C ring may be dispensable for β-carboline: Design, synthesis, and bioactivities evaluation of tryptophan analog derivatives based on the biosynthesis of β-carboline alkaloids

Bioorganic and Medicinal Chemistry

Volumn 24, Issue 3, 2016, Pages 462-473

  Huang, Yuanqiong ^a   Liu, Yongxian ^a   Liu, Yuxiu ^a   Song, Hongjian ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Anti TMV; Biosynthesis; Fungicide; Tryptophan; Carboline

Indexed keywords

2 AMINO 3 (1H INDOL 3 YL) N (1 PHENYLETHYL)PROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N (4 METHOXYBENZYL)PROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N (PROP 2 YNYL)PROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N (PYRIDIN 3 YLMETHYL)PROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N (THIAZOL 2 YL)PROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N ISOPROPYLPROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N OCTYLPROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N PHENETHYLPROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N PHENYLPROPANAMIDE; 2 AMINO 3 (1H INDOL 3 YL) N [(TETRAHYDROFURAN 2 YL)METHYL]PROPANAMIDE; 2 AMINO N (2 CHLOROBENZYL) 3 (1H INDOL 3 YL)PROPANAMIDE; 2 AMINO N (2 HYDROXYETHYL) 3 (1H INDOL 3 YL)PROPANAMIDE; 2 AMINO N (2,4 DIMETHOXYBENZYL) 3 (1H INDOL 3 YL)PROPANAMIDE; 2 AMINO N (3 CHLOROBENZYL) 3 (1H INDOL 3 YL)PROPANAMIDE; 2 AMINO N (4 CHLOROBENZYL) 3 (1H INDOL 3 YL)PROPANAMIDE; 2 AMINO N BENZYL 3 (1H INDOL 3 YL)PROPANAMIDE; 2 AMINO N CYCLOHEXYL 3 (1H INDOL 3 YL)PROPANAMIDE; 2 AMINO N TERT BUTYL 3 (1H INDOL 3 YL) N PROPANAMIDE; 2 AMINO N,N DIETHYL 3 (1H INDOL 3 YL) N PROPANAMIDE; ALKALOID; BETA CARBOLINE DERIVATIVE; ETHYL 2 AMINO 3 (1H INDOL 3 YL)PROPANOATE; METHYL 2 (3 BENZYLUREIDO) 3 3 (1H INDOL 3 YL) 2 (3 ISOPROPYLUREIDO)PROPANOATE; METHYL 2 (3 BUTYLUREIDO) 3 (1H INDOL 3 YL)PROPANOATE; METHYL 2 (3 CYCLOHEXYLUREIDO) 3 3 (1H INDOL 3 YL)PROPANOATE; METHYL 2 (3 CYCLOPENTYLUREIDO) 3 3 (1H INDOL 3 YL)PROPANOATE; METHYL 3 (1H INDOL 3 YL) 2 (3 ISOPROPYLUREIDO)PROPANOATE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [2 AMINO N BUTYL 3 (1H INDOL 3 YL)PROPANAMIDE]; ANTIVIRUS AGENT; BETA CARBOLINE; CARBOLINE DERIVATIVE; FUNGICIDE; INSECTICIDE; TRYPTOPHAN;

ANIMAL EXPERIMENT; ANTIFUNGAL ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BIOASSAY; BIOLOGICAL ACTIVITY; BIOSYNTHESIS; CONTROLLED STUDY; DRUG DESIGN; DRUG DOSE COMPARISON; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; IN VITRO STUDY; IN VIVO STUDY; INSECTICIDAL ACTIVITY; MALE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TOBACCO MOSAIC VIRUS; TOXICITY TESTING; ANALOGS AND DERIVATIVES; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CULEX; DOSE RESPONSE; DRUG EFFECTS; FUNGUS; METABOLISM; MICROBIAL SENSITIVITY TEST;

ANIMALS; ANTIVIRAL AGENTS; CARBOLINES; CULEX; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; FUNGI; FUNGICIDES, INDUSTRIAL; INSECTICIDES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TOBACCO MOSAIC VIRUS; TRYPTOPHAN;

EID: 84954378688     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.08.016     Document Type: Article

References (21)

1. H.J. Song, Y.X. Liu, Y.X. Liu, L.Z. Wang, and Q.M. Wang J. Agric. Food Chem. 62 2014 1010
2. H.J. Song, Y.X. Liu, Y.X. Liu, Y.Q. Huang, Y.Q. Li, and Q.M. Wang Bioorg. Med. Chem. Lett. 24 2014 5228
3. Y.X. Liu, H.J. Song, Y.Q. Huang, J.R. Li, S. Zhao, Y.C. Song, P.W. Yang, Z.X. Xiao, Y.X. Liu, Y.Q. Li, H. Shang, and Q.M. Wang J. Agric. Food Chem. 62 2014 9987
4. Q. Chen, C.T. Ji, Y.X. Song, H.B. Huang, J.Y. Ma, X.P. Tian, and J.H. Ju Angew. Chem., Int. Ed. 52 2013 9980
5. Yan, W.; Ge, H. M.; Wang, G.; Jiang, N.; Mei, Y. N.; Jiang, R.; Li, S. J.; Chen, C. J.; Jiao, R. H.; Xu, Q.; Ng, S. W.; Tan, R. X. PNAS2014, 111, 18138.
6. H.C. Lin, G. Chiou, Y.H. Chooi, T.C. McMahon, W. Xu, N.K. Garg, and Y. Tang Angew. Chem., Int. Ed. 54 2015 3004
7. W.X. Song, and R.M. Wang Acad. Period. Farm Prod. Process. 3 2005 18
8. Z.Z. Zuo, Q.G. Huang, W.B. Wu, A.J. Cai, X.Q. Weng, Y.Y. Zhao, and Q.Q. Shi Anhui. Agric. Sci. Bull. 16 2010 38
9. G.Y. Kang, Z.P. Li, X.L. Liu, X.R. Wu, H.Q. Shen, and Q.I. Wang Carcinog. Teratogenesis. Mutagen. 25 2015 272
10. Hipskind, P. A.; Lobb, K. L. US 005792760 A, 1998.
11. D.H. Wang, P. Wei, and P.K. Ouyang Chem. Ind. Eng. Prog. 21 2002 103
12. Kohki, T.; Keisuke, S.; Yutaka, S. EP 0032708 A1, 1981.
13. C. Appelt, A.K. Schrey, J. Arvid Söderhäll, and P. Schmieder Bioorg. Med. Chem. Lett. 17 2007 2334
14. W.M. Li, H.Z. Tan, J.G. Wang, Y.H. Li, and Z.M. Li Chem. J. Chin. Univ. 30 2009 728
15. A.B. Nongonierma, and R.J. FitzGerald Food Funct. 2013 1843 4
16. A.D. Lu, Z.W. Wang, Z.H. Zhou, J.X. Chen, and Q.M. Wang J. Agric. Food Chem. 63 2015 1378
17. L. Li, Z. Li, K.L. Wang, S. Zhao, J.M. Feng, J.R. Li, P.W. Yang, Y.X. Liu, L.Z. Wang, Y.Q. Li, H. Shang, and Q.M. Wang J. Agric. Food Chem. 62 2014 11080
18. J.C. Xiao, J.L. Xu, S. Cui, H.B. Liu, S. Wang, and Y.L. Li Org. Lett. 10 2008 645
19. L.H.J. Kleijn, F.M. Müskens, S.F. Oppedijk, G.D. Bruin, and N.I. Martin Tetrahedron Lett. 53 2012 6430
20. J. Zhu, T. Chen, L.L. Chen, W.Q. Lu, P. Che, J. Huang, H.L. Li, J. Li, and H.L. Jiang Molecules 14 2009 494
21. K.Y. Yaeko, O. Chiharu, Y. Kiminari, U. Yasuyuki, A. Shiho, S. Noriko, K. Toshitsugu, T. Hiroaki, and H. Yoshihiro Tetrahedron 58 2002 7851