The 2:1 cocrystal of benzamide and pentafluorobenzoic acid.
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Biomedical subjects
Maria Gdaniec
Publications and source records attributed to Maria Gdaniec.
2,2',3,3',4,4',5,5',6,6'-Decafluorodiphenylamine and its 1:1 cocrystal with diphenylamine.
In the structures of decafluorodiphenylamine, C(12)HF(10)N, and its 1:1 cocrystal with diphenylamine, C(12)HF(10)NxC(12)H(11)N, the molecules are located on special positions of C(2) symmetry. The NH groups are not involved in hydrogen bonding and the usual face-to-face stacking interactions between phenyl and pentafluorophenyl rings are not observed in the cocrystal.
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Synthesis and in vitro anti-tumor activity of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides.
A series of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides (2a-z) was obtained by reacting 6,7-dihydro-1H-imidazo[2,1-c][1,2,4]thiadiazol-3-thione (1) with arylsulfonyl chlorides. The relationships between structure and anti-tumor activity revealed that compound 2o with p-Cl substituent at the phenyl ring was most active (-log GI50>8.00, -log TGI=7.66) and was found to exhibit high selectivity toward the leukemia CCRF-CEM cell line (Deltaf=3.08 and 3.31, respectively).
Antineoplastic Agents↗
Synthesis, crystal structure and biological activities of copper(II) complexes with chelating bidentate 2-substituted benzimidazole ligands.
A series of Cu(II) coordination compounds with benzimidazole-derived bidentate chelating ligands have been prepared and characterized by X-ray crystallography. The 2-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazole CuCl2 complex 8 showed very potent superoxide dismutase (Cu,Zn-SOD) activity in vitro with IC50 of 0.09 microM, comparable to those described in the literature for best low molecular weight CuZnSOD mimics. Cytotoxicity studies with seven different human tumor cell lines in vitro showed that the most active 2-(4,5-dihydro-1H-imidazol-2-yl)-5-nitro-1H-benzimidazole CuCl2 complex 10 inhibited the growth of cancer cells with IC50 between 4.76 and 10.84 microM.
Antineoplastic Agents↗
Anion-pi interactions in cyanuric acids: a combined crystallographic and computational study.
Several structures of pi complexes of isocyanuric acid and of several thio derivatives with anions have been computed by using high level ab initio calculations. The nature of the complexes has been studied by means of the method of molecular interaction potential with polarization (MIPp) and Bader's theory of atoms-in-molecules. These molecules form favorable complexes with anions and can be used as binding units for building receptors for the molecular recognition of anions. In several cases, the anion-pi interaction has been demonstrated experimentally by means of X-ray crystallography.
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Synthesis, molecular structure, and in vitro antitumor activity of new 4-chloro-2-mercaptobenzenesulfonamide derivatives.
The reaction of 3-amino-2-(2-alkylthio-4-chlorobenzenesulfonyl)guanidines 2a-j with 1,2-dicarbonyl compounds are described. Depending on structure of 1,2-dicarbonyl reagent novel 2-alkylthio-5-chloro-N-(1,2,4-triazin-3-yl)benzenesulfonamides 3-15, 1-(2-alkylthio-4-chlorobenzenesulfonyl)-3-(2-oxobutane-3-ylidenoimino)guanidines 16-18 and 2-alkylthio-4-chloro-N-(1,2-dihydroxycyclobuta[e]1,2,4-triazin-3-yl)benzenesulfonamides 19-21 are obtained. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data and X-ray analysis. The compounds 4, 5, 7, 9, 10, 12-15, 17, 18 and 20 were screened at the National Cancer Institute (NCI) for their in vitro activities against a panel of 56 tumor cell lines and relationship between structure and antitumor activity are discussed. The compounds 10, 12, 17 and 20 were inactive, whereas the other compounds exhibited reasonable activity against one or more human tumor cell lines. The prominent compound 18 showed significant activity against cell lines of colon cancer (HCT-116), renal cancer (786-0) and melanoma (M14) (GI50 in the range 0.33-1.08 microM) as well as good selectivity toward non-small cell lung cancer (HOP-62) cells (GI50 = 0.05 microM, TGI = 0.38 microM and LC50 = 4.83 microM).
Antineoplastic Agents↗
Synthesis of 2,3,5,6-tetrahydro-3H-imidazo[2,1-b] [1,3,5]benzotriazepines and their oxidative ring contraction into 1-(4,5-dihydro-1H-imidazol-2-yl)-1H-benzimidazoles.
Syntheses of novel 5-aryl-2,3,5,6-tetrahydro-3H-imidazo[2,1-b] [1,3,5]benzotriazepine derivatives 3a-g were performed by reacting 2-(2-aminoarylimino)imidazolidines 1a-b with corresponding aryl aldehydes. The compounds 3 incorporating aminal group upon treatment with 2,3-dichloro-5,6-dicyano-1,2-benzoqinone (DDQ) underwent the oxidative ring contraction to give 1-(4,5-dihydro-1H-imidazol-2-yl)-2-aryl-benzimidazoles 4a-g. Reactions of the compounds 1a-c with carbonyldiimidazole (CDI) afforded novel 2,3,5,6-tetrahydro-1H-imidazo[2,1-b] [1,3,5]benzotriazepin-5-ones 5a-c which when heated in boiling methanol gave the corresponding 1-(4,5-dihydro-1H-imidazol-2-yl)-1,3-dihydro-2H-benzimidazol-2-ones 6a-c. Radioligand binding studies using rat central imidazoline I2 receptors and alpha2-adrenoceptors demonstrated that benzimidazoles 4a-g display a low affinity (microM) for these receptors while benzimidazol-2-ones 6a-b elicited a moderate affinity for I2 receptor with Ki values of 490 and 220 nM, respectively.
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Synthesis, antiviral, and anti-HIV-1 integrase activities of 3-aroyl-1,1-dioxo-1,4,2-benzodithiazines.
HIV-1 integrase (IN) is an essential enzyme for effective viral replication and is an attractive target for selective blockade of viral infection. Previously, we identified a series of sulfones, sulfonamides, and mercaptosalicylhydrazides (MBSAs) as IN inhibitors with antiviral activities in cell-based assays. In an effort to optimize a series of our active site directed lead compounds, we designed and synthesized novel benzodithiazines starting from MBSAs. In contrast to all reported IN inhibitors benzodithiazines are essentially nontoxic. Significant antiviral potency was only observed at concentration exceedingly higher than that required to inhibit purified IN.
Anti-HIV Agents↗
Synthesis, X-ray crystal structures, stabilities, and in vitro cytotoxic activities of new heteroarylacrylonitriles.
Twenty-three acrylonitriles, substituted at position 2 with either triazoles or benzimidazoles and at position 3 with various substituted furan, thiophene, or phenyl rings, were prepared by Knoevenagel condensation and tested for in vitro cytotoxic potency on 11 human cancer cell lines. X-ray crystal analysis of two representative compounds showed that the olfenic bond is E-configured. Structure-activity-relationships (SAR) indicated that position 2 is flexible for substituents with various nitrogen heterocyclics while position 3 is very sensitive to change; the most potent compounds contained a 5-nitrothiophen-2-yl ring at position 3 and either benzimidazol-2-yl (11) or a 5-benzyl-1H-[1,2,4]-triazol-3-yl (7) group at position 2 of acrylonitrile. SARs for the thiophen-2-yl-benzimidazoles show the following trend for position 5: NO2 >> H > Cl = CH3. Compound 11 was on average 10- and 3-fold more potent than cisplatin and etoposide, respectively. However, the acrylonitrile functionality is not an absolute requirement for cytotoxic activity because replacement of the nitrile group for either a hydrogen or a methyl group also gave active compounds. The acrylonitriles caused delayed cell death characterized by giant cells with multilobed nuclei. Compound 11 was found to bring about the increase in the activities of caspases 3 and 9 in the HL-60 cell line in a manner similar to etoposide, strongly indicating that apoptosis is the mechanism of cell death. The selectivity of various compounds toward cancer cells was estimated by comparing the IC50 values obtained from a noncancerous epithelial cell line, h-TERT-RPE1, with the average IC50 value from the cancer cell lines; 11 showed an average 1.7-fold greater activity toward cancer cells. The stabilities of the new compounds under cell culture conditions, estimated by HPLC, indicated that a major fraction of the compounds were lost from the medium over the first 24 h.
Acrylonitrile↗
Hetero di- and trinuclear Cu-Gd complexes with trifluoroacetate bridges: synthesis, structural and magnetic studies.
The synthesis, structural determinations and magnetic properties of an original dinuclear Cu-Gd and two trinuclear Cu-Ln-Cu complexes (Ln = Gd or Dy) made with a Schiff base ligand and carboxylate ligands are reported. In each complex, the copper and gadolinium or dysprosium ions are linked by a double phenoxo bridge and a eta1:eta1:mu trifluoroacetato bridge. The dinuclear Cu-Gd complex exhibits the usual ferromagnetic interaction while the trinuclear (Cu-Gd-Cu) complexes can not be fitted with a simple Hamiltonian that only takes into account the Cu-Gd interaction. Introduction into the Hamiltonian of a Cu-Cu interaction between the terminal copper ions gives a nice fit in the case of a ferromagnetic Cu-Cu interaction (J'(Cu-Cu) = 8.3 and 9.8 cm(-1)). For the first time, the occurrence of a ferromagnetic interaction between the copper ions of the trinuclear entities is evidenced and supported by the field dependence of the magnetization. As there is no direct proof for the existence of an interaction between two centers through a third magnetic center located in between them, we can conclude that the existence of pi-pi stacking interactions through the phenyl rings of the ligands are responsible for the presence of these interactions.
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Planar chiral dianthranilide and dithiodianthranilide molecules: optical resolution, chiroptical spectra, and molecular self-assembly.
Planar chiral dianthranilide (1) was resolved to enantiomers with use of (-)-(1S,4R)-camphanoyl chloride as a chiral derivatizing agent. The (+)-1 enantiomer was assigned the S absolute configuration from the X-ray crystal structure of its N,N'-dicamphanoyl derivative. Optical resolution of dithionodianthranilide (2) was accomplished by inclusion crystallization with (R,R)-1,2-diaminocyclohexane, and the X-ray structure of the corresponding adduct revealed the (-)-2stereoisomer has the R configuration. A slow boat-to-boat ring inversion (DeltaG(++) = 24.1 +/- 0.1 kcal mol(-1)) causes racemization of (+)-1 in solution as manifested by a gradual decrease of the CD spectrum whereas, (-)-2 is configurationally stable at these conditions. The analysis of the CD spectra of the title compounds showed that the n-pi* Cotton effect signs are determined by the helicity of the skewed benzamide and thiobenzamide chromophores. The solid-state structures of the racemic and homochiral forms of 1 and 2 show different self-assembly patterns: the racemate (+/-)-1 prefers the cyclic R(2)(2)(8) hydrogen bond motif, whereas the crystalline DMSO solvates of (+/-)-1 and (+)-1 consist of 1D homochiral hydrogen-bonded assemblies generated by the C(6) motif. In the case of dithionolactams (+/-)-2 and (-)-2 two types of 1D networks were observed: in the racemate they are generated by the centrosymmetric R(2)(2)(8) and R(2)(2)(12) hydrogen bond motifs, whereas the molecules in the homochiral crystals are connected solely with use of the strongly nonplanar R(2)(2)(8) motif.
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N,N'-Bis(2-pyridyl)benzene-1,2-diamine.
Hindered rotation about the partial double C-N bonds between the amine and pyridine moieties in the title molecule, C16H14N4, results in two different conformations of the N-aryl-2-aminopyridine units. One, assuming an E conformation, is involved in a pair of N-H...N hydrogen bonds that generate a centrosymmetric R2(2)(8) motif. The second, adopting a Z conformation, is not engaged in any hydrogen bonding and is flattened, the dihedral angle between the benzene and pyridine rings being 12.07 (7) degrees. This conformation is stabilized by an intramolecular C-H...N interaction [C...N = 2.9126 (19) A, H...N = 2.31 A and C-H...N = 120 degrees ].
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2,4,6-Trimethylbenzamide.
The crystal structure of the title compound, C(10)H(13)NO, displays an infinite one-dimensional network composed of primary amide molecules connected by N-H...O[double bond]C hydrogen bonds involving the anti NH amide H atoms, thus generating a C(4) motif. This network is additionally stabilized by a weak N-H...pi interaction between the syn-oriented amide H atom and the aromatic ring of a neighbouring molecule. The distance between the H atom and the ring centroid is 2.50 A. The amide group and the aryl moiety are nearly perpendicular, forming an intramolecular dihedral angle of 84.69 (6) degrees.
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2-Amino-6-(1-imidazolylmethyl)-4-(3,5,5-trimethyl-2-pyrazolin-1-yl)-1,3,5-triazine and 2-amino-6-(1-benzimidazolylmethyl)-4-(3,5,5-trimethyl-2-pyrazolin-1-yl)-1,3,5-triazine hemihydrate.
The two title compounds, C(13)H(18)N(8) and C(17)H(20)N(8).0.5H(2)O, possess similar molecular shapes, with the pyrazoline moiety and s-triazine ring located approximately in one plane, and the imidazole or benzimidazole ring nearly perpendicular to the s-triazine nucleus. In both crystal structures, despite there being a large number of accessible hydrogen-bond acceptor sites, only one H atom from the NH(2) group is involved in hydrogen bonding; the molecules are assembled into discrete centrosymmetric dimers via a pair of nearly linear N-H.N hydrogen bonds.
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Supramolecular assemblies of hydrogen-bonded carboxylic acid dimers mediated by phenyl-pentafluorophenyl stacking interactions.
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Synthesis, structural characterization and in vitro antitumor activity of novel 6-chloro-1,1-dioxo-1,4,2-benzodithiazie derivatives.
A series of nonconventional aminium N-(6-chloro-7-R-1,1-dioxo-1,4,2-benzodithiazin-3-yl)arylsulfonamidates 7-15 have been synthesized by the reactions of 6-chloro-7-R-3-methylthio-1,4,2-benzodithiazine 1,1-dioxides with 4-dimethylaminopyridine or Et(3)N and some arylsulfonamides. The free N-(6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazin-3-yl)benzenesulfonamides 16-18 were obtained by treatment of their aminium salts with H(2)SO(4) in boiling acetic acid. The in vitro antitumor activity of the compounds 9, 11-14 and 16-18 has been tested in the antitumor screening of the National Cancer Institute (NCI), and relationships between structure and antitumor activity are discussed. 4-Dimethylaminopyridinium 4-chloro-N-(6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazin-3-yl)benzenesulfonamidate 9 is the prominent of the compounds due to its remarkable activity (log GI(50)<-8.00, log TGI=-5.50) and selectivity for the leukemia SR cell line. For that reason experimental and theoretical analysis of the geometric and electronic properties of 9 was carried out.
Antineoplastic Agents↗
Synthesis, molecular structure, and applications of 2-hydroxylamino-4,5-dihydroimidazolium-O-sulfonate to the synthesis of novel heterocyclic ring systems.
2-hydroxylamino-4,5-dihydroimidazolium-O-sulfonate (1) has been prepared by reacting 2-chloro-4,5-dihydroimidazole with hydroxylamine-O-sulfonic acid. Deprotonated compound 1a containing both the nucleophilic endocyclic nitrogen atoms and electrophilic exocyclic nitrogen was used for the syntheses of 3-substituted 6,7-dihydro-5H-imidazo[2,1-c][1,2,4]oxadiazoles 2-9 and 6,7-dihydro-5H-imidazo[2,1-c][1,2,4]thiadiazole-3-thione (10) by tandem nucleophilic addition-electrophilic amination reaction. The method promises utility in the synthesis of a variety of other heterocycles. On the other hand, the convenient routes to 7,8-dihydroimidazo[1,2-c][1,3,5]thiadiazine-2,4(6H)-dithione (16) and 2,6,7,8-tetrahydroimidazo[1,2-a][1,3,5]triazine-4(3H)-thione derivative (17) are reported starting from compound 1. The structures of the compounds prepared were established by elemental analyses, IR, NMR, and MS spectra, and in some instances X-ray analyses.
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Creation of hydrogen bonded 1D networks by co-crystallization of N,N'-bis(2-pyridyl)aryldiamines with dicarboxylic acids.
The preparation and crystal structures of fourteen complexes of N,N'-bis(2-pyridyl)aryldiamines with dicarboxylic acids and two complexes with squaric acid are reported. The recognition between the carboxylic acids and the 2-aminopyridine units occurs through the formation of the cyclic R(2)2 (8) hydrogen bond motif, whereas squaric acid creates the analogous R(2)2 (9) motif. In the 1:1 complexes the cyclic motifs generate infinite hydrogen-bonded 1D networks with the alternating component molecules. These networks are further organised into densely packed layers assembled through weaker C-H...O interactions. Analysis of the intermolecular interactions in these complexes led us to the synthesis of N,N'-bis(2-pyridyl)-2,2'-oxybis(aminobenzene) (5) which acts as a tritopic receptor of the carboxylic group and forms exclusively 2:1 complexes with dicarboxylic acids.
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