SCOPUS 정보 검색 플랫폼

Volumn 36, Issue 10, 2012, Pages 2060-2069

New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: Synthesis and drug-release studies at the air-water interface

(4) Sautrey, Guillaume a Clarot, Igor a Rogalska, Ewa a Regnouf De Vains, Jean Bernard a

a UNIVERSITÉ DE LORRAINE (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 N MONOMETHOXYTRITYL 5' O IMIDAZOLYLCARBONYLACICLOVIR; 2 N MONOMETHOXYTRITYLACICLOVIR; 5,11,17,23 TETRA(TERT BUTYL) 25 (3 HYDROXYPROPOXY) 26,27,28 TRISHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA(TERT BUTYL) 25 [3 (2 N MONOMETHOXYTRITYLACICLOVIR)CARBONYLOXYPROPOXY] 26,27,28 TRISHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA(TERT BUTYL) 25 [3 (5' O ACICLOVIR)CARBONYLOXYPROPOXY] 26,27,28 TRISHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA(TERT BUTYL) 25,27 BIS(3 HYDROXYPROPOXY) 26,27 BISHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA(TERT BUTYL) 25,27 BIS(3 IMIDAZOLYLCARBONYLOXYPROPOXY) 26,28 BISHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA(TERT BUTYL) 25,27 BIS[3 (2 N MONOMETHOXYTRITYLACICLOVIR)CARBONYLOXYPROPOXY] 26,28 BISHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA(TERT BUTYL) 25,27 BIS[3 (5' O ACICLOVIR)CARBONYLOXYPROPOXY] 26,28 BISHYDROXYCALIX[4]ARENE; ACICLOVIR DERIVATIVE; AMPHOPHILE; ANTIVIRUS AGENT; BUFFER; CALIX[4]ARENE; DRUG CARRIER; PRODRUG; TETRA 4 TERT BUTYL CALIX[4]ARENE DERIVATIVE; UNCLASSIFIED DRUG;

AIR WATER INTERFACE; ARTICLE; ARTIFICIAL MEMBRANE; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; DRUG HYDROLYSIS; DRUG RELEASE; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOPHILICITY; MOLECULAR STABILITY; PH; PRIORITY JOURNAL; TEMPERATURE SENSITIVITY;

EID: 84870938694 PISSN: 11440546 EISSN: 13699261 Source Type: Journal
DOI: 10.1039/c2nj40338b Document Type: Article

Times cited : (13)

References (55)

1
- 0026734447
- G. H. Hitchings Annu. Rev. Pharmacol. 1992 32 1
- (1992) Annu. Rev. Pharmacol. , vol.32 , pp. 1
- Hitchings, G.H.¹

2
- 0026605647
- C. Périgaud G. Gosselin J.-L. Imbach Nucleosides Nucleotides 1992 11 903
- (1992) Nucleosides Nucleotides , vol.11 , pp. 903
- Périgaud, C.¹ Gosselin, G.² Imbach, J.-L.³

3
- 2342531101
- H. J. Field E. De Clercq J. Clin. Virol. 2004 30 115
- (2004) J. Clin. Virol. , vol.30 , pp. 115
- Field, H.J.¹ De Clercq, E.²

4
- 1642527146
- A. Matsuda T. Sasaki Cancer Sci. 2004 95 105
- (2004) Cancer Sci. , vol.95 , pp. 105
- Matsuda, A.¹ Sasaki, T.²

5
- 0018214706
- D. C. Baker T. H. Haskell S. R. Putt J. Med. Chem. 1978 21 1218
- (1978) J. Med. Chem. , vol.21 , pp. 1218
- Baker, D.C.¹ Haskell, T.H.² Putt, S.R.³

6
- 0017078110
- W. J. Wechter D. T. Gish M. E. Greig G. D. Gray T. E. Moxley S. L. Kuentzel L. G. Gray A. J. Gibbons R. L. Griffin G. L. Neil J. Med. Chem. 1976 19 1013
- (1976) J. Med. Chem. , vol.19 , pp. 1013
- Wechter, W.J.¹ Gish, D.T.² Greig, M.E.³ Gray, G.D.⁴ Moxley, T.E.⁵ Kuentzel, S.L.⁶ Gray, L.G.⁷ Gibbons, A.J.⁸ Griffin, R.L.⁹ Neil, G.L.¹⁰

7
- 0017128134
- E. K. Hamamura M. Prystasz J. P. H. Verheyden J. G. Moffatt K. Yamaguchi N. Uchida K. Sato A. Nomura O. Shiratori J. Med. Chem. 1976 19 667
- (1976) J. Med. Chem. , vol.19 , pp. 667
- Hamamura, E.K.¹ Prystasz, M.² Verheyden, J.P.H.³ Moffatt, J.G.⁴ Yamaguchi, K.⁵ Uchida, N.⁶ Sato, K.⁷ Nomura, A.⁸ Shiratori, O.⁹

8
- 67649111006
- L. W. Peterson C. E. McKenna Expert Opin. Drug Delivery 2009 6 405
- (2009) Expert Opin. Drug Delivery , vol.6 , pp. 405
- Peterson, L.W.¹ McKenna, C.E.²

9
- 33845333328
- P. Poijarvi-Virta H. Lonnberg Curr. Med. Chem. 2006 13 3441
- (2006) Curr. Med. Chem. , vol.13 , pp. 3441
- Poijarvi-Virta, P.¹ Lonnberg, H.²

10
- 30344486584
- E. De Clercq H. J. Field Br. J. Pharmacol. 2006 147 1
- (2006) Br. J. Pharmacol. , vol.147 , pp. 1
- De Clercq, E.¹ Field, H.J.²

11
- 42949174825
- F. Li H. Maag T. Alfredson J. Pharm. Sci. 2008 97 1109
- (2008) J. Pharm. Sci. , vol.97 , pp. 1109
- Li, F.¹ Maag, H.² Alfredson, T.³

12
- 84863110363
- M. J. Sofia Antiviral Chem. Chemother. 2011 22 23
- (2011) Antiviral Chem. Chemother. , vol.22 , pp. 23
- Sofia, M.J.¹

13
- 78651110499
- D. R. Bobeck R. F. Schinazi S. J. Coats Antiviral Ther. 2010 15 935
- (2010) Antiviral Ther. , vol.15 , pp. 935
- Bobeck, D.R.¹ Schinazi, R.F.² Coats, S.J.³

14
- 70350708165
- E. de Clercq Rev. Med. Virol. 2009 19 287
- (2009) Rev. Med. Virol. , vol.19 , pp. 287
- De Clercq, E.¹

15
- 67649184788
- A. de Fatima S. A. Fernandes A. A. Sabino Curr. Drug Discovery Technol. 2009 6 151
- (2009) Curr. Drug Discovery Technol. , vol.6 , pp. 151
- De Fatima, A.¹ Fernandes, S.A.² Sabino, A.A.³

16
- 67650215632
- R. V. Rodik V. I. Boyko V. I. Kalchenko Curr. Med. Chem. 2009 16 1630
- (2009) Curr. Med. Chem. , vol.16 , pp. 1630
- Rodik, R.V.¹ Boyko, V.I.² Kalchenko, V.I.³

17
- 79959410976
- F. Perret A. W. Coleman Chem. Commun. 2011 47 7303
- (2011) Chem. Commun. , vol.47 , pp. 7303
- Perret, F.¹ Coleman, A.W.²

18
- 81755168068
- B. Mokhtari K. Pourabdollah J. Coord. Chem. 2011 64 3189
- (2011) J. Coord. Chem. , vol.64 , pp. 3189
- Mokhtari, B.¹ Pourabdollah, K.²

19
- 0035479555
- A. Ben Salem J. B. Regnouf-de-Vains Tetrahedron Lett. 2001 42 7033
- (2001) Tetrahedron Lett. , vol.42 , pp. 7033
- Ben Salem, A.¹ Regnouf-De-Vains, J.B.²

20
- 0043171183
- A. Ben Salem J. B. Regnouf-de-Vains Tetrahedron Lett. 2003 44 6769
- (2003) Tetrahedron Lett. , vol.44 , pp. 6769
- Ben Salem, A.¹ Regnouf-De-Vains, J.B.²

21
- 37149031185
- B. Korchowiec A. Ben Salem Y. Corvis J.-B. Regnouf de Vains J. Korchowiec E. Rogalska J. Phys. Chem. B 2007 111 13231
- (2007) J. Phys. Chem. B , vol.111 , pp. 13231
- Korchowiec, B.¹ Ben Salem, A.² Corvis, Y.³ De Vains, J.-B.R.⁴ Korchowiec, J.⁵ Rogalska, E.⁶

22
- 77955569319
- B. Korchowiec M. Orlof G. Sautrey A. Ben Salem J. Korchowiec J.-B. Regnouf-de- Vains E. Rogalska J. Phys. Chem. B 2010 114 10427
- (2010) J. Phys. Chem. B , vol.114 , pp. 10427
- Korchowiec, B.¹ Orlof, M.² Sautrey, G.³ Ben Salem, A.⁴ Korchowiec, J.⁵ Regnouf-De-Vains, J.-B.⁶ Rogalska, E.⁷

23
- 65349158711
- H. Massimba Dibama I. Clarot S. Fontanay A. B. Salem M. Mourer C. Finance R. E. Duval J.-B. Regnouf-de-Vains Bioorg. Med. Chem. Lett. 2009 19 2679
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 2679
- Massimba Dibama, H.¹ Clarot, I.² Fontanay, S.³ Salem, A.B.⁴ Mourer, M.⁵ Finance, C.⁶ Duval, R.E.⁷ Regnouf-De-Vains, J.-B.⁸

24
- 82255175456
- A. Ben Salem G. Sautrey S. Fontanay R. E. Duval J.-B. Regnouf de Vains Bioorg. Med. Chem. 2011 19 7534
- (2011) Bioorg. Med. Chem. , vol.19 , pp. 7534
- Ben Salem, A.¹ Sautrey, G.² Fontanay, S.³ Duval, R.E.⁴ De Vains, J.-B.R.⁵

25
- 84255160917
- G. Sautrey I. Clarot A. Ben Salem E. Rogalska J.-B. Regnouf de Vains New J. Chem. 2012 36 78
- (2012) New J. Chem. , vol.36 , pp. 78
- Sautrey, G.¹ Clarot, I.² Ben Salem, A.³ Rogalska, E.⁴ De Vains, J.-B.R.⁵

26
- 85046525470
- V. Sidorov F. W. Kotch M. El-Kouedi J. F. Davis Chem. Commun. 2000 2369
- (2000) Chem. Commun. , pp. 2369
- Sidorov, V.¹ Kotch, F.W.² El-Kouedi, M.³ Davis, J.F.⁴

27
- 0344667432
- F. W. Kotch V. Sidorov Y.-F. Lam K. J. Kayser H. Li M. S. Kaucher J. F. Davis J. Am. Chem. Soc. 2003 125 15140
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 15140
- Kotch, F.W.¹ Sidorov, V.² Lam, Y.-F.³ Kayser, K.J.⁴ Li, H.⁵ Kaucher, M.S.⁶ Davis, J.F.⁷

28
- 0037009714
- S. J. Kim B. H. Kim Tetrahedron Lett. 2002 43 6367
- (2002) Tetrahedron Lett. , vol.43 , pp. 6367
- Kim, S.J.¹ Kim, B.H.²

29
- 0037930745
- S. J. Kim B. H. Kim Nucleic Acids Res. 2003 31 2725
- (2003) Nucleic Acids Res. , vol.31 , pp. 2725
- Kim, S.J.¹ Kim, B.H.²

30
- 33645851958
- G. M. L. Consoli G. Granata E. Galante F. Cunsolo C. Geraci Tetrahedron Lett. 2006 47 3245
- (2006) Tetrahedron Lett. , vol.47 , pp. 3245
- Consoli, G.M.L.¹ Granata, G.² Galante, E.³ Cunsolo, F.⁴ Geraci, C.⁵

31
- 35148853104
- G. M. L. Consoli G. Granata D. Garozzo T. Mecca C. Geraci Tetrahedron Lett. 2007 48 7974
- (2007) Tetrahedron Lett. , vol.48 , pp. 7974
- Consoli, G.M.L.¹ Granata, G.² Garozzo, D.³ Mecca, T.⁴ Geraci, C.⁵

32
- 46949092125
- G. M. L. Consoli G. Granata R. Lo Nigro G. Malandrino C. Geraci Langmuir 2008 24 6194
- (2008) Langmuir , vol.24 , pp. 6194
- Consoli, G.M.L.¹ Granata, G.² Lo Nigro, R.³ Malandrino, G.⁴ Geraci, C.⁵

33
- 34548669146
- G. M. L. Consoli G. Granata E. Galante I. Di Silvestro L. Salafia C. Geraci Tetrahedron 2007 63 10758
- (2007) Tetrahedron , vol.63 , pp. 10758
- Consoli, G.M.L.¹ Granata, G.² Galante, E.³ Di Silvestro, I.⁴ Salafia, L.⁵ Geraci, C.⁶

34
- 0022483442
- J. C. Martin D. P. C. McGee G. A. Jeffrey D. W. Hobbs D. F. Smee T. R. Matthews J. P. H. Verheyden J. Med. Chem. 1986 29 1384
- (1986) J. Med. Chem. , vol.29 , pp. 1384
- Martin, J.C.¹ McGee, D.P.C.² Jeffrey, G.A.³ Hobbs, D.W.⁴ Smee, D.F.⁵ Matthews, T.R.⁶ Verheyden, J.P.H.⁷

35
- 0004209750
- Academic Press, New York, USA, 2nd edn
- J. T. Davies and E. K. Rideal, Interfacial Phenomena, Academic Press, New York, USA, 2nd edn, 1963
- (1963) Interfacial Phenomena
- Davies, J.T.¹ Rideal, E.K.²

36
- 0003466321
- Wiley Interscience, New York, USA
- G. L. Gaines, Insoluble monolayers at liquid-gas interfaces, Wiley Interscience, New York, USA, 1966
- (1966) Insoluble Monolayers at Liquid-gas Interfaces
- Gaines, G.L.¹

37
- 84870956619
- Int. Patent, WO 2009/085267 A1
- S. Dong and M. C. Schroeder, Int. Patent, 2009, WO 2009/085267 A1
- (2009)
- Dong, S.¹ Schroeder, M.C.²

38
- 78650410911
- T. Rodriguez-Pérez S. Fernandez Y. S. Sanghvi M. Detorio R. F. Schinazi V. Gotor M. Ferrero Bioconjugate Chem. 2010 21 2239
- (2010) Bioconjugate Chem. , vol.21 , pp. 2239
- Rodriguez-Pérez, T.¹ Fernandez, S.² Sanghvi, Y.S.³ Detorio, M.⁴ Schinazi, R.F.⁵ Gotor, V.⁶ Ferrero, M.⁷

39
- 4544237135
- N. S. Pujar N. F. Huang C. L. Daniels L. Dieter M. G. Gayton A. L. Lee Biopolymers 2004 75 71
- (2004) Biopolymers , vol.75 , pp. 71
- Pujar, N.S.¹ Huang, N.F.² Daniels, C.L.³ Dieter, L.⁴ Gayton, M.G.⁵ Lee, A.L.⁶

40
- 79251499743
- A. M. Ramadan J. M. Calatayud Sala T. N. Parac-Vogt Dalton Trans. 2011 40 1230
- (2011) Dalton Trans. , vol.40 , pp. 1230
- Ramadan, A.M.¹ Calatayud Sala, J.M.² Parac-Vogt, T.N.³

41
- 0347623390
- M. K. Chmielewski V. Marchan J. Cieslak A. Grajkowski V. Livengood U. Muench A. Wilk S. L. Beaucage J. Org. Chem. 2003 68 10003
- (2003) J. Org. Chem. , vol.68 , pp. 10003
- Chmielewski, M.K.¹ Marchan, V.² Cieslak, J.³ Grajkowski, A.⁴ Livengood, V.⁵ Muench, U.⁶ Wilk, A.⁷ Beaucage, S.L.⁸

42
- 78650190141
- J. Ho F. M. N. Al-Deen A. Al-Abboodi C. Selomulya S. D. Xiang M. Plebanski G. M. Forde Colloids Surf., B 2011 83 83
- (2011) Colloids Surf., B , vol.83 , pp. 83
- Ho, J.¹ Al-Deen, F.M.N.² Al-Abboodi, A.³ Selomulya, C.⁴ Xiang, S.D.⁵ Plebanski, M.⁶ Forde, G.M.⁷

43
- 34250207688
- A. P. Goodwin S. S. Lam J. M. J. Frechet J. Am. Chem. Soc. 2007 129 6994
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 6994
- Goodwin, A.P.¹ Lam, S.S.² Frechet, J.M.J.³

44
- 75849159202
- L. Zhang L. Song Z. Liu H. Li Y. Lu Z. Li S. Ma Eur. J. Med. Chem. 2010 45 915
- (2010) Eur. J. Med. Chem. , vol.45 , pp. 915
- Zhang, L.¹ Song, L.² Liu, Z.³ Li, H.⁴ Lu, Y.⁵ Li, Z.⁶ Ma, S.⁷

45
- 33749132600
- E. Utagawa M. Sekine K. Seio J. Org. Chem. 2006 71 7668
- (2006) J. Org. Chem. , vol.71 , pp. 7668
- Utagawa, E.¹ Sekine, M.² Seio, K.³

46
- 15144355782
- D.-K. Kim N. Lee Y.-W. Kim K. Chang J.-S. Kim G.-J. Im W.-S. Choi I. Jung T.-S. Kim Y.-Y. Hwang D.-S. Min K. A. Um Y.-B. Cho K. H. Kim J. Med. Chem. 1998 41 3435
- (1998) J. Med. Chem. , vol.41 , pp. 3435
- Kim, D.-K.¹ Lee, N.² Kim, Y.-W.³ Chang, K.⁴ Kim, J.-S.⁵ Im, G.-J.⁶ Choi, W.-S.⁷ Jung, I.⁸ Kim, T.-S.⁹ Hwang, Y.-Y.¹⁰ Min, D.-S.¹¹ Um, K.A.¹² Cho, Y.-B.¹³ Kim, K.H.¹⁴

47
- 77950065199
- M. A. Raviolo P. A. M. Williams S. B. Etcheverry O. E. Piro E. E. Castellano M. S. Gualdesi M. C. Brinon J. Mol. Struct. 2010 970 59
- (2010) J. Mol. Struct. , vol.970 , pp. 59
- Raviolo, M.A.¹ Williams, P.A.M.² Etcheverry, S.B.³ Piro, O.E.⁴ Castellano, E.E.⁵ Gualdesi, M.S.⁶ Brinon, M.C.⁷

48
- 33845423423
- A. Hosseini S. Taylor G. Accorsi N. Armaroli C. A. Reed P. D. W. Boyd J. Am. Chem. Soc. 2006 128 15903
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 15903
- Hosseini, A.¹ Taylor, S.² Accorsi, G.³ Armaroli, N.⁴ Reed, C.A.⁵ Boyd, P.D.W.⁶

49
- 33751498991
- C. Jaime J. De Mendoza P. Prados P. M. Nieto C. Sanchez J. Org. Chem. 1991 56 3372
- (1991) J. Org. Chem. , vol.56 , pp. 3372
- Jaime, C.¹ De Mendoza, J.² Prados, P.³ Nieto, P.M.⁴ Sanchez, C.⁵

50
- 0000065213
- L. C. Groenen J. D. Van Loon W. Verboom S. Harkema A. Casnati R. Ungaro A. Pochini F. Ugozzoli D. N. Reinhoudt J. Am. Chem. Soc. 1991 113 2385
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 2385
- Groenen, L.C.¹ Van Loon, J.D.² Verboom, W.³ Harkema, S.⁴ Casnati, A.⁵ Ungaro, R.⁶ Pochini, A.⁷ Ugozzoli, F.⁸ Reinhoudt, D.N.⁹

51
- 34249819389
- S. Li Y. Lin J. Cao S. Zhang J. Org. Chem. 2007 72 4067
- (2007) J. Org. Chem. , vol.72 , pp. 4067
- Li, S.¹ Lin, Y.² Cao, J.³ Zhang, S.⁴

52
- 50849123743
- F. S. Pereira E. Ribeiro de Azevedo E. F. da Silva T. J. Bonagamba D. L. da Silva Agostini A. Magalhaes A. E. Job E. R. Perez Gonzalez Tetrahedron 2008 64 10097
- (2008) Tetrahedron , vol.64 , pp. 10097
- Pereira, F.S.¹ De Azevedo, E.R.² Da Silva, E.F.³ Bonagamba, T.J.⁴ Da Silva Agostini, D.L.⁵ Magalhaes, A.⁶ Job, A.E.⁷ Perez Gonzalez, E.R.⁸

53
- 45249127652
- D. A. Pearson M. Blanchette M. L. Baker C. A. Guindon Tetrahedron Lett. 1989 30 2739
- (1989) Tetrahedron Lett. , vol.30 , pp. 2739
- Pearson, D.A.¹ Blanchette, M.² Baker, M.L.³ Guindon, C.A.⁴

54
- 58849100861
- P. B. Garland and P. J. Serafinowski, Org. Biomol. Chem., 2009, 7, 451
- (2009) Org. Biomol. Chem. , vol.7 , pp. 451
- Garland, P.B.¹ Serafinowski, P.J.²

55
- 84943008172
- ICH Guidelines Q2(R1): Note for Guidance on Validation of Analytical Procedures: Text and Methodology Ref. CPMP/ICH/381/95
- ICH Guidelines Q2(R1): Note for Guidance on Validation of Analytical Procedures: Text and Methodology Ref. CPMP/ICH/381/95

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.