cheng, J.T. Isosteviol as a potassium channel opener to lower intracellular calcium concentrations in cultured aortic smooth muscle cells. Planta Med. 2004, 70, 108-112
    • (2004) Planta Med. , vol.70 , pp. 108-112
    • Wong, K.L.1    Yang, H.Y.2    Chan, P.3    Cheng, T.H.4    Liu, J.C.5    Hsu, F.L.6    Liu, I.M.7    Cheng, Y.W.8    Cheng, J.T.9
  • 6
    • 34347386462 scopus 로고    scopus 로고
    • Isosteviol reduces plasma glucose levels in the intravenous glucose tolerance test in zucker diabetic fatty rats
    • Ma, J.; Ma, Z.; Wang, J.; Milne, R.W.; Xu, D.; Davey, A.K.; Evans, A.M. Isosteviol reduces plasma glucose levels in the intravenous glucose tolerance test in zucker diabetic fatty rats. Diabetes Obes. Metab. 2007, 9, 597-599
    • (2007) Diabetes Obes. Metab. , vol.9 , pp. 597-599
    • Ma, J.1    Ma, Z.2    Wang, J.3    Milne, R.W.4    Xu, D.5    Davey, A.K.6    Evans, A.M.7
  • 8
    • 47249095856 scopus 로고    scopus 로고
    • The neuroprotective effects of isosteviol against focal cerebral ischemia injury induced by middle cerebral artery occlusion in rats
    • Xu, D.; Du, W.; Zhao, L.; Davey, A.K.; Wang, J. The neuroprotective effects of isosteviol against focal cerebral ischemia injury induced by middle cerebral artery occlusion in rats. Planta Med. 2008, 74, 816-821
    • (2008) Planta Med. , vol.74 , pp. 816-821
    • Xu, D.1    Du, W.2    Zhao, L.3    Davey, A.K.4    Wang, J.5
  • 9
    • 79960017502 scopus 로고    scopus 로고
    • Isosteviol as a starting material in organic synthesis
    • Moons, N.; de Borggraeve, W.; Dehaen, W. Isosteviol as a starting material in organic synthesis. Curr. Org. Chem. 2011, 15, 2731-2741
    • (2011) Curr. Org. Chem. , vol.15 , pp. 2731-2741
    • Moons, N.1    De Borggraeve, W.2    Dehaen, W.3
  • 10
    • 84882912019 scopus 로고    scopus 로고
    • (-)-isosteviol as a versatile ex-chiral-pool building block for organic chemistry
    • Lohoelter, C.; Weckbecker, M.; Waldvogel, S.R. (-)-isosteviol as a versatile ex-chiral-pool building block for organic chemistry. Eur. J. Org. Chem. 2013, 2013, 5539-5554
    • (2013) Eur. J. Org. Chem. , vol.2013 , pp. 5539-5554
    • Lohoelter, C.1    Weckbecker, M.2    Waldvogel, S.R.3
  • 11
    • 84867563740 scopus 로고    scopus 로고
    • Ent-kaurane diterpenoids and glycosides: Isolation, properties, and chemical transformations
    • Kataev, V.E.; Khaybullin, R.N.; Sharipova, R.R.; Strobykina, I.Y. Ent-kaurane diterpenoids and glycosides: Isolation, properties, and chemical transformations. Rev. J. Chem. 2011, 1, 93-160
    • (2011) Rev. J. Chem. , vol.1 , pp. 93-160
    • Kataev, V.E.1    Khaybullin, R.N.2    Sharipova, R.R.3    Strobykina, I.Y.4
  • 12
    • 84875927753 scopus 로고    scopus 로고
    • Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol
    • Hutt, O.E.; Doan, T.L.; Georg, G.I. Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol. Org. Lett. 2013, 15, 1602-1605
    • (2013) Org. Lett. , vol.15 , pp. 1602-1605
    • Hutt, O.E.1    Doan, T.L.2    Georg, G.I.3
  • 13
    • 35348947451 scopus 로고    scopus 로고
    • 16-aza-ent-beyerane and 16-aza-ent-trachylobane: Potent mechanism-based inhibitors of recombinant ent-kaurene synthase from arabidopsis thaliana
    • Roy, A.; Roberts, F.G.; Wilderman, P.R.; Zhou, K.; Peters, R.J.; Coates, R.M. 16-aza-ent-beyerane and 16-aza-ent-trachylobane: Potent mechanism-based inhibitors of recombinant ent-kaurene synthase from arabidopsis thaliana. J. Am. Chem. Soc. 2007, 129, 12453-12460
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12453-12460
    • Roy, A.1    Roberts, F.G.2    Wilderman, P.R.3    Zhou, K.4    Peters, R.J.5    Coates, R.M.6
  • 16
    • 84867923309 scopus 로고    scopus 로고
    • Unfolded and macrocyclic ammonium derivatives of diterpenoids steviol and isosteviol having choline moieties. Synthesis and inhibitory activities toward acetylcholine- and butyrylcholinesterases
    • Korochkina, M.G.; Nikitashina, A.D.; Khaybullin, R.N.; Petrov, K.A.; Strobykina, I.Y.; Zobov, V.V.; Kataev, V.E. Unfolded and macrocyclic ammonium derivatives of diterpenoids steviol and isosteviol having choline moieties. Synthesis and inhibitory activities toward acetylcholine- and butyrylcholinesterases. Med. Chem. Commun. 2012, 3, 1449-1454
    • (2012) Med. Chem. Commun. , vol.3 , pp. 1449-1454
    • Korochkina, M.G.1    Nikitashina, A.D.2    Khaybullin, R.N.3    Petrov, K.A.4    Strobykina, I.Y.5    Zobov, V.V.6    Kataev, V.E.7
  • 17
    • 84865512422 scopus 로고    scopus 로고
    • D-ring modified novel isosteviol derivatives: Design, synthesis and cytotoxic activity evaluation
    • Zhang, T.; Lu, L.H.; Liu, H.; Wang, J.W.; Wang, R.X.; Zhang, Y.X.; Tao, J.C. D-ring modified novel isosteviol derivatives: Design, synthesis and cytotoxic activity evaluation. Bioorg. Med. Chem. Lett. 2012, 22, 5827-5832
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 5827-5832
    • Zhang, T.1    Lu, L.H.2    Liu, H.3    Wang, J.W.4    Wang, R.X.5    Zhang, Y.X.6    Tao, J.C.7
  • 18
    • 84877870367 scopus 로고    scopus 로고
    • Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents
    • Zhu, S.L.; Wu, Y.; Liu, C.J.; Wei, C.Y.; Tao, J.C.; Liu, H.M. Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents. Eur. J. Med. Chem. 2013, 65, 70-82
    • (2013) Eur. J. Med. Chem. , vol.65 , pp. 70-82
    • Zhu, S.L.1    Wu, Y.2    Liu, C.J.3    Wei, C.Y.4    Tao, J.C.5    Liu, H.M.6
  • 19
    • 84874101284 scopus 로고    scopus 로고
    • Cytotoxic and apoptosis-inducing activities of steviol and isosteviol derivatives against human cancer cell lines
    • Ukiya, M.; Sawada, S.; Kikuchi, T.; Kushi, Y.; Fukatsu, M.; Akihisa, T. Cytotoxic and apoptosis-inducing activities of steviol and isosteviol derivatives against human cancer cell lines. Chem. Biodivers. 2013, 10, 177-188
    • (2013) Chem. Biodivers. , vol.10 , pp. 177-188
    • Ukiya, M.1    Sawada, S.2    Kikuchi, T.3    Kushi, Y.4    Fukatsu, M.5    Akihisa, T.6
  • 20
    • 84893783595 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activity of mom-ether analogs of isosteviol
    • Malki, A.; Laha, R.; Bergmeier, S.C. Synthesis and cytotoxic activity of mom-ether analogs of isosteviol. Bioorg. Med. Chem. Lett. 2014, 24, 1184-1187
    • (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 1184-1187
    • Malki, A.1    Laha, R.2    Bergmeier, S.C.3
  • 21
    • 84855756802 scopus 로고    scopus 로고
    • Synthesis of a biologically active triazole-containing analogue of cystatin a through successive peptidomimetic alkyne-azide ligations
    • Valverde, I.E.; Lecaille, F.; Lalmanach, G.; Aucagne, V.; Delmas, A.F. Synthesis of a biologically active triazole-containing analogue of cystatin a through successive peptidomimetic alkyne-azide ligations. Angew. Chem. Int. Ed. Engl. 2012, 51, 718-722
    • (2012) Angew. Chem. Int. Ed. Engl. , vol.51 , pp. 718-722
    • Valverde, I.E.1    Lecaille, F.2    Lalmanach, G.3    Aucagne, V.4    Delmas, A.F.5
  • 22
    • 56249112956 scopus 로고    scopus 로고
    • Novel anthraquinone derivatives: Synthesis via click chemistry approach and their induction of apoptosis in bgc gastric cancer cells via reactive oxygen species (ros)-dependent mitochondrial pathway
    • Wang, S.; Wang, Q.; Wang, Y.; Liu, L.; Weng, X.; Li, G.; Zhang, X.; Zhou, X. Novel anthraquinone derivatives: Synthesis via click chemistry approach and their induction of apoptosis in bgc gastric cancer cells via reactive oxygen species (ros)-dependent mitochondrial pathway. Bioorg. Med. Chem. Lett. 2008, 18, 6505-6508
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 6505-6508
    • Wang, S.1    Wang, Q.2    Wang, Y.3    Liu, L.4    Weng, X.5    Li, G.6    Zhang, X.7    Zhou, X.8
  • 25
    • 84861595329 scopus 로고    scopus 로고
    • Convenient synthesis of novel geiparvarin analogs with potential anti-cancer activity via click chemistry
    • Zhang, Y.; Lv, Z.; Zhong, H.; Geng, D.; Zhang, M.; Zhang, T.; Li, Y.; Li, K. Convenient synthesis of novel geiparvarin analogs with potential anti-cancer activity via click chemistry. Eur. J. Med. Chem. 2012, 53, 356-363
    • (2012) Eur. J. Med. Chem. , vol.53 , pp. 356-363
    • Zhang, Y.1    Lv, Z.2    Zhong, H.3    Geng, D.4    Zhang, M.5    Zhang, T.6    Li, Y.7    Li, K.8
  • 26
    • 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
  • 27
    • 84879468718 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of ursolic acid-triazolyl derivatives as potential anti-cancer agents
    • Rashid, S.; Dar, B.A.; Majeed, R.; Hamid, A.; Bhat, B.A. Synthesis and biological evaluation of ursolic acid-triazolyl derivatives as potential anti-cancer agents. Eur. J. Med. Chem. 2013, 66, 238-245
    • (2013) Eur. J. Med. Chem. , vol.66 , pp. 238-245
    • Rashid, S.1    Dar, B.A.2    Majeed, R.3    Hamid, A.4    Bhat, B.A.5
  • 28
    • 0001387760 scopus 로고
    • Hydrolysis of the diterpenoid glycoside, stevioside
    • Avent, A.G.; Hanson, J.R.; Deoliveira, B.H. Hydrolysis of the diterpenoid glycoside, stevioside. Phytochemistry 1990, 29, 2712-2715
    • (1990) Phytochemistry , vol.29 , pp. 2712-2715
    • Avent, A.G.1    Hanson, J.R.2    Deoliveira, B.H.3
  • 30
    • 80051767323 scopus 로고    scopus 로고
    • Acid-base jointly promoted copper(I)-catalyzed azide-alkyne cycloaddition
    • Shao, C.; Wang, X.; Zhang, Q.; Luo, S.; Zhao, J.; Hu, Y. Acid-base jointly promoted copper(I)-catalyzed azide-alkyne cycloaddition. J. Org. Chem. 2011, 76, 6832-6836
    • (2011) J. Org. Chem. , vol.76 , pp. 6832-6836
    • Shao, C.1    Wang, X.2    Zhang, Q.3    Luo, S.4    Zhao, J.5    Hu, Y.6
  • 32
    • 0037071180 scopus 로고    scopus 로고
    • A convenient synthesis of azido peptides by post-assembly diazo transfer on the solid phase applicable to large peptides
    • Rijkers, D.T.S.; van Vugt, H.H.R.; Jacobs, H.J.F.; Liskamp, R.M.J. A convenient synthesis of azido peptides by post-assembly diazo transfer on the solid phase applicable to large peptides. Tetrahedron Lett. 2002, 43, 3657-3660
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3657-3660
    • Rijkers, D.T.S.1    Van Vugt, H.H.R.2    Jacobs, H.J.F.3    Liskamp, R.M.J.4
  • 33
    • 24044531286 scopus 로고    scopus 로고
    • Organic azides: An exploding diversity of a unique class of compounds
    • Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Organic azides: An exploding diversity of a unique class of compounds. Angew. Chem. Int. Ed. Engl. 2005, 44, 5188-5240
    • (2005) Angew. Chem. Int. Ed. Engl. , vol.44 , pp. 5188-5240
    • Brase, S.1    Gil, C.2    Knepper, K.3    Zimmermann, V.4
  • 34
    • 33845278154 scopus 로고
    • Azides-Their preparation and synthetic uses
    • Scriven, E.F.V.; Turnbull, K. Azides-Their preparation and synthetic uses. Chem. Rev. 1988, 88, 297-368
    • (1988) Chem. Rev. , vol.88 , pp. 297-368
    • Scriven, E.F.V.1    Turnbull, K.2
  • 35
    • 70350175456 scopus 로고    scopus 로고
    • Part 1. Lab-scale synthesis of azido compounds: Safety measures and analysis
    • 1st ed.; John Wiley & Sons: West Sussex, UK
    • Bräse, S.; Banert, K. Part 1. Lab-scale synthesis of azido compounds: Safety measures and analysis. In Organic Azides: Syntheses and Applications, 1st ed.; John Wiley & Sons: West Sussex, UK, 2009; Volume 1, pp. 3-27.
    • (2009) Organic Azides: Syntheses and Applications , vol.1 , pp. 3-27
    • Bräse, S.1    Banert, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.