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1.
J Org Chem ; 84(7): 4000-4008, 2019 04 05.
Article in English | MEDLINE | ID: mdl-30864430

ABSTRACT

An "on water" organocatalytic cyanoarylmethylation of aryl acetonitrile to isatins is developed, giving products in high yields and up to excellent diastereoselectivities. A remarkable enhancement of reaction rates and diastereoselectivities by water was observed under mild conditions. Moreover, this approach provides a highly efficient and environmentally benign access to thermodynamic 3-hydroxy-3-cyanomethyl oxindoles.


Subject(s)
Acetonitriles/chemical synthesis , Isatin/chemistry , Oxindoles/chemical synthesis , Water/chemistry , Acetonitriles/chemistry , Catalysis , Methylation , Models, Molecular , Oxindoles/chemistry , Stereoisomerism
2.
Curr Org Synth ; 16(8): 1149-1160, 2019.
Article in English | MEDLINE | ID: mdl-31984921

ABSTRACT

AIMS AND OBJECTIVE: In the synthesis of heterocyclic compounds, acrylonitrile derivatives are the most important and appropriate precursors. These compounds are the most important intermediates and subunits for the enhancement of molecules having pharmaceutical or biological interests. Nitrogen-containing compounds have received extensive consideration in the literature over the years. MATERIALS AND METHODS: A facile, economic and efficient method has been developed for the synthesis of acrylonitrile derivatives using p-nitrophenylacetonitrile and aromatic/heterocyclic aldehydes in the presence of zinc chloride at room temperature. Spectroscopic data were obtained using the following instruments: Fourier transform infrared spectra (KBr discs, 4000-400 cm-1) by Shimadzu IR-408 Perkin-Elmer 1800 instrument; 1H NMR and 13C NMR spectra by Bruker Avance-II 400 MHz using DMSO-d6 as a solvent containing TMS as the internal standard. RESULTS: To continue our ongoing studies to synthesize heterocyclic and pharmaceutical compounds by mild, facile and efficient protocols, herein we wish to report our experimental results on the synthesis of acrylonitrile derivatives, using various aromatic/heterocyclic aldehydes and p-nitrophenylacetonitrile in the presence of zinc chloride in ethanolic media at room temperature. Some of the new compounds were tested for their human serum albumin activity (HSA) while a study of interaction with HSA protein was performed for compounds 3a and 3b. The results show that compound 3b binds tightly to HSA as compared to compound 3a. CONCLUSION: It can be concluded that acrylonitrile derivatives can be synthesized by an efficient method via the reaction of p-nitrophenylacetonitrile with aromatic/heterocyclic aldehydes by the use of zinc chloride as an effective solid catalyst. The remarkable features of this procedure include excellent yields (90-95%), short reaction period (30 min.), moderate reaction environment, easy workup procedure and managing of the catalyst. This method may find a wide significance in organic synthesis for the synthesis of the Z-acrylonitrile.


Subject(s)
Acetonitriles/chemical synthesis , Acrylonitrile/chemistry , Acrylonitrile/chemical synthesis , Serum Albumin, Human/chemistry , Acetonitriles/chemistry , Aldehydes/chemistry , Catalysis , Chlorides/chemistry , Crystallization , Humans , Protein Binding , Protein Conformation , Solvents/chemistry , X-Rays , Zinc Compounds/chemistry
3.
Molecules ; 23(6)2018 06 08.
Article in English | MEDLINE | ID: mdl-29890669

ABSTRACT

Alkylidene oxindoles are important functional moieties and building blocks in pharmaceutical and synthetic chemistry. Our interest in biologically active compounds focused our studies on the synthesis of novel oxindoles, bearing on the exocyclic double bond at the C8, CN, and S groups. Extending the potential applications of Appel's salt, we developed a new synthetic approach by investigating the reactions of C5-substituted 2-oxindoles with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel's salt) to give original (Z)-3-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)indolin-2-one derivatives, and new 2-mercapto-(2-oxoindolin-3-ylidene)acetonitriles via a dithiazole ring-opening reaction. The work described in this article represents further applications of Appel's salt in the conception of novel heterocyclic rings, in an effort to access original bioactive compounds. Fifteen new compounds were prepared and fully characterized.


Subject(s)
Acetonitriles/chemical synthesis , Indoles/chemistry , Carbon-13 Magnetic Resonance Spectroscopy , Proton Magnetic Resonance Spectroscopy , Spectrometry, Mass, Electrospray Ionization
4.
Sci Rep ; 8(1): 3051, 2018 02 14.
Article in English | MEDLINE | ID: mdl-29445093

ABSTRACT

Hydroxynitrile lyases (HNLs), which are key enzymes in cyanogenesis, catalyze the cleavage of cyanohydrins into carbonyl compounds and hydrogen cyanide. Since HNLs also catalyze the reverse reaction, they are used industrially for the asymmetric synthesis of cyanohydrins, which are valuable building blocks of pharmaceuticals and fine chemicals. HNLs have been isolated from cyanogenic plants and bacteria. Recently, an HNL from the cyanogenic millipede Chamberlinius hualienensis was shown to have the highest specific activity for (R)-mandelonitrile synthesis, along with high stability and enantioselectivity. However, no HNLs have been isolated from other cyanogenic millipedes. We identified and characterized HNLs from 10 cyanogenic millipedes in the Paradoxosomatidae and Xystodesmidae. Sequence analyses showed that HNLs are conserved among cyanogenic millipedes and likely evolved from one ancestral gene. The HNL from Parafontaria tonominea was expressed in Escherichia coli SHuffle T7 and showed high specific activity for (R)-mandelonitrile synthesis and stability at a range of pHs and temperatures. The stability of millipede HNLs is likely due to disulfide bond(s). The E. coli cells expressing HNL produced (R)-mandelonitrile with 97.6% enantiomeric excess without organic solvents. These results demonstrate that cyanogenic millipedes are a valuable source of HNLs with high specific activity and stability.


Subject(s)
Acetonitriles/chemical synthesis , Aldehyde-Lyases/chemistry , Arthropods/enzymology , Aldehyde-Lyases/biosynthesis , Aldehyde-Lyases/metabolism , Animals , Arthropods/genetics , Biocatalysis , Catalysis , Cloning, Molecular/methods , Escherichia coli/genetics , Escherichia coli/metabolism , Nitriles/metabolism
5.
Drug Test Anal ; 10(4): 671-680, 2018 Apr.
Article in English | MEDLINE | ID: mdl-28857492

ABSTRACT

α-Phenylacetoacetonitrile (APAAN) is one of the most important pre-precursors for amphetamine production in recent years. This assumption is based on seizure data but there is little analytical data available showing how much amphetamine really originated from APAAN. In this study, several syntheses of amphetamine following the Leuckart route were performed starting from different organic compounds including APAAN. The organic phases were analysed using gas chromatography-mass spectrometry (GC-MS) to search for signals caused by possible APAAN markers. Three compounds were discovered, isolated, and based on the performed syntheses it was found that they are highly specific for the use of APAAN. Using mass spectra, high resolution MS and nuclear magnetic resonance (NMR) data the compounds were characterised and identified as 2-phenyl-2-butenenitrile, 3-amino-2-phenyl-2-butenenitrile, and 4-amino-6-methyl-5-phenylpyrimidine. To investigate their significance, they were searched in data from seized amphetamine samples to determine to what extent they were present in illicitly produced amphetamine. Data of more than 580 cases from amphetamine profiling databases in Germany and the Netherlands were used for this purpose. These databases allowed analysis of the yearly occurrence of the markers going back to 2009. The markers revealed a trend that was in agreement with seizure reports and reflected an increasing use of APAAN from 2010 on. This paper presents experimental proof that APAAN is indeed the most important pre-precursor of amphetamine in recent years. It also illustrates how important it is to look for new ways to identify current trends in drug production since such trends can change within a few years.


Subject(s)
Acetonitriles/analysis , Amphetamine/analysis , Central Nervous System Stimulants/analysis , Illicit Drugs/analysis , Acetonitriles/chemical synthesis , Amphetamine/chemical synthesis , Central Nervous System Stimulants/chemical synthesis , Databases, Pharmaceutical , Drug Contamination , Gas Chromatography-Mass Spectrometry , Germany , Illicit Drugs/chemical synthesis , Magnetic Resonance Spectroscopy , Netherlands
6.
Carbohydr Polym ; 179: 408-414, 2018 Jan 01.
Article in English | MEDLINE | ID: mdl-29111068

ABSTRACT

A binary grafted copolymer of Psyllium mucilage (Psy) with acrylic acid (AA) and acrylonitrile (An) has been successfully synthesized under microwave conditions for in vitro drug release study. The grafting was confirmed by FTIR spectroscopy, XRD, SEM, EDX, TGA analytical techniques and the intrinsic viscosity study. The swelling behavior of grafted material has been studied in solution of different pH and time. We also prepare Psy-g-Poly (AA-co-An) based beads with anti-cancer drug [(2-Chloro-3-(4-hydroxyphenylamino) naphthalene-1, 4-dione)]. The drug release behavior of Psy-g-Poly (AA-co-An) based beads has been determined in aqueous medium at different pH. It has been observed that highest drug release at pH 1.6. The drug release kinetics was analysed using the different models. This study demonstrates that the release of drug depends on the composition of beads and pH of release medium. Kinetics of drug release from beads is best fitted by zero order and first order model.


Subject(s)
Acetonitriles/chemical synthesis , Acetonitriles/pharmacokinetics , Acrylates/chemical synthesis , Acrylates/pharmacokinetics , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacokinetics , Drug Liberation , Microwaves , Naphthoquinones/pharmacokinetics , Psyllium/chemistry , Acetonitriles/chemistry , Acrylates/chemistry , Acrylonitrile/chemistry , Antineoplastic Agents/chemistry , Chemistry Techniques, Analytical , Drug Delivery Systems , Hydrogen-Ion Concentration , Naphthoquinones/chemistry , Psyllium/chemical synthesis , Psyllium/pharmacokinetics , Time Factors , Viscosity
7.
Sci Rep ; 7(1): 1530, 2017 05 08.
Article in English | MEDLINE | ID: mdl-28484214

ABSTRACT

A novel turn-on two-photon fluorescent probe NS-N 2 H 4 was developed with the 2-benzothiazoleacetonitrile as a new recognition site for the detection of hydrazine (N2H4). The two-photon probe exhibited favorable properties including high selectivity, low cytotoxicity and almost 16-fold fluorescence enhancement in the presence of N2H4 in solution. The probe could be used to image hydrazine in the living cells. Notably, we also used the two-photon fluorescent probe to image hydrazine in the tissue imaging for the first time. Furthermore, by the way of probe-loaded TLC plate, we further monitored vapor of hydrazine. Therefore, the novel two-photon probe is expected to be employed to detect N2H4 in biosamples and environmental pollution and the new recognition site will be widely applied to construct fluorescent probes for the detection of N2H4.


Subject(s)
Acetonitriles/chemistry , Benzothiazoles/chemistry , Fluorescent Dyes/chemistry , Hydrazines/analysis , Molecular Imaging , Photons , Acetonitriles/chemical synthesis , Animals , Benzothiazoles/chemical synthesis , Fluorescence , Fluorescent Dyes/chemical synthesis , Gases , HeLa Cells , Humans , Hydrogen-Ion Concentration , Mice , Rats , Spectrometry, Fluorescence
8.
Drug Test Anal ; 9(7): 966-976, 2017 Jul.
Article in English | MEDLINE | ID: mdl-28332334

ABSTRACT

This perspective examines amphetamine importations into Ireland. Some novel by-products were detected and linked to a change in the method of production of P2P from APAAN. These by-products remained present during subsequent Leuckart reaction conditions. Novel by-products from substituted cathinone synthesis reactions were also isolated and characterized.


Subject(s)
Acetone/analogs & derivatives , Acetonitriles/chemistry , Amphetamine/chemistry , Central Nervous System Stimulants/chemistry , Drug Contamination , Illicit Drugs/chemistry , Acetone/chemical synthesis , Acetone/chemistry , Acetonitriles/chemical synthesis , Amphetamine/chemical synthesis , Central Nervous System Stimulants/chemical synthesis , Gas Chromatography-Mass Spectrometry , Hydrolysis , Illicit Drugs/chemical synthesis , Ireland , Pharmacy
9.
Bioorg Med Chem Lett ; 26(9): 2164-9, 2016 May 01.
Article in English | MEDLINE | ID: mdl-27017113

ABSTRACT

A small library of (Z)-2-(benzo[d][1,3]dioxol-5-yl) and (Z)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl analogs of 2- and 3-phenylacetonitriles has been synthesized and evaluated for their anti-cancer activities against a panel of 60 human cancer cell lines. The dihydrodioxin analog 3j and dioxol analogs 5e and 7e exhibited the most potent anti-cancer activity of all the analogs synthesized in this study, with GI50 values of <100 nM against almost all of the cell lines in the human cancer cell panel. Of these three, only compound 3j inhibited tubulin polymerization to any degree in vitro. The binding modes of 3j and the structurally related tubulin-inhibitor DMU-212 were determined by virtual docking studies with tubulin dimer. Compound 3j docked at the colchicine-binding site at the dimer interface of tubulin. The Full-Fitness (FF) score of 3j was observed to be substantially higher than DMU-212, which agrees well with the observed anti-cancer potency (GI50 values). The mechanism by which dioxol analogs 5e and 7e exert their cytotoxic effects remains unknown at this stage, but it is unlikely that they affect tubulin dynamics. Nevertheless, these findings suggest that both dioxol and dihydrodioxin analogs of phenylacrylonitrile may have potential for development as clinical candidates to treat a variety of human cancers.


Subject(s)
Acetonitriles/pharmacology , Antineoplastic Agents/pharmacology , Benzodioxoles/pharmacology , Dioxanes/pharmacology , Acetonitriles/administration & dosage , Acetonitriles/chemical synthesis , Antineoplastic Agents/administration & dosage , Antineoplastic Agents/chemical synthesis , Benzodioxoles/administration & dosage , Benzodioxoles/chemical synthesis , Cell Line, Tumor , Dioxanes/administration & dosage , Dioxanes/chemical synthesis , Drug Screening Assays, Antitumor , Humans , Molecular Docking Simulation , Stereoisomerism , Stilbenes/pharmacology , Tubulin Modulators/administration & dosage , Tubulin Modulators/chemical synthesis , Tubulin Modulators/pharmacology
10.
Appl Biochem Biotechnol ; 177(6): 1348-63, 2015 Nov.
Article in English | MEDLINE | ID: mdl-26310798

ABSTRACT

The carrier-based and carrier-free (cross-linked enzyme aggregate) covalent immobilizations of Prunus dulcis hydroxynitrile lyase were investigated. The immobilized preparations were tested for enantioselective carbon-carbon bond formation activity in the biphasic medium. Of the tested preparations, only cross-linked enzyme aggregate of P. dulcis hydroxynitrile lyase (PdHNL-CLEA) achieved the synthesis of (R)-mandelonitrile with 93% yield and 99% enantiopurity. PdHNL-CLEA was also used in the synthesis of various (R)-cyanohydrins from corresponding aldehydes/ketones and hydrocyanic acid. When 4-methoxybenzaldehyde, 4-methyl benzaldehyde, and 4-hydroxybenzaldehyde were used as substrates, the yield-enantiomeric excess of corresponding (R)-cyanohydrins were obtained as 95-95, 85-79, and 2-25%, respectively, after 96 h at pH 4.0 and 5 °C. For acetophenone, 4-fluoroacetophenone, 4-chloroacetophenone, 4-bromoacetophenone, and 4-iodoacetophenone, the yield-enantiomeric excess of corresponding (R)-cyanohydrins were 1-99, 20-84, 11-95, 5-99, and 3-24%, respectively at the same conditions. The results demonstrate PdHNL-CLEA can be effectively used in the synthesis of (R)-mandelonitrile.


Subject(s)
Acetonitriles/chemical synthesis , Aldehyde-Lyases/chemistry , Enzymes, Immobilized/chemistry , Plant Proteins/chemistry , Prunus dulcis/enzymology , Acetonitriles/chemistry , Stereoisomerism
11.
Spectrochim Acta A Mol Biomol Spectrosc ; 145: 531-539, 2015 Jun 15.
Article in English | MEDLINE | ID: mdl-25801442

ABSTRACT

Two new bi-anchoring organic sensitizers of type D-(π-A)2 comprising the identical π-spacer (thiophene-2-acetonitrile) and electron acceptor (malonic acid) but different aryl amine as electron donors (diphenylamine and carbazole) were synthesized, characterized and fabricated metal free dye-sensitized solar cell devices. The intra molecular charge transfer property and electrochemical property of these dyes were investigated by molecular absorption, emission, cyclic voltammetric experiments and in addition, quantum chemical calculation studies were performed to provide sufficient driving force for the electron injection into the conduction band of TiO2 which leads to efficient charge collection. Among the fabricated devices, carbazole based device exhibits high current conversion efficiency (η=4.7%) with a short circuit current density (JSC) 15.3 mA/cm(2), an open circuit photo voltage (VOC) of 0.59 V and a fill factor of 0.44 under AM 1.5 illumination (85 mW/cm(2)) compared to diphenylamine based device.


Subject(s)
Acetonitriles/chemistry , Acetonitriles/chemical synthesis , Coloring Agents/chemistry , Electrons , Malonates/chemistry , Solar Energy , Thiophenes/chemistry , Thiophenes/chemical synthesis , Adsorption , Electricity , Electrochemical Techniques , Spectroscopy, Fourier Transform Infrared , Thermodynamics , Titanium/chemistry
12.
Org Lett ; 17(3): 476-9, 2015 Feb 06.
Article in English | MEDLINE | ID: mdl-25590210

ABSTRACT

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.


Subject(s)
Acetonitriles/chemical synthesis , Isoxazoles/chemistry , Palladium/chemistry , Acetonitriles/chemistry , Boronic Acids/chemistry , Catalysis , Microwaves , Molecular Structure
13.
Org Biomol Chem ; 13(6): 1634-8, 2015 Feb 14.
Article in English | MEDLINE | ID: mdl-25519974

ABSTRACT

A chemoenzymatic two-step cascade process, with both steps having incompatible reaction conditions, was successfully performed in continuous flow. The chemoenzymatic aqueous formation of cyanohydrins was integrated with a subsequent organic phase protection step in a single flow process utilising a membrane-based phase separation module. The wider applicability of our setup was demonstrated with the synthesis of nine protected cyanohydrin derivatives, all obtained in good yields and high to excellent enantioselectivity.


Subject(s)
Acetonitriles/chemical synthesis , Acetonitriles/chemistry , Molecular Structure , Stereoisomerism
14.
J Org Chem ; 79(20): 9717-27, 2014 Oct 17.
Article in English | MEDLINE | ID: mdl-25237713

ABSTRACT

Reacting (Z)-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1H-pyrazol-5-amines 5 with Et2NH and then with concd H2SO4 gives 5H-pyrazolo[3,4-e][1,2,4]dithiazine-3-carbonitriles 7 in good yields (74-85%) and 6H-pyrazolo[3,4-f][1,2,3,5]trithiazepine-4-carbonitriles 9 as minor products (0-6%). Furthermore, the 1,3-dimethylpyrazole analogue 5a was transformed into the dithiazine 7a in two discrete steps, allowing the isolation of a disulfide intermediate (Z)-2-[(diethylamino)disulfan-yl]-2-[(1H-pyrazol-5-yl)imino]acetonitrile (8a). The one-pot, two-step reaction also worked with electron-rich hydroxy- and methoxy-substituted anilines. Thermolysis of the pyrazolo[3,4-e][1,2,4]dithiazines 7 gave the ring-contracted 1H-pyrazolo[3,4-d]thiazole-5-carbonitriles 6 (94-100%). With active sulfur, 1,3-dimethyl-5H-pyrazolo[3,4-e][1,2,4]dithiazine-3-carbonitrile (7a) gave 1,3-dimethyl-6H-pyrazolo[3,4-f][1,2,3,5]trithiazepine-4-carbonitrile (9a), but on prolonged reaction times, it gave 5,7-dimethyl-5H-[1,2,3]dithiazolo[4,5-b]pyrazolo[3,4-e][1,4]thiazine (13). Finally, in the absence of acid, heating a solution of (Z)-2-[(diethylamino)disulfanyl]-2-[(1,3-dimethyl-1H-pyrazol-5-yl)imino]acetonitrile (8a) gave 4,6,10,12-tetramethyl-6H-pyrazolo[3,4-f]pyrazolo[3',4':4,5]pyrimido[6,1-d][1,2,3,5]trithiazepine-8,12b(10H)-dicarbonitrile (19) (67%).


Subject(s)
Acetonitriles/chemical synthesis , Nitriles/chemistry , Nitriles/chemical synthesis , Pyrazoles/chemical synthesis , Thiazepines/chemistry , Thiazepines/chemical synthesis , Acetonitriles/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Pyrazoles/chemistry
15.
Ecotoxicol Environ Saf ; 107: 30-5, 2014 Sep.
Article in English | MEDLINE | ID: mdl-24905694

ABSTRACT

Formation of disinfection by-products (DBPs) from chlorination and chloramination of tetracycline antibiotics (TCs) was comprehensively investigated. It was demonstrated that a connection existed between the transformation of TCs and the formation of chloroform (CHCl3), carbon tetrachloride (CCl4), dichloroacetonitrile (DCAN) and dichloroacetone (DCAce). Factors evaluated included chlorine (Cl2) and chloramine(NH2Cl) dosage, reaction time, solution pH and disinfection modes. Increased Cl2/NH2Cl dosage and reaction time improved the formation of CHCl3 and DCAce. Formation of DCAN followed an increasing and then decreasing pattern with increasing Cl2 dosage and prolonged reaction time. pH affected DBPs formation differently, with CHCl3 and DCAN decreasing in chlorination, and having maximum concentrations at pH 7 in chloramination. The total concentrations of DBPs obeyed the following order: chlorination>chloramination>pre-chlorination (0.5h)>pre-chlorination (1h)>pre-chlorination (2h).


Subject(s)
Anti-Bacterial Agents/chemistry , Chloramines/chemistry , Chlorine/chemistry , Disinfection , Tetracyclines/chemistry , Acetonitriles/chemical synthesis , Halogenation , Hydrogen-Ion Concentration
16.
Molecules ; 18(10): 12488-99, 2013 Oct 10.
Article in English | MEDLINE | ID: mdl-24152671

ABSTRACT

We have demonstrated that a cooperative catalytic system comprised of CuCl and Cu(OTf)(2) could be used to effectively catalyse the three-, five- and seven-component coupling reactions of aliphatic or aromatic amines, formaldehyde, and trimethylsilyl cyanide (TMSCN), and selectively produce in good yields the corresponding cyanomethylamines, N,N-bis(cyanomethyl)amines and N,N'-bis(cyanomethyl)methylenediamines.


Subject(s)
Acetonitriles/chemical synthesis , Copper/chemistry , Methylamines/chemical synthesis , Organometallic Compounds/chemistry , Catalysis , Formaldehyde/chemistry , Models, Chemical , Polymers/chemistry
17.
Bioorg Med Chem Lett ; 23(9): 2571-4, 2013 May 01.
Article in English | MEDLINE | ID: mdl-23528295

ABSTRACT

Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE2 productions and was less cytotoxic than arvelexin on macrophage cells.


Subject(s)
Acetonitriles/chemistry , Anti-Inflammatory Agents/chemical synthesis , Dinoprostone/metabolism , Nitric Oxide/metabolism , Acetonitriles/chemical synthesis , Acetonitriles/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Cell Line , Cell Survival/drug effects , Indoles/chemistry , Indoles/pharmacology , Lipopolysaccharides/toxicity , Mice
18.
Org Biomol Chem ; 11(16): 2582-5, 2013 Apr 28.
Article in English | MEDLINE | ID: mdl-23503621

ABSTRACT

A one-pot two-step synthesis of versatile indenones has been developed. This palladium(II)-catalyzed transformation involves generation and condensation of ortho-functionalized 1,2-benzils from 2-(2-arylethynylphenyl)acetonitriles using Ph2SO as the oxidant. The resulting 3-cyanoindenones can be converted to various valuable molecules.


Subject(s)
Acetonitriles/chemistry , Hydrocarbons, Aromatic/chemical synthesis , Nitriles/chemical synthesis , Palladium/chemistry , Acetonitriles/chemical synthesis , Catalysis , Cyclization , Hydrocarbons, Aromatic/chemistry , Nitriles/chemistry , Oxidation-Reduction
19.
J Am Chem Soc ; 134(45): 18534-7, 2012 Nov 14.
Article in English | MEDLINE | ID: mdl-23113730

ABSTRACT

Enzymes and their mimics use hydrogen bonds to catalyze chemical transformations. Small-molecule transition state analogues of oxyanion holes have been characterized by computations, gas-phase IR and photoelectron spectroscopy, and determination of their binding constants in acetonitrile. A new class of hydrogen bond catalysts is proposed (donors that can contribute three hydrogen bonds to a single functional group) and demonstrated in a Friedel-Crafts reaction. The employed catalyst was observed to react 100 times faster than its rotamer that can employ only two hydrogen bonds. The former compound also binds anions more tightly and was found to have a thermodynamic advantage.


Subject(s)
Acetonitriles/chemistry , Oxygen/chemistry , Acetonitriles/chemical synthesis , Anions/chemistry , Catalysis , Hydrogen Bonding , Molecular Structure , Thermodynamics
20.
Bioorg Med Chem Lett ; 22(23): 7011-4, 2012 Dec 01.
Article in English | MEDLINE | ID: mdl-23102653

ABSTRACT

A series of (2-phenyl-4H-benzopyrimodo[2,1-b][1,3]thiazol-4-yliden-4-yliden)acetonitrile derivatives have been prepared by ring transformation reaction of 4-(methylthio)-2-oxo-6-aryl-2H-pyrane-3-carbonitriles. The yield of ring transformation product is moderate to good. Furthermore the glycosidase inhibitory activities were tested by using α-amylase and α-glucosidase pancreatic, intestinal and liver enzymes, responsible for hyperglycemia in type II diabetes. The results revealed that all compounds exhibit significant glycosidase inhibitory activity.


Subject(s)
Acetonitriles/chemistry , Acetonitriles/pharmacology , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors , Hypoglycemic Agents/chemical synthesis , Acetonitriles/chemical synthesis , Acetonitriles/metabolism , Amylases/antagonists & inhibitors , Amylases/metabolism , Animals , Enzyme Activation/drug effects , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/metabolism , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/metabolism , Intestines/enzymology , Liver/enzymology , Mice , Pancreas/enzymology , Protein Binding , Swine , alpha-Glucosidases/metabolism
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