Design, synthesis and preliminary activity assay of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as novel Histone deacetylases (HDACs) inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 5, 2010, Pages 1761-1772

  Zhang, Yingjie ^a   Feng, Jinhong ^a   Liu, Chunxi ^a   Zhang, Lei ^a   Jiao, Jie ^a   Fang, Hao ^a   Su, Li ^a   Zhang, Xiaopan ^a   Zhang, Jian ^a   Li, Minyong ^a   Wang, Binghe ^b   Xu, Wenfang ^a  

^a SHANDONG UNIVERSITY   (China)

^b GEORGIA STATE UNIVERSITY   (United States)

Author keywords

1,2,3,4 Tetrahydroisoquinoline 3 carboxylic acid derivatives; Histone deacetylases; Inhibitor; Synthesis

Indexed keywords

1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID DERIVATIVE; 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] N (4 METHOXYPHENYL) 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDE; 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] N (NAPHTHALEN 1 YL) 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDE HYDROCHLORIDE; 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] N 2 TOLYL 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDE; 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] N 4 TOLYL 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDE; 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] N PHENETHYL 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDE; 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] N PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDE; BENZYL 3 (BIPHENYL 4 YLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXYLATE; BENZYL 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3 (PHENETHYLCARBAMOYL) 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; BENZYL 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3 (PHENYLCARBAMOYL) 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; HISTONE DEACETYLASE 8; HISTONE DEACETYLASE INHIBITOR; N BENZYL 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXAMIDE; TERT BUTYL 3 (2,4 DIMETHYLPHENYLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXYLATE; TERT BUTYL 3 (3 CHLORO 4 FLUOROPHENYLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXYLATE; TERT BUTYL 3 (3 CHLOROPHENYLCARBAMOYL) 7 [2 (HYDROXYAMINO 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 3 (3 CHLOROPHENYLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXYLATE; TERT BUTYL 3 (4 FLUOROPHENYLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXYLATE; TERT BUTYL 3 (BIPHENYL 4 YLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 3 (HEXYLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 3 (HEXYLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXYLATE; TERT BUTYL 3 (TERT BUTYLCARBAMOYL) 7 [2 (HYDROXYAMINO 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 3 (TERT BUTYLCARBAMOYL) 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 7 (2 (HYDROXYAMINO) 2 OXOETHOXY) 3 (NAPHTHALEN 1 YLCARBAMOYL) 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3 (4 METHOXYPHENYLCARBAMOYL) 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3 (PENTYLCARBAMOYL) 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; TERT BUTYL 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3 (PENTYLCARBAMOYL) 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXYLATE; TERT BUTYL 7 [2 (HYDROXYAMINO) 2 OXOETHOXY] 3 (PHENYLCARBAMOYL) 3,4 DIHYDROISOQUINOLINE 2 (1H) CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VORINOSTAT;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50;

ANTINEOPLASTIC AGENTS; BINDING SITES; CATALYTIC DOMAIN; CELL LINE, TUMOR; COMPUTER SIMULATION; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HL-60 CELLS; HUMANS; HYDROXAMIC ACIDS; ISOQUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROISOQUINOLINES;

EID: 77249167010     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.01.060     Document Type: Article

References (38)

1. Christian A.H., and Stuart L.S. Curr. Opin. Chem. Biol. 1 (1997) 300
2. Kouzarides T. Curr. Opin. Genet. Dev. 9 (1999) 40
3. Wolffe A.P. Science (Washington) 272 (1996) 371
4. Polo S.E., and Almouzni G. Cancer Lett. 220 (2005) 1
5. Vidanes G.M., Bonilla C.Y., and Toczyski D.P. Cell 121 (2005) 973
6. Glozak M.A., Sengupta N., Zhang X.H., and Seto E. Gene 363 (2005) 15
7. Yang X., and Seto E. Nat. Rev. Mol. Cell Biol. 9 (2008) 206
8. Fraga M.F., Ballestar E., Villar-Garea A., Boix-Chornet M., Espada J., Schotta G., Bonaldi T., Haydon C., Ropero S., Petrie K., Iyer N.G., Perez-Rosado A., Calvo E., Lopez J.A., Cano A., Calasanz M.J., Colomer D., Piris M.A., Ahn N., Imhof A., Caldas C., Jenuwein T., and Esteller M. Nat. Genet. 37 (2005) 391
9. Halkidou K., Gaughan L., Cook S., Leung H.Y., Neal D.E., and Robson C.N. Prostate 59 (2004) 177
10. Choi J.H., Kwon H.J., Yoon B.-I., Kim J.H., Han S.U., Joo H.J., and Kim D.-Y. Jpn. J. Cancer Res. 92 (2001) 1300
11. Wilson A.J., Byun D.-S., Popova N., Murray L.B., L'Italien K., Sowa Y., Arango D., Velcich A., Augenlicht L.H., and Mariadason J.M. J. Biol. Chem. 281 (2006) 13548
12. Zhang Z.H., Yamashita H., Toyama T., Sugiura H., Ando Y., Mita K., Hamaguchi M., Hara Y., Kobayashi S., and Iwase H. Breast Cancer Res. Treat. 94 (2005) 11
13. Zhu P., Martin E., Mengwasser J., Schlag P., Janssen K.-P., and Gottlicher M. Cancer Cell. 5 (2004) 455
14. Huang B.H., Laban M., Leung C.H.-W., Lee L., Lee C.K., Salto-Tellez M., Raju G.C., and Hooi S.C. Cell Death Differ. 12 (2005) 395
15. Song J., Noh J.H., Lee J.H., Eun J.W., Ahn Y.M., Kim S.Y., Lee S.H., Park W.S., Yoo N.J., Lee J.Y., and Nam S.W. APMIS 113 (2005) 264
16. Zhang Z.H., Yamashita H., Toyama T., Sugiura H., Omoto Y., Ando Y., Mita K., Hamaguchi M., Hayashi S.-I., and Iwase H. Clin. Cancer Res. 10 (2004) 6962
17. Butler L.M., Agus D.B., Scher H.I., Higgins B., Rose A., Cordon-Cardo C., Thaler H.T., Rifkind R.A., Marks P.A., and Richon V.M. Cancer Res. 60 (2000) 5165
18. Garber K. Nat. Biotechnol. 25 (2007) 17
19. Grant S., Easley C., and Kirkpatrick P. Nat. Rev. Drug Disc. 6 (2007) 21
20. Marks P.A., and Breslow R. Nat. Biotechnol. 25 (2007) 84
21. Sangthongpitag K., Wu X., Khng H., Goh S., Ng P., Hu C., Bonday Z., Wang H., Wood J., and Entzeroth M. Eur. J. Cancer Suppl. 4 (2006) 52
22. Fiskus W., Pranpat M., Bali P., Balasis M., Kumaraswamy S., Boyapalle S., Rocha K., Wu J., Giles F., Manley P.W., Atadja P., and Bhalla K. Blood 108 (2006) 645
23. Armeanu S., Pathil A., Venturelli S., Mascagni P., Weiss T.S., Gottlicher M., Gregor M., Lauer U.M., and Bitzer M. J. Hepatol. 42 (2005) 210
24. Arts J., Angibaud P., Marien A., Floren W., Janssens B., King P., van Dun J., Janssen L., Geerts T., Tuman R.W., Johnson D.L., Andries L., Jung M., Janicot M., and van Emelen K. Br. J. Cancer 97 (2007) 1344
25. Wang, A.; U'Prichard, D. C.; Marder, V. J. US Patent 2002/0061885 A1.
26. Vendeville S., Goossens F., Debreu-Fontaine M.A., Landry V., Davioud-Charvet E., Grellier P., Scharpe S., and Sergheraert G. Bioorg. Med. Chem. 10 (2002) 1719
27. Balboni G., Salvadori S., Guerrini R., Negri L., Giannini E., Jinsmaa Y., Bryant S.D., and Lazarus L.H. J. Med. Chem. 45 (2002) 5556
28. Balboni G., Guerrini R., Salvadori S., Bianchi C., Rizzi D., Bryant S.D., and Lazarus L.H. J. Med. Chem. 45 (2002) 713
29. Kotha S., and Sreenivasachary N. Eur. J. Org. Chem. 17 (2001) 3375
30. Cueva J.P., Cai T.B., Mascarella S.W., Thomas J.B., Navarro H.A., and Carroll F.I. J. Med. Chem. 52 (2009) 7463
31. Matter H., Schudok M., Schwab W., Thorwart W., Barbier D., Billen G., Haase B., Neises B., Weithmann K.U., and Wollmann T. Bioorg. Med. Chem. 10 (2002) 3529
32. Klutchko S., Blankley C.J., Fleming R.W., Hinkley J.M., Werner A.E., Nordin I., Holmes A., Hoefle M.L., Cohen D.M., Essenburg A.D., and Kaplan H.R. J. Med. Chem. 29 (1986) 1953
33. Verschueren K., Toth G., Tourwé D., Lebl M., Van Binst G., and Hruby V. Synthesis 5 (1992) 458
34. Bodanszky M., Scheehan T.J., Ohdetti A.M., and Lande S. J. Am. Chem. Soc. 85 (1963) 991
35. Maclaren A.J. Aust. J. Chem. 11 (1958) 360
36. Dekker A.C., Taylor P.S., and Rruton S.J. J. Biol. Chem. 180 (1949) 155
37. Faul M.M., Winneroski L.L., York J.S., Reinhard M.R., Hoying R.C., Gritton W.H., and Dominianni S.J. Heterocycles 55 (2001) 689
38. Vannini A., Volpari C., Filocamo G., Caroli Casavola E., Brunetti M., Renzoni D., Chakravarty P., Paolini C., De Francesco R., Gallinari P., Steinkuhler C., and Di Marco S. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 15064