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Volumn 4, Issue 7, 2013, Pages 651-655

Semisynthesis, cytotoxic activity, and oral availability of new lipophilic 9-substituted camptothecin derivatives

Author keywords

9 substituted camptothecins; Lipophilic camptothecin; oral administration; Tscherniac Einhorn derivatives

Indexed keywords

ANTINEOPLASTIC AGENT; CAMPTOTHECIN DERIVATIVE; DNA TOPOISOMERASE; TOPOTECAN;

EID: 84880164399     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400125z     Document Type: Article
Times cited : (18)

References (36)
  • 1
    • 7144248725 scopus 로고
    • Plant antitumor agents I. the isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata
    • Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; Mc Phail, A. T.; Sim, G. A. Plant antitumor agents I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata J. Am. Chem. Soc. 1966, 88, 3888-3890
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 3888-3890
    • Wall, M.E.1    Wani, M.C.2    Cook, C.E.3    Palmer, K.H.4    Mc Phail, A.T.5    Sim, G.A.6
  • 2
    • 0015378084 scopus 로고
    • Phase i trial of weekly and daily treatment with camptothecin (NSC-1000880): Correlation with preclinical studies
    • Muggia, F. M.; Creaven, P. J.; Hansen, H. H.; Cohen, M. H.; Selawry, O. S. Phase I trial of weekly and daily treatment with camptothecin (NSC-1000880): Correlation with preclinical studies Cancer Chemother. Rep., Part 1 1972, 56, 515-521
    • (1972) Cancer Chemother. Rep., Part 1 , vol.56 , pp. 515-521
    • Muggia, F.M.1    Creaven, P.J.2    Hansen, H.H.3    Cohen, M.H.4    Selawry, O.S.5
  • 4
    • 59649105538 scopus 로고    scopus 로고
    • Camptothecins: A SAR/QSAR study
    • Verma, R. P.; Hansch, C. Camptothecins: a SAR/QSAR study Chem. Rev. 2009, 109, 213-235
    • (2009) Chem. Rev. , vol.109 , pp. 213-235
    • Verma, R.P.1    Hansch, C.2
  • 7
    • 0344074659 scopus 로고    scopus 로고
    • 7-Silylcamptothecins (silatecans): A new family of camptothecin antitumor agents
    • Josien, H.; Bom, D.; Curran, D. P.; Zeng, Y. H.; Chou, T. C. 7-Silylcamptothecins (silatecans): A new family of camptothecin antitumor agents Bioorg. Med. Chem. Lett. 1997, 7, 3189-3194
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 3189-3194
    • Josien, H.1    Bom, D.2    Curran, D.P.3    Zeng, Y.H.4    Chou, T.C.5
  • 8
    • 0033549870 scopus 로고    scopus 로고
    • Novel A,B,E-ring-modified camptothecins displaying high lipophilicity and markedly improved human blood stabilities
    • Bom, D.; Curran, D. P.; Chavan, A. J.; Kruszewski, S.; Zimmer, S. G.; Fraley, K. A.; Burke, T. G. Novel A,B,E-ring-modified camptothecins displaying high lipophilicity and markedly improved human blood stabilities J. Med. Chem. 1999, 42, 3018-3022
    • (1999) J. Med. Chem. , vol.42 , pp. 3018-3022
    • Bom, D.1    Curran, D.P.2    Chavan, A.J.3    Kruszewski, S.4    Zimmer, S.G.5    Fraley, K.A.6    Burke, T.G.7
  • 10
    • 84863768731 scopus 로고    scopus 로고
    • Namitecan: A hydrophilic camptothecin with a promising preclinical profile
    • Beretta, G. L.; Zuco, V.; De Cesare, M.; Perego, P.; Zaffaroni, N. Namitecan: a hydrophilic camptothecin with a promising preclinical profile Curr. Med. Chem. 2012, 19, 3488-3501
    • (2012) Curr. Med. Chem. , vol.19 , pp. 3488-3501
    • Beretta, G.L.1    Zuco, V.2    De Cesare, M.3    Perego, P.4    Zaffaroni, N.5
  • 14
    • 0025948430 scopus 로고
    • Chemical modification of an antitumor alkaloid camptothecin: Synthesis and antitumor activity of 7-C-substituted camptothecins
    • Sawada, S.; Nokata, K.; Furuta, T.; Yokokura, T.; Miyasaka, T. Chemical modification of an antitumor alkaloid camptothecin: synthesis and antitumor activity of 7-C-substituted camptothecins Chem. Pharm. Bull. 1991, 39, 2574-2580
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 2574-2580
    • Sawada, S.1    Nokata, K.2    Furuta, T.3    Yokokura, T.4    Miyasaka, T.5
  • 15
    • 28844476795 scopus 로고    scopus 로고
    • Novel route for preparation of 7-methl-camptothecin and its possible mechanism
    • Wang, X.; Wen, J.; Li, G.; You, T. Novel route for preparation of 7-methl-camptothecin and its possible mechanism Synth. Commun. 2005, 35, 3163-3166
    • (2005) Synth. Commun. , vol.35 , pp. 3163-3166
    • Wang, X.1    Wen, J.2    Li, G.3    You, T.4
  • 19
    • 10044237834 scopus 로고    scopus 로고
    • Phase II evaluation of 9-aminocamptothecin (9-AC, NSC #603071) in platinum-resistant ovarian and primary peritoneal carcinoma: A gynecologic oncology group study
    • Miller, D. S.; Blessing, J. A.; Waggoner, S.; Schilder, J.; Sorosky, J.; Bloss, J.; Schilder, R. Phase II evaluation of 9-aminocamptothecin (9-AC, NSC #603071) in platinum-resistant ovarian and primary peritoneal carcinoma: a gynecologic oncology group study Gynecol. Oncol. 2005, 96, 67-71
    • (2005) Gynecol. Oncol. , vol.96 , pp. 67-71
    • Miller, D.S.1    Blessing, J.A.2    Waggoner, S.3    Schilder, J.4    Sorosky, J.5    Bloss, J.6    Schilder, R.7
  • 20
    • 46349105443 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of 9-methyl-10-hydroxycamptothecin
    • Wang, S.; Li, Y. Y.; You, Q. D. Synthesis and antitumor activity of 9-methyl-10-hydroxycamptothecin Chin. Chem. Lett. 2008, 19, 918-920
    • (2008) Chin. Chem. Lett. , vol.19 , pp. 918-920
    • Wang, S.1    Li, Y.Y.2    You, Q.D.3
  • 21
    • 33745749456 scopus 로고    scopus 로고
    • A practical regiospecific synthesis of 9-nitrocamptothecin
    • Fu, Q.; Chen, Z. A practical regiospecific synthesis of 9-nitrocamptothecin Synthesis 2006, 12, 1940-1942
    • (2006) Synthesis , vol.12 , pp. 1940-1942
    • Fu, Q.1    Chen, Z.2
  • 22
    • 0027430831 scopus 로고
    • Superelectrophilic Tscherniac amidomethylation of aromatics with N -hydroxymethylphthalimide in trifluoromethanesulfonic acid
    • Olah, G. A.; Wang, Q.; Sandford, G.; Oxyzoglou, A. B.; Prakash, G. K. S. Superelectrophilic Tscherniac amidomethylation of aromatics with N -hydroxymethylphthalimide in trifluoromethanesulfonic acid Synthesis 1993, 11, 1077-1079
    • (1993) Synthesis , vol.11 , pp. 1077-1079
    • Olah, G.A.1    Wang, Q.2    Sandford, G.3    Oxyzoglou, A.B.4    Prakash, G.K.S.5
  • 23
    • 85067856671 scopus 로고
    • Advances in the chemistry of Mannich bases
    • Tramontini, M. Advances in the chemistry of Mannich bases Synthesis 1973, 703
    • (1973) Synthesis , pp. 703
    • Tramontini, M.1
  • 24
    • 50649086342 scopus 로고    scopus 로고
    • Synthesis development of an aminomethylcycline antibiotic via an electronically tuned acyliminium Friedel-Crafts reaction
    • Chung, J.; Hartner, F. W.; Cvetovich, R. J. Synthesis development of an aminomethylcycline antibiotic via an electronically tuned acyliminium Friedel-Crafts reaction Tetrahedron Lett. 2008, 49, 6095-6100
    • (2008) Tetrahedron Lett. , vol.49 , pp. 6095-6100
    • Chung, J.1    Hartner, F.W.2    Cvetovich, R.J.3
  • 26
    • 4644248597 scopus 로고    scopus 로고
    • Hydrophilic camptothecin analogs that form extreamly stable cleavable complexes with DNA and topoisomerase i
    • Wadkins, R. M.; Bearss, D.; Manikumar, G.; Wani, M. C.; Wall, M. E.; Von Hoff, D. D. Hydrophilic camptothecin analogs that form extreamly stable cleavable complexes with DNA and topoisomerase I Cancer Res. 2004, 64, 6679-6683
    • (2004) Cancer Res. , vol.64 , pp. 6679-6683
    • Wadkins, R.M.1    Bearss, D.2    Manikumar, G.3    Wani, M.C.4    Wall, M.E.5    Von Hoff, D.D.6
  • 28
    • 0031006728 scopus 로고    scopus 로고
    • Investigation of new degradation products arising from encapsulation of an oil-based suspension formulation of topotecan
    • Patel, K.; Kerarney, A. S.; Palepu, N. R. Investigation of new degradation products arising from encapsulation of an oil-based suspension formulation of topotecan Int. J. Pharm. 1997, 151, 7-13
    • (1997) Int. J. Pharm. , vol.151 , pp. 7-13
    • Patel, K.1    Kerarney, A.S.2    Palepu, N.R.3
  • 30
    • 35349012642 scopus 로고    scopus 로고
    • Animal data: The contributions of the Ussing Chamber and perfusion systems to predicting human oral drug delivery in vivo
    • Lennernas, H. Animal data: the contributions of the Ussing Chamber and perfusion systems to predicting human oral drug delivery in vivo Adv. Drug Delivery Rev. 2007, 59, 1103-1120
    • (2007) Adv. Drug Delivery Rev. , vol.59 , pp. 1103-1120
    • Lennernas, H.1
  • 31
    • 0004767983 scopus 로고
    • The Sommelet reaction in the synthesis of aromatic dialdehydes
    • Wood, J. H.; Tung, C. C.; Perry, R. E.; Gibson, R. E. The Sommelet reaction in the synthesis of aromatic dialdehydes J. Am. Chem. Soc. 1950, 7, 2992-2993
    • (1950) J. Am. Chem. Soc. , vol.7 , pp. 2992-2993
    • Wood, J.H.1    Tung, C.C.2    Perry, R.E.3    Gibson, R.E.4
  • 33
    • 28844451574 scopus 로고    scopus 로고
    • Camptothecin analogs with enhanced activity against human breast cancer cells I. Correlation of potency with lipophilicity and persistence in the cleavage complex
    • Adams, D. J.; da Silva, M. W.; Flowers, J. L.; Kohlhagen, G.; Pommier, Y.; Colvin, O. M.; Manikumar, G.; Wani, M. C. Camptothecin analogs with enhanced activity against human breast cancer cells I. Correlation of potency with lipophilicity and persistence in the cleavage complex Cancer Chemother. Pharmacol. 2006, 57, 135-144
    • (2006) Cancer Chemother. Pharmacol. , vol.57 , pp. 135-144
    • Adams, D.J.1    Da Silva, M.W.2    Flowers, J.L.3    Kohlhagen, G.4    Pommier, Y.5    Colvin, O.M.6    Manikumar, G.7    Wani, M.C.8
  • 35
    • 0027146389 scopus 로고
    • Transport of celiprolol across human intestinal epithelial (Caco-2) cells: Mediation of secretion by multiple transporters including P-glycoprotein
    • Karlsson, J.; Kuo, S. M.; Ziemniak, J.; Artursson, P. Transport of celiprolol across human intestinal epithelial (Caco-2) cells: mediation of secretion by multiple transporters including P-glycoprotein Br. J. Pharmacol. 1993, 110, 1009-1016
    • (1993) Br. J. Pharmacol. , vol.110 , pp. 1009-1016
    • Karlsson, J.1    Kuo, S.M.2    Ziemniak, J.3    Artursson, P.4
  • 36
    • 0030797273 scopus 로고    scopus 로고
    • Human jejunal effective permeability and its correlation with preclinical drug absorption models
    • Lennernas, H. Human jejunal effective permeability and its correlation with preclinical drug absorption models J. Pharm. Pharmacol. 1997, 49, 627-638
    • (1997) J. Pharm. Pharmacol. , vol.49 , pp. 627
    • Lennernas, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.