Benzimidazole derivatives. Part 1: Synthesis and structure–activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists

López-Rodrı́guez, Marı́a L.; Benhamú, Bellinda; Viso, Alma; Morcillo, M. J.; Murcia, Marta; Orensanz, Luis M.; Alfaro, M.J.; Martı́n, Marı́a Isabel

doi:10.1016/s0968-0896(99)00172-8

Cited by 35 publications

(22 citation statements)

References 45 publications

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“…Furthmore, benzimidazole carboxylic acids and their derivatives are widely used due to their biological activites such as antifilarial, antineoplastic, anthelmintic and antiviral activities [6][7][8][9]. Up to now, several complexes have been synthesized using the benzimidazole carboxylic acid [10][11][12][13][14][15][16].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C₂₂H₂₇CuN₄O_12.50

Zhang

Chen

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C₂₂H₂₇CuN₄O_12.50

Zhang

Chen

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Imidazole and benzimidazole carboxylic acids have gained great interst for their functional properties of antifilarial, antineoplastic, anthelmintic and antiviral activities, and lead to their widely use in the design of therapeutic agents, such as antifilarial and antineoplastic, anthelmintic, antiviral compounds and 5-HT 4 receptor antagonists [1][2][3][4]. In addition, these special amino acids are known as good ligands in the supramolecular chemistry, as an Natom in the imidazole ring and the Oatoms in the carboxylate groups can be donor sites [5][6][7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(carboxymethyl)-2-methyl-1,3-benzimidazol- 3-ium-3-acetate hydrate, [C10H9N2O2][CH3CO2] · H2O

Chen¹,

Huang²,

Jiang³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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C 12 H 14 N 2 O 5 ,triclinic, P1 (no. 2), a =8.117(1) Å, b =8.848(2) Å, c =9.675(2) Å, a =89.020(2)°,Source of material 2-Methyl-1H-benzimidazole (3.96 g, 0.03 mol) and chloroacetic acid (7.2 g, 0.075 mol) were dissolved in water (70 ml). The pH of the solution was kept to 8bythe addition of NaOH for 4h.The solution was cooled to room temperature, then the pH was adjusted to 2-3byaddition of hydrochloric acid and awhite precipitate began to form. The precipitate was filtered off and recrystallized from water (yield 74 %). Experimental details

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“…Imidazole and benzimidazole carboxylic acids and their derivatives have attracted broad interest because of their functional properties such as antifilarial, antineoplastic, anthelmintic and antiviral activities [2][3][4]. In addition, these compounds are used widely as ligands in the coordination chemistry of supramolecular metal complexes, because the Na tom in the imidazole or benzimidazole ring and the Oatoms in the carboxylate groups can act as donor sites [5].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of hexaaquanickel(II) bis[1-(carboxylatomethyl)-1,3- benzimidazol-3-ium-3-acetato] dihydrate, [Ni(H2O)6](C11H9N2O4)2 · 2H2O

Huang¹,

Chen²

2008

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe starting material 1-(carboxymethyl)-1H-benzimidazol-3-ium-3-acetate was prepared from chloroacetic acid and benzimidazole [1]. 1-(Carboxymethyl)-1H-benzimidazol-3-ium-3-acetate (0.0937 g, 0.4 mmol) was dissolved in 50% ethanol (20 ml) containing NaOH (0.0161 g, 0.4 mmol). The resulting solution was added dropwise to ahot solution of nickel dichloride hexahydrate (0.0952 g, 0.4 mmol) dissolved in the same solvent (10 ml) under continuous stirring for 3h.After filtration, the bluegreen filtrate was kept at room temperature. By slow evaporation of the solvent blue block-like crystals suitable for X-ray diffraction were obtained. Experimental detailsThe two Hatoms (H1A and H1B) were positioned geometrically and refined as riding on their parent atom O1W. The remaining H atoms were located in difference Fourier maps, and were refined with distance restraints giving DiscussionImidazole and benzimidazole carboxylic acids and their derivatives have attracted broad interest because of their functional properties such as antifilarial, antineoplastic, anthelmintic and antiviral activities [2][3][4]. In addition, these compounds are used widely as ligands in the coordination chemistry of supramolecular metal complexes, because the Na tom in the imidazole or benzimidazole ring and the Oatoms in the carboxylate groups can act as donor sites [5]. However, studies of metal complexes with these ligands as zwitterions are still rare [6,7]. In the molecular structure of the title compound the Ni II atom lies at acrystallographic inversion center and is coordinated by six O atoms from water molecules with aslightly distorted octahedral environment ( figure, top). The metal-oxygen bonds are in the range from 2.055(1) to 2.065(1) Å,the bond angles around each metal center range from 88.86(4)°to 180°. Both bond lengths and angles are in good agreement with those of comparable hexaaquanickel complex, e.g. theophylline-7-acetate hexaaquanickel(II) tetrahydrate [8] or hexaaquanickel(II) bis(diphenyl aminosquarate) dihydrate [9]. Within the asymmetric unit, each2+ cation is connected with neighboring 1-(carboxymethyl)-1,3-benzimidazol-3-ium-3-acetato anions via hydrogen bonds betweencoordinated water Oatom and the uncoordinated carboxyl Oa tom, namely O5-H5A···O4ii ,O 5 -H5B···O2, O6-H6B···O3 iv ,O7-H7A···O1 v (symmetry codes: (ii) x,y,z+1; (iv) 3-x,-y+2,-z;(v) -x+1,-y+2,-z+1). Besides, the water molecules act as hydrogen-bond donors to carboxylate Oatom as well as hydrogen-bond acceptors of coordinated water Oa toms. Thus, the relative independent components [Ni(H 2O)6] 2+ ,1-(carboxymethyl)-1,3-benzimidazol-3-ium-3-acetato anions and lattice H 2 Omolecules are assembled into two-dimensional layers parallel to (001). The non-classical hydrogen bonds (C-H···O) link adjacent layers to form athree-dimensional network (figure, bottom).

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Benzimidazole derivatives. Part 1: Synthesis and structure–activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists

Cited by 35 publications

References 45 publications

Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C₂₂H₂₇CuN₄O_12.50

Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C₂₂H₂₇CuN₄O_12.50

Crystal structure of 1-(carboxymethyl)-2-methyl-1,3-benzimidazol- 3-ium-3-acetate hydrate, [C10H9N2O2][CH3CO2] · H2O

Crystal structure of hexaaquanickel(II) bis[1-(carboxylatomethyl)-1,3- benzimidazol-3-ium-3-acetato] dihydrate, [Ni(H2O)6](C11H9N2O4)2 · 2H2O

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Benzimidazole derivatives. Part 1: Synthesis and structure–activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists

Cited by 35 publications

References 45 publications

Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50

Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50

Crystal structure of 1-(carboxymethyl)-2-methyl-1,3-benzimidazol- 3-ium-3-acetate hydrate, [C10H9N2O2][CH3CO2] · H2O

Crystal structure of hexaaquanickel(II) bis[1-(carboxylatomethyl)-1,3- benzimidazol-3-ium-3-acetato] dihydrate, [Ni(H2O)6](C11H9N2O4)2 · 2H2O

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Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C₂₂H₂₇CuN₄O_12.50

Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C₂₂H₂₇CuN₄O_12.50