Quantitative structure-activity relationships of 1,3,4-thiadiazol-2(3H)- ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 1, 2012, Pages 296-304

  Zuo, Yang ^a   Yang, Sheng Gang ^a   Jiang, Li Li ^a   Hao, Ge Fei ^a   Wang, Zhi Fang ^a,b   Wu, Qiong You ^a   Xi, Zhen ^b   Yang, Guang Fu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

1,3,4 Oxadiazol 2(3H) ones; 1,3,4 Thiadiazol 2(3H) ones; Human protoporphyrinogen oxidase inhibitors; Molecular docking; QSAR

Indexed keywords

1,3,4 OXADIAZOL 2[3H] ONE DERIVATIVE; 1,3,4 OXADIAZOLE DERIVATIVE; 1,3,4 THIADIAZOLE 2[3H] ONE DERIVATIVE; 1,3,4 THIADIAZOLE DERIVATIVE; ENZYME INHIBITOR; PROTOPORPHYRINOGEN OXIDASE; PROTOPORPHYRINOGEN OXIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CORRELATIONAL STUDY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; IN VITRO STUDY; MATHEMATICAL PARAMETERS; MOLECULAR DOCKING; POISSON BOLTZMANN SURFACE AREA; QUANTITATIVE STUDY; STRUCTURE ACTIVITY RELATION;

BENZOTHIAZOLES; BINDING SITES; COMPUTER SIMULATION; ENZYME ACTIVATION; ENZYME INHIBITORS; HUMANS; MOLECULAR CONFORMATION; OXADIAZOLES; PROTEIN STRUCTURE, TERTIARY; PROTOPORPHYRINOGEN OXIDASE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; THIADIAZOLES;

PUFFINUS AURICULARIS;

EID: 84855192918     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.10.079     Document Type: Article

References (48)

1. S.M. Gerald Bot. Rev. 32 1966 56
2. R. Poulson, and W.J. Polglase J. Biol. Chem. 250 1975 1269
3. R. Poulson J. Biol. Chem. 251 1976 3730
4. J.C. Deybach, V. Da Silva, B. Grandchamp, and Y. Nordmann Eur. J. Biochem. 149 1985 431
5. G.C. Ferreira, T.L. Andrew, S.W. Karr, and H.A. Dailey J. Biol. Chem. 263 1988 3835
6. G.C. Ferreira, and H.A. Dailey Biochem. J. 250 1988 597
7. S.I. Beale Photosynth. Res. 60 1999 43
8. I.U. Heinemann, N. Diekmann, A. Masoumi, M. Koch, A. Messerschmidt, M. Jahn, and D. Jahn Biochem. J. 402 2007 575
9. J.M. Jacobs, and N.J. Jacobs Arch. Biochem. Biophys. 229 1984 312
10. S. Jung, Y. Lee, K. Yang, S.B. Lee, S.M. Jang, S.B. Ha, and K. Back Plant Cell Environ. 27 2004 1436
11. I. Lermontova, E. Kruse, H.P. Mock, and B. Grimm Proc. Natl. Acad. Sci. U.S.A. 94 1997 8895
12. D.A. Brenner, and J.R. Bloomer N. Engl. J. Med. 302 1980 765
13. J.C. Deybach, H. De Verneuil, and Y. Nordmann Hum. Genet. 58 1981 425
14. P.N. Meissner, R.S. Day, M.R. Moore, P.B. Disler, and E. Harley Eur. J. Clin. Invest. 16 1986 257
15. Y. Nordmann, and H. Puy Clin. Chim. Acta. 325 2002 17
16. S.D. Whatley, H. Puy, R.R. Morgan, A.M. Robreau, A.G. Roberts, Y. Nordmann, G.H. Elder, and J.C. Deybach Am. J. Hum. Genet. 65 1999 984
17. G. Dean The porphyrias: A story of inheritance and environment 2nd ed. 1971 Pitman Medical London
18. T. Jenkins Nat. Genet. 13 1996 7
19. R.S. Day Semin. Dermatol. 5 1986 138
20. J.C. Deybach, H. Puy, A.M. Robreau, J. Lamoril, V. Da Silva, B. Grandchamp, and Y. Nordmann Hum. Mol. Genet. 5 1996 407
21. P.N. Meissner, T.A. Dailey, R.J. Hift, M. Ziman, A.V. Corrigall, A.G. Roberts, D.M. Meissner, R.E. Kirsch, and H.A. Dailey Nat. Genet. 13 1996 95
22. S.O. Duke, J. Lydon, J.M. Becerril, T.D. Sherman, L.P. Lehnen Jr., and H. Matsumoto Weed Sci. 1991 465
23. Y.X. Liu, Z.P. Cui, B. Liu, B.L. Cai, Y.H. Li, and Q.M. Wang J. Agric. Food Chem. 58 2009 2685
24. Nagano, E.; Hashimoto, S.; Yoshida, R.; Matsumoto, H.; Oshio, H.; Kamoshita, K. EP Patent 61,741, 1982.
25. T.K. Gitsopoulos, and R.J. Froud-Williams Weed Res. 44 2004 329
26. M. Hiraki, S. Ohki, Y. Sato, I. Jablonkai, P. Boger, and K. Wakabayashi Pestic. Biochem. Phys. 70 2001 159
27. Theodoridis, G. U.S. Patent 5798,316, 1989.
28. Theodoridis, G.; Princetons, N. J. U.S. Patent 4818,275, 1989.
29. H.R. Corradi, A.V. Corrigall, E. Boix, C.G. Mohan, E.D. Sturrock, P.N. Meissner, and K.R. Acharya J. Biol. Chem. 281 2006 38625
30. M. Koch, C. Breithaupt, R. Kiefersauer, J. Freigang, R. Huber, and A. Messerschmidt J. EMBO 23 2004 1720
31. S.O. Duke, and C.A. Rebeiz ACS Symposium Series Vol. 559 1994 American Chemical Society Washington, DC 71
32. V.H. Fingar, T.J. Wieman, K.S. McMahon, P.S. Haydon, B.P. Halling, D.A. Yuhas, and J.W. Winkelman Cancer Res. 57 1997 4551
33. Volker, A.; Burkhard, G. U.S. Patent 20050049228, 2005.
34. D.E.J.G.J. Dolmans, D. Fukumura, and R.K. Jain Nat. Rev. Cancer 3 2003 380
35. B.P. Halling, D.A. Yuhas, V.F. Fingar, and J.W. Winkelmann Protophyrinogen Oxidase Inhibitors for Tumor Therapy, in Porphyric Pesticides: Chemistry, Toxicology and Pharmaceutical Applications 1994 American Chemical Society Washington, DC
36. X.H. Qin, Y. Tan, L.L. Wang, Z.F. Wang, B.F. Wang, X. Wen, G.F. Yang, Z. Xi, and Y.Q. Shen FASEB J. 25 2011 653
37. L.L. Jiang, Y. Tan, X.L. Zhu, Z.F. Wang, Y. Zuo, Q. Chen, Z. Xi, and G.F. Yang J. Agric. Food Chem. 58 2010 2643
38. J. Bosch, T. Roca, J.L. Catena, C. Farrerons, and I. Miquel Synthesis 2000 721
39. L. Zhu, M.B. Zhang, and M. Dai J. Heterocycl. Chem. 42 2005 727
40. Bruker. SMART (Version 5.628), Bruker AXS, Inc., Madison, Wisconsin, USA, 2001.
41. Bruker. SAINT-Plus (Version 6.45), Bruker AXS, Inc., Madison, Wisconsin, USA, 2001.
42. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112
43. Y. Tan, L. Sun, Z. Xi, G.F. Yang, D.Q. Jiang, X.P. Yan, X. Yang, and H.Y. Li Anal. Biochem. 383 2008 200
44. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639
45. M.F. Sanner J. Mol. Graphics Modell. 17 1999 57
46. Y. Xiong, Y. Li, H. He, and C.G. Zhan Bioorg. Med. Chem. Lett. 17 2007 5186
47. Case, D. A.; Darden, T. A.; Cheatham; Iii, T. E.; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Merz, K. M.; Pearlman, D. A.; Crowley, M. AMBER 9, University of California, San Francisco, 2006.
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghava-chari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B-03, Gaussian, Inc.: Pittsburgh, PA, 2003.