SCOPUS 정보 검색 플랫폼

Volumn 7, Issue 4, 2009, Pages 706-716

Synthesis of new aza-analogs of staurosporine, K-252a and rebeccamycin by nucleophilic opening of C2-symmetric bis-aziridines

(2) Delarue Cochin, Sandrine a,b McCort Tranchepain, Isabelle a

a UNIVERSITÉ PARIS DESCARTES (France)

b UNIVERSITÉ PARIS SUD (France)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

AZIRIDINES; PYRROLIDINES; REBECCAMYCIN; STAUROSPORINES; WATERSOLUBLE;

ORGANIC COMPOUNDS;

EID: 59849125064 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b815737e Document Type: Article

Times cited : (15)

References (58)

1
- 0017745032
- Y. Nishizuka Y. Takai A. Kishimoto J. Biol. Chem. 1977 252 7603
- (1977) J. Biol. Chem. , vol.252 , pp. 7603
- Nishizuka, Y.¹ Takai, Y.² Kishimoto, A.³

2
- 0032209522
- A. Toker Front. Biosci. 1998 3 D1134
- (1998) Front. Biosci. , vol.3 , pp. 1134
- Toker, A.¹

3
- 0027180238
- N. R. Murray G. P. Baumgardner D. J. Burns A. P. Fields J. Biol. Chem. 1993 268 15847
- (1993) J. Biol. Chem. , vol.268 , pp. 15847
- Murray, N.R.¹ Baumgardner, G.P.² Burns, D.J.³ Fields, A.P.⁴

4
- 0030458055
- G. K. Schwartz Exp. Opin. Invest. Drugs 1996 5 1601
- (1996) Exp. Opin. Invest. Drugs , vol.5 , pp. 1601
- Schwartz, G.K.¹

5
- 0034725601
- K. R. Santhamma I. Sen J. Biol. Chem. 2000 275 23253
- (2000) J. Biol. Chem. , vol.275 , pp. 23253
- Santhamma, K.R.¹ Sen, I.²

6
- 0033543693
- Y. A. Chen V. Duvvuri H. Schulman R. H. Scheller J. Biol. Chem. 1999 274 26469
- (1999) J. Biol. Chem. , vol.274 , pp. 26469
- Chen, Y.A.¹ Duvvuri, V.² Schulman, H.³ Scheller, R.H.⁴

7
- 0035657643
- P. G. Goekjian M. R. Jirousek Exp. Opin. Invest. Drugs 2001 10 2117
- (2001) Exp. Opin. Invest. Drugs , vol.10 , pp. 2117
- Goekjian, P.G.¹ Jirousek, M.R.²

8
- 5744224686
- C. A. Carter C. J. M. Kane Curr. Med. Chem. 2004 11 2883
- (2004) Curr. Med. Chem. , vol.11 , pp. 2883
- Carter, C.A.¹ Kane, C.J.M.²

9
- 1542619344
- J. Hofmann Curr. Cancer Drug Targets 2004 4 125
- (2004) Curr. Cancer Drug Targets , vol.4 , pp. 125
- Hofmann, J.¹

10
- 0036839948
- A. Boneh Trends Mol. Med. 2002 8 524
- (2002) Trends Mol. Med. , vol.8 , pp. 524
- Boneh, A.¹

11
- 0036527429
- P. Cohen Nat. Rev. Drug Discov. 2002 1 309
- (2002) Nat. Rev. Drug Discov. , vol.1 , pp. 309
- Cohen, P.¹

12
- 59849123715
- P. J. Parker, and L. V. Dekker, Springer, London, p. 75
- S. Ohno, In Protein kinase C, ed., P. J. Parker, and, L. V. Dekker, Springer, London, 1997, p. 75
- (1997) Protein Kinase C, Ed.
- Ohno In, S.¹

13
- 0034194092
- K. J. Way E. Chou G. L. King Trends Pharm. Sci. 2000 181
- (2000) Trends Pharm. Sci. , pp. 181
- Way, K.J.¹ Chou, E.² King, G.L.³

14
- 0031922295
- K. Hinterding D. Alonso-Diaz H. Waldmann Angew. Chim. Int. Ed. Engl. 1998 37 688
- (1998) Angew. Chim. Int. Ed. Engl. , vol.37 , pp. 688
- Hinterding, K.¹ Alonso-Diaz, D.² Waldmann, H.³

15
- 0035413601
- A. C. Newton Chem. Rev. 2001 101 2353
- (2001) Chem. Rev. , vol.101 , pp. 2353
- Newton, A.C.¹

16
- 0032936474
- U. Pindur Y. S. Kim F. Mehrabani Curr. Med. Chem. 1999 6 29
- (1999) Curr. Med. Chem. , vol.6 , pp. 29
- Pindur, U.¹ Kim, Y.S.² Mehrabani, F.³

17
- 0345455075
- B. Testa, E. Kyburz, W. Fuhrer, and R. Giger, VCH-Verlag, Weinheim, p. 101
- J. H. Harteinstein, J. Aranda, H. Barth, H. J. Betche, J. Kleinschroth, R. Reck, C. Rudolph, U. Trostmann, and C. Schächtele, In Perspectives in Medicinal Chemistry, ed., B. Testa, E. Kyburz, W. Fuhrer, and, R. Giger, VCH-Verlag, Weinheim, 1993, p. 101
- (1993) Perspectives in Medicinal Chemistry, Ed.
- Harteinstein, J.H.¹ Aranda, J.² Barth, H.³ Betche, H.J.⁴ Kleinschroth, J.⁵ Reck, R.⁶ Rudolph, C.⁷ Trostmann, U.⁸ Schächtele In, C.⁹

18
- 0029951570
- J. Zimmermann E. Buchdunger H. Mett T. Meyer N. Lydon P. Traxler Bioorg. Med. Chem. Lett. 1996 6 1221
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1221
- Zimmermann, J.¹ Buchdunger, E.² Mett, H.³ Meyer, T.⁴ Lydon, N.⁵ Traxler, P.⁶

19
- 14444281388
- J. M. Hamby C. J. Connolly M. C. Schroeder R. T. Winters H. D. Showalter R. L. Panek T. C. Major A. M. Doherty J. Med. Chem. 1997 40 2296
- (1997) J. Med. Chem. , vol.40 , pp. 2296
- Hamby, J.M.¹ Connolly, C.J.² Schroeder, M.C.³ Winters, R.T.⁴ Showalter, H.D.⁵ Panek, R.L.⁶ Major, T.C.⁷ Doherty, A.M.⁸

20
- 19244370071
- L. Sun N. Tran C. Liang F. Tang A. Rice R. Schreck K. Waltz L. K. Shawver G. McMahon C. Tang J. Med. Chem. 1999 42 5120
- (1999) J. Med. Chem. , vol.42 , pp. 5120
- Sun, L.¹ Tran, N.² Liang, C.³ Tang, F.⁴ Rice, A.⁵ Schreck, R.⁶ Waltz, K.⁷ Shawver, L.K.⁸ McMahon, G.⁹ Tang, C.¹⁰

21
- 8944246315
- M. R. Jirousek J. R. Gillig C. M. Gonzalez W. F. Heath J. H. McDonald III D. A. Neel C. J. Rito U. Singh L. E. Stramm A. Melikian-Badalian M. Baevsky L. M. Ballas S. E. Hall M. M. Faul L. L. Winneroski J. Med. Chem. 1996 39 2664
- (1996) J. Med. Chem. , vol.39 , pp. 2664
- Jirousek, M.R.¹ Gillig, J.R.² Gonzalez, C.M.³ Heath, W.F.⁴ McDonald Iii, J.H.⁵ Neel, D.A.⁶ Rito, C.J.⁷ Singh, U.⁸ Stramm, L.E.⁹ Melikian-Badalian, A.¹⁰ Baevsky, M.¹¹ Ballas, L.M.¹² Hall, S.E.¹³ Faul, M.M.¹⁴ Winneroski, L.L.¹⁵

22
- 0346957401
- G. X. Shen Curr. Drug Targets 2003 3 301
- (2003) Curr. Drug Targets , vol.3 , pp. 301
- Shen, G.X.¹

23
- 0028220466
- B. B. Shankar A. Q. Viet R. Rizvi M. P. Kirkup S. W. McCombie A. K. Ganguly Bioorg. Med. Chem. Lett. 1994 4 495
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 495
- Shankar, B.B.¹ Viet, A.Q.² Rizvi, R.³ Kirkup, M.P.⁴ McCombie, S.W.⁵ Ganguly, A.K.⁶

24
- 0021816422
- D. E. Nettleton T. W. Doyle B. Knishnan G. K. Matsumoto J. Clardy Tetrahedron Lett. 1985 26 4011
- (1985) Tetrahedron Lett. , vol.26 , pp. 4011
- Nettleton, D.E.¹ Doyle, T.W.² Knishnan, B.³ Matsumoto, G.K.⁴ Clardy, J.⁵

25
- 0023178261
- J. A. Bush B. H. Long J. J. Catino W. T. Bradner K. Tomita J. Antibiot. 1987 40 668
- (1987) J. Antibiot. , vol.40 , pp. 668
- Bush, J.A.¹ Long, B.H.² Catino, J.J.³ Bradner, W.T.⁴ Tomita, K.⁵

26
- 0037075811
- C. Marminon F. Anizon P. Moreau S. Léonce A. Pierré B. Pfeiffer P. Renard M. Prudhomme J. Med. Chem 2002 45 1330
- (2002) J. Med. Chem , vol.45 , pp. 1330
- Marminon, C.¹ Anizon, F.² Moreau, P.³ Léonce, S.⁴ Pierré, A.⁵ Pfeiffer, B.⁶ Renard, P.⁷ Prudhomme, M.⁸

27
- 33947176009
- C. Asche M. Demeunynck Curr. Med. Chem.: Anti-Cancer Agents 2007 7 247
- (2007) Curr. Med. Chem.: Anti-Cancer Agents , vol.7 , pp. 247
- Asche, C.¹ Demeunynck, M.²

28
- 0030014783
- J. C. Wang Ann. Rev. Biochem. 1996 65 635
- (1996) Ann. Rev. Biochem. , vol.65 , pp. 635
- Wang, J.C.¹

29
- 0033049569
- C. Bailly X. Qu F. Anizon M. Prudhomme J.-F. Riou J. B. Chaires Mol. Pharmacol. 1999 55 377
- (1999) Mol. Pharmacol. , vol.55 , pp. 377
- Bailly, C.¹ Qu, X.² Anizon, F.³ Prudhomme, M.⁴ Riou, J.-F.⁵ Chaires, J.B.⁶

30
- 0042121548
- F. Anizon P. Moreau M. Sancelme W. Laine C. Bailly M. Prudhomme Bioorg. Med. Chem. 2003 11 3709
- (2003) Bioorg. Med. Chem. , vol.11 , pp. 3709
- Anizon, F.¹ Moreau, P.² Sancelme, M.³ Laine, W.⁴ Bailly, C.⁵ Prudhomme, M.⁶

31
- 33845183778
- A. Duréault I. Tranchepain J.-C. Depezay J. Org. Chem. 1989 54 5324
- (1989) J. Org. Chem. , vol.54 , pp. 5324
- Duréault, A.¹ Tranchepain, I.² Depezay, J.-C.³

32
- 0028351528
- J. Fitremann A. Duréault J.-C. Depezay Tetrahedron Lett. 1994 35 1201
- (1994) Tetrahedron Lett. , vol.35 , pp. 1201
- Fitremann, J.¹ Duréault, A.² Depezay, J.-C.³

33
- 0028851854
- L. Campanini A. Duréault J.-C. Depezay Tetrahedron Lett. 1995 36 8015
- (1995) Tetrahedron Lett. , vol.36 , pp. 8015
- Campanini, L.¹ Duréault, A.² Depezay, J.-C.³

34
- 0030586151
- L. Campanini A. Duréault J.-C. Depezay Tetrahedron Lett. 1996 37 5095
- (1996) Tetrahedron Lett. , vol.37 , pp. 5095
- Campanini, L.¹ Duréault, A.² Depezay, J.-C.³

35
- 84862413090
- J. Fitremann A. Duréault J.-C. Depezay Synlett 1995 3 235
- (1995) Synlett , vol.3 , pp. 235
- Fitremann, J.¹ Duréault, A.² Depezay, J.-C.³

36
- 0000639058
- M. Brenner H. Rexhausen B. Steffan W. Steglich Tetrahedron 1988 44 2887
- (1988) Tetrahedron , vol.44 , pp. 2887
- Brenner, M.¹ Rexhausen, H.² Steffan, B.³ Steglich, W.⁴

37
- 0029603572
- M. Faul K. A. Sullivan L. L. Winneroski Synthesis 1995 12 1511
- (1995) Synthesis , vol.12 , pp. 1511
- Faul, M.¹ Sullivan, K.A.² Winneroski, L.L.³

38
- 1542632600
- S. Edge A. Charlon T. K. Hansen K. S. Varma A. E. Underhill P. Kathirgamanathan J. Becher Chemistry & Industry 1991 4 130
- (1991) Chemistry & Industry , vol.4 , pp. 130
- Edge, S.¹ Charlon, A.² Hansen, T.K.³ Varma, K.S.⁴ Underhill, A.E.⁵ Kathirgamanathan, P.⁶ Becher, J.⁷

39
- 0033530871
- M. Ohkubo T. Nishimura T. Honma I. Nishimura S. Ito T. Yoshinari H. Arakawa H. Suda H. Morishima S. Nishimura Bioorg. Med. Chem. Lett. 1999 9 3307
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 3307
- Ohkubo, M.¹ Nishimura, T.² Honma, T.³ Nishimura, I.⁴ Ito, S.⁵ Yoshinari, T.⁶ Arakawa, H.⁷ Suda, H.⁸ Morishima, H.⁹ Nishimura, S.¹⁰

40
- 0031032851
- M. Ohkubo H. Kawamoto T. Ohno M. Nakano H. Morishima Tetrahedron 1997 53 585
- (1997) Tetrahedron , vol.53 , pp. 585
- Ohkubo, M.¹ Kawamoto, H.² Ohno, T.³ Nakano, M.⁴ Morishima, H.⁵

41
- 0034304929
- G. E. Burtin D. J. Madge D. L. Selwood Heterocycles 2000 53 2119
- (2000) Heterocycles , vol.53 , pp. 2119
- Burtin, G.E.¹ Madge, D.J.² Selwood, D.L.³

42
- 0027729427
- W. Harris C. H. Hill E. Keech P. Malsher Tetrahedron Lett. 1993 34 8361
- (1993) Tetrahedron Lett. , vol.34 , pp. 8361
- Harris, W.¹ Hill, C.H.² Keech, E.³ Malsher, P.⁴

43
- 0001472509
- A. Duréault C. Greck J.-C. Depezay Tetrahedron Lett. 1986 27 4157
- (1986) Tetrahedron Lett. , vol.27 , pp. 4157
- Duréault, A.¹ Greck, C.² Depezay, J.-C.³

44
- 0000112744
- Y. Le Merrer A. Duréault C. Greck D. Micas-Languin C. Gravier J.-C. Depezay Heterocycles 1987 25 541
- (1987) Heterocycles , vol.25 , pp. 541
- Le Merrer, Y.¹ Duréault, A.² Greck, C.³ Micas-Languin, D.⁴ Gravier, C.⁵ Depezay, J.-C.⁶

45
- 0029084192
- J. Fitremann A. Duréault J.-C. Depezay Tetrahedron 1995 51 9581
- (1995) Tetrahedron , vol.51 , pp. 9581
- Fitremann, J.¹ Duréault, A.² Depezay, J.-C.³

46
- 0034007669
- See ESI for the preparation and characterization of compounds 9b-d and 10a-b
- I. McCort S. Fort A. Duréault J.-C. Depezay Bioorg. Med. Chem. 2000 8 135
- (2000) Bioorg. Med. Chem. , vol.8 , pp. 135
- McCort, I.¹ Fort, S.² Duréault, A.³ Depezay, J.-C.⁴

47
- 59849101528
- U. Rosentreter H. Boeshagen F. Lieb H. Oediger V.-B. Fiedler E. Perzborn F. Seuter US patent, US4843091 1989
- US Patent, US4843091 , pp. 1989
- Rosentreter, U.¹ Boeshagen, H.² Lieb, F.³ Oediger, H.⁴ Fiedler, V.-B.⁵ Perzborn, E.⁶ Seuter, F.⁷

48
- 84985648237
- A. Onistschenko H. Stamm Cherm. Ber. 1989 122 2397
- (1989) Cherm. Ber. , vol.122 , pp. 2397
- Onistschenko, A.¹ Stamm, H.²

49
- 0037286391
- P. R. Giles M. Rogers-Evans M. Soukup J. Knight Organic Process Research & Development 2003 7 22
- (2003) Organic Process Research & Development , vol.7 , pp. 22
- Giles, P.R.¹ Rogers-Evans, M.² Soukup, M.³ Knight, J.⁴

50
- 0023244608
- P. Assithianakis A. Onistschenko H. Stamm Arch. Pharm. 1987 320 604
- (1987) Arch. Pharm. , vol.320 , pp. 604
- Assithianakis, P.¹ Onistschenko, A.² Stamm, H.³

51
- 0026502719
- S. Farooq W. E. Swain, Jr R. Daeppen Tetrahedron: Asymmetry 1992 3 51
- (1992) Tetrahedron: Asymmetry , vol.3 , pp. 51
- Farooq, S.¹ Swain Jr, W.E.² Daeppen, R.³

52
- 0029148957
- J. M. Gardiner C. R. Loyns Tetrahedron 1995 42 11515
- (1995) Tetrahedron , vol.42 , pp. 11515
- Gardiner, J.M.¹ Loyns, C.R.²

53
- 0029055613
- J. M. Gardiner C. R. Loyns A. Burke A. Khan N. Mahmood Bioorg. Med. Chem. Lett. 1995 12 1251
- (1995) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1251
- Gardiner, J.M.¹ Loyns, C.R.² Burke, A.³ Khan, A.⁴ Mahmood, N.⁵

54
- 0346787849
- J. Thierry V. Servajean Tetrahedron Lett. 2004 45 821
- (2004) Tetrahedron Lett. , vol.45 , pp. 821
- Thierry, J.¹ Servajean, V.²

55
- 1542375289
- To avoid the formation of the anhydride 17′, in addition to obvious anhydrous conditions, bis-aziridines 9 and 10 were dried under vacum 12 h prior to use. When 9d was dried only 1 h, 17d and 17′d have been obtained in 15% and 61% yields, respectively
- X. E. Hu Tetrahedron 2004 60 2701
- (2004) Tetrahedron , vol.60 , pp. 2701
- Hu, X.E.¹

56
- 0003463148
- John Wiley & Sons Eds, Wiley-Interscience, New York, p. 101 Later on, the yields of acetonide hydrolysis were improved by use of HCl 1 M in THF or in THF-EtOH
- rd ed. John Wiley & Sons Eds, Wiley-Interscience, New York, 1999, p. 101
- (1999) rd Ed.
- Greene, T.W.¹ Wuts In, P.G.M.²

57
- 4644229467
- During the course of the reaction, difficulties were met monitoring by TLC because of the similarity of the retention factors of the starting material and the product Likewise, bis-indolylmaleimide 32b has been obtained from 35b following the same reaction sequence
- U. Jacquemard V. Bénéteau M. Lefoix S. Routier J.-Y. Mérour G. Coudert Tetrahedron 2004 60 10039
- (2004) Tetrahedron , vol.60 , pp. 10039
- Jacquemard, U.¹ Bénéteau, V.² Lefoix, M.³ Routier, S.⁴ Mérour, J.-Y.⁵ Coudert, G.⁶

58
- 26444518787
- For the same reasons about polarity, these hypotheses are also suitable for 32b
- S. Messaoudi F. Anizon S. Léonce A. Pierré B. Pfeiffer M. Prudhomme Eur. J. Med. Chem. 2005 40 961
- (2005) Eur. J. Med. Chem. , vol.40 , pp. 961
- Messaoudi, S.¹ Anizon, F.² Léonce, S.³ Pierré, A.⁴ Pfeiffer, B.⁵ Prudhomme, M.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.