1,3-Difurfurylbenzimidazolium chloride monohydrate

The title compound, C17H15N2O2 +·Cl−·H2O, was synthesized from benzimidazole and furfryl chloride in dimethyl­formamide. The cationic benzimidazolium ring is connected to two furan rings via methyl­ene bridges. The furan rings make dihedral angle of 79.09 (18)° with respect to each other, and make dihedral angles of 73.92 (12) and 72.58 (13)° with respect to the benzimidazole ring. O—H⋯Cl, C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π inter­actions contribute to the stabilization of the crystal structure. Furthermore, there is a π–π inter­action between adjacent five- and six-membered rings of the benzimidazole groups [centroid–centroid distance = 3.5305 (8) Å]

Synthesis and carbonic anhydrase I, II, IV and XII inhibitory properties of N-protected amino acid – sulfonamide conjugates

N-protected amino acids (Gly, Ala and Phe protected with Boc and Z groups) were reacted with sulfonamide derivatives, leading to the corresponding N-protected amino acid-sulfonamide conjugates. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IV and hCA XII. Among them, hCA II, IV and XII are antiglaucoma drug targets, being involved in aqueous humor secretion within the eye. Low nanomolar inhibition was measured against all four isoforms with the 20 reported sulfonamides, but no selective inhibitory profiles, except for some CA XII-selective derivatives, were observed. hCA I, II and XII were generally better inhibited by sulfonamides incorporating longer scaffolds and Gly/Ala, whereas the best hCA IV inhibitors were homosulfanilamide derivatives, incorporating Phe moieties. The amino acid-sulfonamide conjugates show good water solubility and effective hCA II, IV and XII inhibition, and may be considered as interesting candidates for antiglaucoma studies

Synthesis and carbonic anhydrase inhibitory properties of amino acid – coumarin/quinolinone conjugates incorporating glycine, alanine and phenylalanine moieties

N-Protected amino acids (Gly, Ala and Phe) were reacted with amino substituted coumarin and quinolinone derivatives, leading to the corresponding N-protected amino acid-coumarin/quinolinone conjugates. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against various human (h) isoforms, such as hCA I, hCA II, hCA IV and hCA XII. The quinolinone conjugates were inactive as enzyme inhibitors, whereas the coumarins were ineffective hCA I/II inhibitors (KIs > 50 μM) but were submicromolar hCA IV and XII inhibitors, with inhibition constants ranging between 92 nM and 1.19 μM for hCA IV, and between 0.11 and 0.79 μM for hCA XII. These coumarin derivatives, as many others reported earlier, thus show an interesting selective inhibitory profile for the membrane-bound over the cytosolic CA isoforms

1-Benzyl-3-[(trimethyl­sil­yl)meth­yl]benzimidazolium chloride monohydrate

The title compound, C18H23N2Si+·Cl−·H2O, was synthesized from 1-[(trimethyl­sil­yl)meth­yl]benzimidazole and benzyl chloride in dimethyl­formamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) Å, and makes an angle of 74.80 (12)° with the phenyl ring. The crystal packing is stabilized by O—H⋯Cl, C—H⋯Cl, C—H⋯O and C—H⋯π inter­actions between symmetry-related mol­ecules together with π–π stacking inter­actions between the imidazolium and benzene rings [centroid–centroid distance = 3.5690 (15) Å] and between the benzene rings [centroid–centroid distance = 3.7223 (14) Å]

1-(Prop-2-en-1-yl)-3-[(trimethyl­sil­yl)meth­yl]benzimidazolium bromide monohydrate

In the title compound, C14H21N2Si+·Br−·H2O, the benzimidazole ring system is almost planar [maximum deviation = 0.021 (2) Å]. In the crystal, O—H⋯Br and C—H⋯O hydrogen bonds link the ions via the O atoms of the water mol­ecules. In addition, there are π–π stacking inter­actions between the centroids of the benzene and imidazole rings of the benzimidazole ring system [centroid–centroid distances = 3.521 (3) and 3.575 (2) Å]

Dichloridobis[5-nitro-1-trimethyl­silyl­methyl-1H-benzimidazole-κN 3]cobalt(II) N,N-dimethyl­formamide solvate

The title compound, [CoCl2(C11H15N3O2Si)2]·C3H7NO, was synthesized from 5-nitro-1-trimethyl­silylmethyl-1H-benzimid­azole and cobalt(II) chloride in dimethyl­formamide. The CoII atom is coordinated in a distorted tetra­hedral environment by two Cl atoms and two N atoms. In the crystal structure, there are a number of C—H⋯Cl and C—H⋯O hydrogen-bonding inter­actions between symmetry-related mol­ecules

1,3-Bis(3-phenyl­prop­yl)benzimidazolium bromide monohydrate

In the title compound, C25H27N2 +·Br−·H2O, the benzimidazole unit is essentially planar, with a maximum deviation of 0.020 (6) Å. The benzimidazole unit makes dihedral angles of 83.6 (3) and 81.0 (3)° with the two terminal phenyl rings. The dihedral angle between the phenyl rings is 58.5 (4)°. In the crystal structure, there are C—H⋯O hydrogen bonds, a C—H⋯π inter­action between a phenyl H atom and the phenyl ring of a neighbouring mol­ecule, and a π–π inter­action [3.512 (3) Å] between the centroids of the five-membered ring and the benzene ring of the benzimidazole unit of an adjacent mol­ecule

1,3-Bis(3-phenyl­prop­yl)-1H-benzimidazol-3-ium-2-carbodithio­ate

The title compound, C26H26N2S2, was synthesized from bis­[1,3-bis­(3-phenyl­prop­yl)benzimidazolidine-2-yl­idene] and CS2 in toluene. The mol­ecular structure is composed of a benzimidazole ring system with two phenyl­propyl substituents and a dithio­carboxyl­ate group in the 2-position. The benzimidazole unit is essentially planar, with a maximum atomic deviation of 0.008 (2) Å, and makes dihedral angles of 72.72 (10) and 27.62 (12)°, with the two phenyl rings. The dihedral angle between the two phenyl rings is 55.98 (15)°. The mol­ecular packing is stabilized by a C—H⋯S inter­molecular hydrogen-bonding inter­action and a C—H⋯π inter­action between a benzene H atom and the phenyl ring of a neighbouring mol­ecule

(E)-1,1′-Bis[(E)-but-2-en­yl]-3,3′-(propane-1,3-di­yl)bis­(1H-benzimidazol-3-ium) dibromide monohydrate

The title compound, C25H30N4 2+·2Br−·H2O, was synthesized from 1,1′-propyl­enedibenzimidazole and (E)-1-bromo­but-2-ene in dimethyl­formamide solution. The two benzimidazole ring systems are essentially planar, with maximum deviations of 0.011 (4) and 0.023 (3) Å. The dihedral angle between these two ring systems is 25.87 (15)°. The crystal structure is stabilized by inter­molecular O—H⋯Br and C—H⋯Br hydrogen-bonding inter­actions. Atmospheric water was incorporated into the crystal structure

1-Cyclo­hexyl­methyl-3-methyl-2-[(phenyl­imino)(sulfido)meth­yl]benzimidazolium

In the zwitterionic title compound, C22H25N3S, the benzimid­azole ring system makes a dihedral angle of 55.69 (11)° with the phenyl ring. In the crystal structure, inter- and intra­molecular C—H⋯S inter­actions occur