SCOPUS 정보 검색 플랫폼

Volumn 68, Issue 32, 2012, Pages 6447-6455

Regioselective synthesis of the 1-bromo-4-phenyl-tetrahydro-7-amino- benzocyclohepten-6-one, a subnanomolar aminopeptidase-N/CD13 inhibitor

(8) Al Lakkis Wehbe, Mira a Roux, Lionel a Charrier, Cédric a Alavi, Sarah a Le Nouën, Didier a Defoin, Albert a Tarnus, Céline a Albrecht, Sébastien a

a UNIVERSITÉ DE HAUTE ALSACE (France)

Author keywords

APN inhibitor; Aromatic substitution; Regioselective synthesis; Silyl enol ethers

Indexed keywords

1 [(TERT BUTOXYCARBONYL) TERT BUTYLDIMETHYLSILYLAMINO] 7 TERT BUTYLDIMETHYLSILYLOXY 6,9 DIHYDRO 5H BENZOCYCLOHEPTENE; 1 BROMO 4 PHENYL TETRAHYDRO 7 AMINO BENZOCYCLOHEPTEN 6 ONE; 1 BROMO 4 TERT BUTOXYCARBONYLAMINO 7 BENZYLOXYCARBONYLAMINO 6,7 DIHYDRO 5H BENZOCYCLOHEPTENE; 1 TERT BUTOXYCARBONYL AMINO 7 BENZYLOXYCARBONYLAMINO 6,7 DIHYDRO 5H BENZOCYCLOHEPTENE; 1 TERT BUTOXYCARBONYLAMINO 5,6,8,9 TETRAHYDRO BENZOCYCLOHEPTEN 7 ONE; 4 [(TERT BUTOXYCARBONYL) TERT BUTYLDIMETHYLSILYLAMINO] 7 TERTBUTYLDIMETHYLSILYLOXY 6,9 DIHYDRO 5H BENZOCYCLOHEPTENE; 4 BROMO 1 TERTBUTOXYCARBONYLAMINO 7 BENZYLOXYCARBONYLAMINO 6,7 DIHYDRO 5H BENZOCYCLOHEPTENE; 4 BROMO N TERT BUTYLOXYCARBONYL 2,3 BIS(BROMOMETHYL)ANILINE; 4 TERT BUTOXYCARBONYLAMINO 7 BENZYLOXYCARBONYLAMINO 6,7 DIHYDRO 5H BENZOCYCLOHEPTENE; AMIDE; CHLORIDE; ENZYME INHIBITOR; ETHER DERIVATIVE; KETONE; N TERT BUTYLOXYCARBONYL 2,3 BIS(BROMOMETHYL)ANILINE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; PRIORITY JOURNAL; SANDMEYER REACTION; SUZUKI REACTION;

EID: 84862775461 PISSN: 00404020 EISSN: 14645416 Source Type: Journal
DOI: 10.1016/j.tet.2012.05.121 Document Type: Article

Times cited : (3)

References (29)

1
- 0003931970
- Elsevier Academic Oxford pp 233
- A.J. Barret, N.D. Rawling, and J.F. Woessner Handbook of Proteolytic Enzymes Vol. 2 2004 Elsevier Academic Oxford pp 233
- (2004) Handbook of Proteolytic Enzymes , vol.2
- Barret, A.J.¹ Rawling, N.D.² Woessner, J.F.³

2
- 84862771603
- P. Mina-Osorio Trends Mol. Med. 2008 361
- (2008) Trends Mol. Med. , pp. 361
- Mina-Osorio, P.¹

3
- 0037372507
- S.V. Bhagwat, N. Petrovic, Y. Okamoto, and L.H. Shapiro Blood 2003 1818
- (2003) Blood , pp. 1818
- Bhagwat, S.V.¹ Petrovic, N.² Okamoto, Y.³ Shapiro, L.H.⁴

4
- 34347407791
- N. Petrovic, W. Schacke, J.R. Gahagan, C.A. O'Conor, B. Winnicka, R.E. Conway, P. Mina-Osorio, and L.H. Shapiro Blood 2007 142
- (2007) Blood , pp. 142
- Petrovic, N.¹ Schacke, W.² Gahagan, J.R.³ O'Conor, C.A.⁴ Winnicka, B.⁵ Conway, R.E.⁶ Mina-Osorio, P.⁷ Shapiro, L.H.⁸

5
- 71749104742
- G.Y. Sato Biol. Pharm. Bull. 2004 772
- (2004) Biol. Pharm. Bull. , pp. 772
- Sato, G.Y.¹

6
- 84862770391
- H.Y. Aozuka, K. Koisumi, Y. Saitoh, Y. Ueda, H. Sakurai, and I. Saiki Cancer Res. 2004 35
- (2004) Cancer Res. , pp. 35
- Aozuka, H.Y.¹ Koisumi, K.² Saitoh, Y.³ Ueda, Y.⁴ Sakurai, H.⁵ Saiki, I.⁶

7
- 78149359487
- A. Mucha, M. Drag, J.P. Dalton, and P. Kafarski Biochimie 2010 1509
- (2010) Biochimie , pp. 1509
- Mucha, A.¹ Drag, M.² Dalton, J.P.³ Kafarski, P.⁴

8
- 33644875741
- B. Bauvois, and D. Dauzonne Med. Res. Rev. 2006 88
- (2006) Med. Res. Rev. , pp. 88
- Bauvois, B.¹ Dauzonne, D.²

9
- 79951556666
- S. Albrecht, M. Al-Lakkis-Wehbe, A. Orsini, A. Defoin, P. Pale, C. Tarnus, J.-M. Weibel, and E. Salomon Bioorg. Med. Chem. 2011 1434
- (2011) Bioorg. Med. Chem. , pp. 1434
- Albrecht, S.¹ Al-Lakkis-Wehbe, M.² Orsini, A.³ Defoin, A.⁴ Pale, P.⁵ Tarnus, C.⁶ Weibel, J.-M.⁷ Salomon, E.⁸

10
- 80052588946
- C. Maiereanu, C. Schmitt, N. Schifano-Faux, D. Le Nouën, A. Defoin, and C. Tarnus Bioorg. Med. Chem. 2011 5716
- (2011) Bioorg. Med. Chem. , pp. 5716
- Maiereanu, C.¹ Schmitt, C.² Schifano-Faux, N.³ Le Nouën, D.⁴ Defoin, A.⁵ Tarnus, C.⁶

11
- 84862774068
- French Patent FR2908131, W2008059141
- Tarnus-Rondeau, C.; Defoin, A.; Albrecht, S.; Maiereanu, C.; Faux, N.; Pale, P. French Patent FR2908131, W2008059141, 2008.
- (2008)
- Tarnus-Rondeau, C.¹ Defoin, A.² Albrecht, S.³ Maiereanu, C.⁴ Faux, N.⁵ Pale, P.⁶

12
- 0343663002
- N.L. Allinger, and W. Szkrybalo J. Org. Chem. 1962 722
- (1962) J. Org. Chem. , pp. 722
- Allinger, N.L.¹ Szkrybalo, W.²

13
- 0000953130
- G.A. Russell, R.L. Blankespoor, K.D. Trahanovsky, C.S.C. Chung, P.R. Whittle, J. Mattox, C.L. Myers, R. Penny, T. Ku, Y. Kosugi, and R.S. Givens J. Am. Chem. Soc. 1975 1906
- (1975) J. Am. Chem. Soc. , pp. 1906
- Russell, G.A.¹ Blankespoor, R.L.² Trahanovsky, K.D.³ Chung, C.S.C.⁴ Whittle, P.R.⁵ Mattox, J.⁶ Myers, C.L.⁷ Penny, R.⁸ Ku, T.⁹ Kosugi, Y.¹⁰ Givens, R.S.¹¹

14
- 33845282358
- S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, and M. Tashiro J. Org. Chem. 1987 2653
- (1987) J. Org. Chem. , pp. 2653
- Mataka, S.¹ Takahashi, K.² Mimura, T.³ Hirota, T.⁴ Takuma, K.⁵ Kobayashi, H.⁶ Tashiro, M.⁷

15
- 84862759109
- G. Simchen, and W. Kober Synthesis 1976 261
- (1976) Synthesis , pp. 261
- Simchen, G.¹ Kober, W.²

16
- 0002775378
- L. Blanco, P. Amice, and J.M. Conia Synthesis 1976 194
- (1976) Synthesis , pp. 194
- Blanco, L.¹ Amice, P.² Conia, J.M.³

17
- 0001002063
- R.H. Reuss, and A. Hassner J. Org. Chem. 1974 1785
- (1974) J. Org. Chem. , pp. 1785
- Reuss, R.H.¹ Hassner, A.²

18
- 0742324457
- B. Miriyala, S. Bhattacharyya, and J. Williamson Tetrahedron 2004 1463
- (2004) Tetrahedron , pp. 1463
- Miriyala, B.¹ Bhattacharyya, S.² Williamson, J.³

19
- 84862767030
- D.L. Boger, J.A. McKie, and C.W. Boyce Synlett 1990 515
- (1990) Synlett , pp. 515
- Boger, D.L.¹ McKie, J.A.² Boyce, C.W.³

20
- 84862759722
- 141
- R.K. Boeckman Jr., P. Shao, and J.J. Mullins Organic Syntheses 2000 141
- (2000) Organic Syntheses
- Boeckman Jr., R.K.¹ Shao, P.² Mullins, J.J.³

21
- 33644528891
- D.B. Dess, and J.C. Martin J. Org. Chem. 1983 4155
- (1983) J. Org. Chem. , pp. 4155
- Dess, D.B.¹ Martin, J.C.²

22
- 0000911417
- 2O
- 2O: H.O. House J. Am. Chem. Soc. 1954 3070
- (1954) J. Am. Chem. Soc. , pp. 3070
- House, H.O.¹

23
- 33745700327
- 4
- 4: Y. Kita, R. Inoguchi, J.K. Ganesh, and H. Fujioka J. Org. Chem. 2006 5191
- (2006) J. Org. Chem. , pp. 5191
- Kita, Y.¹ Inoguchi, R.² Ganesh, J.K.³ Fujioka, H.⁴

24
- 0025973358
- 2
- 2: S.F. Martin, and W. Li J. Org. Chem. 1990 642
- (1990) J. Org. Chem. , pp. 642
- Martin, S.F.¹ Li, W.²

25
- 0000578843
- S. Hulasegaram, and R.J. Kulawiec J. Org. Chem. 1997 6547
- (1997) J. Org. Chem. , pp. 6547
- Hulasegaram, S.¹ Kulawiec, R.J.²

26
- 77958020967
- The configuration cis of the amido-alcohol 15a was not specified
- P.L. Roux, C. Charrier, A. Defoin, P. Bisseret, and C. Tarnus Tetrahedron 2010 8722 The configuration cis of the amido-alcohol 15a was not specified
- (2010) Tetrahedron , pp. 8722
- Roux, P.L.¹ Charrier, C.² Defoin, A.³ Bisseret, P.⁴ Tarnus, C.⁵

27
- 0000249892
- M.P. Doyle, B. Siegfried, and J.F. Dellaria Jr. J. Org. Chem. 1977 2426
- (1977) J. Org. Chem. , pp. 2426
- Doyle, M.P.¹ Siegfried, B.² Dellaria Jr., J.F.³

28
- 24944552764
- K. Rudolf, W. Eberlein, W. Engel, H. Pieper, M. Entzeroth, G. Hallermayer, and H. Doods J. Med. Chem. 2005 5921
- (2005) J. Med. Chem. , pp. 5921
- Rudolf, K.¹ Eberlein, W.² Engel, W.³ Pieper, H.⁴ Entzeroth, M.⁵ Hallermayer, G.⁶ Doods, H.⁷

29
- 0000807997
- G.-D. Zhu, M.A. Staeger, and S.A. Boyd Org. Lett. 2000 3345
- (2000) Org. Lett. , pp. 3345
- Zhu, G.-D.¹ Staeger, M.A.² Boyd, S.A.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.