SCOPUS 정보 검색 플랫폼

Volumn 68, Issue 4, 2012, Pages 1029-1051

Synthesis of sansalvamide A peptidomimetics: Triazole, oxazole, thiazole, and pseudoproline containing compounds

(10) Davis, Melinda R b Singh, Erinprit K b Wahyudi, Hendra a Alexander, Leslie D b Kunicki, Joseph B b Nazarova, Lidia A b Fairweather, Kelly A c Giltrap, Andrew M c Jolliffe, Katrina A c McAlpine, Shelli R a

a UNIVERSITY OF NEW SOUTH WALES (Australia)

b SAN DIEGO STATE UNIVERSITY (United States)

c UNIVERSITY OF SYDNEY (Australia)

Author keywords

Macrocycle; Oxazole; Peptide; Peptidomimetic; Pseudoproline; Sansalvamide A; Thiazole; Triazole

Indexed keywords

OXAZOLE DERIVATIVE; PEPTIDOMIMETIC AGENT; PROLINE; SANSALVAMIDE A; THIAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CLICK CHEMISTRY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HANTZSCH REACTION; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

EID: 84855453441 PISSN: 00404020 EISSN: 14645416 Source Type: Journal
DOI: 10.1016/j.tet.2011.11.089 Document Type: Article

Times cited : (72)

References (48)

1
- 77956339835
- R.P. Sellers, L.D. Alexander, V.A. Johnson, C.-C. Lin, J. Savage, R. Corral, J. Moss, T.S. Slugocki, E.K. Singh, M.R. Davis, S. Ravula, J.E. Spicer, J.L. Oelrich, A. Thornquist, C.-M. Pan, and S.R. McAlpine Bioorg. Med. Chem. 18 2010 6822 6856
- (2010) Bioorg. Med. Chem. , vol.18 , pp. 6822-6856
- Sellers, R.P.¹ Alexander, L.D.² Johnson, V.A.³ Lin, C.-C.⁴ Savage, J.⁵ Corral, R.⁶ Moss, J.⁷ Slugocki, T.S.⁸ Singh, E.K.⁹ Davis, M.R.¹⁰ Ravula, S.¹¹ Spicer, J.E.¹² Oelrich, J.L.¹³ Thornquist, A.¹⁴ Pan, C.-M.¹⁵ McAlpine, S.R.¹⁶

2
- 39149096281
- K. Otrubova, G.H. Lushington, D. Vander Velde, K.L. McGuire, and S.R. McAlpine J. Med. Chem. 51 2008 530 544
- (2008) J. Med. Chem. , vol.51 , pp. 530-544
- Otrubova, K.¹ Lushington, G.H.² Vander Velde, D.³ McGuire, K.L.⁴ McAlpine, S.R.⁵

3
- 0033538036
- G.N. Belofsky, P.R. Jensen, and W. Fenical Tetrahedron Lett. 40 1999 2913 2916
- (1999) Tetrahedron Lett. , vol.40 , pp. 2913-2916
- Belofsky, G.N.¹ Jensen, P.R.² Fenical, W.³

4
- 68149175130
- P.-S. Pan, R.C. Vasko, S.A. Lapera, V.A. Johnson, R.P. Sellers, C.-C. Lin, C.-M. Pan, M.R. Davis, V.C. Ardi, and S.R. McAlpine Bioorg. Med. Chem. 17 2009 5806 5825
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 5806-5825
- Pan, P.-S.¹ Vasko, R.C.² Lapera, S.A.³ Johnson, V.A.⁴ Sellers, R.P.⁵ Lin, C.-C.⁶ Pan, C.-M.⁷ Davis, M.R.⁸ Ardi, V.C.⁹ McAlpine, S.R.¹⁰

5
- 34247580055
- K. Otrubova, K.L. McGuire, and S.R. McAlpine J. Med. Chem. 50 2007 1999 2002
- (2007) J. Med. Chem. , vol.50 , pp. 1999-2002
- Otrubova, K.¹ McGuire, K.L.² McAlpine, S.R.³

6
- 34547855100
- P.S. Pan, K. McGuire, and S.R. McAlpine Bioorg. Med. Chem. Lett. 17 2007 5072 5077
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 5072-5077
- Pan, P.S.¹ McGuire, K.² McAlpine, S.R.³

7
- 77956640526
- R.C. Vasko, R.A. Rodriguez, C.N. Cunningham, V.C. Ardi, D.A. Agard, and S.R. McAlpine ACS Med. Chem. Lett. 1 2010 4 8
- (2010) ACS Med. Chem. Lett. , vol.1 , pp. 4-8
- Vasko, R.C.¹ Rodriguez, R.A.² Cunningham, C.N.³ Ardi, V.C.⁴ Agard, D.A.⁵ McAlpine, S.R.⁶

8
- 0036219609
- L. Neckers Trends Mol. Med. 8 2002 S55 S61
- (2002) Trends Mol. Med. , vol.8
- Neckers, L.¹

9
- 0042855994
- G. Chiosis, H. Huezo, N. Rosen, E. Mimnaugh, L. Whitesell, and L. Neckers Mol. Cancer Ther. 2 2003 123 129
- (2003) Mol. Cancer Ther. , vol.2 , pp. 123-129
- Chiosis, G.¹ Huezo, H.² Rosen, N.³ Mimnaugh, E.⁴ Whitesell, L.⁵ Neckers, L.⁶

10
- 21244462689
- E.A. Sausville, M. Hollingshead, M. Alley, A.M. Burger, S. Borgel, C. Pacula-Cox, and H.H. Fiebig Cancer Chemother. Pharmacol. 56 2005 115 125
- (2005) Cancer Chemother. Pharmacol. , vol.56 , pp. 115-125
- Sausville, E.A.¹ Hollingshead, M.² Alley, M.³ Burger, A.M.⁴ Borgel, S.⁵ Pacula-Cox, C.⁶ Fiebig, H.H.⁷

11
- 29544446133
- N. Sueoka, M. Senju, A. Sato, K. Iwanaga, Y. Sakao, S. Tomimitsu, M. Tominaga, K. Irie, S. Hayashi, and E. Sueoka J. Cancer Res. Clin. Oncol. 132 2006 150 158
- (2006) J. Cancer Res. Clin. Oncol. , vol.132 , pp. 150-158
- Sueoka, N.¹ Senju, M.² Sato, A.³ Iwanaga, K.⁴ Sakao, Y.⁵ Tomimitsu, S.⁶ Tominaga, M.⁷ Irie, K.⁸ Hayashi, S.⁹ Sueoka, E.¹⁰

12
- 30044440611
- Y.S. Chang, L.C. Lee, F.C. Sun, C.C. Chao, H.W. Fu, and Y.K. Lai J. Cell. Biochem. 97 2006 156 165
- (2006) J. Cell. Biochem. , vol.97 , pp. 156-165
- Chang, Y.S.¹ Lee, L.C.² Sun, F.C.³ Chao, C.C.⁴ Fu, H.W.⁵ Lai, Y.K.⁶

13
- 33846982944
- D. Matei, M. Satpathy, L. Cao, Y.C. Lai, H. Nakshatri, and D.B. Donner J. Biol. Chem. 282 2007 445 453
- (2007) J. Biol. Chem. , vol.282 , pp. 445-453
- Matei, D.¹ Satpathy, M.² Cao, L.³ Lai, Y.C.⁴ Nakshatri, H.⁵ Donner, D.B.⁶

14
- 70350548428
- S.Z. Usmani, R. Bona, and Z.H. Li Curr. Mol. Med. 9 2009 654 664
- (2009) Curr. Mol. Med. , vol.9 , pp. 654-664
- Usmani, S.Z.¹ Bona, R.² Li, Z.H.³

15
- 64949083563
- F. Koga, K. Kihara, and L. Neckers Anticancer Res. 29 2009 797 807
- (2009) Anticancer Res. , vol.29 , pp. 797-807
- Koga, F.¹ Kihara, K.² Neckers, L.³

16
- 51349083634
- M.F. Barginear, C. Van Poznak, N. Rosen, S. Miodi, C.A. Hudis, and D.R. Budman Curr. Cancer Drug Targets 8 2008 522 535
- (2008) Curr. Cancer Drug Targets , vol.8 , pp. 522-535
- Barginear, M.F.¹ Van Poznak, C.² Rosen, N.³ Miodi, S.⁴ Hudis, C.A.⁵ Budman, D.R.⁶

17
- 58849160500
- U. Banerji Clin. Cancer Res. 15 2009 9 14
- (2009) Clin. Cancer Res. , vol.15 , pp. 9-14
- Banerji, U.¹

18
- 0141596326
- E.A. Sausville, J.E. Tomaszewski, and P. Ivy Curr. Cancer Drug Targets 3 2003 377 383
- (2003) Curr. Cancer Drug Targets , vol.3 , pp. 377-383
- Sausville, E.A.¹ Tomaszewski, J.E.² Ivy, P.³

19
- 0033951278
- L.H. Pearl, and C. Prodromou Curr. Opin. Struct. Biol. 10 2000 46 51
- (2000) Curr. Opin. Struct. Biol. , vol.10 , pp. 46-51
- Pearl, L.H.¹ Prodromou, C.²

20
- 0141683523
- A. Dehner, J. Furrer, K. Richter, I. Schuster, J. Buchner, and H. Kessler ChemBioChem 4 2003 870 877
- (2003) ChemBioChem , vol.4 , pp. 870-877
- Dehner, A.¹ Furrer, J.² Richter, K.³ Schuster, I.⁴ Buchner, J.⁵ Kessler, H.⁶

21
- 79960895660
- Hagn, F. X.; Richter, K.; Buchner, J.; Kessler, H. In Proc. Experimental Nuclear Magnetic Resonance Conference, 2005; p 211.
- (2005) Proc. Experimental Nuclear Magnetic Resonance Conference , pp. 211
- Hagn, F.X.¹ Richter, K.² Buchner, J.³ Kessler, H.⁴

22
- 0344511727
- J.M. Jez, J.C. Chen, G. Rastelli, R.M. Stroud, and D.V. Santi Chem. Biol. 10 2003 361 368
- (2003) Chem. Biol. , vol.10 , pp. 361-368
- Jez, J.M.¹ Chen, J.C.² Rastelli, G.³ Stroud, R.M.⁴ Santi, D.V.⁵

23
- 0030026167
- T.W. von Geldern, J.A. Kester, R. Bal, J.R. Wu-Wong, W. Chiou, D.B. Dixon, and T.J. Opgenorth J. Med. Chem. 39 1996 968 981
- (1996) J. Med. Chem. , vol.39 , pp. 968-981
- Von Geldern, T.W.¹ Kester, J.A.² Bal, R.³ Wu-Wong, J.R.⁴ Chiou, W.⁵ Dixon, D.B.⁶ Opgenorth, T.J.⁷

24
- 14444286696
- J. Bartroli, E. Turmo, M. Algueró, E. Boncompte, M.L. Vericat, L. Conte, J. Ramis, M. Merlos, J. García-Rafanell, and J. Forn J. Med. Chem. 41 1998 1869 1882
- (1998) J. Med. Chem. , vol.41 , pp. 1869-1882
- Bartroli, J.¹ Turmo, E.² Algueró, M.³ Boncompte, E.⁴ Vericat, M.L.⁵ Conte, L.⁶ Ramis, J.⁷ Merlos, M.⁸ García-Rafanell, J.⁹ Forn, J.¹⁰

25
- 0031028387
- P. Dumy, M. Keller, D.E. Ryan, B. Rohwedder, T. Wöhr, and M. Mutter J. Am. Chem. Soc. 119 1997 918 925
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 918-925
- Dumy, P.¹ Keller, M.² Ryan, D.E.³ Rohwedder, B.⁴ Wöhr, T.⁵ Mutter, M.⁶

26
- 77957226741
- Academic London
- B.A. Morgan, J.A. Gainor, and C.A. Richard Annual Reports in Medicinal Chemistry 1989 Academic London 243 252
- (1989) Annual Reports in Medicinal Chemistry , pp. 243-252
- Morgan, B.A.¹ Gainor, J.A.² Richard, C.A.³

27
- 0026766974
- J. Rizo, and L.M. Gierasch Annu. Rev. Biochem. 61 1992 387 418
- (1992) Annu. Rev. Biochem. , vol.61 , pp. 387-418
- Rizo, J.¹ Gierasch, L.M.²

28
- 70349956393
- W.S. Horne, C.A. Olsen, J.M. Beierle, A. Montero, and M.R. Ghadiri Angew. Chem., Int. Ed. 48 2009 4718 4724
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 4718-4724
- Horne, W.S.¹ Olsen, C.A.² Beierle, J.M.³ Montero, A.⁴ Ghadiri, M.R.⁵

29
- 77949488829
- F. Cohen, M.F.T. Koehler, P. Bergeron, L.O. Elliott, J.A. Flygare, M.C. Franklin, L. Gazzard, S.F. Keteltas, K. Lau, C.Q. Ly, V. Tsui, and W.J. Fairbrother Bioorg. Med. Chem. Lett. 20 2010 2229 2233
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 2229-2233
- Cohen, F.¹ Koehler, M.F.T.² Bergeron, P.³ Elliott, L.O.⁴ Flygare, J.A.⁵ Franklin, M.C.⁶ Gazzard, L.⁷ Keteltas, S.F.⁸ Lau, K.⁹ Ly, C.Q.¹⁰ Tsui, V.¹¹ Fairbrother, W.J.¹²

30
- 77955662126
- J. Sperry, and C.J. Moody Tetrahedron 66 2010 6483 6495
- (2010) Tetrahedron , vol.66 , pp. 6483-6495
- Sperry, J.¹ Moody, C.J.²

31
- 0034405086
- M. Keller, T. Wöhr, P. Dumy, L. Patiny, and M. Mutter Chem. - Eur. J. 6 2000 4358 4363
- (2000) Chem. - Eur. J. , vol.6 , pp. 4358-4363
- Keller, M.¹ Wöhr, T.² Dumy, P.³ Patiny, L.⁴ Mutter, M.⁵

32
- 79954617765
- D.S. Pedersen, and A. Abell Eur. J. Org. Chem. 2011 2399 2411
- (2011) Eur. J. Org. Chem. , pp. 2399-2411
- Pedersen, D.S.¹ Abell, A.²

33
- 33845309676
- J. Chatterjee, D.F. Mierke, and H. Kessler J. Am. Chem. Soc. 128 2006 15164 15172
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 15164-15172
- Chatterjee, J.¹ Mierke, D.F.² Kessler, H.³

34
- 33750309548
- M. Heller, M. Sukopp, N. Tsomaia, M. John, D.F. Mierke, B. Reif, and H. Kessler J. Am. Chem. Soc. 128 2006 13806 13814
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 13806-13814
- Heller, M.¹ Sukopp, M.² Tsomaia, N.³ John, M.⁴ Mierke, D.F.⁵ Reif, B.⁶ Kessler, H.⁷

35
- 33947246678
- R.A. Rodriguez, P.-S. Pan, C.-M. Pan, S. Ravula, S.A. Lapera, E.K. Singh, T.J. Styers, J.D. Brown, J. Cajica, E. Parry, K. Otrubova, and S.R. McAlpine J. Org. Chem. 72 2007 1980 2002
- (2007) J. Org. Chem. , vol.72 , pp. 1980-2002
- Rodriguez, R.A.¹ Pan, P.-S.² Pan, C.-M.³ Ravula, S.⁴ Lapera, S.A.⁵ Singh, E.K.⁶ Styers, T.J.⁷ Brown, J.D.⁸ Cajica, J.⁹ Parry, E.¹⁰ Otrubova, K.¹¹ McAlpine, S.R.¹²

36
- 0029952823
- T. Wöhr, F. Wahl, A. Nefzi, B. Rohwedder, T. Sato, X. Sun, and M. Mutter J. Am. Chem. Soc. 118 1996 9218 9227
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9218-9227
- Wöhr, T.¹ Wahl, F.² Nefzi, A.³ Rohwedder, B.⁴ Sato, T.⁵ Sun, X.⁶ Mutter, M.⁷

37
- 0033543486
- T. Rückle, P. de Lavallaz, M. Keller, P. Dumy, and M. Mutter Tetrahedron 55 1999 11281 11288
- (1999) Tetrahedron , vol.55 , pp. 11281-11288
- Rückle, T.¹ De Lavallaz, P.² Keller, M.³ Dumy, P.⁴ Mutter, M.⁵

38
- 77952099836
- H. Sun, L. Liu, J. Lu, S. Qiu, C.Y. Yang, H. Yi, and S. Wang Bioorg. Med. Chem. Lett. 20 2010 3043 3046
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3043-3046
- Sun, H.¹ Liu, L.² Lu, J.³ Qiu, S.⁴ Yang, C.Y.⁵ Yi, H.⁶ Wang, S.⁷

39
- 0000096835
- H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
- Kolb, H.C.¹ Finn, M.G.² Sharpless, K.B.³

40
- 77954557903
- K.A. Fairweather, N. Sayyadi, I.J. Luck, J.K. Clegg, and K.A. Jolliffe Org. Lett. 12 2010 3136 3139
- (2010) Org. Lett. , vol.12 , pp. 3136-3139
- Fairweather, K.A.¹ Sayyadi, N.² Luck, I.J.³ Clegg, J.K.⁴ Jolliffe, K.A.⁵

41
- 23744439852
- K.C. Nicolaou, M. Zak, B.S. Safina, A.A. Estrada, S.H. Lee, and M. Nevalainen J. Am. Chem. Soc. 127 2005 11176 11183
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 11176-11183
- Nicolaou, K.C.¹ Zak, M.² Safina, B.S.³ Estrada, A.A.⁴ Lee, S.H.⁵ Nevalainen, M.⁶

42
- 0037065656
- S. Deng, and J. Taunton J. Am. Chem. Soc. 124 2002 916 917
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 916-917
- Deng, S.¹ Taunton, J.²

43
- 33947293559
- D. Seyferth, R.S. Marmor, and P. Hilbert J. Org. Chem. 36 1971 1379 1386
- (1971) J. Org. Chem. , vol.36 , pp. 1379-1386
- Seyferth, D.¹ Marmor, R.S.² Hilbert, P.³

44
- 0001174986
- J.C. Gilbert, and U. Weerasooriya J. Org. Chem. 47 1982 1837 1845
- (1982) J. Org. Chem. , vol.47 , pp. 1837-1845
- Gilbert, J.C.¹ Weerasooriya, U.²

45
- 84855446757
- S.G. Mahler, G. Serra, I. Viera, and E. Manta Rev. Latinoam. Quim. 35 2007 74 82
- (2007) Rev. Latinoam. Quim. , vol.35 , pp. 74-82
- Mahler, S.G.¹ Serra, G.² Viera, I.³ Manta, E.⁴

46
- 0033550173
- R. Saladino, M. Mezzetti, E. Mincione, I. Torrini, M.P. Paradisi, and G. Mastropietro J. Org. Chem. 64 1999 8468 8474
- (1999) J. Org. Chem. , vol.64 , pp. 8468-8474
- Saladino, R.¹ Mezzetti, M.² Mincione, E.³ Torrini, I.⁴ Paradisi, M.P.⁵ Mastropietro, G.⁶

47
- 77951430489
- S.V. Malhotra, Z. Chengdong, and W. Hao Lett. Org. Chem. 7 2010 168 171
- (2010) Lett. Org. Chem. , vol.7 , pp. 168-171
- Malhotra, S.V.¹ Chengdong, Z.² Hao, W.³

48
- 79952743243
- S.M. Bronner, A.E. Goetz, and N.K. Garg J. Am. Chem. Soc. 133 2011 3832 3835
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 3832-3835
- Bronner, S.M.¹ Goetz, A.E.² Garg, N.K.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.