SCOPUS 정보 검색 플랫폼

Volumn 7, Issue 12, 2009, Pages 2525-2533

Synthesis, transacylation kinetics and computational chemistry of a set of arylacetic acid 1β-O-acyl glucuronides

(11) Stachulski, Andrew V a Berry, Neil G a Iddon, Lisa a Iqbal, Mazhar a,d Meng, Xiaoli a Jayapal, Prabha a,e Johnson, Caroline H b Nicholson, Jeremy K b Lindon, John C b Harding, John R c Wilson, Ian D c

a UNIVERSITY OF LIVERPOOL (United Kingdom)

b IMPERIAL COLLEGE LONDON (United Kingdom)

c ASTRAZENECA (United Kingdom)

d NATIONAL INSTITUTE FOR BIOTECHNOLOGY AND GENETIC ENGINEERING NIBGE (Pakistan)

e UNIVERSITY OF BONN (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL MIGRATION; ACYL TRANSFER; ANOMERS; ANTI-INFLAMMATORY AGENTS; ARYLACETIC ACIDS; COMPUTATIONAL CHEMISTRY; CONCENTRATION DEPENDENCE; DEGREE OF CORRELATIONS; DRUG SAFETY; GLUCURONIDES; GOOD YIELD; H NMR SPECTROSCOPY; HALF LIVES; KINETIC DATA; MODELLING STUDIES; PHENYLACETIC ACID; STRUCTURE REACTIVITY; TRANSITION STATE;

ACIDS; ACTIVATION ENERGY; DRUG PRODUCTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANTS (BOTANY); STRUCTURAL ANALYSIS;

ISOMERS;

GLUCURONIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PHENYLACETIC ACID; PHENYLACETIC ACID DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; KINETICS; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ACYLATION; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; COMPUTER SIMULATION; GLUCURONIDES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENYLACETATES; STEREOISOMERISM;

EID: 67650496987 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b822777b Document Type: Article

Times cited : (27)

References (49)

1
- 0023576733
- F. M. Kaspersen C. A. A. Van Boeckel Xenobiotica 1987 17 1451 71
- (1987) Xenobiotica , vol.17 , pp. 1451-71
- Kaspersen, F.M.¹ Van Boeckel, C.A.A.²

2
- 0032054655
- A. V. Stachulski G. N. Jenkins Nat. Prod. Rep. 1998 15 173 86
- (1998) Nat. Prod. Rep. , vol.15 , pp. 173-86
- Stachulski, A.V.¹ Jenkins, G.N.²

3
- 0343674416
- W. F. Goebel J. Biol. Chem. 1938 122 649 653
- (1938) J. Biol. Chem. , vol.122 , pp. 649-653
- Goebel, W.F.¹

4
- 0022634988
- R. B. Vanbreemen C. C. Fenselau Drug Metab. Dispos. 1986 14 197 201
- (1986) Drug Metab. Dispos. , vol.14 , pp. 197-201
- Vanbreemen, R.B.¹ Fenselau, C.C.²

5
- 0021707968
- E. M. Faed Drug Metab. Rev. 1984 15 1213 49
- (1984) Drug Metab. Rev. , vol.15 , pp. 1213-49
- Faed, E.M.¹

6
- 0026532030
- H. Spahn-Langguth L. Z. Benet Drug Metab. Rev. 1992 24 5 48
- (1992) Drug Metab. Rev. , vol.24 , pp. 5-48
- Spahn-Langguth, H.¹ Benet, L.Z.²

7
- 33845356772
- A. V. Stachulski J. R. Harding J. C. Lindon J. L. Maggs B. K. Park I. D. Wilson J. Med. Chem. 2006 49 6931 45
- (2006) J. Med. Chem. , vol.49 , pp. 6931-6945
- Stachulski, A.V.¹ Harding, J.R.² Lindon, J.C.³ Maggs, J.L.⁴ Park, B.K.⁵ Wilson, I.D.⁶

8
- 2442635266
- J. R. Kenny J. L. Maggs X. Meng D. Sinnott S. E. Clarke B. K. Park A. V. Stachulski J. Med. Chem. 2004 47 2816 25
- (2004) J. Med. Chem. , vol.47 , pp. 2816-2825
- Kenny, J.R.¹ Maggs, J.L.² Meng, X.³ Sinnott, D.⁴ Clarke, S.E.⁵ Park, B.K.⁶ Stachulski, A.V.⁷

9
- 0035998265
- K. Akira T. Uchijima T. Hashimoto Chem. Res. Toxicol. 2002 15 765 72
- (2002) Chem. Res. Toxicol. , vol.15 , pp. 765-772
- Akira, K.¹ Uchijima, T.² Hashimoto, T.³

10
- 0029917396
- N. Presle F. Lapicque S. Fournel-Gigleux J. Magdalou P. Netter Drug Metab. Dispos. 1996 24 1050 7
- (1996) Drug Metab. Dispos. , vol.24 , pp. 1050-1057
- Presle, N.¹ Lapicque, F.² Fournel-Gigleux, S.³ Magdalou, J.⁴ Netter, P.⁵

11
- 4644317079
- J. Wang M. Davis F. Li F. Azam J. Scatina R. Talaat Chem. Res. Toxicol. 2004 17 1206 1216
- (2004) Chem. Res. Toxicol. , vol.17 , pp. 1206-1216
- Wang, J.¹ Davis, M.² Li, F.³ Azam, F.⁴ Scatina, J.⁵ Talaat, R.⁶

12
- 0033973127
- H. Georges N. Presle T. Buronfosse S. Fournel-Gigleux P. Netter J. Magdalou F. Lapicque Chirality 2000 12 53 62
- (2000) Chirality , vol.12 , pp. 53-62
- Georges, H.¹ Presle, N.² Buronfosse, T.³ Fournel-Gigleux, S.⁴ Netter, P.⁵ Magdalou, J.⁶ Lapicque, F.⁷

13
- 0025872002
- C. Volland H. Sun J. Dammeyer L. Z. Benet Drug Metab. Dispos. 1991 19 1080 1086
- (1991) Drug Metab. Dispos. , vol.19 , pp. 1080-1086
- Volland, C.¹ Sun, H.² Dammeyer, J.³ Benet, L.Z.⁴

14
- 0442282104
- S. J. Vanderhoeven J. C. Lindon J. Troke G. E. Tranter I. D. Wilson J. K. Nicholson Xenobiotica 2004 34 73 85
- (2004) Xenobiotica , vol.34 , pp. 73-85
- Vanderhoeven, S.J.¹ Lindon, J.C.² Troke, J.³ Tranter, G.E.⁴ Wilson, I.D.⁵ Nicholson, J.K.⁶

15
- 0021961277
- P. C. Smith J. Hasegawa P. N. Langendijk L. Z. Benet Drug Metab. Dispos. 1985 13 110 112
- (1985) Drug Metab. Dispos. , vol.13 , pp. 110-112
- Smith, P.C.¹ Hasegawa, J.² Langendijk, P.N.³ Benet, L.Z.⁴

16
- 26644452079
- E. Skordi I. D. Wilson J. C. Lindon J. K. Nicholson Xenobiotica 2005 35 715 725
- (2005) Xenobiotica , vol.35 , pp. 715-725
- Skordi, E.¹ Wilson, I.D.² Lindon, J.C.³ Nicholson, J.K.⁴

17
- 0036222938
- R. W. Mortensen U. G. Sidelmann J. Tjornelund S. H. Hansen Chirality 2002 14 305 312
- (2002) Chirality , vol.14 , pp. 305-312
- Mortensen, R.W.¹ Sidelmann, U.G.² Tjornelund, J.³ Hansen, S.H.⁴

18
- 36448976239
- C. H. Johnson I. D. Wilson J. R. Harding A. V. Stachulski L. Iddon J. K. Nicholson J. C. Lindon Anal. Chem. 2007 79 8720 8727
- (2007) Anal. Chem. , vol.79 , pp. 8720-8727
- Johnson, C.H.¹ Wilson, I.D.² Harding, J.R.³ Stachulski, A.V.⁴ Iddon, L.⁵ Nicholson, J.K.⁶ Lindon, J.C.⁷

19
- 0034935377
- H. Hasegawa K. Akira Y. Shinohara Y. Kasuya T. Hashimoto Biol. Pharm. Bull. 2001 24 852 855
- (2001) Biol. Pharm. Bull. , vol.24 , pp. 852-855
- Hasegawa, H.¹ Akira, K.² Shinohara, Y.³ Kasuya, Y.⁴ Hashimoto, T.⁵

20
- 0001526431
- U. G. Sidelmann S. H. Hansen C. Gavaghan H. A. J. Carless J. C. Lindon R. D. Farrant I. D. Wilson J. K. Nicholson Anal. Chem. 1996 68 2564 2572
- (1996) Anal. Chem. , vol.68 , pp. 2564-2572
- Sidelmann, U.G.¹ Hansen, S.H.² Gavaghan, C.³ Carless, H.A.J.⁴ Lindon, J.C.⁵ Farrant, R.D.⁶ Wilson, I.D.⁷ Nicholson, J.K.⁸

21
- 0024452796
- G. Bradow L. S. Kan C. Fenselau Chem. Res. Toxicol. 1989 2 316 324
- (1989) Chem. Res. Toxicol. , vol.2 , pp. 316-324
- Bradow, G.¹ Kan, L.S.² Fenselau, C.³

22
- 0032826052
- T. Ebner G. Heinzel A. Prox K. Beschke H. Wachsmuth Drug Metab. Dispos. 1999 27 1143 1149
- (1999) Drug Metab. Dispos. , vol.27 , pp. 1143-1149
- Ebner, T.¹ Heinzel, G.² Prox, A.³ Beschke, K.⁴ Wachsmuth, H.⁵

23
- 0027158963
- P. C. Smith J. H. Liu Xenobiotica 1993 23 337 348
- (1993) Xenobiotica , vol.23 , pp. 337-348
- Smith, P.C.¹ Liu, J.H.²

24
- 0029744251
- H. Spahn-Langguth M. Dahms A. Hermening Adv. Exper. Med. Biol. 1996 387 313 328
- (1996) Adv. Exper. Med. Biol. , vol.387 , pp. 313-328
- Spahn-Langguth, H.¹ Dahms, M.² Hermening, A.³

25
- 0035064592
- R. W. Mortensen O. Corcoran C. Cornett U. G. Sidelmann J. C. Lindon J. K. Nicholson S. H. Hansen Drug Metab. Dispos. 2001 29 375 380
- (2001) Drug Metab. Dispos. , vol.29 , pp. 375-380
- Mortensen, R.W.¹ Corcoran, O.² Cornett, C.³ Sidelmann, U.G.⁴ Lindon, J.C.⁵ Nicholson, J.K.⁶ Hansen, S.H.⁷

26
- 0029988911
- U. G. Sidelmann A. W. Nicholls P. E. Meadows J. W. Gilbert J. C. Lindon I. D. Wilson J. K. Nicholson J. Chromatogr., A 1996 728 377 385
- (1996) J. Chromatogr., A , vol.728 , pp. 377-385
- Sidelmann, U.G.¹ Nicholls, A.W.² Meadows, P.E.³ Gilbert, J.W.⁴ Lindon, J.C.⁵ Wilson, I.D.⁶ Nicholson, J.K.⁷

27
- 10644294707
- S. J. Vanderhoeven J. Troke G. E. Tranter I. D. Wilson J. K. Nicholson J. C. Lindon Xenobiotica 2004 34 889 900
- (2004) Xenobiotica , vol.34 , pp. 889-900
- Vanderhoeven, S.J.¹ Troke, J.² Tranter, G.E.³ Wilson, I.D.⁴ Nicholson, J.K.⁵ Lindon, J.C.⁶

28
- 33646548989
- S. J. Vanderhoeven J. C. Lindon J. Troke J. K. Nicholson I. D. Wilson J. Pharm. Biomed. Anal. 2006 41 1002 1006
- (2006) J. Pharm. Biomed. Anal. , vol.41 , pp. 1002-1006
- Vanderhoeven, S.J.¹ Lindon, J.C.² Troke, J.³ Nicholson, J.K.⁴ Wilson, I.D.⁵

29
- 0019995539
- J. Hasegawa P. C. Smith L. Z. Benet Drug Metab. Dispos. 1982 10 469 473
- (1982) Drug Metab. Dispos. , vol.10 , pp. 469-473
- Hasegawa, J.¹ Smith, P.C.² Benet, L.Z.³

30
- 0031925696
- K. Akira T. Taira H. Hasegawa C. Sakuma Y. Shinohara Drug Metab. Dispos. 1998 26 457 464
- (1998) Drug Metab. Dispos. , vol.26 , pp. 457-464
- Akira, K.¹ Taira, T.² Hasegawa, H.³ Sakuma, C.⁴ Shinohara, Y.⁵

31
- 0029851431
- A. W. Nicholls K. Akira J. C. Lindon R. D. Farrant I. D. Wilson J. Harding D. A. Killick J. K. Nicholson Chem. Res. Toxicol. 1996 9 1414 1424
- (1996) Chem. Res. Toxicol. , vol.9 , pp. 1414-1424
- Nicholls, A.W.¹ Akira, K.² Lindon, J.C.³ Farrant, R.D.⁴ Wilson, I.D.⁵ Harding, J.⁶ Killick, D.A.⁷ Nicholson, J.K.⁸

32
- 29844439969
- J. A. Perrie J. R. Harding D. W. Holt A. Johnston P. Meath A. V. Stachulski Org. Lett. 2005 7 2591 2594
- (2005) Org. Lett. , vol.7 , pp. 2591-2594
- Perrie, J.A.¹ Harding, J.R.² Holt, D.W.³ Johnston, A.⁴ Meath, P.⁵ Stachulski, A.V.⁶

33
- 34250704682
- E. R. Bowkett J. R. Harding J. L. Maggs B. K. Park J. A. Perrie A. V. Stachulski Tetrahedron 2007 63 7596 7605
- (2007) Tetrahedron , vol.63 , pp. 7596-7605
- Bowkett, E.R.¹ Harding, J.R.² Maggs, J.L.³ Park, B.K.⁴ Perrie, J.A.⁵ Stachulski, A.V.⁶

34
- 0000341264
- F. H. C. Stewart Aust. J. Chem. 1968 21 2543 2550
- (1968) Aust. J. Chem. , vol.21 , pp. 2543-2550
- Stewart, F.H.C.¹

35
- 57449121750
- Wiley-Interscience:
- P. G. M. Wuts and T. W. Greene, Greene's Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience: 2007
- (2007) Greene's Protective Groups in Organic Synthesis, 4th Ed.;
- Wuts, P.G.M.¹ Greene, T.W.²

36
- 10044225737
- M. Shoji T. Uno Y. Hayashi Org. Lett. 2004 6 4535 4538
- (2004) Org. Lett. , vol.6 , pp. 4535-4538
- Shoji, M.¹ Uno, T.² Hayashi, Y.³

37
- 0027572366
- M. Tanaka M. Okita I. Yamatsu Carbohydr. Res. 1993 241 81 88
- (1993) Carbohydr. Res. , vol.241 , pp. 81-88
- Tanaka, M.¹ Okita, M.² Yamatsu, I.³

38
- 0042233651
- M. Warrier L. S. Kaanumalle V. Ramamurthy Can. J. Chem. 2003 81 620 631
- (2003) Can. J. Chem. , vol.81 , pp. 620-631
- Warrier, M.¹ Kaanumalle, L.S.² Ramamurthy, V.³

39
- 33847086252
- G. A. Kraus M. J. Taschner J. Org. Chem. 1980 45 1175 1176
- (1980) J. Org. Chem. , vol.45 , pp. 1175-1176
- Kraus, G.A.¹ Taschner, M.J.²

40
- 0037019992
- H. Neuvonen K. Neuvonen A. Koch E. Kleinpeter P. Pasanen J. Org. Chem. 2002 67 6995 7003
- (2002) J. Org. Chem. , vol.67 , pp. 6995-7003
- Neuvonen, H.¹ Neuvonen, K.² Koch, A.³ Kleinpeter, E.⁴ Pasanen, P.⁵

41
- 35748973588
- E. A. Pritchina N. P. Gritsan G. T. Burdzinski M. S. Platz J. Phys. Chem. A 2007 111 10483 10489
- (2007) J. Phys. Chem. A , vol.111 , pp. 10483-10489
- Pritchina, E.A.¹ Gritsan, N.P.² Burdzinski, G.T.³ Platz, M.S.⁴

42
- 0029269288
- J. K. Nicholson P. J. Foxall M. Spraul R. D. Farrant J. C. Lindon Anal. Chem. 1995 67 793 811
- (1995) Anal. Chem. , vol.67 , pp. 793-811
- Nicholson, J.K.¹ Foxall, P.J.² Spraul, M.³ Farrant, R.D.⁴ Lindon, J.C.⁵

43
- 43049140325
- A. A. Granovsky, PC GAMESS version 7.1, http://classic.chem.msu.su/gran/ gamess/index.html
- PC GAMESS Version 7.1
- Granovsky, A.A.¹

44
- 2042478652
- J. H. Lii B. Y. Ma N. L. Allinger J. Computational Chem. 1999 20 1593 1603
- (1999) J. Computational Chem. , vol.20 , pp. 1593-1603
- Lii, J.H.¹ Ma, B.Y.² Allinger, N.L.³

45
- 0034811661
- M. Hoffmann J. Rychlewski J. Am. Chem. Soc. 2001 123 2308 2316
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 2308-2316
- Hoffmann, M.¹ Rychlewski, J.²

46
- 84986435825
- R. Cammi J. Tomasi J. Computational Chem. 1995 16 1449 1458
- (1995) J. Computational Chem. , vol.16 , pp. 1449-1458
- Cammi, R.¹ Tomasi, J.²

47
- 0001728908
- M. Karelson V. S. Lobanov A. R. Katritzky Chem. Rev. 1996 96 1027 1043
- (1996) Chem. Rev. , vol.96 , pp. 1027-1043
- Karelson, M.¹ Lobanov, V.S.² Katritzky, A.R.³

48
- 0347291894
- R. G. Parr R. G. Pearson J. Am. Chem. Soc. 1983 105 7512 7516
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 7512-7516
- Parr, R.G.¹ Pearson, R.G.²

49
- 59949083740
- Manno (Switzerland)
- P. Flükiger, H. P. Lüthi, S. Portmann and J. Weber, MOLEKEL 4.0: Swiss National Supercomputing Centre CSCS, Manno (Switzerland), 2000
- (2000) MOLEKEL 4.0: Swiss National Supercomputing Centre CSCS
- Flükiger, P.¹ Lüthi, H.P.² Portmann, S.³ Weber, J.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.