Synthesis and activity of benzimidazole N-Acylhydrazones against Trypanosoma cruzi, Leishmania amazonensis and Leishmania infantum.

In this study, we present the design, synthesis, and cytotoxic evaluation of a series of benzimidazole N-acylhydrazones against strains of T. cruzi (Y and Tulahuen) and Leishmania species (L. amazonensis and L.

Antileishmanial Activity of 4,8-Dimethoxynaphthalenyl Chalcones on .

Leishmaniasis is a neglected tropical disease caused by species. Available therapeutic options have several limitations. The drive to develop new, more potent, and selective antileishmanial agents is thus a major goal.

Different conformations and packing motifs in the crystal structures of four thio-phene-carbohydrazide-pyridine derivatives.

The crystal structures of four thio-phene-carbohydrazide-pyridine derivatives, '-[()-pyridin-3-yl-methyl-idene]thio-phene-2-carbohydrazide, CHNOS, (I), '-[()-pyridin-2-yl-methyl-idene]thio-phene-2-carbohydrazide, CHNOS, (II), -methyl-'-[()-pyridin-2-yl-methyl-idene]thio-phene-2-carbohydrazide, CHNOS, (III) and '-[()-pyridin-2-yl-methyl-idene]-2-(thio-phen-2-yl)ethano-hydrazide, CHNOS, (IV) are described. The dihedral angles between the thio-phene ring and the pyridine ring are 21.4 (2), 15.

Synthesis and trypanocidal activity of novel pyridinyl-1,3,4-thiadiazole derivatives.

Herein, we present the design, synthesis and trypanocidal evaluation of sixteen new 1,3,4-thiadiazole derivatives from N-aminobenzyl or N-arylhydrazone series. All derivatives were assayed against the trypomastigote form of Trypanosoma cruzi, showing IC values ranging from 3 to 226 μM, and a better trypanocidal profile was demonstrated for the 1,3,4-thiadiazole-N-arylhydrazones (3a-g). In this series, the 2-pyridinyl fragment bound to the imine subunit of the hydrazine moiety presented pharmacophoric behavior for trypanocidal activity.

Crystal structures of 3β,19-dihydroxyandrost-5-en-17-one, 5, and its monohydrate, [(5).HO]: A survey of the structures of related di- and tri-substituted hydroxy derivatives and their solvated compounds.

The crystal structures of 3β,19-dihydroxyandrost-5-en-17-one, 5, and its monohydrate, [((5).HO]], are reported. The monohydrate, isolated from a solution of 5 in 50% aqueous methanol, recrystallizes in the orthorhombic space group, P222, while that of the anhydrous compound, isolated from solutions of THF, MeCO, EtOAc or dry MeOH, recrystallizes in the monoclinic space group, P2.

Synthesis, Antitrypanosomal and Antimycobacterial Activities of Coumarin N-acylhydrazonic Derivatives.

Background: Near to 5-7 million people are infected with T. cruzi in the world, and about 10,000 people per year die of problems associated with this disease.

Methods: Herein, the synthesis, antitrypanosomal and antimycobacterial activities of seventeen coumarinic N-acylhydrazonic derivatives have been reported.

Erratum: Crystal structures and Hirshfeld surface analyses of ()-'-benzyl-idene-2-oxo-2-chromene-3-carbo-hydrazide and the disordered hemi-DMSO solvate of ()-2-oxo-'-(3,4,5-trimeth-oxybenzyl-idene)-2-chromene-3-carbohydrazide: lattice energy and inter-molecular inter-action energy calculations for the former. Corrigendum.

[This corrects the article DOI: 10.1107/S2056989019012015.].

Crystal structure, Hirshfeld surface analysis and PIXEL calculations of a 1:1 epimeric mixture of 3-[(4-nitro-benzyl-idene)amino]-2()-(4-nitro-phenyl)-5()-(propan-2-yl)imidazolidin-4-one.

A 1:1 epimeric mixture of 3-[(4-nitro-benzyl-idene)amino]-2()-(4-nitro-phen-yl)-5()-(propan-2-yl)imidazolidin-4-one, CHNO, was isolated from a reaction mixture of 2()-amino-3-methyl-1-oxo-butane-hydrazine and 4-nitro-benz-alde-hyde in ethanol. The product was derived from an initial reaction of 2()-amino-3-methyl-1-oxo-butane-hydrazine at its hydrazine group to provide a 4-nitro-benzyl-idene derivative, followed by a cyclization reaction with another mol-ecule of 4-nitro-benzaldehyde to form the chiral five-membered imidazolidin-4-one ring. The formation of the five-membered imidazolidin-4-one ring occurred with retention of the configuration at the 5-position, but with racemization at the 2-position.

Different packing motifs mediated by weak inter-actions and polymorphism in the crystal structures of five 2-(benzyl-idene)benzosuberone derivatives.

The syntheses and crystal structures of five 2-benzyl-idene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetra-hydro-5-benzo[7]annulen-5-one] derivatives, 2-(4-meth-oxy-benzyl-idene)-1-benzosuberone, CHO, (I), 2-(4-eth-oxy-benzyl-idene)-1-benzosuberone, CHO, (II), 2-(4-benzyl-benzyl-idene)-1-benzosuberone, CHO, (III), 2-(4-chloro-benzyl-idene)-1-benzosuberone, CHClO, (IV) and 2-(4-cyano-benzyl-idene)-1-benzosuberone, CHNO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.

Crystal structures and Hirshfeld surface analyses of ()-'-benzyl-idene-2-oxo-2-chromene-3-carbo-hydrazide and the disordered hemi-DMSO solvate of ()-2-oxo-'-(3,4,5-trimeth-oxybenzyl-idene)-2-chromene-3-carbohydrazide: lattice energy and inter-molecular inter-action energy calculations for the former.

The crystal structures of the disordered hemi-DMSO solvate of ()-2-oxo-'-(3,4,5-tri-meth-oxy-benzyl-idene)-2-chromene-3-carbohydrazide, CHNO·0.5CHOS, and ()-'-benzyl-idene-2-oxo-2-chromene-3-carbohydrazide, CHNO (: = CH), are discussed. The non-hydrogen atoms in compound [: = (3,4,5-MeO)CH)] exhibit a distinct curvature, while those in compound, (: = CH), are essential coplanar.

Bis(mefloquinium) butane-dioate ethanol monosolvate: crystal structure and Hirshfeld surface analysis.

The asymmetric unit of the centrosymmetric title salt solvate, 2CHFNO· CHO ·CHCHOH, (systematic name: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium butane-dioate ethanol monosolvate) comprises two independent cations, with almost superimposable conformations and each approximating the shape of the letter , a butane-dioate dianion with an all- conformation and an ethanol solvent mol-ecule. In the crystal, supra-molecular chains along the -axis direction are sustained by charge-assisted hy-droxy-O-H⋯O(carboxyl-ate) and ammonium-N-H⋯O(carboxyl-ate) hydrogen bonds. These are connected into a layer C-F⋯π(pyrid-yl) contacts and π-π stacking inter-actions between quinolinyl-C and -NC rings of the independent cations of the asymmetric unit [inter-centroid separations = 3.

'-(1,3-Benzo-thia-zol-2-yl)benzene-sulfono-hydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry.

The asymmetric unit of the title compound, CHNOS, comprises two independent mol-ecules ( and ); the crystal structure was determined by employing synchrotron radiation. The mol-ecules exhibit essentially the same features with an almost planar benzo-thia-zole ring (r.m.

2-{[2,8-Bis(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium tri-chloro-acetate: crystal structure and Hirshfeld surface analysis.

The asymmetric unit of the centrosymmetric title salt, CHFNO·CClO , comprises a single ion-pair. The hy-droxy-O and ammonium-N atoms lie to the same side of the cation, a disposition maintained by a charge-assisted ammonium-N-H⋯O(hy-droxy) hydrogen bond [the O-C-C-N (h = hy-droxy, m = methine, a = ammonium) torsion angle is 58.90 (19)°].

Crystal structures of the 1:1 salts of 2-amino-4-nitro-benzoate with each of (2-hy-droxy-eth-yl)di-methyl-aza-nium, -but-yl(2-hy-droxy-eth-yl)aza-nium and 1,3-dihy-droxy-2-(hy-droxy-meth-yl)propan-2-aminium.

The crystal and mol-ecular structures of the title mol-ecular salts, CHNO·CHNO , (I), CHNO·CHNO , (II), and CHNO ·CHNO , (III), are described. The common feature of these salts is the presence of the 2-amino-4-nitro-benzoate anion, which exhibit non-chemically significant variations in the conformational relationships between the carboxyl-ate and nitro groups, and between these and the benzene rings they are connected to. The number of ammonium-N-H H atoms in the cations increases from one to three in (I) to (III), respectively, and this variation significantly influences the supra-molecular aggregation patterns in the respective crystals.

Crystal structures and Hirshfeld surfaces of four meth-oxy-benzaldehyde oxime derivatives, 2-MeO-CHC=NOH ( = H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns.

The crystal structures of four ()-meth-oxy-benzaldehyde oxime derivatives, namely (2-meth-oxy-benzaldehyde oxime, , 2,3-di-meth-oxy-benzaldehyde oxime, , 4-di-meth-oxy-benzaldehyde oxime, , and 2,5-di-meth-oxy-benzaldehyde oxime, , are discussed. The arrangements of the 2-meth-oxy group and the H atom of the oxime unit are in compounds -, but in both independent mol-ecules of compound , the arrangements are . There is also a difference in the conformation of the two mol-ecules in , involving the orientations of the 2- and 5-meth-oxy groups.

Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-CHC=NOH ( = Me, OH and MeO).

The crystal structures of three salicyaldoxime compounds, namely 2-hy-droxy-4-methyl-benzaldehyde oxime, CHNO, , 2,4-di-hydroxy-benzaldehyde oxime, CHNO, , and 2-hy-droxy-4-meth-oxy-benzaldehyde oxime, CHNO, , are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The inter-planar angles between the C=N-O moieties of the oxime unit and their attached phenyl rings are 0.

Crystal structures and Hirshfeld surface analyses of the di- and tri-hydrates of (5α,17E)-17-hydrazonoandrostan-3-ol: Significant differences in the hydrogen bonding patterns and supramolecular arrangements.

The crystal structures, Hirshfeld surface analyses and electrostatic potential surfaces of the di- and tri-hydrates of (5α,17E)-17-hydrazonoandrostan-3-ol, 3, namely [3·(HO)] and [3·(HO)], are reported. The trihydrate, isolated from a solution of 3 in moist methanol, recrystallizes in the orthorhombic space group, P222, while that of the dihydrate, isolated from a 1:1 aqueous methanol solution, recrystallizes in the monoclinic space group, P2. The asymmetric unit of the trihydrate involves one steroid and three water molecules, while that of the dihydrate has two similar but independent steroid molecules and four hydrate molecules.

Crystal structures and Hirshfeld surface analyses of the hemi-hydrate and hemi-methanolate of 3α-hydroxy-16α-bromoandrostan-17-one, 3: Differences in supramolecular arrangements.

The crystal structures and Hirshfeld surface analyses of two hemi-solvates of 3α-hydroxy-16α-bromoandrostan-17-one, 3, namely [(3).(HO)] and [(3).(MeOH)], are reported.

Racemic mefloquinium chloro-difluoro-acetate: crystal structure and Hirshfeld surface analysis.

In the racemic title mol-ecular salt, CHFNO·CClFO (systematic name: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium chloro-difluoro-acetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, , with the piperidin-1-ium group being approximately orthogonal to the quinolinyl residue [the C-C-C-N (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79 (18)°]. An intra-molecular, charge-assisted ammonium--⋯(hydrox-yl) hydrogen bond ensures the hy-droxy-O and ammonium-N atoms lie to the same side of the mol-ecule [O-C-C-N (h = hydrox-yl) = -59.

Expected and unexpected products of reactions of 2-hydrazinylbenzo-thia-zole with 3-nitro-benzene-sulfonyl chloride in different solvents.

The syntheses and crystal structures of 2-[2-(propan-2-yl-idene)hydrazin-yl]-1,3-benzo-thia-zol-3-ium 3-nitro-benzene-sulfonate (CHNS·CHNOS), (I), 2-[2-(3-nitro-benzene-sulfon-yl)hydrazin-yl]-1,3-benzo-thia-zole (CHNOS), (II) and 2-[2-(3-nitro-benzene-sulfon-yl)hydrazin-yl]-1,3-benzo-thia-zol-3-ium 3-nitro-benzene-sulfonate (CHNOS·CHNOS), (III) are reported. Salt (I) arose from an unexpected reaction of 2-hydrazinylbenzo-thia-zole with the acetone solvent in the presence of 3-nitro-benzene-sulfonyl chloride, whereas (II) and (III) were recovered from the equivalent reaction carried out in methanol. The crystal of (I) features ion pairs linked by pairs of N-H⋯O (s = sulfonate) hydrogen bonds; adjacent cations inter-act by way of short π-π stacking inter-actions between the thia-zole rings [centroid-centroid separation = 3.

Different mol-ecular conformations in the crystal structures of three 5-nitro-imidazolyl derivatives.

The crystal structures of ()-1-methyl-5-nitro-1-imidazole-2-carbaldehyde -benzyl-oxime, CHNO, (I), ()-1-methyl-5-nitro-1-imidazole-2-carb-alde-hyde -(4-fluoro-benz-yl) oxime, CHFNO, (II), and ()-1-methyl-5-nitro-1-imidazole-2-carbaldehyde -(4-bromo-benz-yl) oxime, CHBrNO, (III), are described. The dihedral angle between the ring systems in (I) is 49.66 (5)° and the linking N-C-C=N (m = methyl-ated) bond shows an conformation [torsion angle = 175.

Different packing motifs of isomeric ()-'-(halo-phenyl-methyl-idene)--methyl-2-(thio-phen-2-yl)acetohydrazides controlled by C-H⋯O inter-actions.

The crystal structures of three isomeric ()-'-(chloro-phenyl-methyl-idene)--methyl-2-(thio-phen-2-yl)acetohydrazides (CHClNOS) are described, with the Cl atom in (I), (III) and (IV) positions in the benzene ring. The -bromo derivative (II) (CHBrNOS), which is isostructural with its chloro congener (I), is also reported. Mol-ecules (I)-(III) have similar conformations, which approximate to l-shapes, as indicated by their N-C-C-C (t = thio-phene) torsion angles of -90.

Crystal structures and Hirshfeld surfaces of two 1,3-benzoxa-thiol-2-one derivatives.

The crystal structures of 6-meth-oxy-1,3-benzoxa-thiol-2-one, CHOS, (I), and 2-oxo-1,3-benzoxa-thiol-6-yl acetate, CHOS, (II), are described. Compound (I) is almost planar (r.m.

Crystal structures and Hirshfeld surfaces of differently substituted ()-'-benzyl-idene--methyl-2-(thio-phen-2-yl)acetohydrazides.

The syntheses and crystal structures of ()-'-(3-cyano-benzyl-idene)--methyl-2-(thio-phen-2-yl)acetohydrazide, CHNOS, (I), and ()-'-(4-meth-oxy-benzyl-idene)--methyl-2-(thio-phen-2-yl)acetohydrazide, CHNOS, (II), with different substituents in the and position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol-ecules in the asymmetric unit, with generally similar conformations [r.m.

Evaluation of 1,3-benzoxathiol-2-one Derivatives as Potential Antifungal Agents.

Background: Over the last few years, fungal infections have emerged as a worrisome global public health problem. Candidiasis is a disease caused by Candida species and has been a problem worldwide mainly for immunosuppressed patients. Lately, the resistant strains and side effects have been reported as important issues for treating Candidiasis, which have to be solved by identifying new drugs.