Structures of arylaldehyde 7-chloroquinoline-4-hydrazones: Supramolecular arrangements derived from N-H⋯N, C-H⋯X (X = N, O, or π) and π⋯π interactions

Zeitschrift fur Kristallographie

Volumn 225, Issue 10, 2010, Pages 440-447

  Howie, R Alan ^a   De Souza, Marcus V N ^b   Ferreira, Marcelle De Lima ^b   Kaiser, Carlos R ^c   Wardell, James L ^b   Wardell, Solange M S V ^d  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

^b INSTITUTO OSWALDO CRUZ   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^d CHEMSOL   (United Kingdom)

Author keywords

interactions; 7 chloroquinoline 4 hydrazone; Hydrogen bonds; Single crystal structure analysis; X ray diffraction

Indexed keywords

EID: 79951665399     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.2010.1291     Document Type: Article

References (29)

1. Wardell, S. M. S. V.; de Souza, M. V. N.;Wardell, J. L.; Low, J. N.; Glidewell, C.: Supramolecular structures in N-isonicotinoyl arylaldehyde hydrazones: multiple hydrogen-bonding modes in series of geometric isomers. Acta Crystallogr. B63 (2007) 879-895. (Pubitemid 350126592)
2. Wardell, S. M. S. V.; de Souza, M. V. N.; Vasconcelos, T. R. A.; Ferreira, M. de L.; Wardell, J. L.; Low, J. N.; Glidewell, C.: Patterns of hydrogen bonding in mono- and di-substituted N-arylpyrazine- carboxamides. Acta Crystallogr. B64 (2008) 84-100. (Pubitemid 351177153)
3. Baddeley, T. C.; Howie, R. A.; da Silva Lima, C. H.; Kaiser, C. R.; de Souza, M. V. N.; Wardell, J. L.; Wardell, S. M. S. V.: Syntheses and crystal structures of (pyrazinecarbonyl)hydrazones of mono-halo-benzaldehydes. Z. Kristallogr. 224 (2009) 461-470.
4. Howie, R. A.; da Silva Lima, C. H.; Kaiser, C.R.; de Souza, M. V. N.; Wardell, J. L.; Wardell, S. M. S. V.: Structures of (pyrazinecarbonyl)hydrazones of substituted benzaldehydes: supramolecular arrangements generated by various intermolecular contacts. Z. Kristallogr. 225 (2010) 19-28.
5. Howie, R. A.; da Silva Lima, C. H.; Kaiser, C.R.; de Souza, M. V. N.; Wardell, J. L.; Wardell, S. M. S. V.: Structures of (pyrazinecarbonyl)hydrazones of substituted benzaldehydes: different supramolecular arrangements from C-H⋯X (X = O, N, π) hydrogen bonds. Z. Kristallogr. 225 (2010) 158-166.
6. Kaiser, C. R.; Pais, K. C.; de Souza, M. V. N.; Wardell, J. L.; Wardell, S. M. S. V.; Tiekink, E. R. T.: Assessing the persistence of the N-H/N hydrogen bonding leading to supramolecular chains in molecules related to the anti-malarial drug, chloroquine. CrystEngComm. 11 (2009) 1133-1140.
7. Tanenbaum, L.; Tuffanelli, D. L.: Antimalarial Agents: Chloroquine, Hydroxychloroquine, and Quinacrine. Arch. Dermatol. 116 (1980) 587-591. (Pubitemid 10101721)
8. Font, M.; Monge, A.; Ruiz, I.; Heras, B.: Structure-activity relationships in quinoline Reissert derivatives with HIV-1 reverse transcriptase inhibitory activity. Drug Design Disc. 14 (1997) 259-272. (Pubitemid 27234611)
9. Nakamura, T.; Oka, M.; Aizawa, K.; Soda, H.; Fukuda, M.; Terashi, K.; Ikeda, K.; Mizuta, Y.; Noguchi, Y.; Kimura, Y.; Tsuruo, T.; Kohno, S.: Direct interaction between a quinoline derivative, MS-209, and multidrug resistance protein (MRP) in human gastric cancer cells. Biochem. Biophys. Res. Commun. 255 (1999) 618-624. (Pubitemid 29294848)
10. Kaminsky, D.; Meltzer, R. I.: Quinoline antibacterial agents. Oxolinic acid and related compounds. J. Med. Chem. 11 (1968) 160-163.
11. Musiol, R.; Jampilek, J.; Buchta, V.; Silva, L.; Niedbala, H.; Podeszwa, B.; Palka, A.; Majerz-Maniecka, K.; Oleksyn, B.; Polanski, J.: Antifungal properties of new series of quinoline derivatives. Bioorg. Med. Chem. 14 (2006) 3592-3598.
12. Warshakoon, N. C.; Sheville, J.; Bhatt, R. T.; Ji, W.; Mendez- Andino, J. L.; Meyers, K. M.; Kim, N.; Wos, J. A.; Mitchell, C.; Paris, J. L.; Pinney, B. B.; Reizes, O.; Hu, X. E.: Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents. Bioorg. Med. Chem. Letters 16 (2006) 5207-5211. (Pubitemid 44247686)
13. Sloboda, A. E.; Powell, D.; Poletto, J. F.; Pickett, W. C.; Gibbons, J. J.; Bell, D. H.; Oronsky, A. L.; Kerwar, S. S.: Antiinflammatory and antiarthritic properties of a substituted quinoline carboxylic acid: CL 306, 293. J. Rheumatol. 18 (1991) 855-860.
14. Palmer, K. J.; Holliday, S. M.; Brogden, R. N.: Mefloquine: a review of its antimalarial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 45 (1993) 430-475. (Pubitemid 23104127)
15. Elslager, E. F.; Tendick, F. H.; Werbel, L. M.: Repository drugs. VIII. Ester and amide congeners of amodiaquine, hydroxychloroquine, oxychloroquine, primaquine, quinacrine, and related substances as potential long-acting antimalarial agents. J. Med. Chem. 12 (1969) 600-607.
16. Candéa, A. L. P.; Ferreira, M. L.; Pais, K. C.; Laura N. de F. Cardoso, L. N. F.; Carlos R. Kaiser, C. R.; Maria das Graças M. de O. Henriques, M. G. M. O.; Maria C. S. Lourenço, M. C. S.; Flávio Bezerra; F. A. F. M.; de Souza, M. V. N.: Synthesis and antitubercular activity of 7-chloro-4-quinolinylhydrazones derivatives. Bioorg.Med.l Chem. Letters 19 (2009) 6272-6274.
17. de Souza, M. V. N.; Howie, R. A.; Tiekink, E. R. T.; Wardell. J. L.; Wardell, S. M. S. V.: 7-Chloro-4-[(E)-N-(4-fluorobenzylidene) hydrazinyl]quinoline monohydrate. Acta Crystallogr. E66 (2010) o152-o153.
18. de Souza, M. V. N.; Howie, R. A.; Tiekink, E. R. T.;Wardell, J. L.; Wardell, S. M. S. V.; Kaiser, C. R.: 7-Chloro-4-[(E)-2-(2-methoxybenzylidene) hydrazin-1-yl]quinoline monohydrate, Acta Crystallogr. E66 (2010) o698-o699.
19. de Lima Ferreira, M.; de Souza, M. V. N.; Howie, R. A.; Tiekink, E. R. T.; Wardell, J. L.; Wardell, S. M. S. V.: 7-Chloro-4- [(E)-2-(4- methoxybenzylidene)hydrazin-1-yl]quinoline monohydrate, Acta Crystallogr. E66 (2010) o696-o697.
20. de Ferreira, M. L.; de Souza, M. V. N.; Howie, R. A.; Tiekink, E. R. T.; Wardell, J. L.; Wardell, S. M. S. V.: 3-[(E)-(7-Chloro- 4-quinolyl) hydrazonomethyl]benzonitrile monohydrate, Acta Crystallogr. E65 (2009) o3239-o3240.
21. de Souza, M. V. N.; Howie, R. A.; Tiekink, E. R. T.;Wardell, J. L.; Wardell, S M. S. V.: 7-Chloro-4-[(E)-(3-chlorobenzylidene)hydrazinyl]- 1λ4-quinolinium 3-chlorobenzoate, Acta Crystallogr. E65 (2009) o3204-o3205.
22. Pellerano, C.; Savini, L.; Fiorini, I.: Atti Accad. Fisiocritic Siena 8 (1976) 43-57.
23. Al-Sha'alan, N. H.: Antimicrobial Activity and Spectral, Magnetic and Thermal Studies of Some Transition Metal Complexes of a Schiff Base Hydrazone Containing a Quinoline Moiety Molecules Molecules 12 (2007) 1080-1091.
24. Hooft, R. W. W.: COLLECT, data collection software. Nonius BV, Delft, The Netherlands, (1998).
25. Otwinowski, Z.; Minor, W.: Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by Carter Jr, C. W.; Sweet, R. M. pp. 307-326. New York: Academic Press, (1997). (Pubitemid 27085611)
26. Sheldrick, G. M.: SADABS Version 2007/2, Bruker AXS Inc., Madison, Wisconsin, USA (2007).
27. Farrugia, L. J.: ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr. 30 (1997) 565. (Pubitemid 127791756)
28. Sheldrick, G. M.: A short history of SHELX. Acta Cryst. A64 (2008) 112-122.
29. Spek, A. L.: Single-crystal structure validation with the program PLATON. J. Appl. Crystallogr. 36 (2003) 7-13.