A tolbutamide–metformin salt based on antidiabetic drug combinations: synthesis, crystal structure analysis and pharmaceutical properties

2019 ◽  
Vol 75 (9) ◽  
pp. 1250-1258 ◽  
Author(s):  
Lina Jia ◽  
Songgu Wu ◽  
Junbo Gong
Keyword(s):  
Crystal Packing ◽  
Parent Drug ◽  
Crystal Structure Analysis ◽  
Drug Combinations ◽  
X Ray Diffraction ◽  
Antidiabetic Drug ◽  
Salt Crystal ◽  
H Nmr ◽  
Accelerated Stability ◽  
Pharmaceutical Properties

A drug–drug anhydrous pharmaceutical salt containing tolbutamide {systematic name: 3-butyl-1-[(4-methylbenzene)sulfonyl]urea, TOL, C12H18N2O3S} and metformin (systematic name: 1-carbamimidamido-N,N-dimethylmethanimidamide, MET, C4H11N5) was created based on antidiabetic drug combinations to overcome the poor pharmaceutical properties of the parent drugs. Proton transfer and the proportion of the two components were confirmed by 1H NMR spectroscopy and single-crystal X-ray diffraction analysis. Comprehensive characterization of the new pharmaceutical salt crystal, 2-[(dimethylamino)(iminiumyl)methyl]guanidine (butylcarbamoyl)[(4-methylbenzene)sulfonyl]azanide, C4H12N5 +·C12H17N2O3S−, was performed and showed enhancement of the pharmaceutical properties, such as lower hygroscopicity and greater accelerated stability than the parent drug MET, and higher solubility and dissolution rate than TOL. The property alterations were correlated with the crystal packing features and potential hydrogen-bonding sites through observed changes in the crystal structures.

scholarly journals A Glimepiride-Metformin Multidrug Crystal: Synthesis, Crystal Structure Analysis, and Physicochemical Properties

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3786 ◽  
Author(s):  
Xufei Bian ◽  
Lan Jiang ◽  
Zongjie Gan ◽  
Xiaoshu Guan ◽  
Li Zhang ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Physicochemical Properties ◽  
Structure Analysis ◽  
Parent Drug ◽  
Crystal Structure Analysis ◽  
Solvent Evaporation Method ◽  
X Ray ◽  
Accelerated Stability ◽  
Crystal Synthesis ◽  
Pharmaceutical Properties

A multidrug crystal based on drug combinations was synthesized by the solvent evaporation method. This multicomponent crystal consisted of antidiabetic drugs Glimepiride (Gli) and Metformin (Met), which was performed by single crystal X-ray structure analysis. The results showed an enhancement of the pharmaceutical properties such as lower hygroscopicity and greater accelerated stability than the parent drug Met, and a higher solubility and dissolution rate than Gli.

Reaction of 2-[(2-aminoethyl)amino]ethanol with pyridine-2-carbaldehyde and complexation of the products with CuII and CdII along with docking studies

2019 ◽  
Vol 75 (7) ◽  
pp. 951-959 ◽  
Author(s):  
Zahra Mardani ◽  
Mohammad Hakimi ◽  
Keyvan Moeini ◽  
Fabian Mohr
Keyword(s):  
Crystal Packing ◽  
Docking Studies ◽  
Molar Ratio ◽  
Distorted Octahedral Geometry ◽  
X Ray Diffraction ◽  
Donor Ligand ◽  
X Ray ◽  
H Nmr ◽  
Distorted Octahedral ◽  
Ft Ir

The reaction between 2-[2-(aminoethyl)amino]ethanol and pyridine-2-carbaldehyde in a 1:2 molar ratio affords a mixture containing 2-({2-[(pyridin-2-ylmethylidene)amino]ethyl}amino)ethanol (PMAE) and 2-[2-(pyridin-2-yl)oxazolidin-3-yl]-N-(pyridin-2-ylmethylidene)ethanamine (POPME). Treatment of this mixture with copper(II) chloride or cadmium(II) chloride gave trichlorido[(2-hydroxyethyl)({2-[(pyridin-2-ylmethylidene)amino]ethyl})azanium]copper(II) monohydrate, [Cu(C10H16N3O)Cl3]·H2O or [Cu(HPMAE)Cl3]·H2O, 1, and dichlorido{2-[2-(pyridin-2-yl)oxazolidin-3-yl]-N-(pyridin-2-ylmethylidene)ethanamine}cadmium(II), [CdCl2(C16H18N4O)] or [CdCl2(POPME)], 2, which were characterized by elemental analysis, FT–IR, Raman and 1H NMR spectroscopy and single-crystal X-ray diffraction. PMAE is potentially a tetradentate N3O-donor ligand but coordinates to copper here as an N2 donor. In the structure of 1, the geometry around the Cu atom is distorted square pyramidal. In 2, the Cd atom has a distorted octahedral geometry. In addition to the hydrogen bonds, there are π–π stacking interactions between the pyridine rings in the crystal packing of 1 and 2. The ability of PMAE, POPME and 1 to interact with ten selected biomolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II and B-DNA) was investigated by docking studies and compared with doxorubicin.

Structural elucidation and study of intermolecular interactions in meso-tetratolylporphyrins

2016 ◽  
Vol 20 (07) ◽  
pp. 833-842
Author(s):  
Rahul Soman ◽  
Subramaniam Sujatha ◽  
Chellaiah Arunkumar
Keyword(s):  
Surface Analysis ◽  
Intermolecular Interactions ◽  
Crystal Packing ◽  
Crystal Structure Analysis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Axial Position ◽  
X Ray Diffraction ◽  
Synthesis And Crystal Structure ◽  
Porphyrin Core

Synthesis and crystal structure analysis of meso-tetratolylporphyrins, 1–5 combined with computational Hirshfeld surface analysis were investigated. The crystal packing of porphyrins 1, 3 and 4 are arranged in an “orthogonal fashion” whereas 2 and 5 are in a “slip-stack or off-set fashion” through various intermolecular interactions. Compound 2 exhibits saddle geometry whereas 5 showed a domed geometry as evident from the single crystal X-ray diffraction studies. The enhancement of non-planarity in 2 is probably due to the presence of numerous intermolecular interactions caused by the presence of trifluoroacetate anions on both faces of the porphyrin in addition to the bulky bromine groups at the [Formula: see text]-pyrrole positions. In 5, the non-planarity is merely due to the metal coordination at the porphyrin core as pentacoordinated Mn[Formula: see text] center with a chloro ligand in the axial position. Hirshfeld surface analysis was performed in order to analyze the various intermolecular interactions present in these porphyrins and the result was discussed.

Synthesis, crystal structure and studies on the interaction with albumin of a new silver(I) complex based on 2-(4-nitrobenzenesulfonamido)benzoic acid

2019 ◽  
Vol 75 (7) ◽  
pp. 1011-1020
Author(s):  
Lucius Flavius Ourives Bomfim Filho ◽  
Cleidivania Rocha ◽  
Bernardo Lages Rodrigues ◽  
Heloisa Beraldo ◽  
Leticia Regina Teixeira
Keyword(s):  
Hydrogen Bonds ◽  
Benzoic Acid ◽  
Crystal Packing ◽  
Linear Chain ◽  
X Ray Diffraction ◽  
H Nmr ◽  
Polymeric Chains ◽  
Ft Ir ◽  
Bridging Groups ◽  
2D Polymer

In the present work, the two-dimensional (2D) polymer poly[[μ4-2-(4-nitrobenzenesulfonamido)benzoato-κ4 O 1:O 1:O 1′:N 6]silver(I)] (AgL), [Ag(C13H9N2O6S)] n , was obtained from 2-(4-nitrobenzenesulfonamido)benzoic acid (HL), C13H10N2O6S. FT–IR, 1H and 13C{1H} NMR spectroscopic analyses were used to characterize both compounds. The crystal structures of HL and AgL were determined by single-crystal X-ray diffraction. In the structure of HL, O—H...O hydrogen bonds between neighbouring molecules result in the formation of dimers, while the silver(I) complex shows polymerization associated with the O atoms of three distinct deprotonated ligands (L −). Thus, the structure of the Ag complex can be considered as a coordination polymer consisting of a one-dimensional linear chain, constructed by carboxylate bridging groups, running parallel to the b axis. Neighbouring polymeric chains are further bridged by Ag—C monohapto contacts, resulting in a 2D framework. Fingerprint analysis of the Hirshfeld surfaces show that O...H/H...O hydrogen bonds are responsible for the most significant contacts in the crystal packing of HL and AgL, followed by the H...H and O...C/C...O interactions. The Ag...Ag, Ag...O/O...Ag and Ag...C/C...Ag interactions in the Hirshfeld surface represent 12.1% of the total interactions in the crystal packing. Studies of the interactions of the compounds with human serum albumin (HSA) indicated that both HL and AgL interact with HSA.

scholarly journals Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine

2022 ◽  
Vol 78 (2) ◽  
Author(s):  
Paulina Kalle ◽  
Sergei V. Tatarin ◽  
Marina A. Kiseleva ◽  
Alexander Yu. Zakharov ◽  
Daniil E. Smirnov ◽  
...  
Keyword(s):  
Water Molecule ◽  
Crystal Structures ◽  
Crystal Packing ◽  
Rotation Axis ◽  
Point Group ◽  
Group Symmetry ◽  
X Ray Diffraction ◽  
Hydrogen Atoms ◽  
H Nmr ◽  
Rotation Axes

The title compounds, 2-(4-methylphenyl)-1H-perimidine hemihydrate (1, C18H14N2·0.5H2O) and 1-methyl-2-(4-methylphenyl)-1H-perimidine (2, C19H16N2), were prepared and characterized by 1H NMR and single-crystal X-ray diffraction. The organic molecule of the hemihydrate lies on a twofold rotation axis while the water molecule lies on the intersection of three twofold rotation axes (point group symmetry 222). As a consequence, the hydrogen atoms that are part of the N—H group and the water molecule as well as the CH3 group of the p-tolyl ring are disordered over two positions. In compound 1, the perimidine and the 2-aryl rings are slightly twisted while its N-methylated derivative 2 has a more distorted conformation because of the steric repulsion between the N-methyl group and the 2-aryl ring. In the crystal structures, molecules of perimidine 2 are held together only by C—H...π contacts while the parent perimidine 1 does not exhibit this type of interaction. Its crystal packing is established by intermolecular N—H...O hydrogen bonds with the solvent water molecules and additionally stabilized by π–π stacking.

scholarly journals Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide

2021 ◽  
Vol 77 (2) ◽  
pp. 184-189
Author(s):  
Cong Nguyen Tien ◽  
Trung Vu Quoc ◽  
Dat Nguyen Dang ◽  
Giang Le Duc ◽  
Luc Van Meervelt
Keyword(s):  
Title Compound ◽  
Crystal Packing ◽  
Asymmetric Unit ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Hydrogen Bonding Interactions ◽  
Hirshfeld Analysis ◽  
Phenyl Rings ◽  
C Nmr

The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide, C24H21NO4, was prepared from reaction of N-(4-methoxyphenyl)-2-chloroacetamide and (E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one, which was obtained from the reaction of 4-hydroxybenzaldehyde and acetophenone. The structure of the title compound was determined by IR, 1H-NMR, 13C-NMR and HR–MS spectroscopic data and further characterized by single-crystal X-ray diffraction. The asymmetric unit contains four molecules, each displaying an E-configuration of the C=C bond. The dihedral angle between the phenyl rings in each molecule varies between 14.9 (2) and 45.8 (2)°. In the crystal, C—H...O hydrogen-bonding interactions link the molecules into chains running along the [001] direction. In addition, C—H...π interactions further stabilize the crystal packing. A Hirshfeld analysis indicates that the most important contributions to the surface contacts are from H...H (43.6%), C...H/H...C (32.1%) and O...H/H...O (18.1%) interactions.

Polysulfonylamine Polysulfonylamine, CXXXVIII [1], 1.1-Di(organosu!fonyl)-3,3-diorganylharnstoffe: Synthese von acht Vertretern und Kristallstruktur des Prototyps (MeSO2)2N-C(O)-NMe2 / Polysulfonylamines, CXXXVIII [1]. 1.1-Di(organosulfonyl)-3,3-diorganylureas: Synthesis of Eight Representatives and Crystal Structure of the Prototype (MeSO2)2N-C(O)-NMe2

2001 ◽  
Vol 56 (7) ◽  
pp. 680-688 ◽  
Author(s):  
Jörg Dalluhn ◽  
Hans-Heinrich Pröhl ◽  
Armand Blaschette ◽  
Peter G. Jones
Keyword(s):  
Crystal Packing ◽  
Three Dimensional ◽  
Acetonitrile Solution ◽  
X Ray Diffraction ◽  
Dimethylamino Group ◽  
Triclinic Space Group ◽  
H Nmr ◽  
Dimensional Network ◽  
Electrophilic Activation ◽  
High Degree

Eight compounds of the type (RSO2)2N-C(O)-NR'2 , where R = Me or 4-tolyl and R' = Me, Et, iPr or Ph, were obtained in good yields by treating the corresponding carbamoyl chlorides R'2NC(0)C1 with silver salts AgN (SO2R)2 in acetonitrile solution. The pronounced sensitivity of the compounds towards atmospheric moisture is indicative of a high degree of electrophilic activation at the carbonyl centre; bulk hydrolysis rapidly leads to carbon dioxide and the corresponding ammonium salt R'2NH+2'N (SO2R)2. In the 1H and 13C NMR solution spectra, the R4N groups of the ureas give rise to distinct R' resonances at room temperature, reflecting unusually high barriers to rotation about the C(O)-NR'2 bonds. For ( MeSO2)2N-C(O)-NMe2 (1a) and the analogous ditosyl compound, the 1H NMR signals of the dimethylamino group were found to coalesce at 107 °C and 93 °C, respectively, which corresponds to a rotational barrier of ⊿G#c ≈ 80 kJ mol-1. In the crystal of la (triclinic, space group P1̄, Z = 2; X-ray diffraction at -75 °C), the molecule possesses an essentially planar Me2N-C(O)-N moiety (except H atoms), whereas the C-NS2 grouping is pyramidalized to such an extent that N lies 27.8(2) pm out of the plane defined by the carbonyl C atom and the two sulfonyl S atoms [S-N-S 120.52(11)°, C-N-S 115.73(14) and 115.06(14)°]. The most remarkable features of the molecular structure are the exceedingly long C(O)-NS2 bond [148.6(3) pm] and the concomitantly short C-O and C(O)-NC2 bonds [121.4(3) and 132.2(3) pm]. The crystal packing of la is governed by a three-dimensional network of nine intermolecular C-H···O hydrogen bonds originating from the activated M e-S and M e -N donor groups (H···O 230-266 pm, C-H···O 123-173°).

scholarly journals Crystal structure of (E)-4-nitro-2-(((3-(tetrahydro-8λ4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxaborol-8-yl)phenyl)imino)methyl)phenol – water (1/2), C17H18BN3O5·2H2O

2016 ◽  
Vol 231 (1) ◽  
pp. 89-91
Author(s):  
Chunhua Ge ◽  
Juanjuan Liu ◽  
Zhe Xü ◽  
Yang Zhang ◽  
Xiangdong Zhang
Keyword(s):  
Crystal Structure ◽  
Nitrogen Atom ◽  
Carbon Atom ◽  
Boron Atom ◽  
Crystal Structure Analysis ◽  
Coordination Bond ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Phenol Water

AbstractThe title compound has been synthesized and characterized by IR, 1H NMR, elemental analysis as well as single crystal X-ray diffraction techniques. Crystal structure analysis reveals that the boron atom is tetrahedrally bonding with one carbon atom, one nitrogen atom, and two oxygen atoms. The bond between nitrogen atom and boron atom is a coordination bond.

scholarly journals Crystal structure of (R)-5-[(R)-3-(4-chlorophenyl)-5-methyl-4,5-dihydroisoxazol-5-yl]-2-methylcyclohex-2-enone

2020 ◽  
Vol 76 (3) ◽  
pp. 400-403
Author(s):  
Ali Oubella ◽  
My Youssef Ait Itto ◽  
Aziz Auhmani ◽  
Abdelkhalek Riahi ◽  
Jean-Claude Daran ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Column Chromatography ◽  
Title Compound ◽  
Crystal Packing ◽  
Three Dimensional ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Compound C ◽  
Dimensional Network

The title compound, C17H18ClNO2, was prepared and isolated as a pure diastereoisomer, using column chromatography followed by a succession of fractional crystallizations. Its exact structure was fully identified via 1H NMR and confirmed by X-ray diffraction. It is built up from a central five-membered dihydroisoxazole ring to which a p-chlorophenyl group and a cyclohex-2-enone ring are attached in the 3 and 5 positions. The cyclohex-2-one and isoxazoline rings each exhibit an envelope conformation. The crystal packing features C—H...O, C—H...N and C—H...π interactions, which generate a three-dimensional network.

scholarly journals Crystal structure of (E)-4-hydroxy-6-methyl-3-{1-[2-(4-nitrophenyl)hydrazinylidene]ethyl}-2H-pyran-2-one

2017 ◽  
Vol 73 (2) ◽  
pp. 223-226 ◽  
Author(s):  
Kirandeep ◽  
Ahmad Husain ◽  
Pooja Negi ◽  
Girijesh Kumar ◽  
Ramesh Kataria
Keyword(s):  
Single Crystal ◽  
Crystal Packing ◽  
Molar Ratio ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Dehydroacetic Acid ◽  
Compound C ◽  
Ft Ir ◽  
C Nmr

The title compound, C14H13N3O5(HMNP), was synthesized by the simple condensation ofp-nitrophenylhydrazine with dehydroacetic acid (DHA) in a 1:1 molar ratio in ethanol. HMNP has been characterized by using FT–IR,1H and13C NMR and UV–Vis spectroscopic and single-crystal X-ray diffraction techniques. The crystal packing reveals strong hydrogen bonds between the NH group and the carbonyl O atom of dihydropyranone moiety, forming chains along [101]. The thermal stability of the synthesized compound was confirmed by thermogravimetric analysis and it was found to be stable up to 513 K. The UV–Vis spectrum shows the presence of a strong band at λmax394 nm.1H NMR and single-crystal X-ray analyses confirmed the presence of theenolform of the ligand and dominance over theketoform. The crystal studied was a non-merohedral twin with the refined ratio of the twin components being 0.3720 (19):0.6280 (19).

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