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Volumn 24, Issue 6, 2016, Pages 1241-1254

Design and synthesis of a series of serine derivatives as small molecule inhibitors of the SARS coronavirus 3CL protease

(5) Konno, Hiroyuki a Wakabayashi, Masaki a Takanuma, Daiki a Saito, Yota a Akaji, Kenichi b

a YAMAGATA UNIVERSITY (Japan)

b KYOTO PHARMACEUTICAL UNIVERSITY (Japan)

Author keywords

Cathepsin B; Cytotoxicity; Docking simulation; SARS 3CL protease; SARS CoV; Serine derivative

Indexed keywords

CATHEPSIN B; N (PARA HYDROXYPHENYL)PROPIONYLSERINECYCLOHEXYLAMIDE; N 2' METHOXY 3 PHENYLPROP 2 ENOICSERINECYCLOHEXYLAMIDE; N 3' METHOXY 3 PHENYLPROP 2 ENOICSERINECYCLOHEXYLAMIDE; N 3',4' DIMETHOXY 3 PHENYLPROP 2 ENOICSERINECYCLOHEXYLAMIDE; N 3',4',5' TRIMETHOXY 3 PHENYLPROP 2 ENOICSERINECYCLOHEXYLAMIDE; N 3',5' DIMETHOXY 3 PHENYLPROP 2 ENOICSERINECYCLOHEXYLAMIDE; N 4 PHENYLBUT 2 ENOICSERINECYCLOHEXYLAMIDE; N 4' HYDROXY 3 PHENYLPROP 2 ENOICSERINECYCLOHEXYLAMIDE; N 4' METHOXY 3 PHENYLPROP 2 ENOICSERINECYCLOHEXYLAMIDE; N BENZOYLSERINECYCLOHEXYLAMIDE; N CINNAMOYL SERINE(BENZOYL)CYCLOHEXYLAMIDE; N CINNAMOYL SERINE(CINNAMOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(2,4,6 TRICHLOROBENZOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(3 PYROGLUTAMOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(ACETYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(BENZOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(BUTANOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(ISONICOTINOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(PHENYLACETYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(PHENYLPROPANOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINE(PIVALOYL)CYCLOHEXYLAMIDE; N CINNAMOYLSERINEBENZYLAMIDE; N CINNAMOYLSERINECYCLOHEXANEMETHYLAMIDE; N CINNAMOYLSERINECYCLOHEXYLAMIDE; N CINNAMOYLSERINEMORPHOLINEAMIDE; N CINNAMOYLSERINEPIPERIDINEAMIDE; SERINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRUS ENZYME; 3C-LIKE PROTEASE, SARS CORONAVIRUS; CYSTEINE PROTEINASE; MOLECULAR LIBRARY; PROTEINASE INHIBITOR; SERINE; VIRAL PROTEIN;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY TEST; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SPECIFICITY; HUMAN; HUMAN CELL; IC50; MOLECULAR DOCKING; NONHUMAN; SARS CORONAVIRUS; SIMULATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CELL DEATH; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; ENZYMOLOGY; HELA CELL LINE; METABOLISM; MOLECULAR LIBRARY; PHARMACOLOGY;

CELL DEATH; CYSTEINE ENDOPEPTIDASES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HELA CELLS; HUMANS; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; PROTEASE INHIBITORS; SARS VIRUS; SERINE; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL PROTEINS;

EID: 84958891590 PISSN: 09680896 EISSN: 14643391 Source Type: Journal
DOI: 10.1016/j.bmc.2016.01.052 Document Type: Article

Times cited : (23)

References (32)

1
- 0013074820
- N. Lee, D. Hui, A. Wu, P. Chan, P. Cameron, G.M. Joynt, A. Ahuja, M.Y. Yung, C.B. Leung, and K.F. To N. Engl. J. Med. 348 2003 1986
- (2003) N. Engl. J. Med. , vol.348 , pp. 1986
- Lee, N.¹ Hui, D.² Wu, A.³ Chan, P.⁴ Cameron, P.⁵ Joynt, G.M.⁶ Ahuja, A.⁷ Yung, M.Y.⁸ Leung, C.B.⁹ To, K.F.¹⁰

2
- 0038523806
- C. Drosten, S. Gunther, W. Preiser, S. Ven der Werf, H.R. Brodt, S. Becker, H. Rabenau, M. Panning, L. Kolensnikova, R.A.M. Fouchier, A. Berger, A.M. Burguiere, J. Cinatl, M. Eickmann, N. Escriou, K. Grywna, S. Kramme, J. Manuguerra, S. Muller, V. Rickerts, M. Sturmer, S. Vieth, H.D. Klenk, A.D.E.E. Osterhaus, H. Schemitz, and H.W. Doerr N. Engl. J. Med. 348 2003 1967
- (2003) N. Engl. J. Med. , vol.348 , pp. 1967
- Drosten, C.¹ Gunther, S.² Preiser, W.³ Ven Der Werf, S.⁴ Brodt, H.R.⁵ Becker, S.⁶ Rabenau, H.⁷ Panning, M.⁸ Kolensnikova, L.⁹ Fouchier, R.A.M.¹⁰ Berger, A.¹¹ Burguiere, A.M.¹² Cinatl, J.¹³ Eickmann, M.¹⁴ Escriou, N.¹⁵ Grywna, K.¹⁶ Kramme, S.¹⁷ Manuguerra, J.¹⁸ Muller, S.¹⁹ Rickerts, V.²⁰ more..

3
- 0038076030
- T.G. Ksiazek, D. Erdman, C.S. Goldsmith, S.R. Zaki, T. Peret, S. Emery, S. Tong, C. Urbani, J.A. Comer, W. Lim, R.E. Rollin, S.F. Dowell, A.E. Ling, C.D. Humphrey, G.J. Shieh, J.Y. Guarner, C.D. Paddock, P. Rota, B. Fields, L.J. DeRisi, J.Y. Yang, N. Cox, J.M. Hughes, J.W. LeDuc, W.J. Bellinim, and J.W. Anderson N. Engl. J. Med. 348 2003 1953
- (2003) N. Engl. J. Med. , vol.348 , pp. 1953
- Ksiazek, T.G.¹ Erdman, D.² Goldsmith, C.S.³ Zaki, S.R.⁴ Peret, T.⁵ Emery, S.⁶ Tong, S.⁷ Urbani, C.⁸ Comer, J.A.⁹ Lim, W.¹⁰ Rollin, R.E.¹¹ Dowell, S.F.¹² Ling, A.E.¹³ Humphrey, C.D.¹⁴ Shieh, G.J.¹⁵ Guarner, J.Y.¹⁶ Paddock, C.D.¹⁷ Rota, P.¹⁸ Fields, B.¹⁹ Derisi, L.J.²⁰ more..

4
- 33947376439
- K. Pyrc, B. Berkhout, and L. Van der Hoek J. Virol. 81 2007 3051
- (2007) J. Virol. , vol.81 , pp. 3051
- Pyrc, K.¹ Berkhout, B.² Van Der Hoek, L.³

5
- 79952410434
- R. MacBride, and B.C. Fielding Future Microbiol. 6 2011 153
- (2011) Future Microbiol. , vol.6 , pp. 153
- MacBride, R.¹ Fielding, B.C.²

6
- 84881030100
- No. 129134
- L.-J. Cui, C. Zhang, T. Zhang, R.-J. Lu, Z.-D. Xie, L.-L. Zhang, C.-Y. Liu, W.-M. Zhou, X.-J. Ma, and W.-J. Tan Adv. Virol. 2011 No. 129134
- (2011) Adv. Virol.
- Cui, L.-J.¹ Zhang, C.² Zhang, T.³ Lu, R.-J.⁴ Xie, Z.-D.⁵ Zhang, L.-L.⁶ Liu, C.-Y.⁷ Zhou, W.-M.⁸ Ma, X.-J.⁹ Tan, W.-J.¹⁰

7
- 84976230519
- A.M. Zaki, S. van Boheemen, T.M. Bestebroer, A.D. Osterhaus, and R.A. Fouchier N. Engl. J. Med. 2012 1814 367
- (1814) N. Engl. J. Med. , vol.2012 , pp. 367
- Zaki, A.M.¹ Van Boheemen, S.² Bestebroer, T.M.³ Osterhaus, A.D.⁴ Fouchier, R.A.⁵

8
- 85044010389
- A. Bermingham, C.S. Brown, E. Aarons, C. Tong, C. Langrish, K. Hoschler, K. Brown, M. Galiano, R. Myers, R.G. Pebody, H.K. Green, N.L. Boddington, R. Gopai, W. Newsholme, C. Drosten, R.A. Fouchier, and M. Zambon Euro. Surveill. 17 2012 20290
- (2012) Euro. Surveill. , vol.17 , pp. 20290
- Bermingham, A.¹ Brown, C.S.² Aarons, E.³ Tong, C.⁴ Langrish, C.⁵ Hoschler, K.⁶ Brown, K.⁷ Galiano, M.⁸ Myers, R.⁹ Pebody, R.G.¹⁰ Green, H.K.¹¹ Boddington, N.L.¹² Gopai, R.¹³ Newsholme, W.¹⁴ Drosten, C.¹⁵ Fouchier, R.A.¹⁶ Zambon, M.¹⁷

9
- 84871415482
- e00473-12
- S. Van Boheemen, M. Graaf, C. Lauber, T.M. Bestebroer, V.S. Raj, A.M. Zaki, A.D.M. Osterhaus, B.L. Haagmans, A.E. Gorbalenya, E.J. Snijder, and R.A.M. Fouchier MBio 3 2012 e00473-12
- (2012) MBio , vol.3
- Van Boheemen, S.¹ Graaf, M.² Lauber, C.³ Bestebroer, T.M.⁴ Raj, V.S.⁵ Zaki, A.M.⁶ Osterhaus, A.D.M.⁷ Haagmans, B.L.⁸ Gorbalenya, A.E.⁹ Snijder, E.J.¹⁰ Fouchier, R.A.M.¹¹

10
- 0042377358
- V. Thiel, K.A. Ivanov, A. Putics, T. Hertzig, B. Schelle, S. Bayer, B. Weiβbrich, E.J. Snijider, H. Rabenau, H.W. Doerr, A.E. Gorbalenya, and J.J. Ziebuhr J. Gen. Virol. 84 2003 2305
- (2003) J. Gen. Virol. , vol.84 , pp. 2305
- Thiel, V.¹ Ivanov, K.A.² Putics, A.³ Hertzig, T.⁴ Schelle, B.⁵ Bayer, S.⁶ Weiß⁷ brich, B.⁸ Snijider, E.J.⁹ Rabenau, H.¹⁰ Doerr, H.W.¹¹ Gorbalenya, A.E.¹² Ziebuhr, J.J.¹³

11
- 84878735186
- P. Thanigaimaalai, S. Konno, T. Yamamoto, Y. Koiwai, A. Taguchi, K. Takayama, F. Yakushiji, K. Akaji, Y. Kiso, Y. Kawasaki, S.-E. Chen, A. Naser-Tavakolian, A. Scheön, E. Freire, and Y. Hayashi Eur. J. Med. Chem. 65 2013 436
- (2013) Eur. J. Med. Chem. , vol.65 , pp. 436
- Thanigaimaalai, P.¹ Konno, S.² Yamamoto, T.³ Koiwai, Y.⁴ Taguchi, A.⁵ Takayama, K.⁶ Yakushiji, F.⁷ Akaji, K.⁸ Kiso, Y.⁹ Kawasaki, Y.¹⁰ Chen, S.-E.¹¹ Naser-Tavakolian, A.¹² Scheön, A.¹³ Freire, E.¹⁴ Hayashi, Y.¹⁵

12
- 84862783612
- T.T.H. Nguyen, H.-J. Woo, H.-K. Kang, V.D. Nguyen, Y.-M. Kim, D.-W. Kim, S.-A. Ahn, Y. Xia, and D. Kim Biotechnol. Lett. 34 2012 831
- (2012) Biotechnol. Lett. , vol.34 , pp. 831
- Nguyen, T.T.H.¹ Woo, H.-J.² Kang, H.-K.³ Nguyen, V.D.⁴ Kim, Y.-M.⁵ Kim, D.-W.⁶ Ahn, S.-A.⁷ Xia, Y.⁸ Kim, D.⁹

13
- 84878584191
- J.-Y. Park, J.H. Kim, J.M. Kwon, H.-J. Kwon, H.J. Jeong, Y.M. Kim, D. Kim, W.S. Lee, and Y.B. Ryu Bioorg. Med. Chem. 21 2013 3730
- (2013) Bioorg. Med. Chem. , vol.21 , pp. 3730
- Park, J.-Y.¹ Kim, J.H.² Kwon, J.M.³ Kwon, H.-J.⁴ Jeong, H.J.⁵ Kim, Y.M.⁶ Kim, D.⁷ Lee, W.S.⁸ Ryu, Y.B.⁹

14
- 84872775313
- J. Jacobs, V. Grum-Tokars, Y. Zhou, M. Turlington, S.A. Saldanha, P. Chase, A. Eggler, E.C. Dawson, Y.M. Baez-Santos, S. Tomar, A.M. Mielech, S.C. Baker, C.W. Lindsley, P. Hodder, A. Mesecar, and S.R. Stauffer J. Med. Chem. 56 2013 534
- (2013) J. Med. Chem. , vol.56 , pp. 534
- Jacobs, J.¹ Grum-Tokars, V.² Zhou, Y.³ Turlington, M.⁴ Saldanha, S.A.⁵ Chase, P.⁶ Eggler, A.⁷ Dawson, E.C.⁸ Baez-Santos, Y.M.⁹ Tomar, S.¹⁰ Mielech, A.M.¹¹ Baker, S.C.¹² Lindsley, C.W.¹³ Hodder, P.¹⁴ Mesecar, A.¹⁵ Stauffer, S.R.¹⁶

15
- 84891482162
- W. Liu, H.-M. Zhu, G.-J. Niu, E.-Z. Shi, J. Chen, B. Sun, W.-Q. Chen, H.-G. Zhou, and C. Yang Bioorg. Med. Chem. 22 2014 292
- (2014) Bioorg. Med. Chem. , vol.22 , pp. 292
- Liu, W.¹ Zhu, H.-M.² Niu, G.-J.³ Shi, E.-Z.⁴ Chen, J.⁵ Sun, B.⁶ Chen, W.-Q.⁷ Zhou, H.-G.⁸ Yang, C.⁹

16
- 84964199951
- Y. Shimamoto, Y. Hattori, K. Kobayashi, K. Teruya, A. Sanjoh, A. Nakagawa, E. Yamashita, and K. Akaji Bioorg. Med. Chem. 23 2015 876
- (2015) Bioorg. Med. Chem. , vol.23 , pp. 876
- Shimamoto, Y.¹ Hattori, Y.² Kobayashi, K.³ Teruya, K.⁴ Sanjoh, A.⁵ Nakagawa, A.⁶ Yamashita, E.⁷ Akaji, K.⁸

17
- 53749084338
- K. Akaji, H. Konno, M. Onozuka, A. Makino, and K. Nosaka Bioorg. Med. Chem. 16 2008 9400
- (2008) Bioorg. Med. Chem. , vol.16 , pp. 9400
- Akaji, K.¹ Konno, H.² Onozuka, M.³ Makino, A.⁴ Nosaka, K.⁵

18
- 82555185535
- K. Akaji, H. Konno, H. Mitsui, K. Teruya, Y. Shimamoto, Y. Hattori, T. Ozaki, M. Kusunoki, and A. Sanjoh J. Med. Chem. 54 2011 7962
- (2011) J. Med. Chem. , vol.54 , pp. 7962
- Akaji, K.¹ Konno, H.² Mitsui, H.³ Teruya, K.⁴ Shimamoto, Y.⁵ Hattori, Y.⁶ Ozaki, T.⁷ Kusunoki, M.⁸ Sanjoh, A.⁹

19
- 84881120157
- H. Konno, Y. Sema, M. Ishii, Y. Hattori, K. Nosak, and K. Akaji Tetrahedron Lett. 54 2013 4848
- (2013) Tetrahedron Lett. , vol.54 , pp. 4848
- Konno, H.¹ Sema, Y.² Ishii, M.³ Hattori, Y.⁴ Nosak, K.⁵ Akaji, K.⁶

20
- 84937761704
- H. Konno, Y. Sema, and Y. Tokairin Tetrahedron 71 2015 3433
- (2015) Tetrahedron , vol.71 , pp. 3433
- Konno, H.¹ Sema, Y.² Tokairin, Y.³

21
- 54349125060
- D. Bai, Q. Yang, L. Chem, X. He, Z. Gao, and X. Shen Chem. Pharm. Bull. 56 2008 1400
- (2008) Chem. Pharm. Bull. , vol.56 , pp. 1400
- Bai, D.¹ Yang, Q.² Chem, L.³ He, X.⁴ Gao, Z.⁵ Shen, X.⁶

22
- 12044258245
- L.A. Carpino J. Am. Chem. Soc. 115 1993 4397
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397
- Carpino, L.A.¹

23
- 0001304727
- L.A. Carpino, H. Imazumi, A. El-Faham, F.J. Ferrer, C. Zhang, Y. Lee, B.M. Foxman, P. Henklein, C. Hanay, C. Mugge, H. Wenschuh, J. Klose, M. Beyerman, and M. Bienert Angew. Chem., Int. Ed. 41 2002 442
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 442
- Carpino, L.A.¹ Imazumi, H.² El-Faham, A.³ Ferrer, F.J.⁴ Zhang, C.⁵ Lee, Y.⁶ Foxman, B.M.⁷ Henklein, P.⁸ Hanay, C.⁹ Mugge, C.¹⁰ Wenschuh, H.¹¹ Klose, J.¹² Beyerman, M.¹³ Bienert, M.¹⁴

24
- 0035906028
- M. Kunishima, C. Wamachi, K. Hioki, K. Terao, and S. Tani Tetrahedron 57 2001 1551
- (2001) Tetrahedron , vol.57 , pp. 1551
- Kunishima, M.¹ Wamachi, C.² Hioki, K.³ Terao, K.⁴ Tani, S.⁵

25
- 84894260334
- I. Shiina Bull. Chem. Soc. Jpn. 87 2014 196
- (2014) Bull. Chem. Soc. Jpn. , vol.87 , pp. 196
- Shiina, I.¹

26
- 0001616071
- J. Inanaga, K. Hirata, H. Saeki, Y. Katsuki, and M. Yamaguchi Bull. Chem. Soc. Jpn. 52 1979 1989
- (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 1989
- Inanaga, J.¹ Hirata, K.² Saeki, H.³ Katsuki, Y.⁴ Yamaguchi, M.⁵

27
- 84872775313
- J. Jacobs, V. Grum-Tokars, Y. Zhou, M. Turlington, S.A. Saldanha, P. Chase, A. Eggler, E.S. Dawson, Y.M. Baez-Santos, S. Tomar, A.M. Mielech, S.C. Baker, C.W. Lindsley, P. Hodder, A. Mesecar, and S.R. Stauffer J. Med. Chem. 56 2013 534
- (2013) J. Med. Chem. , vol.56 , pp. 534
- Jacobs, J.¹ Grum-Tokars, V.² Zhou, Y.³ Turlington, M.⁴ Saldanha, S.A.⁵ Chase, P.⁶ Eggler, A.⁷ Dawson, E.S.⁸ Baez-Santos, Y.M.⁹ Tomar, S.¹⁰ Mielech, A.M.¹¹ Baker, S.C.¹² Lindsley, C.W.¹³ Hodder, P.¹⁴ Mesecar, A.¹⁵ Stauffer, S.R.¹⁶

28
- 80054768857
- H. Konno, K. Nosaka, and K. Akaji Tetrahedron 67 2011 9067
- (2011) Tetrahedron , vol.67 , pp. 9067
- Konno, H.¹ Nosaka, K.² Akaji, K.³

29
- 34547563523
- K. Konno, K. Kubo, H. Makabe, E. Toshiro, K. Nosaka, and K. Akaji Tetrahedron 63 2007 9502
- (2007) Tetrahedron , vol.63 , pp. 9502
- Konno, K.¹ Kubo, K.² Makabe, H.³ Toshiro, E.⁴ Nosaka, K.⁵ Akaji, K.⁶

30
- 0027198637
- T. Hiwasa, J. Fujita-Yoshigaki, M. Shirouzu, H. Koide, T. Sawada, S. Sakiyama, and S. Yokoyama Cancer Lett. 69 1993 161
- (1993) Cancer Lett. , vol.69 , pp. 161
- Hiwasa, T.¹ Fujita-Yoshigaki, J.² Shirouzu, M.³ Koide, H.⁴ Sawada, T.⁵ Sakiyama, S.⁶ Yokoyama, S.⁷

31
- 0019765848
- A.J. Barrett, and H. Kirschke Method Enzymol. 380 1981 535
- (1981) Method Enzymol. , vol.380 , pp. 535
- Barrett, A.J.¹ Kirschke, H.²

32
- 4143073625
- I.T. Lim, S.O. Meroueh, M. Lee, M.J. Heeg, and S. Mobashery J. Am. Chem. Soc. 126 2004 10271
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 10271
- Lim, I.T.¹ Meroueh, S.O.² Lee, M.³ Heeg, M.J.⁴ Mobashery, S.⁵

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