Synthesis and characterization of novel hydrazide–hydrazones and the study of their structure–antituberculosis activity

Koçyığıt‐Kaymakcioğlu, Bedia; Elçin, Oruç; Ünsalan, Seda; Kandemi̇rlı, Fatma; Shvets, N.; Rollas, Sevım; Димогло, А. С.

doi:10.1016/j.ejmech.2006.06.009

Cited by 247 publications

(145 citation statements)

References 26 publications

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“…Hyrazone compounds, obtained from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties [1][2][3]. Recently, we have reported a few hydrazone compounds [4][5][6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 4-hydroxy-3-methoxy-N'-(5-chloro-2-hydroxybenzylidene) benzohydrazide – methanol (1:1), C15H13CIN2O4CH3OH

Qiu¹

2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was prepared by the Schiff base condensation of equimolar (0.5 mmol each) solutions of 5-chlorosalicylaldehyde and 4-hydroxy-3-methoxybenzohydrazide in methanol (20 ml). Excess methanol was removed from the reaction mixture by distillation. The colourless solid was filtered and dried in air. Colourless block-shaped crystals suitable for X-ray diffraction were obtained from a methanol solution. Experimental detailsThe i mino Η atom was located in a difference map and refined with Ν-Η distance restrained to 0.90(1) Â. The remaining Η atoms were positioned geometrically [d(C-H) = 0.93 -0.96 Â, d(0-H) = 0.82 Â] and refmed using a riding model, with C/iso(H) = 1.2 U e q(C) and 1.5 i/eq(Cmethyi and O). Rotating group models were used for the methyl groups.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 4-hydroxy-3-methoxy-N'-(5-chloro-2-hydroxybenzylidene) benzohydrazide – methanol (1:1), C15H13CIN2O4CH3OH

Qiu¹

2009

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Hydrazone compounds, which derived from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties [1][2][3][4][5][6]. The crystal structure of the title compound consists of aSchiff base molecule and amethanol molecule of crystallization.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 4-hydroxy-3-methoxy-N'-(2-hydroxy- naphthylidene) benzohydrazide methanol solvate, C19H16N2O4 ·CH3OH

Qiu¹

2008

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was prepared by the Schiff base condensation of equimolar (0.5 mmol each) 2-hydroxy-1-naphthylaldehyde and 4-hydroxy-3-methoxybenzohydrazide in methanol (20 ml). Excess methanol was removed from the reaction mixture with distillation. The colorless solid was filtered and dried in air. Colorless block-shaped crystals suitable for X-ray diffraction were obtained from amethanol solution. and refined using ariding model, with U iso(H) =1.2 U eq (C) and 1.5 U eq (C methyl and O). Rotating group models were used for the methyl groups. Experimental details DiscussionHydrazone compounds, which derived from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties [1][2][3][4][5][6]. The crystal structure of the title compound consists of aSchiff base molecule and amethanol molecule of crystallization. The Schiff base molecule is in a trans configuration with respect to the methylidene group. The dihedral angle between the phenyl ring and the naphthyl ring is 1.5(2)°, indicating anearly planar configuration of the molecule. The bond lengths and angles in the compound are found to have normal values and comparable to the values in the similar compounds [7][8][9]. The methanol molecules are linked to the Schiff base molecules through intermolecular N−H···O and O−H···O hydrogen bonds. In the crystal structure, molecules are linked by intermolecular O−H···O and N−H···O hydrogen bonds into wave-shaped twodimensional layers parallel to (010).

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“…This versatility has made hydrazones good polydentate chelating agents that can form a variety of complexes with various transition metals. In recent years, a number of hydrazone compounds have been prepared and investigated for their biological properties such as antibacterial, antifungal, 5 anticonvulsant, 6 anti-inflammatory, 7 antimalarial, 8 analgesic, 9 antiplatelets, 10 antituberculosis, 11 and anticancer activities. 12 Hydrazones also act as herbicides, insecticides, nematocides, rodenticides, and plant growth regulators, and are used as plasticizers and stabilizers for polymers, polymerization initiators, antioxidants, etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structures, and Antibacterial Activity of a Series of Hydrazone Compounds Derived From 4-Methylbenzohydrazide

Yan¹,

Li²,

Fu³

et al. 2015

J. Chil. Chem. Soc.

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A series of hydrazone compounds, 4-methyl-N'-(4-nitrobenzylidene)benzohydrazide methanol solvate (1), N'-(4-hydroxy-3-nitrobenzylidene)-4-methylbenzohydrazide dimethanol solvate (2), and N'-(3,5-dibromobenzylidene)-4-methylbenzohydrazide (3), derived from 4-methylbenzohydrazide with different benzaldehydes, were synthesized and characterized by physico-chemical methods and single crystal X-ray diffraction. Crystals of the compounds are stabilized by intermolecular hydrogen bonds, as well as π···π stacking interactions. Antibacterial activity of the compounds against Staphylococcus aureus, Escherichia coli, and Klebsielle pneumoniae strains was studied. Compounds 1 and 2 have moderate minimum inhibition concentration values on the tested bacteria strains. Compound 3, with the Br-substituent groups, showed the highest activity on the bacterial strains.

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Synthesis and characterization of novel hydrazide–hydrazones and the study of their structure–antituberculosis activity

Cited by 247 publications

References 26 publications

Crystal structure of 4-hydroxy-3-methoxy-N'-(5-chloro-2-hydroxybenzylidene) benzohydrazide – methanol (1:1), C15H13CIN2O4CH3OH

Crystal structure of 4-hydroxy-3-methoxy-N'-(5-chloro-2-hydroxybenzylidene) benzohydrazide – methanol (1:1), C15H13CIN2O4CH3OH

Crystal structure of 4-hydroxy-3-methoxy-N'-(2-hydroxy- naphthylidene) benzohydrazide methanol solvate, C19H16N2O4 ·CH3OH

Synthesis, Crystal Structures, and Antibacterial Activity of a Series of Hydrazone Compounds Derived From 4-Methylbenzohydrazide

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