SCOPUS 정보 검색 플랫폼

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 8, 2011, Pages 2183-2187

Synthesis and evaluation of arylquinones as BACE1 inhibitors, β-amyloid peptide aggregation inhibitors, and destabilizers of preformed β-amyloid fibrils

(7) Ortega, Andrea a Rincón, Ángela b Jiménez Aliaga, Karim L a Bermejo Bescós, Paloma a Martín Aragón, Sagrario a Molina, María Teresa c Csákÿ, Aurelio G b

a UNIVERSIDAD COMPLUTENSE DE MADRID (Spain)

b UNIVERSIDAD COMPLUTENSE DE MADRID (Spain)

c INSTITUTO DE QUÍMICA MÉDICA (Spain)

Author keywords

A fibrils; Alzheimer's disease; Amyloid aggregation; BACE1; Quinones

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; AMYLOID BETA PROTEIN; ANTIDIABETIC AGENT; BETA AMYLOID PEPTIDE AGGREGATION INHBITOR; BETA SECRETASE 1; BETA SECRETASE 1 INHIBITOR; CYCLOOXYGENASE 1; NATURAL PRODUCT; PROTEIN INHIBITOR; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HUMAN; NONHUMAN; PROTEIN AGGREGATION; PROTEIN PROCESSING;

ALZHEIMER DISEASE; AMYLOID; AMYLOID BETA-PEPTIDES; AMYLOID PRECURSOR PROTEIN SECRETASES; ASPARTIC ACID ENDOPEPTIDASES; ENZYME INHIBITORS; HUMANS; QUINONES;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 79953285877 PISSN: 0960894X EISSN: None Source Type: Journal
DOI: 10.1016/j.bmcl.2011.03.023 Document Type: Article

Times cited : (33)

References (58)

1
- 33847613885
- M.T. Heneka, and M.K. O'Banion J. Neuroimmunol. 184 2007 69
- (2007) J. Neuroimmunol. , vol.184 , pp. 69
- Heneka, M.T.¹ O'Banion, M.K.²

2
- 67651047153
- W.H. Huang, R. Sheng, and Y.Z. Hu Curr. Med. Chem. 16 2009 1806
- (2009) Curr. Med. Chem. , vol.16 , pp. 1806
- Huang, W.H.¹ Sheng, R.² Hu, Y.Z.³

3
- 77951776829
- M. Citron Nat. Rev. Drug. Disc. 9 2010 387
- (2010) Nat. Rev. Drug. Disc. , vol.9 , pp. 387
- Citron, M.¹

4
- 33746310315
- K. Blennow, M.J. de Leon, and H. Zetterberg Lancet 368 2006 387
- (2006) Lancet , vol.368 , pp. 387
- Blennow, K.¹ De Leon, M.J.² Zetterberg, H.³

5
- 0029379605
- F. Checler J. Neurochem. 65 1995 1431
- (1995) J. Neurochem. , vol.65 , pp. 1431
- Checler, F.¹

6
- 0033213875
- M. Racchi, and S. Govone Trends Pharmacol. Sci. 20 1999 418
- (1999) Trends Pharmacol. Sci. , vol.20 , pp. 418
- Racchi, M.¹ Govone, S.²

7
- 0034516988
- D. Selkoe Ann. N.Y. Acad. Sci. 924 2000 17
- (2000) Ann. N.Y. Acad. Sci. , vol.924 , pp. 17
- Selkoe, D.¹

8
- 0034057378
- C. Couglan, and K.C. Breen Pharm. Ther. 86 2000 111
- (2000) Pharm. Ther. , vol.86 , pp. 111
- Couglan, C.¹ Breen, K.C.²

9
- 4344580888
- M. Citron Neuroscience 5 2004 677
- (2004) Neuroscience , vol.5 , pp. 677
- Citron, M.¹

10
- 34548812551
- M.A. Findeis Pharmacol. Ther. 116 2007 266
- (2007) Pharmacol. Ther. , vol.116 , pp. 266
- Findeis, M.A.¹

11
- 9144267815
- R.K. Hom, A.F. Gailunas, S. Mamo, L.Y. Fang, J.S. Tung, D.E. Walker, D. Davis, R.E.D. Thorsett, N.E. Jewett, J.B. Moon, and V. John J. Med. Chem. 47 2004 158
- (2004) J. Med. Chem. , vol.47 , pp. 158
- Hom, R.K.¹ Gailunas, A.F.² Mamo, S.³ Fang, L.Y.⁴ Tung, J.S.⁵ Walker, D.E.⁶ Davis, D.⁷ Thorsett, R.E.D.⁸ Jewett, N.E.⁹ Moon, J.B.¹⁰ John, V.¹¹

12
- 33645091918
- A.K. Ghosh, N. Kumaragurubaran, and J. Tang Curr. Top. Med. Chem. 5 2005 1609
- (2005) Curr. Top. Med. Chem. , vol.5 , pp. 1609
- Ghosh, A.K.¹ Kumaragurubaran, N.² Tang, J.³

13
- 20844450922
- J. Tang, X. He, X. Huang, and L. Hong Curr. Alzheimer Res. 2 2005 261
- (2005) Curr. Alzheimer Res. , vol.2 , pp. 261
- Tang, J.¹ He, X.² Huang, X.³ Hong, L.⁴

14
- 33646189389
- V. John Curr. Top. Med. Chem. 6 2006 569
- (2006) Curr. Top. Med. Chem. , vol.6 , pp. 569
- John, V.¹

15
- 33847368052
- M.C. Maillard, R.K. Hom, T.E. Benson, J.B. Moon, S. Mamo, M. Bienkowski, A.G. Tomasselli, D.D. Woods, D.B. Prince, D.J. Paddock, T.L. Emmons, J.A. Tucker, M.S. Dappen, L. Brogley, E.D. Thorsett, N. Jewett, S. Sinha, and V. John J. Med. Chem. 50 2007 776
- (2007) J. Med. Chem. , vol.50 , pp. 776
- Maillard, M.C.¹ Hom, R.K.² Benson, T.E.³ Moon, J.B.⁴ Mamo, S.⁵ Bienkowski, M.⁶ Tomasselli, A.G.⁷ Woods, D.D.⁸ Prince, D.B.⁹ Paddock, D.J.¹⁰ Emmons, T.L.¹¹ Tucker, J.A.¹² Dappen, M.S.¹³ Brogley, L.¹⁴ Thorsett, E.D.¹⁵ Jewett, N.¹⁶ Sinha, S.¹⁷ John, V.¹⁸

16
- 23944450549
- M.G. Kornacker, Z. Lai, M. Witmer, J. Ma, J. Hendrick, V.G. Lee, D.J. Riexinger, C. Mapelli, W. Metzler, and R.A. Copeland Biochemistry 44 2005 11567
- (2005) Biochemistry , vol.44 , pp. 11567
- Kornacker, M.G.¹ Lai, Z.² Witmer, M.³ Ma, J.⁴ Hendrick, J.⁵ Lee, V.G.⁶ Riexinger, D.J.⁷ Mapelli, C.⁸ Metzler, W.⁹ Copeland, R.A.¹⁰

17
- 85056027895
- A. Robles Open Neurol. J. 3 2009 27
- (2009) Open Neurol. J. , vol.3 , pp. 27
- Robles, A.¹

18
- 20044370990
- F. Yang, G.P. Lim, A.N. Begum, O.J. Ubeda, M.R. Simmons, S.S. Ambegaokar, P.P. Chen, R. Kayed, C.G. Glabe, S.A. Frautschy, and G.M. Cole J. Biol. Chem. 280 2005 5892
- (2005) J. Biol. Chem. , vol.280 , pp. 5892
- Yang, F.¹ Lim, G.P.² Begum, A.N.³ Ubeda, O.J.⁴ Simmons, M.R.⁵ Ambegaokar, S.S.⁶ Chen, P.P.⁷ Kayed, R.⁸ Glabe, C.G.⁹ Frautschy, S.A.¹⁰ Cole, G.M.¹¹

19
- 0003868021
- Blackie Academic and Professional London
- R.H. Thomson In: Naturally Occurring Quinones IV 1997 Blackie Academic and Professional London
- (1997) Naturally Occurring Quinones IV
- Thomson, R.H.¹

20
- 5444237056
- See for example: R.S. Coleman, F.-X. Felpin, and W. Chen J. Org. Chem. 69 2004 7309
- (2004) J. Org. Chem. , vol.69 , pp. 7309
- Coleman, R.S.¹ Felpin, F.-X.² Chen, W.³

21
- 0035098507
- W.T. Bradner Cancer Treat. Rev. 27 2001 35
- (2001) Cancer Treat. Rev. , vol.27 , pp. 35
- Bradner, W.T.¹

22
- 0032493424
- W. Wang, T. Li, R. Milburn, J. Yates, E. Hinnant, M.J. Luzzio, S.A. Noble, and G. Attardo Bioorg. Med. Chem. Lett. 8 1998 1579
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1579
- Wang, W.¹ Li, T.² Milburn, R.³ Yates, J.⁴ Hinnant, E.⁵ Luzzio, M.J.⁶ Noble, S.A.⁷ Attardo, G.⁸

23
- 85010175135
- See for example: K. Arai, S. Shimizu, Y. Taguchi, and Y. Yamamoto Chem. Pharm. Bull. 29 1981 991
- (1981) Chem. Pharm. Bull. , vol.29 , pp. 991
- Arai, K.¹ Shimizu, S.² Taguchi, Y.³ Yamamoto, Y.⁴

24
- 0019950047
- S. Shuimizu, Y. Yamamoto, and S. Koshimura Chem. Pharm. Bull. 30 1982 1896
- (1982) Chem. Pharm. Bull. , vol.30 , pp. 1896
- Shuimizu, S.¹ Yamamoto, Y.² Koshimura, S.³

25
- 0028129409
- A. Kaji, R. Saito, Y. Hata, N. Kiriyama, S. Wakusawa, and K. Miyamoto Chem. Pharm. Bull. 42 1994 1682
- (1994) Chem. Pharm. Bull. , vol.42 , pp. 1682
- Kaji, A.¹ Saito, R.² Hata, Y.³ Kiriyama, N.⁴ Wakusawa, S.⁵ Miyamoto, K.⁶

26
- 0033532347
- B. Zhang, G. Salituro, D. Szalkowski, Z. Li, Y. Zhang, I. Royo, D. Vitella, M.T. Diez, F. Peláez, C. Ruby, R.L. Kendall, X. Mao, P. Griffin, J. Calaycay, J.R. Zierath, J.V. Heck, R.G. Smith, and D.E. Moller Science 284 1999 974
- (1999) Science , vol.284 , pp. 974
- Zhang, B.¹ Salituro, G.² Szalkowski, D.³ Li, Z.⁴ Zhang, Y.⁵ Royo, I.⁶ Vitella, D.⁷ Diez, M.T.⁸ Peláez, F.⁹ Ruby, C.¹⁰ Kendall, R.L.¹¹ Mao, X.¹² Griffin, P.¹³ Calaycay, J.¹⁴ Zierath, J.R.¹⁵ Heck, J.V.¹⁶ Smith, R.G.¹⁷ Moller, D.E.¹⁸

27
- 0025896061
- See for example: Y. Fukuyama, J. Okino, and M. Kodama Chem. Pharm. Bull. 39 1991 1877
- (1991) Chem. Pharm. Bull. , vol.39 , pp. 1877
- Fukuyama, Y.¹ Okino, J.² Kodama, M.³

28
- 0027365911
- Y. Fukuyama, Y. Kiriyama, J. Okino, and M. Kodama Tetrahedron Lett. 34 1993 7633
- (1993) Tetrahedron Lett. , vol.34 , pp. 7633
- Fukuyama, Y.¹ Kiriyama, Y.² Okino, J.³ Kodama, M.⁴

29
- 79953290697
- M.K. Hadden, S.A. Hill, J. Davenport, R.L. Matts, and B.S. Blagg Bioorg. Med. Chem. 37 2009 634
- (2009) Bioorg. Med. Chem. , vol.37 , pp. 634
- Hadden, M.K.¹ Hill, S.A.² Davenport, J.³ Matts, R.L.⁴ Blagg, B.S.⁵

30
- 66049133428
- F. Mancini, M.L. Bolognesi, C. Melchiorre, and V.J. Andrisano Pharm. Biomed. Anal. 50 2009 164
- (2009) Pharm. Biomed. Anal. , vol.50 , pp. 164
- Mancini, F.¹ Bolognesi, M.L.² Melchiorre, C.³ Andrisano, V.J.⁴

31
- 0030905125
- T. Tomiyama, H. Kaneko, K. Kataoka, S. Asano, and N. Endo Biochem. J. 322 1997 859
- (1997) Biochem. J. , vol.322 , pp. 859
- Tomiyama, T.¹ Kaneko, H.² Kataoka, K.³ Asano, S.⁴ Endo, N.⁵

32
- 57749099247
- M.L. Bolognesi, A. Cavalli, and C. Melchiorre Neurotherapeutics 6 2009 152
- (2009) Neurotherapeutics , vol.6 , pp. 152
- Bolognesi, M.L.¹ Cavalli, A.² Melchiorre, C.³

33
- 0029863551
- T. Tomiyama, A. Shoji, K. Kataoka, Y. Suwa, S. Asano, H. Kaneko, and N. Endo J. Biol. Chem. 271 1996 6839
- (1996) J. Biol. Chem. , vol.271 , pp. 6839
- Tomiyama, T.¹ Shoji, A.² Kataoka, K.³ Suwa, Y.⁴ Asano, S.⁵ Kaneko, H.⁶ Endo, N.⁷

34
- 22544478124
- H.T. Li, D.H. Lin, X.Y. Luo, F. Zhang, L.N. Ji, H.N. Du, G.Q. Song, J. Hu, J.W. Zhou, and H.Y. Hu J. FEBS 272 2005 3661
- (2005) J. FEBS , vol.272 , pp. 3661
- Li, H.T.¹ Lin, D.H.² Luo, X.Y.³ Zhang, F.⁴ Ji, L.N.⁵ Du, H.N.⁶ Song, G.Q.⁷ Hu, J.⁸ Zhou, J.W.⁹ Hu, H.Y.¹⁰

35
- 0033022771
- C. Pereira, M.S. Santos, and C. Oliveira Neurobiol. Dis. 6 2009 209
- (2009) Neurobiol. Dis. , vol.6 , pp. 209
- Pereira, C.¹ Santos, M.S.² Oliveira, C.³

36
- 0032898672
- K. Yamada, T. Tanaka, D. Han, K. Senzaki, T. Kameyama, and T. Nabeshima Eur. J. Neurosci. 11 1999 83
- (1999) Eur. J. Neurosci. , vol.11 , pp. 83
- Yamada, K.¹ Tanaka, T.² Han, D.³ Senzaki, K.⁴ Kameyama, T.⁵ Nabeshima, T.⁶

37
- 79953282113
- P. Bermejo-Bescós, S. Martín-Aragón, K.L. Jiménez-Aliaga, A. Ortega, M.T. Molina, E. Buxaderas, G. Orellana, and A.G. Csákÿ Biochim. Biophys. Res. Commun. 400 2009 169
- (2009) Biochim. Biophys. Res. Commun. , vol.400 , pp. 169
- Bermejo-Bescós, P.¹ Martín-Aragón, S.² Jiménez-Aliaga, K.L.³ Ortega, A.⁴ Molina, M.T.⁵ Buxaderas, E.⁶ Orellana, G.⁷ Csákÿ, A.G.⁸

38
- 85050430499
- S. Patai, Z. Rappoport, Wiley New York
- Reviews: S. Patai, Z. Rappoport, In: The Chemistry of the Quinonoid Compounds 1988 Wiley New York Vol. 2, Parts 1 and 2
- (1988) The Chemistry of the Quinonoid Compounds

39
- 26444548133
- N.G. Batenko, G. Karlivans, and R. Valters Chem. Heterocycl. Compd. 41 2005 691
- (2005) Chem. Heterocycl. Compd. , vol.41 , pp. 691
- Batenko, N.G.¹ Karlivans, G.² Valters, R.³

40
- 79953278426
- M. Balci, M.S. Gultekin, and M. Celik Sci. Synth. 28 2006 131
- (2006) Sci. Synth. , vol.28 , pp. 131
- Balci, M.¹ Gultekin, M.S.² Celik, M.³

41
- 12344258791
- See also: S.-L. Zhang, Z.-S. Huang, L.-K. An, X.-Z. Bu, L. Ma, Y.-M. Li, A.S.C. Chan, and L.-Q. Gu Org. Lett. 6 2004 4853
- (2004) Org. Lett. , vol.6 , pp. 4853
- Zhang, S.-L.¹ Huang, Z.-S.² An, L.-K.³ Bu, X.-Z.⁴ Ma, L.⁵ Li, Y.-M.⁶ Chan, A.S.C.⁷ Gu, L.-Q.⁸

42
- 16844378606
- M.C. Pirrung, Y. Liu, L. Deng, D.K. Halstead, Z. Li, J.F. May, M. Wedel, D.A. Austin, and N.J.G. Webster J. Am. Chem. Soc. 127 2005 106
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 106
- Pirrung, M.C.¹ Liu, Y.² Deng, L.³ Halstead, D.K.⁴ Li, Z.⁵ May, J.F.⁶ Wedel, M.⁷ Austin, D.A.⁸ Webster, N.J.G.⁹

43
- 31544444995
- H.-B. Zhang, L. Liu, Y.-J. Chen, D. Wang, and C.-J. Li Adv. Synth. Catal. 348 2006 229
- (2006) Adv. Synth. Catal. , vol.348 , pp. 229
- Zhang, H.-B.¹ Liu, L.² Chen, Y.-J.³ Wang, D.⁴ Li, C.-J.⁵

44
- 77956471191
- Y. Zhao, Y. Zhang, J. Wang, H. Li, L. Wu, and Z. Liu Synlett 2010 2352 and references cited therein
- (2010) Synlett , pp. 2352
- Zhao, Y.¹ Zhang, Y.² Wang, J.³ Li, H.⁴ Wu, L.⁵ Liu, Z.⁶

45
- 0000392051
- See for example: L.S. Liebeskind, and S.W. Riesinger J. Org. Chem. 58 1993 408
- (1993) J. Org. Chem. , vol.58 , pp. 408
- Liebeskind, L.S.¹ Riesinger, S.W.²

46
- 0000568291
- A. Palmgren, A. Thorarensen, and J.-E. Bäckvall J. Org. Chem. 63 1998 3764
- (1998) J. Org. Chem. , vol.63 , pp. 3764
- Palmgren, A.¹ Thorarensen, A.² Bäckvall, J.-E.³

47
- 67449103167
- I. Ullah, R.A. Khera, M. Hussain, A. Villinger, and P. Langers Tetrahedron Lett. 50 2009 4651
- (2009) Tetrahedron Lett. , vol.50 , pp. 4651
- Ullah, I.¹ Khera, R.A.² Hussain, M.³ Villinger, A.⁴ Langers, P.⁵

48
- 33646594410
- R. Shintani, W.-L. Duan, and T. Hayashi J. Am. Chem. Soc. 128 2006 5628
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 5628
- Shintani, R.¹ Duan, W.-L.² Hayashi, T.³

49
- 34447558049
- W.-L. Duan, Y. Imazaki, R. Shintani, and T. Hayashi Tetrahedron 63 2007 8529
- (2007) Tetrahedron , vol.63 , pp. 8529
- Duan, W.-L.¹ Imazaki, Y.² Shintani, R.³ Hayashi, T.⁴

50
- 67649404713
- For additions of aryltrifluoroborates, see: O.M. Demchuk, and K.M. Pietrusiewicz Synlett 2009 1149
- (2009) Synlett , pp. 1149
- Demchuk, O.M.¹ Pietrusiewicz, K.M.²

51
- 34547163506
- For the addition of arylboronic acids to quinone monoacetals see: N. Tokunaga, and T. Hayashi Adv. Synth. Catal. 349 2007 513
- (2007) Adv. Synth. Catal. , vol.349 , pp. 513
- Tokunaga, N.¹ Hayashi, T.²

52
- 46049105895
- G. Lalic, and E.J. Corey Tetrahedron Lett. 49 2008 4894
- (2008) Tetrahedron Lett. , vol.49 , pp. 4894
- Lalic, G.¹ Corey, E.J.²

53
- 33846350928
- Reviews: Y. Yamamoto, T. Nishikata, and N.J. Miyaura Synth. Org. Chem., Jpn. 64 2006 1112
- (2006) Synth. Org. Chem., Jpn. , vol.64 , pp. 1112
- Yamamoto, Y.¹ Nishikata, T.² Miyaura, N.J.³

54
- 53849111957
- A. Gutnov Eur. J. Org. Chem. 2008 4547
- (2008) Eur. J. Org. Chem. , pp. 4547
- Gutnov, A.¹

55
- 44649128461
- Y. Yamamoto, T. Nishikata, and N. Miyaura Pure Appl. Chem. 80 2008 807
- (2008) Pure Appl. Chem. , vol.80 , pp. 807
- Yamamoto, Y.¹ Nishikata, T.² Miyaura, N.³

56
- 68949151956
- N. Miyaura Synlett 2009 2039
- (2009) Synlett , pp. 2039
- Miyaura, N.¹

57
- 70350676942
- M.T. Molina, C. Navarro, A. Moreno, and A.G. Csákÿ Org. Lett. 11 2009 4938
- (2009) Org. Lett. , vol.11 , pp. 4938
- Molina, M.T.¹ Navarro, C.² Moreno, A.³ Csákÿ, A.G.⁴

58
- 27944473247
- T. Richard, X. Vitrac, J.M. Merillon, and J.P. Monti Biochim. Biophys. Acta. 1726 2005 238
- (2005) Biochim. Biophys. Acta. , vol.1726 , pp. 238
- Richard, T.¹ Vitrac, X.² Merillon, J.M.³ Monti, J.P.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.