5-Phenyl-2-(benzalhydrazonyl)-1,3,4-thiadiazoles, potential trypanocidal agents: consistent dimer formation via N-H center dot center dot center dot N intermolecular hydrogen bonds

Samir A. Carvalho, William T. A. Harrison, Carlos A. M. Fraga, Edson E. da Silva, James L. Wardell, Solange M. S. V. Wardell

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The molecular and crystal structures of a series of 5-Ph-2-(arylCH=NNH)-1,3,4-thiadiazoles [2: aryl = 4-XC6H4 (X = H [2a], 4-Cl [2b], 4-Br [2c], 4-F3CO [2d], 2-HO [2e], 2-HO-3-MeO [2f] as well as [5-Ph-2-(4-HOC6H4CH=NNH)-1,3,4-thiadiazole](3)(H2O)(2)] [(2g)(3) center dot 2 (H2O)] are reported. The compounds were prepared as part of a study on typanocide reagents as possible treatments for Chagas' disease. The asymmetric unit of [(2g)(3) center dot 2 (H2O)] consists of three independent molecules and two water molecules, in contrast to the single molecules comprising the asymmetric units of 2a-2f. In all cases, N-H center dot center dot center dot N intermolecular hydrogen bonding results in the formation of dimers linked by R-2(2)(8) rings. As well as the hydrogen-bonded dimers, the molecules of 2a-2f are also linked by other weak interactions including aromatic pi-pi stacking and C-H center dot center dot center dot X bonds.

Original languageEnglish
Pages (from-to)598-606
Number of pages9
JournalZeitschrift für Kristallographie
Volume224
Issue number12
DOIs
Publication statusPublished - Dec 2009

Keywords

  • Chagas' disease
  • hydrazones
  • thiadiazoles
  • hydrogen bonding
  • pi-pi stacking interactions
  • single crystal structure analysis
  • synchrotron X-ray radiation
  • 1,3,4-thiadiazole-2-arylhydrazone derivatives
  • trypanosoma-cruzi
  • crystal-structure
  • megazol
  • analogs
  • 2-amino-1,3,4-thiadiazole
  • chloride
  • drug

Cite this

5-Phenyl-2-(benzalhydrazonyl)-1,3,4-thiadiazoles, potential trypanocidal agents: consistent dimer formation via N-H center dot center dot center dot N intermolecular hydrogen bonds. / Carvalho, Samir A.; Harrison, William T. A.; Fraga, Carlos A. M.; da Silva, Edson E.; Wardell, James L.; Wardell, Solange M. S. V.

In: Zeitschrift für Kristallographie, Vol. 224, No. 12, 12.2009, p. 598-606.

Research output: Contribution to journalArticle

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abstract = "The molecular and crystal structures of a series of 5-Ph-2-(arylCH=NNH)-1,3,4-thiadiazoles [2: aryl = 4-XC6H4 (X = H [2a], 4-Cl [2b], 4-Br [2c], 4-F3CO [2d], 2-HO [2e], 2-HO-3-MeO [2f] as well as [5-Ph-2-(4-HOC6H4CH=NNH)-1,3,4-thiadiazole](3)(H2O)(2)] [(2g)(3) center dot 2 (H2O)] are reported. The compounds were prepared as part of a study on typanocide reagents as possible treatments for Chagas' disease. The asymmetric unit of [(2g)(3) center dot 2 (H2O)] consists of three independent molecules and two water molecules, in contrast to the single molecules comprising the asymmetric units of 2a-2f. In all cases, N-H center dot center dot center dot N intermolecular hydrogen bonding results in the formation of dimers linked by R-2(2)(8) rings. As well as the hydrogen-bonded dimers, the molecules of 2a-2f are also linked by other weak interactions including aromatic pi-pi stacking and C-H center dot center dot center dot X bonds.",
keywords = "Chagas' disease, hydrazones, thiadiazoles, hydrogen bonding, pi-pi stacking interactions, single crystal structure analysis, synchrotron X-ray radiation, 1,3,4-thiadiazole-2-arylhydrazone derivatives, trypanosoma-cruzi, crystal-structure, megazol, analogs, 2-amino-1,3,4-thiadiazole, chloride, drug",
author = "Carvalho, {Samir A.} and Harrison, {William T. A.} and Fraga, {Carlos A. M.} and {da Silva}, {Edson E.} and Wardell, {James L.} and Wardell, {Solange M. S. V.}",
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T1 - 5-Phenyl-2-(benzalhydrazonyl)-1,3,4-thiadiazoles, potential trypanocidal agents: consistent dimer formation via N-H center dot center dot center dot N intermolecular hydrogen bonds

AU - Carvalho, Samir A.

AU - Harrison, William T. A.

AU - Fraga, Carlos A. M.

AU - da Silva, Edson E.

AU - Wardell, James L.

AU - Wardell, Solange M. S. V.

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N2 - The molecular and crystal structures of a series of 5-Ph-2-(arylCH=NNH)-1,3,4-thiadiazoles [2: aryl = 4-XC6H4 (X = H [2a], 4-Cl [2b], 4-Br [2c], 4-F3CO [2d], 2-HO [2e], 2-HO-3-MeO [2f] as well as [5-Ph-2-(4-HOC6H4CH=NNH)-1,3,4-thiadiazole](3)(H2O)(2)] [(2g)(3) center dot 2 (H2O)] are reported. The compounds were prepared as part of a study on typanocide reagents as possible treatments for Chagas' disease. The asymmetric unit of [(2g)(3) center dot 2 (H2O)] consists of three independent molecules and two water molecules, in contrast to the single molecules comprising the asymmetric units of 2a-2f. In all cases, N-H center dot center dot center dot N intermolecular hydrogen bonding results in the formation of dimers linked by R-2(2)(8) rings. As well as the hydrogen-bonded dimers, the molecules of 2a-2f are also linked by other weak interactions including aromatic pi-pi stacking and C-H center dot center dot center dot X bonds.

AB - The molecular and crystal structures of a series of 5-Ph-2-(arylCH=NNH)-1,3,4-thiadiazoles [2: aryl = 4-XC6H4 (X = H [2a], 4-Cl [2b], 4-Br [2c], 4-F3CO [2d], 2-HO [2e], 2-HO-3-MeO [2f] as well as [5-Ph-2-(4-HOC6H4CH=NNH)-1,3,4-thiadiazole](3)(H2O)(2)] [(2g)(3) center dot 2 (H2O)] are reported. The compounds were prepared as part of a study on typanocide reagents as possible treatments for Chagas' disease. The asymmetric unit of [(2g)(3) center dot 2 (H2O)] consists of three independent molecules and two water molecules, in contrast to the single molecules comprising the asymmetric units of 2a-2f. In all cases, N-H center dot center dot center dot N intermolecular hydrogen bonding results in the formation of dimers linked by R-2(2)(8) rings. As well as the hydrogen-bonded dimers, the molecules of 2a-2f are also linked by other weak interactions including aromatic pi-pi stacking and C-H center dot center dot center dot X bonds.

KW - Chagas' disease

KW - hydrazones

KW - thiadiazoles

KW - hydrogen bonding

KW - pi-pi stacking interactions

KW - single crystal structure analysis

KW - synchrotron X-ray radiation

KW - 1,3,4-thiadiazole-2-arylhydrazone derivatives

KW - trypanosoma-cruzi

KW - crystal-structure

KW - megazol

KW - analogs

KW - 2-amino-1,3,4-thiadiazole

KW - chloride

KW - drug

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JO - Zeitschrift für Kristallographie

JF - Zeitschrift für Kristallographie

SN - 0044-2968

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ER -