Synthesis and antidepressant evaluation of new 3-phenyl-5-sulfonamidoindole derivatives

Ergenç, N.; Gunay, Nur Sibel; Demirdamar, R.

doi:10.1016/s0223-5234(98)80039-1

Cited by 98 publications

(53 citation statements)

References 3 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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“…3-Phenyl-5-sulfonamidoindole-2-carboxylic acid 3,4-methylenedioxy / 4-methyl / 4-nitrobenzylidene-hydrazide showed antidepresant activity at 100 mg/kg [10]. …”

Section: Antidepressant Activitymentioning

confidence: 97%

“…When they are used as intermediates, coupling products can be synthesized by using the active hydrogen component of -CONHN=CH-azometine group [9]. N-Alkyl hydrazides can be synthesized by reduction of hydrazones with NaBH 4 [10], substituted 1,3,4-oxadiazolines can be synthesized when hydrazones are heated in the presence of acetic anhydride [1,11,12]. 2-Azetidinones can be synthesized when hydrazones react with trietylamine chloro acetylchloride [13].…”

Section: Nifuroxazide Isoniazidmentioning

confidence: 99%

Biological Activities of Hydrazone Derivatives

2007

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There has been considerable interest in the development of novel compounds with anticonvulsant, antidepressant, analgesic, antiinflammatory, antiplatelet, antimalarial, antimicrobial, antimycobacterial, antitumoral, vasodilator, antiviral and antischistosomiasis activities. Hydrazones possessing an azometine -NHN=CH-proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. These observations have been guiding for the development of new hydrazones that possess varied biological activities.

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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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Synthesis and antidepressant evaluation of new 3-phenyl-5-sulfonamidoindole derivatives

Cited by 98 publications

References 3 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

Biological Activities of Hydrazone Derivatives

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

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