Vanillin derivatives as the selective small molecule inhibitors of FtsZ

Medicinal Chemistry Research

Volumn 23, Issue 6, 2014, Pages 2985-2994

  Sun, Juan ^a   Li, Ming Hui ^a   Wang, Xin Yi ^b   Zhang, Yang ^b   Yuan, Rong Ju ^b   Liu, Han Yu ^b   Zhu, Hai Liang ^a,b  

^a NANJING UNIVERSITY   (China)

^b SHANDONG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Antibacterial activity; FtsZ inhibitors; Schiff base; Vanillin derivatives

Indexed keywords

2 METHOXY 3 NITRO 4 [(M TOLYLIMINO)METHYL]PHENOL; 2 METHOXY 3 NITRO 4 [(O TOLYLIMINO)METHYL]PHENOL; 2 METHOXY 3 NITRO 4 [(P TOLYLIMINO)METHYL]PHENOL; 2 METHOXY 3 NITRO 4 [[(2 NITROPHENYL)IMINO]METHYL]PHENOL; 2 METHOXY 3 NITRO 4 [[(3 NITROPHENYL)IMINO]METHYL]PHENOL; 2 METHOXY 3 NITRO 4 [[(4 NITROPHENYL)IMINO]METHYL]PHENOL; 2 METHOXY 4 [[(2 METHOXYPHENYL)IMINO]METHYL] 3 NITROPHENOL; 2 METHOXY 4 [[(3 METHOXYPHENYL)IMINO]METHYL] 3 NITROPHENOL; 2 METHOXY 4 [[(4 METHOXYPHENYL)IMINO]METHYL] 3 NITROPHENOL; 4 [[(2 CHLOROPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(2,4 D DICHLOROPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(2,5 DICHLOROPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(2,5 DIMETHYLPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(2,6 DIISOPROPYLPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(2,6 DIMETHYLPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(3 CHLORO 4 METHYLPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(3 FLUOROPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(3,4 DICHLOROPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(3,4 DIMETHYLPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(4 BROMOPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; 4 [[(4 CHLORO 2 NITROPHENYL)IMINO]METHYL] 2 METHOXY 3 NITROPHENOL; ANTIINFECTIVE AGENT; FTSZ PROTEIN; PROTEIN INHIBITOR; UNCLASSIFIED DRUG; VANILLIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; IC 50; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; POLYMERIZATION; PROTEIN BINDING; PROTEIN CONFORMATION; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84898859245     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0886-8     Document Type: Article

References (29)

1. Akihiro T, Takeshi S, Futoshi Y, Hideyuki I et al (2011) Evaluation of antioxidant activity of vanillin by using multiple antioxidant assays. Biochim Biophys Acta 1810:170-177
2. Ana OS, Fabio CSG, Célio LS, Beatriz B et al (2007) Antimycobacterial and cytotoxicity activity of synthetic and natural compounds. Quim Nova 30:1563-1566
3. Bringmann G, Dreyer M, Faber JH, Dalsgaard PW et al (2004) Ancistrotanzanine C and related 5,1'-And 7,3'-couple naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. J Nat Prod 67:743-748
4. Bythrow JD (2005) Vanilla as a medicinal plant. Semin Integr Med 3:129-131
5. Chohan ZH, Arif M, Sarfraz M (2007) Metal-based antibacterial and antifungal amino acid derived Schiff bases: their synthesis, characterization and in vitro biological activity. Appl Organomet Chem 21:294-302
6. Claudio VJ, Amanda D, da Vanderlan SB, Eliezer JB, Carlos AMF (2007) Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 14:1829-1852
7. Cleiton MS, Daniel LS, Luzia VM et al (2011) Schiff bases: a short review of their antimicrobial activities. J Adv Res 2:1-8
8. Daniel JF, Malcolm S, Arjan N (2003) Analysis of the inhibition of food spoilage yeasts by vanillin. Int J Food Microbiol 86:113-122
9. Faridbod F, Ganjali MR (2007) Ion recognition: application of symmetric and asymmetric schiff bases and their complexes for the fabrication of cationic and anionic membrane sensors to determine ions in real samples. Comb Chem High Throughput Screen 10:527-546
10. Fitzgerald DJ, Stratford M, Gasson MJ, Narbad A (2004) The potential application of vanillin in preventing yeast spoilage of soft drinks and fruit juices. J Food Protect 67:391-395
11. Fraga CAM (2009) Drug hybridization strategies: before or after lead identification? Expert Opin Drug Dis 4:605-609
12. Frederico JG, Richard L (2002) A widely conserved bacterial cell division protein that promotes assembly of the tubulin-like protein FtsZ. Genes Dev 16:2544-2566
13. Frye SV (2010) The art of the chemical probe. Nat Chem Biol 6:159-161
14. Hacer B, Ahmet D, Sengül AK, Neslihan D (2009) Synthesis of some new 1,2,4-riazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. N Eur J Med Chem 44:1057-1066
15. Jeffery E, Richard AD (2003) Cytokinesis in bacteria. Microbiol Mol Biol Rev 67:52-65
16. Laura R, Petra AL (2003) Assembly dynamics of the bacterial cell division protein FtsZ: poised at the edge of stability. Annu Rev Microbiol 57:125-154
17. Lei S, Hui-Ming G, Shu-Hua T, Huan-Qiu L, Yong-Chun S, Hai-Liang Z, Ren-Xiang T (2007) Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde. Eur J Med Chem 42:558-564
18. Lloyd GC, Neil RS, Steve R, David JH (2012) Antibacterial inhibitors of the essential cell division protein FtsZ. Antibiotic Discov Dev 30:957-968
19. Mari SK, Dasappa JP, Boja P (2006) Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety. Bioorg Med Chem 14:7482-7489
20. Mariana GP, Jeff E (2003) Dispersed mode of Staphylococcus aureus cell wall synthesis in the absence of the division machinery. Mol Microbiol 50:871-881
21. Martin L (2004) Antibiotics: a shot in the arm. Nature 431:892-893
22. Piotr P, Adam H, Krystian P, Bogumil B, Franz B (2009) Biological properties of schiff bases and azo derivatives of phenols. Curr Org Chem 13:124-148
23. Sardari S, Nishibe S, Daneshtalab M (2000) Coumarins, the bioactive structures with antifungal property. Stud Nat Prod Chem 23:335-393
24. Seshaiah KS, Atmakuru R (2001) Synthesis and pharmacological activities of hydrazones, schiff and mannich bases of isatin derivatives. Biol Pharm Bull 24:1149-1152
25. Ti-Feng J, Ming-Hua L (2005) Supramolecular assemblies and molecular recognition of amphiphilic Schiff bases with barbituric acid in organized molecular films. J Phys Chem B 109:2532-2539
26. Venugopala KN, Jayashree BS (2008) Microwave-induced synthesis of Schiff bases of aminothiazolyl bromocoumarins as antibacterials. Indian J Pharm Sci 70:88-91
27. Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. Phytochem 63:505-515
28. White EL, Ross LJ, Reynolds RC, Seitz LE, Moore GD, Borhani DW (2000) Slow polymerization of Mycobacterium tuberculosis FtsZ. J Bacteriol 182:4028-4034
29. Zhan-Yong G, Ronge X, Song L, Zhi-Mei Z, Xia J, Peng-Cheng L (2007) Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. Carbohydr Res 342:1329-1332