Synthesis, antiproliferative and apoptotic activities of N-(6(4)-indazolyl)-benzenesulfonamide derivatives as potential anticancer agents

Abbassi, Najat; Chicha, Hakima; Rakib, El Mostapha; Hannioui, A.; Alaoui, Mdaghri; Hajjaji, Abdelouahed; Geffken, Detlef; Aiello, Cinzia; Gangemi, Rosaria; Rosano, Camillo; Viale, Maurizio

doi:10.1016/j.ejmech.2012.09.013

Cited by 59 publications

(68 citation statements)

References 27 publications

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“…The synthesis of sulfonamide indazole derivatives using SnCl 2 / ArSO 2 Cl/Pyridine in ethanol is reported and it gives anti-proliferative activities (Scheme-70) [84]. In other example 1, 6-dihydro indazole derivatives synthesized via Larock indole annulations (Scheme-71) [85].…”

Section: Scheme-69mentioning

confidence: 98%

Synthesis of indazole motifs and their medicinal importance: An overview

Gaikwad¹,

Chapolikar²,

Devkate³

et al. 2015

European Journal of Medicinal Chemistry

273

115

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Section: Scheme-69mentioning

confidence: 98%

Synthesis of indazole motifs and their medicinal importance: An overview

Gaikwad¹,

Chapolikar²,

Devkate³

et al. 2015

European Journal of Medicinal Chemistry

273

115

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“…We thus, have reported the synthesis of 7-alkoxy-and 4-alkoxyindazole derivatives via the reduction of 4-, 6-and 7-nitroindazoles in the presence of anhydrous SnCl 2 in various alcohol solvents, followed by the coupling of the newly formed amine with arylsulfonyl chlorides in pyridine [10][11][12][13][14][15][16][17] . We selected arylsulfonyl chloride as a protective agent of aminoindazole because in our previous study, we observed significant degradation of aromatic primary amine.…”

Section: Introductionmentioning

confidence: 99%

“…In view of its inherent properties such as reusability, greater selectivity, operational simplicity, non-corrosiveness, low cost and ease of isolation, several groups have accomplished efficient syntheses of different heterocyclic compounds employing the reduction of nitro derivatives with stannous chloride [6][7][8][9] . Our research program during the last ten years has been focused on the synthesis of heterocyclic compounds using anhydrous SnCl 2 as reductive reagent [10][11][12][13][14][15][16][17] .…”

Section: Introductionmentioning

confidence: 99%

SnCl₂/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties

Chicha

Bouissane

Ammari

et al. 2015

Synthetic Communications

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The treatment of N-alkyl-5-nitroindazole with stannous chloride in ethanol gave after coupling of the obtained amines with arylsulfonyl chloride in pyridine the new 4-ethoxyand 4-chloroindazoles bearing sulfonamide in moderate to good yields. Chlorination and ethoxylation of indazole is observed during the reduction of the nitro group with anhydrous SnCl 2 in ethanol. The influence of the N-alkylation in N-1 and N-2 position of 5-nitroindazole on the reduction is investigated. The presence of ethoxy group and chlorine atom at position C-4 of indazole is confirmed by X-ray diffraction analysis of compounds 7a and 8a

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“…In our previous work, we have found that indazoles bearing arylsulfonamide groups showed anti-proliferative activity against human (colon and prostate) and murine (leukaemia) cell lines (Abbassi et al, 2012(Abbassi et al, , 2014Bouissane, et al, 2006).…”

Section: Structure Descriptionmentioning

confidence: 99%

4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate

et al. 2017

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The asymmetric unit of the title compound, 2C 15 H 15 N 3 O 3 SÁH 2 O, comprises two crystallographically independent organic molecules and one water molecule, all in general positions. Each organic molecule comprises an indazolyl system linked through a sulfonamide group to a methoxybenzene ring. The most important difference between the two organic molecules is the dihedral angle between the fused-ring system and the methoxybenzene ring, which is 56.32 (7) in one molecule and 35.35 (8) in the other. In the crystal, the organic and water molecules are connected into supramolecular chains along the c axis through O-HÁ Á ÁN, O-HÁ Á ÁO, N-HÁ Á ÁO and N--HÁ Á ÁN hydrogen bonds; in addition, a -interaction between pyrazolyl rings [inter-centroid separation = 3.7547 (12) Å ] is noted. Structure descriptionSulfonamides and their derivatives constitute an important class of therapeutic agents that exhibit a broad spectrum of pharmacological profiles, such as anti-bacterial, diuretic, hypoglycaemic, anti-thyroid, anti-viral, anti-inflammatory and anti-parasitic activities among others (Ranjith et al., 2014;Shah et al., 2013;Scozzafava et al., 2013;Greig et al., 2013). In our previous work, we have found that indazoles bearing arylsulfonamide groups showed anti-proliferative activity against human (colon and prostate) and murine (leukaemia) cell lines (Abbassi et al., 2012(Abbassi et al., , 2014Bouissane, et al., 2006).The asymmetric unit of the title compound contains two independent organic molecules and one water molecule, as shown in Fig. 1. The fused five-and six-membered rings of each molecule are almost coplanar, with the maximum deviation from the mean plane being 0.020 (2) Å for the C12 atom and 0.022 (2) Å for the C27 atom in the first and data reports second molecules, respectively. The dihedral angles between the indazolyl system and the methoxybenzene ring are 56.32 (7) and 35.35 (8) in the first and second molecules, respectively.In the crystal, the organic molecules are connected through the water molecule by O7-H7AÁ Á ÁN6, O7-H7BÁ Á ÁO2, N1-HN1Á Á ÁO7 and N4-HN4Á Á ÁN3 hydrogen bonds (Table 1), in addition to -interactions between pyrazole rings as shown in Fig. 2. Synthesis and crystallizationA mixture of 1-methyl-7-nitroindazole (1.22 mmol) and anhydrous SnCl 2 (1.1 g, 6.1 mmol) in ethanethiol (25 ml) was heated at 308 K for 4 h. After reduction, the starting material had been consumed and the solution was allowed to cool. The pH of the solution was made slightly basic (pH = 7-8) by addition of 5% aqueous potassium bicarbonate. Extraction with EtOAc followed. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methoxybenzenesulfonyl chloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture had been concentrated in vacuo, the resulting residue was purified by flash chromatography (elution was with EtOAc/hexane 1:9). The title compoun...

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Synthesis, antiproliferative and apoptotic activities of N-(6(4)-indazolyl)-benzenesulfonamide derivatives as potential anticancer agents

Cited by 59 publications

References 27 publications

Synthesis of indazole motifs and their medicinal importance: An overview

Synthesis of indazole motifs and their medicinal importance: An overview

SnCl₂/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties

4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate

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Synthesis, antiproliferative and apoptotic activities of N-(6(4)-indazolyl)-benzenesulfonamide derivatives as potential anticancer agents

Cited by 59 publications

References 27 publications

Synthesis of indazole motifs and their medicinal importance: An overview

Synthesis of indazole motifs and their medicinal importance: An overview

SnCl2/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties

4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate

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Product

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About

SnCl₂/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties