Crystal structures of four thio-glycosides involving carbamimido-thio-ate groups.

The compounds 2',3',4',6'-tetra--acetyl-β-d-gluco-pyranosyl '-cyano--phenyl-carbamimido-thio-ate (CHNOS, ), 2',3',4',6'-tetra--acetyl-β-d-galacto-pyranosyl '-cyano-phenyl-carbamimido-thio-ate, (CHNOS, ), 2',3',4',6'-tetra--acetyl-β-d-galacto-pyranosyl '-cyano--methyl-carbamimido-thio-ate (CHNOS, ), and 2',3',4',6'-tetra--acetyl-β-d-galacto-pyranosyl '-cyano---tolyl-carbamimido-thio-ate (CHNOS, ) all crystallize in 222 with = 4. For all four structures, the configuration across the central (formal) C=N(CN) double bond of the carbamimido-thio-ate group is . The torsion angles C5-O1-C1-S (standard sugar numbering) are all close to 180°, confirming the β position of the substituent.

Novel synthesis of the first new class of triazine sulfonamide thioglycosides and the evaluation of their anti-tumor and anti-viral activities against human coronavirus.

Novel class of triazine sulfonamide thioglycosides was designed and synthesized. Those novel structures comprising three essential and pharmacological significant moieties such as the triazine, sulfonamide, and thioglycosidic scaffolds. The triazine sulfonamides were furnished a direct approach starting from potassium cyanocarbonimidodithioate, then the corresponding triazine sulfonamide thioglycosides were generated using the peracylated -d-- and galacto-pyranosyl bromides.

Design and synthesis of novel 1,3,4-thiadiazole thioglycosides as promising antimicrobial potent structures.

Thiosemicarbazide was used as a key starting material for the building of a diversity of novel heterocyclic moieties. The heterocyclization reaction of thiosemicarbazide derivatives with carbon disulfide in basic conditions afforded novel heterocyclic 1,3,4-thiadiazolethiolate derivatives. 1,3,4-thiadiazole-2-thiol was successfully reacted with protected α-D-gluco- and galacto-pyranosyl bromides in dimethylformamide at room temperature to give the matching 1,3,4-thiadiazole -glycosides in good yields.

Crystal structure of ()--(4-bromo-phen-yl)-2-cyano-3-[3-(2-methyl-prop-yl)-1-phenyl-1-pyrazol-4-yl]prop-2-enamide.

The structure of the title compound, CHBrNO, contains two independent mol-ecules connected by hydrogen bonds of the type N-H⋯N≡C to form a dimer. The configuration at the exocyclic C=C double bond is . The mol-ecules are roughly planar except for the isopropyl groups.

Synthesis and crystal structure of -phenyl-2-(phenyl-sulfan-yl)acetamide.

-Phenyl-2-(phenyl-sulfan-yl)acetamide, CHNOS, was synthesized and structurally characterized. In the crystal, N-H⋯O hydrogen bonding leads to the formation of chains of mol-ecules along the [100] direction. The chains are linked by C-H⋯π inter-actions, forming a three-dimensional network.

Crystal structure of 2,4-di-amino-5-(4-hy-droxy-3-meth-oxy-phen-yl)-8,8-dimethyl-6-oxo-6,7,8,9-tetra-hydro-5-chromeno[2,3-]pyridine-3-carbo-nitrile-di-methyl-formamide-water (1/1/1).

In the structure of the title compound, CHNO·CHNO·HO, the entire tricyclic system is approximately planar except for the carbon atom bearing the two methyl groups; the meth-oxy-phenyl ring is approximately perpendicular to the tricycle. All seven potential hydrogen-bond donors take part in classical hydrogen bonds. The main mol-ecule and the DMF combine to form broad ribbons parallel to the axis and roughly parallel to the plane; the water mol-ecules connect the residues in the third dimension.

Novel synthesis of new triazine sulfonamides with antitumor, anti-microbial and anti-SARS-CoV-2 activities.

Novel approach for synthesizing triazine sulfonamide derivatives is accomplished via reacting the sulfaguanidine derivatives with N-cyanodithioiminocarbonate. Further reaction of the novel triazine sulfonamide analogues with various secondary amines and anilines generated various substituted triazine sulfonamide analogues of promising broad-spectrum activities including anti-microbial, anti-tumor, and anti-viral properties. The in vitro anti-proliferative activities of most of the novel compounds were evaluated on the NCI-60 cell line panel.

Crystal structure of 4-(benzo[]thia-zol-2-yl)-1,2-dimethyl-1-pyrazol-3(2)-one.

In the title compound, CHNOS, the inter-planar angle between the pyrazole and benzo-thia-zole rings is 3.31 (7)°. In the three-dimensional mol-ecular packing, the carbonyl oxygen acts as acceptor to four C-H donors (with one H⋯O as short as 2.

An unexpected tautomer: synthesis and crystal structure of -[6-amino-4-(methyl-sulfan-yl)-1,2-di-hydro-1,3,5-triazin-2-yl-idene]benzenesulfonamide.

The title compound, CHNOS, consists of an unexpected tautomer with a protonated nitro-gen atom in the triazine ring and a formal exocyclic double bond C=N to the sulfonamide moiety. The ring angles at the unsubstituted nitro-gen atoms are narrow, at 115.57 (12) and 115.

Crystal structure of 2-[(5-amino-1-tosyl-1-pyrazol-3-yl)-oxy]-1-(4-meth-oxy-phen-yl)ethan-1-one 1,4-dioxane monosolvate.

In the structure of the title compound, CHNOS·CHO, the two independent dioxane mol-ecules each display inversion symmetry. The pyrazole ring is approximately parallel to the aromatic ring of the oxy-ethanone group and approximately perpendicular to the tolyl ring of the sulfonyl substituent. An extensive system of classical and 'weak' hydrogen bonds connects the residues to form a layer structure parallel to (201), within which dimeric subunits are conspicuous; neighbouring layers are connected by classical hydrogen bonds to dioxanes and by 'weak' hydrogen bonds from H donors.

Naphthyl cyanoketene ,-acetals in glycoside synthesis: a new preparative route to a new class of -naphthylcyanoacrylamide thioglycosides and their conversions to naphthyl-pyrazole hybrids.

The novel -naphthylcyanoacrylamide thioglycosides were readily prepared by the reaction of -napthylcyanoacetamide with aryl isothiocyanates in the presence of potassium hydroxide, followed by coupling of the produced salts with 2,3,4,6-tetra--acetyl-α-d-gluco- and galacto-pyranosyl bromides . The -naphthyl acrylamide thioglycoside was prepared by the reaction of -napthylcyanoacetamide with glucose isothiocyante in the presence of potassium hydroxide, followed by alkylation of the produced salt with methyl iodide. The reaction of thioglycoside compounds with hydrazines afforded the corresponding naphthyl-pyrazole hybrids.

Synthesis and Biological Evaluation of Benzothiazolyl-pyridine Hybrids as New Antiviral Agents against H5N1 Bird Flu and SARS-COV-2 Viruses.

A novel series of benzothiazolyl-pyridine hybrids - and - were produced from the reaction of enamine derivative with each of the arylcyanoacetamides - and cyanoacetohydrazides -. The new products were characterized by spectral techniques (IR, H NMR, C NMR, and MS). Biological evaluation of - and - in against H5N1 and SARS-COV-2 viruses showed that several compounds had significant activity.

Crystal structure of 2-{[5-(methyl-sulfan-yl)-4-phenyl-4-1,2,4-triazol-3-yl]meth-yl}benzo[]thia-zole.

In the structure of the title compound, CHNO, the triazole ring exhibits inter-planar angles of 63.86 (2) and 76.96 (2)° with the phenyl and benzo-thia-zole planes, respectively.

Crystal structure of 5-(β-d-gluco-pyran-osyl-thio)--(4-methyl-phen-yl)-1,3,4-thia-diazol-2-amine.

In the structure of the title compound, CHNOS, the bond lengths at the linking sulfur atom are significantly different [1.7473 (17) and 1.811 (2) Å], and the angle at the exocyclic nitro-gen atom is wide at 128.

Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations.

This study revealed the design and preparation of new 3-(benzo[]thiazol-2-yl)-2-chromen-2-one derivatives . The structures of the synthesized products were elucidated by their spectroscopic data and X-ray crystallography for compounds and . The prepared new compounds were measured for their fluorescence, and a good result indicated that the emission efficiency was decreased by increasing the electron-withdrawing groups from the unsubstituted compound to the highly substituted derivative (2 Br heavy atoms).

Crystal structure of 3-(benzo[]thia-zol-2-yl)-6-methyl-2-chromen-2-one.

The mol-ecule of the title compound, CHNOS, is almost planar, with an inter-planar angle of 3.01 (3)° between the benzo-thia-zole and chromene ring systems. A short intra-molecular S⋯O=C contact of 2.

Crystal structure of -[3-(benzo[]thia-zol-2-yl)-6-bromo-2-chromen-2-yl-idene]-4-methyl-benzenamine.

The title compound, CHBrNOS, was the unexpected product in an attempted synthesis of the isomeric 3-(benzo[]thia-zol-2-yl)-6-bromo-1--tolyl-quinolin-2(1)-one. The C=N-C angle is wide [125.28 (8)°].

Crystal structures of three homologues with increasing ring size: 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8-tetra-hydro-quinoline-3-carbo-nitrile, 2-meth-oxy-4-(thio-phen-2-yl)-6,7,8,9-tetra-hydro-5-cyclo-hepta-[]pyridine-3-carbo-nitrile and 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8,9,10-hexa-hydrocyclo-octa[]pyridine-3-carbo-nitrile.

The title compounds, CHNOS (), CHNOS (), and CHNOS (), form a homologous series in which the size of the saturated ring increases from six- to eight-membered (with four, five and six methyl-ene groups respectively). For and , the central (CH) moieties are all displaced to the same side of their ring, and the CH-CH-CH angles are much wider than the standard value; a database search indicates that these are general features of such ring systems. For , the thio-phene ring lies with the sulfur atom on the opposite side of the C-C bond to the cyano group, in contrast to and .

Synthesis, Physicochemical Properties and Molecular Docking of New Benzothiazole Derivatives as Antimicrobial Agents Targeting DHPS Enzyme.

The drug-resistance problem is widely spread and becoming more common in community-acquired and nosocomial strains of bacteria. Therefore, finding new antimicrobial agents remains an important drug target. From this perspective, new derivatives of benzothiazole were synthesized and evaluated for their antimicrobial activity and ability to inhibit the DHPS enzyme.

3-(Benzo[]thia-zol-2-yl)-2-chromen-2-one.

In the title compound, CHNOS, the inter-planar angle is 6.47 (6)°. An intra-molecular S⋯O=C contact of 2.

4-Amino-5-(4-bromo-benzo-yl)-3-(benzo[]thia-zol-2-yl)-2-[(2',3',4',6'-tetra--acetyl-β-d-galacto-pyran-osyl-)sulfanyl]-thio-phene.

In the title compound, CHBrNOS, the benzo-thia-zole and thio-phene ring systems subtend an inter-planar angle of 7.43 (12)°. The NH group forms intra-molecular hydrogen bonds to N and O.

Medicinal Chemistry of Pyrazolopyrimidine Scaffolds Substituted with Different Heterocyclic Nuclei.

Background: Medicinal chemistry of pyrazolopyrimidine scaffolds substituted with different heterocyclic nuclei has attracted great attention due to their wide range of biological activities that have been reported. Pyrazolopyrimidine scaffold is an important privileged heterocycle nucleus in drug discovery.

Methods: All pharmacological activities of pyrazolopyrimidine scaffold have been mentioned, such as anticancer, anti-inflammatory, antihypertensive, antitubercular, antiviral, antibacterial, antifungal, antidiabetic, and anti-obesity agents.

Novel Thiophene Thioglycosides Substituted with the Benzothiazole Moiety: Synthesis, Characterization, Antiviral and Anticancer Evaluations, and NS3/4A and USP7 Enzyme Inhibitions.

Novel derivatives of benzothiazole-2-thiophene -glycoside were synthesized and tested for their antiviral and anticancer potency and NS3/4A and USP7 enzyme inhibitions. The ring system was formed by first synthesizing new derivatives of 5-mercaptothiophene substituted with the benzothiazole moiety, followed by coupling with various halo sugar derivatives. New compounds were tested in vitro for the cytotoxic effect on five types of normal cell lines and for antiviral activity using a plaque reduction assay against CBV4, HSV-1, HCVcc genotype 4 viruses, HAV HM 175, and HAdV7.

Crystal structure of 2-amino-5,6,7,8-tetra-hydro-7,7-dimethyl-4-(naphthalen-2-yl)-5-oxo-4-chromene-3-carbo-nitrile.

In the title compound, CHNO, both six-membered rings of the fused heterocyclic system display envelope conformations; the two carbon atoms bearing the methyl groups and the naphthyl substituent both lie outside the planes of the other atoms of each ring. In the crystal, the amino group forms hydrogen bonds of the types N-H⋯O=C and N-H⋯N≡C, leading to the formation of a double layer structure propagating parallel to the plane. Weak C-H⋯O and C-H⋯π inter-actions may reinforce the layers.

Purine analogs: synthesis, evaluation and molecular dynamics of pyrazolopyrimidines based benzothiazole as anticancer and antimicrobial CDK inhibitors.

Cyclin dependent kinases (CDKs) enzymes regulate cell proliferation and transcriptional processes and can be considered as important targets for the development of anticancer and antimicrobial drugs. In this work, novel benzothiazolyl pyrazolopyrimidine carboxamide and benzothiazolyl pyrazolopyrimidine carbonitrile derivatives were synthesized and characterized. The synthetic process was carried out via the reaction of ylidine benzothiazole derivatives with pyrazolocarboxamide and pyrazolocarbonitrile through a Michael addition pathway.