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Volumn 4, Issue 39, 2014, Pages 20164-20176

The pentafluorosulfanyl group in cannabinoid receptor ligands: Synthesis and comparison with trifluoromethyl and tert-butyl analogues

(5) Altomonte, Stefano a Baillie, Gemma L b Ross, Ruth A b Riley, Jennifer c Zanda, Matteo a,d

a UNIVERSITY OF ABERDEEN (United Kingdom)

b UNIVERSITY OF TORONTO (Canada)

c UNIVERSITY OF DUNDEE (United Kingdom)

d CNR (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; DISSOCIATION;

ALIPHATIC GROUPS; CANNABINOID LIGANDS; CANNABINOID RECEPTORS; ELECTRONWITHDRAWING; EQUILIBRIUM DISSOCIATION CONSTANT; NANOMOLAR RANGE; PHARMACOLOGICAL ACTIVITY; TRIFLUOROMETHYL;

LIGANDS;

EID: 84901252134 PISSN: None EISSN: 20462069 Source Type: Journal
DOI: 10.1039/c4ra01212g Document Type: Article

Times cited : (45)

References (48)

1
- 0000362773
- D. O'Hagan D. B. Harper J. Fluorine Chem. 1999 100 127 133
- (1999) J. Fluorine Chem. , vol.100 , pp. 127-133
- O'Hagan, D.¹ Harper, D.B.²

2
- 38149070200
- S. Purser P. R. Moore S. Swallow V. Gouverneur Chem. Soc. Rev. 2008 37 320 330
- (2008) Chem. Soc. Rev. , vol.37 , pp. 320-330
- Purser, S.¹ Moore, P.R.² Swallow, S.³ Gouverneur, V.⁴

3
- 11244267140
- M. Zanda New J. Chem. 2004 28 1401 1411
- (2004) New J. Chem. , vol.28 , pp. 1401-1411
- Zanda, M.¹

4
- 77958039726
- D. O'Hagan J. Fluorine Chem. 2010 131 1071 1081
- (2010) J. Fluorine Chem. , vol.131 , pp. 1071-1081
- O'Hagan, D.¹

5
- 0001653490
- W. A. Sheppard J. Am. Chem. Soc. 1960 82 4751 4752
- (1960) J. Am. Chem. Soc. , vol.82 , pp. 4751-4752
- Sheppard, W.A.¹

6
- 84874640730
- Imperial college press
- J. T. Welch, in Fluorine In Pharmaceutical And Medicinal Chemistry, Imperial college press, 2012, vol. 6, pp. 175-207
- (2012) Fluorine in Pharmaceutical and Medicinal Chemistry , vol.6 , pp. 175-207
- Welch, J.T.¹

7
- 84867404690
- S. Altomonte M. Zanda J. Fluorine Chem. 2012 143 57 93
- (2012) J. Fluorine Chem. , vol.143 , pp. 57-93
- Altomonte, S.¹ Zanda, M.²

8
- 48249141548
- ed. V. A. Soloshonok, American Chemical Society, Washington, DC
- R. W. Winter, R. A. Dodean, and G. L. Gard, in Fluorine-Containing Synthons, ed., V. A. Soloshonok, American Chemical Society, Washington, DC, 2005, vol. 911, pp. 87-118
- (2005) Fluorine-Containing Synthons , vol.911 , pp. 87-118
- Winter, R.W.¹ Dodean, R.A.² Gard, G.L.³

9
- 0001645508
- W. A. Sheppard J. Am. Chem. Soc. 1965 87 2410 2420
- (1965) J. Am. Chem. Soc. , vol.87 , pp. 2410-2420
- Sheppard, W.A.¹

10
- 0005910987
- C. Hansch R. M. Muir T. Fujita P. P. Maloney F. Geiger M. Streich J. Am. Chem. Soc. 1963 85 2817 2824
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 2817-2824
- Hansch, C.¹ Muir, R.M.² Fujita, T.³ Maloney, P.P.⁴ Geiger, F.⁵ Streich, M.⁶

11
- 0000908552
- W. A. Sheppard J. Am. Chem. Soc. 1962 84 3072 3076
- (1962) J. Am. Chem. Soc. , vol.84 , pp. 3072-3076
- Sheppard, W.A.¹

12
- 34548540174
- J. T. Welch D. S. Lim Bioorg. Med. Chem. 2007 15 6659 6666
- (2007) Bioorg. Med. Chem. , vol.15 , pp. 6659-6666
- Welch, J.T.¹ Lim, D.S.²

13
- 84891565619
- Wiley-VCH, Weinheim
- P. Kirsch, Modern fluoroorganic chemistry synthesis, reactivity, applications, Wiley-VCH, Weinheim, 2004
- (2004) Modern Fluoroorganic Chemistry Synthesis, Reactivity, Applications
- Kirsch, P.¹

14
- 0037891239
- ed. K. Akiba, Wiley-VCH, New York
- D. Lentz and K. Seppelt, in Chemistry of Hypervalent Compounds, ed., K. Akiba, Wiley-VCH, New York, 1999, pp. 295-323
- (1999) Chemistry of Hypervalent Compounds , pp. 295-323
- Lentz, D.¹ Seppelt, K.²

15
- 0035980214
- L. J. Sæthre N. Berrah J. D. Bozek K. J. Børve T. X. Carroll E. Kukk G. L. Gard R. Winter T. D. Thomas J. Am. Chem. Soc. 2001 123 10729 10737
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 10729-10737
- Sæthre, L.J.¹ Berrah, N.² Bozek, J.D.³ Børve, K.J.⁴ Carroll, T.X.⁵ Kukk, E.⁶ Gard, G.L.⁷ Winter, R.⁸ Thomas, T.D.⁹

16
- 41149089767
- A. Kapur P. Samaniego G. A. Thakur A. Makriyannis M. E. Abood J. Pharmacol. Exp. Ther. 2008 325 341 348
- (2008) J. Pharmacol. Exp. Ther. , vol.325 , pp. 341-348
- Kapur, A.¹ Samaniego, P.² Thakur, G.A.³ Makriyannis, A.⁴ Abood, M.E.⁵

17
- 0027515373
- S. Munro K. L. Thomas M. Abu-Shaar Nature 1993 365 61 65
- (1993) Nature , vol.365 , pp. 61-65
- Munro, S.¹ Thomas, K.L.² Abu-Shaar, M.³

18
- 18444376760
- A. C. Howlett F. Barth T. I. Bonner G. Cabral P. Casellas W. A. Devane C. C. Felder M. Herkenham K. Mackie B. R. Martin R. Mechoulam R. G. Pertwee Pharmacol. Rev. 2002 54 161 202
- (2002) Pharmacol. Rev. , vol.54 , pp. 161-202
- Howlett, A.C.¹ Barth, F.² Bonner, T.I.³ Cabral, G.⁴ Casellas, P.⁵ Devane, W.A.⁶ Felder, C.C.⁷ Herkenham, M.⁸ Mackie, K.⁹ Martin, B.R.¹⁰ Mechoulam, R.¹¹ Pertwee, R.G.¹²

19
- 0028931849
- D. Shire C. Carillon M. Kaghad B. Calandra M. Rinaldi-Carmona G. L. Fur D. Caput P. Ferrara J. Biol. Chem. 1995 270 3726 3731
- (1995) J. Biol. Chem. , vol.270 , pp. 3726-3731
- Shire, D.¹ Carillon, C.² Kaghad, M.³ Calandra, B.⁴ Rinaldi-Carmona, M.⁵ Fur, G.L.⁶ Caput, D.⁷ Ferrara, P.⁸

20
- 11144263163
- E. Ryberg H. K. Vu N. Larsson T. Groblewski S. Hjorth T. Elebring S. Sjögren P. J. Greasley FEBS Lett. 2005 579 259 264
- (2005) FEBS Lett. , vol.579 , pp. 259-264
- Ryberg, E.¹ Vu, H.K.² Larsson, N.³ Groblewski, T.⁴ Hjorth, S.⁵ Elebring, T.⁶ Sjögren, S.⁷ Greasley, P.J.⁸

21
- 0025236913
- M. Herkenham A. B. Lynn M. D. Little M. R. Johnson L. S. Melvin B. R. de Costa K. C. Rice Proc. Natl. Acad. Sci. U. S. A. 1990 87 1932 1936
- (1990) Proc. Natl. Acad. Sci. U. S. A. , vol.87 , pp. 1932-1936
- Herkenham, M.¹ Lynn, A.B.² Little, M.D.³ Johnson, M.R.⁴ Melvin, L.S.⁵ De Costa, B.R.⁶ Rice, K.C.⁷

22
- 0031578457
- G. Griffin S. R. Fernando R. A. Ross N. G. McKay M. L. J. Ashford D. Shire J. W. Huffman S. Yu J. A. H. Lainton R. G. Pertwee Eur. J. Pharmacol. 1997 339 53 61
- (1997) Eur. J. Pharmacol. , vol.339 , pp. 53-61
- Griffin, G.¹ Fernando, S.R.² Ross, R.A.³ McKay, N.G.⁴ Ashford, M.L.J.⁵ Shire, D.⁶ Huffman, J.W.⁷ Yu, S.⁸ Lainton, J.A.H.⁹ Pertwee, R.G.¹⁰

23
- 0033538346
- R. G. Pertwee Life Sci. 1999 65 597 605
- (1999) Life Sci. , vol.65 , pp. 597-605
- Pertwee, R.G.¹

24
- 33244493807
- J. C. Ashton D. Friberg C. L. Darlington P. F. Smith Neurosci. Lett. 2006 396 113 116
- (2006) Neurosci. Lett. , vol.396 , pp. 113-116
- Ashton, J.C.¹ Friberg, D.² Darlington, C.L.³ Smith, P.F.⁴

25
- 80053246977
- J. Horder M. Browning M. Di Simplicio P. J. Cowen C. J. Harmer J. Psychopharmacol. 2012 26 125 132
- (2012) J. Psychopharmacol. , vol.26 , pp. 125-132
- Horder, J.¹ Browning, M.² Di Simplicio, M.³ Cowen, P.J.⁴ Harmer, C.J.⁵

26
- 58149138840
- G. Kunos D. Osei-Hyiaman S. Bátkai K. A. Sharkey A. Makriyannis Trends Pharmacol. Sci. 2009 30 1 7
- (2009) Trends Pharmacol. Sci. , vol.30 , pp. 1-7
- Kunos, G.¹ Osei-Hyiaman, D.² Bátkai, S.³ Sharkey, K.A.⁴ Makriyannis, A.⁵

27
- 84858984433
- E. Kirilly X. Gonda G. Bagdy Acta Physiol. 2012 205 41 60
- (2012) Acta Physiol. , vol.205 , pp. 41-60
- Kirilly, E.¹ Gonda, X.² Bagdy, G.³

28
- 79955473886
- B.-C. Ho T. H. Wassink S. Ziebell N. C. Andreasen Schizophr. Res. 2011 128 66 75
- (2011) Schizophr. Res. , vol.128 , pp. 66-75
- Ho, B.-C.¹ Wassink, T.H.² Ziebell, S.³ Andreasen, N.C.⁴

29
- 20444459375
- B. Costa A. E. Trovato M. Colleoni G. Giagnoni E. Zarini T. Croci Pain 2005 116 52 61
- (2005) Pain , vol.116 , pp. 52-61
- Costa, B.¹ Trovato, A.E.² Colleoni, M.³ Giagnoni, G.⁴ Zarini, E.⁵ Croci, T.⁶

30
- 34249671248
- P. Gazzerro M. G. Caruso M. Notarnicola G. Misciagna V. Guerra C. Laezza M. Bifulco Int. J. Obes. 2006 31 908 912
- (2006) Int. J. Obes. , vol.31 , pp. 908-912
- Gazzerro, P.¹ Caruso, M.G.² Notarnicola, M.³ Misciagna, G.⁴ Guerra, V.⁵ Laezza, C.⁶ Bifulco, M.⁷

31
- 0028129936
- M. Rinaldi-Carmona F. Barth M. Héaulme D. Shire B. Calandra C. Congy S. Martinez J. Maruani G. Néliat D. Caput P. Ferrara P. Soubrié J. C. Brelière G. Le Fur FEBS Lett. 1994 350 240 244
- (1994) FEBS Lett. , vol.350 , pp. 240-244
- Rinaldi-Carmona, M.¹ Barth, F.² Héaulme, M.³ Shire, D.⁴ Calandra, B.⁵ Congy, C.⁶ Martinez, S.⁷ Maruani, J.⁸ Néliat, G.⁹ Caput, D.¹⁰ Ferrara, P.¹¹ Soubrié, P.¹² Brelière, J.C.¹³ Le Fur, G.¹⁴

32
- 0033602129
- R. Lan Q. Liu P. Fan S. Lin S. R. Fernando D. McCallion R. Pertwee A. Makriyannis J. Med. Chem. 1999 42 769 776
- (1999) J. Med. Chem. , vol.42 , pp. 769-776
- Lan, R.¹ Liu, Q.² Fan, P.³ Lin, S.⁴ Fernando, S.R.⁵ McCallion, D.⁶ Pertwee, R.⁷ Makriyannis, A.⁸

33
- 84901285367
- P. Lazzari, S. Ruiu, G. A. Pinna and G. Murineddu, US Pat., 0 261 281, 2005
- (2005) US Pat.
- Lazzari, P.¹ Ruiu, S.² Pinna, G.A.³ Murineddu, G.⁴

34
- 0034685768
- R. D. Bowden P. J. Comina M. P. Greenhall B. M. Kariuki A. Loveday D. Philp Tetrahedron 2000 56 3399 3408
- (2000) Tetrahedron , vol.56 , pp. 3399-3408
- Bowden, R.D.¹ Comina, P.J.² Greenhall, M.P.³ Kariuki, B.M.⁴ Loveday, A.⁵ Philp, D.⁶

35
- 51849098198
- S.-L. Tseng M.-S. Hung C.-P. Chang J.-S. Song C.-L. Tai H.-H. Chiu W.-P. Hsieh Y. Lin W.-L. Chung C.-W. Kuo C.-H. Wu C.-M. Chu Y.-S. Tung Y.-S. Chao K.-S. Shia J. Med. Chem. 2008 51 5397 5412
- (2008) J. Med. Chem. , vol.51 , pp. 5397-5412
- Tseng, S.-L.¹ Hung, M.-S.² Chang, C.-P.³ Song, J.-S.⁴ Tai, C.-L.⁵ Chiu, H.-H.⁶ Hsieh, W.-P.⁷ Lin, Y.⁸ Chung, W.-L.⁹ Kuo, C.-W.¹⁰ Wu, C.-H.¹¹ Chu, C.-M.¹² Tung, Y.-S.¹³ Chao, Y.-S.¹⁴ Shia, K.-S.¹⁵

36
- 8644243613
- A. Leo C. Hansch D. Elkins Chem. Rev. 1971 71 525 616
- (1971) Chem. Rev. , vol.71 , pp. 525-616
- Leo, A.¹ Hansch, C.² Elkins, D.³

37
- 33846449169
- H. Fan H. T. Ravert D. P. Holt R. F. Dannals A. G. Horti J. Labelled Compd. Radiopharm. 2006 49 1021 1036
- (2006) J. Labelled Compd. Radiopharm. , vol.49 , pp. 1021-1036
- Fan, H.¹ Ravert, H.T.² Holt, D.P.³ Dannals, R.F.⁴ Horti, A.G.⁵

38
- 34548313831
- S. Tobiishi T. Sasada Y. Nojiri F. Yamamoto T. Mukai K. Ishiwata M. Maeda Chem. Pharm. Bull. 2007 55 1213 1217
- (2007) Chem. Pharm. Bull. , vol.55 , pp. 1213-1217
- Tobiishi, S.¹ Sasada, T.² Nojiri, Y.³ Yamamoto, F.⁴ Mukai, T.⁵ Ishiwata, K.⁶ Maeda, M.⁷

39
- 0032982010
- R. A. Ross H. C. Brockie L. A. Stevenson V. L. Murphy F. Templeton A. Makriyannis R. G. Pertwee Br. J. Pharmacol. 1999 126 665 672
- (1999) Br. J. Pharmacol. , vol.126 , pp. 665-672
- Ross, R.A.¹ Brockie, H.C.² Stevenson, L.A.³ Murphy, V.L.⁴ Templeton, F.⁵ Makriyannis, A.⁶ Pertwee, R.G.⁷

40
- 31544467861
- J.-Z. Chen X.-W. Han Q. Liu A. Makriyannis J. Wang X.-Q. Xie J. Med. Chem. 2006 49 625 636
- (2006) J. Med. Chem. , vol.49 , pp. 625-636
- Chen, J.-Z.¹ Han, X.-W.² Liu, Q.³ Makriyannis, A.⁴ Wang, J.⁵ Xie, X.-Q.⁶

41
- 24044539957
- M. R. Price G. L. Baillie A. Thomas L. A. Stevenson M. Easson R. Goodwin A. McLean L. McIntosh G. Goodwin G. Walker P. Westwood J. Marrs F. Thomson P. Cowley A. Christopoulos R. G. Pertwee R. A. Ross Mol. Pharmacol. 2005 68 1484 1495
- (2005) Mol. Pharmacol. , vol.68 , pp. 1484-1495
- Price, M.R.¹ Baillie, G.L.² Thomas, A.³ Stevenson, L.A.⁴ Easson, M.⁵ Goodwin, R.⁶ McLean, A.⁷ McIntosh, L.⁸ Goodwin, G.⁹ Walker, G.¹⁰ Westwood, P.¹¹ Marrs, J.¹² Thomson, F.¹³ Cowley, P.¹⁴ Christopoulos, A.¹⁵ Pertwee, R.G.¹⁶ Ross, R.A.¹⁷

42
- 77949389182
- D. A. Jackson S. A. Mabury Environ. Toxicol. Chem. 2009 28 1866
- (2009) Environ. Toxicol. Chem. , vol.28 , pp. 1866
- Jackson, D.A.¹ Mabury, S.A.²

43
- 65249098311
- B. Hoelke S. Gieringer M. Arlt C. Saal Anal. Chem. 2009 81 3165 3172
- (2009) Anal. Chem. , vol.81 , pp. 3165-3172
- Hoelke, B.¹ Gieringer, S.² Arlt, M.³ Saal, C.⁴

44
- 58149392408
- M. M. C. van D. Lee M. Bras C. J. van Koppen G. J. R. Zaman J. Biomol. Screening 2008 13 986 998
- (2008) J. Biomol. Screening , vol.13 , pp. 986-998
- Van D. Lee, M.M.C.¹ Bras, M.² Van Koppen, C.J.³ Zaman, G.J.R.⁴

45
- 84874441447
- B. D. Kangas M. S. Delatte V. K. Vemuri G. A. Thakur S. P. Nikas K. V. Subramanian V. G. Shukla A. Makriyannis J. Bergman J. Pharmacol. Exp. Ther. 2013 344 561 567
- (2013) J. Pharmacol. Exp. Ther. , vol.344 , pp. 561-567
- Kangas, B.D.¹ Delatte, M.S.² Vemuri, V.K.³ Thakur, G.A.⁴ Nikas, S.P.⁵ Subramanian, K.V.⁶ Shukla, V.G.⁷ Makriyannis, A.⁸ Bergman, J.⁹

46
- 0002714675
- W. C. Still M. Kahn A. Mitra J. Org. Chem. 1978 43 2923 2925
- (1978) J. Org. Chem. , vol.43 , pp. 2923-2925
- Still, W.C.¹ Kahn, M.² Mitra, A.³

47
- 80051720314
- For Economic Co-Operation And Development O. OECD Publishing, Paris
- Organisation for Economic Co-operation and Development, Test No. 117: Partition Coefficient (n-octanol/water), HPLC Method, OECD Publishing, Paris, 2004
- (2004) Test No. 117: Partition Coefficient (N-octanol/water), HPLC Method

48
- 15944368026
- X. Fei Q. Zheng J. Liq. Chromatogr. Relat. Technol. 2005 28 939 945
- (2005) J. Liq. Chromatogr. Relat. Technol. , vol.28 , pp. 939-945
- Fei, X.¹ Zheng, Q.²

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