Syntheses, crystal structures, and antimicrobial activities of n'-(5-hydroxy-2-nitrobenzylidene)-4-dimethylaminobenzohydrazide methanol solvate and 2-fluoro-n'-(5-hydroxy-2-nitrobenzylidene)benzohydrazide

Jiegou Huaxue

Volumn 31, Issue 8, 2012, Pages 1075-1082

  Zhu, Hai Yun ^a  

^a BAOJI UNIVERSITY OF ARTS AND SCIENCES   (China)

Author keywords

Antimicrobial activity; Hydrazone; Hydrogen bonding; Synthesis; X ray structure analysis

Indexed keywords

EID: 84865257713     PISSN: 02545861     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Rasras, A. J. M.; Al-Tel, T. H.; Al-Aboudi, A. F.; Al-Qawasmeh, R. A. Synthesis and antimicrobial activity of cholic acid hydrazone analogues. Eur. J. Med. Chem. 2010, 45, 2307-2313.
2. Fan, C. D.; Su, H.; Zhao, J.; Zhao, B. X.; Zhang, S. L.; Miao, J. Y. A novel copper complex of salicylaldehyde pyrazole hydrazone induces apoptosis through up-regulating integrin beta 4 in H322 lung carcinoma cells. Eur. J. Med. Chem. 2010, 45, 1438-1446.
3. Ajani, O. O.; Obafemi, C. A.; Nwinyi, O. C.; Akinpelu, D. A. Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives. Bioorg. Med. Chem. 2010, 18, 214-221.
4. Avaji, P. G.; Kumar, C. H. V.; Patil, S. A.; Shivananda, K. N.; Nagaraju, C. Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bis hydrazone. Eur. J. Med. Chem. 2009, 44, 3552-3559.
5. Gokce, M.; Utku, S.; Kupeli, E. Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p- substituted/nonsubstitutedbenzal)hydrazone derivatives. Eur. J. Med. Chem. 2009, 44, 3760-3764.
6. Gurkok, G.; Coban, T.; Suzen, B. Melatonin analogue new indole hydrazide/hydrazone derivatives with antioxidant behavior: Synthesis and structure-activity relationships. J. Enzyme Inhib. Med. Chem. 2009, 24, 506-515.
7. Zheng, L. W.; Wu, L. L.; Zhao, B. X.; Dong, W. L.; Miao, J. Y. Synthesis of novel substituted pyrazole-5-carbohydrazide hydrazone derivatives and discovery of a potent apoptosis inducer in A549 lung cancer cells. Bioorg. Med. Chem. 2009, 17, 1957-1962.
8. Sonar, V. N.; Crooks, P. A. Synthesis and antitubercular activity of a series of hydrazone and nitrovinyl analogs derived from heterocyclic aldehydes. J. Enzyme Inhib. Med. Chem. 2009, 24, 117-124.
9. Felton, L. C.; Brewer, J. H. Action of substituted salicylaldehydes on bacteria and fungi. Science 1947, 105, 409-410.
10. Jin, L.; Chen, J.; Song, B.; Chen, Z.; Yang, S.; Li, Q.; Hu, D.; Xu, R. Synthesis, structure, and bioactivity of Ń-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives. Bioorg. Med. Chem. Lett. 2006, 16, 5036-5040.
11. Zhu, H. Y. Syntheses, crystal structures, and antimicrobial activities of 3-bromo-Ń-(2-chloro-5-nitrobenzylidene)benzohydrazide and 3-bromo-N'-(4-nitrobenzylidene)benzohydrazide. Chin. J. Struct. Chem. 2011, 30, 724-730.
12. Yang, D. S. Ń-(5-Hydroxy-2-nitrobenzylidene)-2- methoxybenzohydrazide. Acta Crystallogr. 2009, E65, o2864.
13. Sheldrick, G. M. SADABS Program for Empirical Absorption Correction of Area Detector, University of Göttingen, Germany 1996.
14. Sheldrick, G. M. SHELXS-97. Program for Crystal Structure Solution, University of Göttingen, Germany 1990.
15. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany 1997.
16. Indu, M. N.; Hatha, A. A. M.; Abirosh, C.; Harsha, U.; Vivekanandan, G. Antimicrobial activity of some of the South-Indian spices against serotypes of Escherichia coli, Salmonella, Listeria monocytogenes and Aeromonas hydrophila. Braz. J. Microbiol. 2006, 37, 153-158.
17. Saghatforoush, L. A.; Chalabian, F.; Aminkhani, A.; Karimnezhad, G.; Ershad, S. Synthesis, spectroscopic characterization and antibacterial activity of new cobalt(II) complexes of unsymmetrical tetradentate (OSN2) Schiff base ligands. Eur. J. Med. Chem. 2009, 44, 4490-4495.
18. Zou, X. W.; Yu, H. T.; Guo, H.; Meng, J. B. Syntheses and crystal structures of two new compounds containing triarylamine and benzoic hydrazide units. Chin. J. Struct. Chem. 2004, 23, 164-170.
19. Lin, H. W. Synthesis and crystal structure of isonicotinic acid [1-(3,5-dibromo-2-hydroxyphenyl)methylidene]hydrazide methanol. Chin. J. Struct. Chem. 2007, 26, 773-776.
20. Wang, N.; Li, J. P.; Pu, Y. L. Synthesis and crystal structure of 2-hydroxybenzoic acid [1-(3,5-dibromo-2-hydroxyphenyl)methylidene]hydrazide methanol. Chin. J. Struct. Chem. 2007, 26, 547-550.
21. Yang, D. S. Syntheses, characterization and crystal structures of two structurally similar Schiff bases isonicotinic acid [1-(3-methoxy-2- hydroxyphenyl)methylidene]hydrazide and isonicotinic acid [1-(4- dimethylaminophenyl)methylidene]hydrazide monohydrate. J. Chem. Crystallogr. 2007, 37, 343-348.
22. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr. 2009, D65, 148-155.