Synthesis and Antitumor Activity of Some Substituted Indazole Derivatives

Abbassi, Najat; Rakib, El Mostapha; Chicha, Hakima; Bouissane, Latifa; Hannioui, A.; Aiello, Cinzia; Gangemi, Rosaria; Castagnola, Patrizio; Rosano, Camillo; Viale, Maurizio

doi:10.1002/ardp.201300390

Cited by 40 publications

(43 citation statements)

References 25 publications

(24 reference statements)

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“…This is undoubtedly due to a broad variety of biological functions of indazole derivatives such as anti-inflammatory (Schmidt et al, 2008), antibacterial (Shafakat Ali et al, 2012) and antitumor activities (Abbassi et al, 2014). The present work is a continuation of our work on indazole derivatives (El Brahmi et al, 2011).…”

Section: Structure Descriptionmentioning

confidence: 69%

5-Nitro-1-(prop-2-yn-1-yl)-1H-indazole

Boulhaoua¹,

Hafi²,

Benchidmi³

et al. 2016

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Section: Structure Descriptionmentioning

confidence: 69%

5-Nitro-1-(prop-2-yn-1-yl)-1H-indazole

Boulhaoua¹,

Hafi²,

Benchidmi³

et al. 2016

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“…Studies of the structure and physicochemical properties of the indazole ring have been reviewed (Abbassi et al, 2014;Li et al, 2003;Lee et al, 2001). Indazole is a frequently found motif in drug substances with important biological activities, such as antimicrobial (Patel et al, 1999) and anti-inflammatory activities (Lin et al, 2008), and anticancer effects (Zhu et al, 2007).…”

Section: Structure Descriptionmentioning

confidence: 99%

1-(3-Chloro-6-nitro-1H-indazol-1-yl)ethan-1-one

et al. 2017

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The asymmetric unit of the title compound, C 9 H 6 ClN 3 O 3 , contains one full molecule in a general position and a half molcule sitting on a crystallographic mirror plane. In the crystal, molecules form stacks extending along the b-axis direction through a combination of offset -stacking between indazole units and C-ClÁ Á Á (ring) interactions with the six-membered rings of the same units. Elaboration of the C-ClÁ Á Á (ring) interactions along the a-axis direction forms slabs of molecules parallel to [001]. The stacks are joined by a combination of C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds. Structure descriptionStudies of the structure and physicochemical properties of the indazole ring have been reviewed (Abbassi et al., 2014;Li et al., 2003;Lee et al., 2001). Indazole is a frequently found motif in drug substances with important biological activities, such as antimicrobial (Patel et al., 1999) and anti-inflammatory activities (Lin et al., 2008), and anticancer effects (Zhu et al., 2007). As a continuation of our studies of indazole derivatives (Mohamed Abdelahi et al., 2017a,b,c), we report the synthesis and structure of the title compound (Fig. 1).The asymmetric unit of the title compound consists of one molecule in a general position and a half molecule located on a crystallographic mirror plane at y = 1/4. The indazole portion of the former is planar to within 0.007 (1) Å (C16) and the dihedral angle between its mean plane and the mirror on which the latter lies is 4.82 (3) Å . For the overlay of the two independent molecules, values of 0.0130 and 0.0288 Å are obtained, respectively, for the r.m.s. deviation and the maximum deviation. In the crystal, molecules form stacks extending along the b-axis direction. One element of the stack is a dimer formed by pairwise head-to-tail offset -stacking interactions between the indazole (Table 1 and Fig. 4). As shown in Fig. 3, an R 3 3 (19) graph set is formed by two C-HÁ Á ÁO hydrogen bonds and one ClÁ Á ÁO interaction for the molecule in the general position. A corresponding set is formed with the molecule in the special position.

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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 and Antitumor Activity of Some Substituted Indazole Derivatives

Cited by 40 publications

References 25 publications

5-Nitro-1-(prop-2-yn-1-yl)-1H-indazole

5-Nitro-1-(prop-2-yn-1-yl)-1H-indazole

1-(3-Chloro-6-nitro-1H-indazol-1-yl)ethan-1-one

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

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