- A novel class for carbonic anhydrases inhibitors and evaluation of their non-zinc binding
-
In this study, 23 different imidazole derivatives were synthesized, and the inhibitory properties of these derivatives against carbonic anhydrase I and II isoenzymes were investigated for the first time. The inhibition concentrations of the imidazole derivatives were found to be in the range of 2.89–115.5 nM. Docking studies examined the binding properties of the imidazole derivatives, and the structure–activity relationship is discussed. Theoretical calculations showed that the binding mode of the imidazole ring was non-zinc binding.
- Kuzu, Burak,Tan, Meltem,Gül?in, ?lhami,Menges, Nurettin
-
-
- Green and efficient synthesis of new β-amido-aroyl carbonyl derivatives catalyzed by choline chloride/urea as a deep eutectic solvent
-
A green and highly efficient synthesis of some new β-amido-aroyl carbonyl derivatives has been achieved through a one-pot, three-component reaction of dimedone/barbituric acid derivatives, arylglyoxals, and amides in choline chloride/urea as a deep eutectic solvent (DES). The use of biodegradable materials, short reaction time and high yields of products introduced this protocol as an efficient environmentally friendly method. The DES could be easily recovered and reused about four times with satisfied catalytic activity.
- ANARAKI-ARDAKANI, HOSSEIN,BERJIS, ANITA,MIRZA, BEHROOZ
-
p. 547 - 553
(2021/07/26)
-
- Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides
-
Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.
- Jeong, Hye-Min,Nam, Dong Guk,Ryu, Do Hyun,Shim, Su Yong
-
supporting information
p. 22236 - 22240
(2021/09/13)
-
- Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls
-
2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.
- Dubovtsev, Alexey Yu.,Shcherbakov, Nikolay V.,Dar'in, Dmitry V.,Kukushkin, Vadim Yu.
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p. 745 - 757
(2020/02/04)
-
- Antiproliferative Activity of 2-Aroyland 2-Heteroyl-1,1,3,3-Tetracyanoprop-2-en-1-ides
-
The influence of previously synthesized 2-aroyl-1,1,3,3-tetracyanoprop-2-en-1-ides on the growth of conditionally normal and tumor cells was studied in continuation of a search for new anticancer drugs. Cytotoxicities of the compounds were studied with respect to human tumor cell lines from the ATCC. All compounds were ineffective against melanoma and lung and ovary cancer cell lines and exhibited moderate activity in the other cases. The tested compounds exhibited highly selective effects because they were safe for conditionally normal skin fibroblasts.
- Kayukov, Ya. S.,Mar’yasov, M. A.,Nasakin, O. E.
-
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- Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases
-
Mono- or di-substituted imidazole derivatives were synthesized using a one-pot, two-step strategy. All imidazole derivatives were tested for AChE and BChE inhibition and showed nanomolar activity similar to that of the test compound donepezil and higher than that of tacrine. Structure activity relationship studies, docking studies to on X-ray crystal structure of AChE with PDB code 1B41, and adsorption, distribution, metabolism, and excretion (ADME) predictions were performed. The synthesized core skeleton was bound to important regions of the active site of AChE such as the peripheral anionic site (PAS), oxyanion hole (OH), and anionic subsite (AS). Selectivity of the reported test compounds was calculated and enzyme kinetic studies revealed that they behave as competitive inhibitors, while two of the test compounds showed noncompetitive inhibitory behavior. ADME predictions revealed that the synthesized molecules might pass through the blood brain barrier and intestinal epithelial barrier and circulate freely in the blood stream without binding to human serum albumin. While the toxicity of one compound on the WS1 (skin fibroblast) cell line was 1790 μM, its toxicity on the SH-SY5Y (neuroblastoma) cell line was 950 μM.
- Kuzu, Burak,Tan, Meltem,Taslimi, Parham,Gül?in, ?lhami,Ta?p?nar, Mehmet,Menges, Nurettin
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p. 187 - 196
(2019/02/06)
-
- A simple route for synthesis of 5-(furan-3-yl)barbiturate/thiobarbiturate derivatives via a multi-component reaction between arylglyoxals, acetylacetone and barbituric/thiobarbituric acid
-
An effective protocol for the synthesis of 5-(furan-3-yl)barbiturate and 5-(furan-3-yl)thiobarbiturate derivatives through a one-pot three-component reaction of readily available starting materials arylglyoxals, barbituric acid or thiobarbituric acid and acetylacetone in water as solvent is reported.
- Dehghanzadeh, Fatemeh,Shahrokhabadi, Fereshteh,Anary-Abbasinejad, Mohammad
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p. 133 - 141
(2019/04/17)
-
- INHIBITORS OF HEPATITIS C VIRUS REPLICATION
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The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.
- -
-
Paragraph 0554-0555
(2019/05/15)
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- Exocyclic N-Acyliminium Ion (NAI) Cyclization: Access to Fully Substituted Oxazoles and Furocoumarins
-
A concise, one-pot route to oxazoles and furocoumarins has been reported. The key step in this transformation involves in situ generation of N-acyliminium ion (NAI) precursor under catalyst and solvent-free conditions and their further transformations promoted by superacid in the same pot. We have also presented the experimental evidence for the involvement of proto-solvated novel exocyclic N-acyliminium ion. Further, the UV-visible and fluorescence studies revealed that few of the compounds reported here exhibited emission of blue light upon irradiation in EtOH in the region of 404-422 nm.
- Babu, Venkata Nagarjuna,Murugan, Arumugavel,Katta, Narenderreddy,Devatha, Suman,Sharada, Duddu S.
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p. 6631 - 6641
(2019/06/07)
-
- Modular Synthesis of Di- A nd Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors
-
A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.
- De Toledo, Ian,Grigolo, Thiago A.,Bennett, James M.,Elkins, Jonathan M.,Pilli, Ronaldo A.
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p. 14187 - 14201
(2019/10/16)
-
- Synthesis of fused pyrroles containing 4-hydroxycoumarins by regioselective metal-free multicomponent reactions
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The reaction of arylglyoxals, 4-hydroxycoumarin, and aromatic amines such as 7-amino-2-methylchromone, 6/7-aminoflavone, 7-amino-4-methylcoumarin, 1-amino-9-fluorenone, 1-aminoanthraquinone and aniline derivatives in acetic acid medium under microwave conditions provides the corresponding regioselective fused pyrroles having hydroxycoumarin and aryl substituents. Alternatively, we have developed another method using in situ arylglyoxals from acetophenone derivatives by I2/DMSO promoted C-H oxidation followed by one-pot three component cyclization reactions to provide similar fused pyrroles. Using both the methods a series of novel pyrroles fused with pharmacologically important chromone, flavone, coumarin, fluorenone, and anthraquinone moieties were synthesized under metal-free reaction conditions in good to very good yields within a short reaction time. The structures of the synthesized fused pyrroles have been unambiguously confirmed by spectroscopic techniques, mass analysis and single crystal XRD.
- Mishra, Richa,Jana, Asim,Panday, Anoop Kumar,Choudhury, Lokman H.
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p. 3289 - 3302
(2018/05/22)
-
- Oxidative C-C Bond Cleavage for the Synthesis of Aryl Carboxylic Acids from Aryl Alkyl Ketones
-
A metal-free and one-pot two-step synthesis of aryl carboxylic acids from aryl alkyl ketones has been achieved. The reactions were performed with iodine as the catalyst, DMSO and TBHP as the oxidants. Under the optimal reaction conditions, a number of aryl alkyl ketones could be converted into their corresponding aryl carboxylic acids in good to excellent yields (up to 94%).
- Xu, Liang,Wang, Shengpeng,Chen, Bajin,Li, Meichao,Hu, Xinquan,Hu, Baoxiang,Jin, Liqun,Sun, Nan,Shen, Zhenlu
-
supporting information
p. 1505 - 1509
(2018/05/25)
-
- Enantioselective Cyanosilylation of α,α-Dialkoxy Ketones by Using Phosphine-Thiourea Dual-Reagent Catalysis
-
The first highly enantioselective cyanosilylation of α,α-dialkoxy ketones enabled by a dual-reagent catalysis has been developed. With the combination of a chiral bifunctional phosphine-thiourea and methyl acrylate, the key organophosphorus zwitterion intermediate was generated in situ as a novel Lewis base, which catalyzed the enantioselective cyanosilylation reaction in excellent yields (up to 99 %) with good-to-excellent enantioselectivities (up to 94 % ee).
- Yu, Qi-Wen,Wu, Lu-Ping,Kang, Tian-Chen,Xie, Jin,Sha, Feng,Wu, Xin-Yan
-
supporting information
p. 3992 - 3996
(2018/07/31)
-
- 9-Ethyl-3-{6-(het)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl}-9H-carbazoles: synthesis and study of sensitivity to nitroaromatic compounds
-
5-(9-Ethyl-9H-carbazol-3-yl)-substituted 6-(het)aryl[1,2,5]oxadiazolo[3,4-b]pyrazines were synthesized by direct transition metal-free C—H functionalization in the pyrazine ring. Their photophysical and sensory properties with respect to nitrobenzene and
- Verbitskiy,Kvashnin, Yu. A.,Baranova,Yakovleva, Yu. A.,Khokhlov,Rusinov,Charushin
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p. 1078 - 1082
(2018/10/02)
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- Visible-light assisted one-pot preparation of aryl glyoxals from acetoarylones via in-situ arylacyl bromides formation: Selenium-free approach to acetoarylones oxidation
-
A novel visible-light (blue LEDs: hν?=?425?±?15?nm) photocatalyzed one-pot method for the synthesis of electronically diverse aryl glyoxals in good to excellent yields from acetoarylones and green regents such as air, vitamin C and dioxane dibromide has been described. In addition, an application of the current methodology has been demonstrated for the oxidation of monoamine oxidase-B inhibitors, i.e., 1-(4-((4-fluorobenzyl)oxy)phenyl)ethanone and 1-(3-((4-chlorobenzyl)oxy)phenyl)ethanone. This finding may serves as a valuable alternative to the traditional acetoarylones oxidation reactions conducted using selenium dioxide a harmful and unselective reagent known to simultaneously oxidize allylic, benzylic, [sbnd]CH3and so on.
- Natarajan, Palani,Manjeet,Kumar, Naveen,Devi, Sapna,Mer, Kalyani
-
supporting information
p. 658 - 662
(2017/01/25)
-
- Synthesis of 2-acyl-benzo[1,3-d]selenazoles via domino oxidative cyclization of methyl ketones with bis(2-aminophenyl) diselenide
-
A general, practical and simple one-pot synthesis of 2-acyl-benzo[1,3-d]selenazoles was developed by reacting a wide range of 2-arylethane-1,2-diones, generated in situ from commercially available aryl methyl ketones, with bis(2-aminophenyl) diselenide, promoted by Na2S2O5 in DMSO at 100 °C. Comparatively, the reactions were conducted under conventional heating and microwave irradiation. The use of focused microwave irradiation drastically decreased the reaction time from 48 to 2 h with a gain in the reaction yield for most cases. Still, 2-phenylacyl-benzo[1,3-d]selenazole was elected to react with sodium borohydride and butylmagnesium bromide, giving the respective secondary and tertiary alcohols under mild reaction conditions.
- Balaguez, Renata A.,Betin, Eduardo S.,Barcellos, Thiago,Lenard?o, Eder J.,Alves, Diego,Schumacher, Ricardo F.
-
supporting information
p. 1483 - 1487
(2017/02/23)
-
- A direct phosphine-mediated synthesis of polyfunctionalized 1-aminopyrroles from arylglyoxals, phenylhydrazine and acetylene diesters
-
A new and efficient one-pot synthesis of 1-Aminopyrrole derivatives by three-component reaction of dialkyl acetylenedicarboxylates, phenylhydrazine and arylglyoxals in the presence of triphenylphosphine is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded good yields of products.
- Poorand, Mahboobe Amirani,Anary-Abbasinejad, Mohammad,Darehkordi, Ali
-
supporting information
p. 141 - 147
(2017/10/31)
-
- Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
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A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of "green chemistry". Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
- Karpov, Sergey V.,Grigor'Ev, Arthur A.,Kayukov, Yakov S.,Karpova, Irina V.,Nasakin, Oleg E.,Tafeenko, Victor A.
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p. 6402 - 6408
(2016/08/16)
-
- Computer-guided design, synthesis, and biological evaluation of quinoxalinebisarylureas as FLT3 inhibitors
-
Activating mutations of FMS-like tyrosine kinase 3 (FLT3) are present in ~30% of patients with acute myeloid leukemia (AML) and are associated with poor prognosis. Point mutations in the tyrosine kinase domain (TKD) are observed as primary mutations or are acquired as secondary mutations in FLT3 with internal tandem duplications (ITDs) after treatment with tyrosine kinase inhibitors (TKIs). Although dozens of potent inhibitors against FLT3 ITD have been reported, activating TKD point mutations, especially at residues F691 and D835, remain the leading cause for therapy resistance, highlighting the consistent need for new potent inhibitors. Herein we report the identification and characterization of novel quinoxaline-based FLT3 inhibitors. We used the pharmacophore features of diverse known inhibitors as a starting point for a new optimization algorithm for type II TKIs, starting from an in silico library pharmacophore search and induced-fit docking in the known FLT3 structure. This led to the design of a set of diverse quinoxaline-bisarylureas, which were profiled in an FLT3 kinase activity assay. The most promising compounds were further evaluated in a zebrafish embryo phenotype assay.
- G?ring, Stefan,Bensinger, Dennis,Naumann, Eva C.,Schmidt, Boris
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p. 511 - 522
(2015/03/13)
-
- Two efficient one-pot approaches for regioselective synthesis of new 3-arylpyridazino[4,3-c]quinolin-5(6H)-ones
-
Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.
- Rimaz, Mehdi
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p. 1529 - 1534
(2015/10/20)
-
- Regiospecific one-pot, combinatorial synthesis of new substituted pyrimido[4,5-c]pyridazines as potential monoamine oxidase inhibitors
-
New 3-aryl-6-methylpyrimido[4,5-c]pyridazine-5,7(6H ,8H)-diones and 3-aryl-6-ethyl-7-thioxo-7,8-dihydropyrimido[4,5- c]pyridazin-5(6H)-ones were efficiently synthesized via a regiospecific one-pot reaction of N -methylbarbituric acid and N -ethyl-2-thiobarbituric acid with various arylglyoxal monohydrates in the presence of hydrazine dihydrochloride in ethanol at 50°C. The target compounds were obtained in high yields and were regioisomerically pure after recrystallization. These new heterocycles may act as potential MAOB inhibitors.
- Rimaz, Mehdi,Pourhossein, Paria,Khalili, Behzad
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p. 244 - 254
(2015/05/27)
-
- Syntheses, Cholinesterases Inhibition, and Molecular Docking Studies of Pyrido[2,3-b]pyrazine Derivatives
-
Cholinesterases, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), have a role in cholinergic deficit which evidently leads to Alzheimer's disease (AD). Inhibition of cholinesterases with small molecules is an attractive strategy in AD therapy. This study demonstrates synthesis of pyrido[2,3-b]pyrazines (6a-6q) series, their inhibitory activities against both cholinesterases, AChE and BChE, and molecular docking studies. The bioactivities data of pyrido[2,3-b]pyrazines showed 3-(3′-nitrophenyl)pyrido[2,3-b]pyrazine 6n a potent dual inhibitor among the series against both AChE and BChE with IC50 values of 0.466 ± 0.121 and 1.89 ± 0.05 μm, respectively. The analogues 3-(3′-methylphenyl)pyrido[2,3-b]pyrazine 6c and 3-(3′-fluorophenyl)pyrido[2,3-b]pyrazine 6f were found to be selective inhibition for BChE with IC50 values of 0.583 ± 0.052 μm and AChE with IC50 value of 0.899 ± 0.10 μm, respectively. Molecular docking studies of the active compounds suggested the putative binding modes with cholinesterases. The potent compounds among the series could potentially serves as good leads for the development of new cholinesterase inhibitors. A series of pyrido[2,3-b]pyrazine (6a-6q) derivatives has been synthesized and evaluated for inhibitory activities against cholinesterases; acetylcholinesterase, and butyrylcholinesterase. Molecular docking of active compounds was also performed to suggest the putative binding modes with cholinesterases.
- Hameed, Abdul,Zehra, Syeda T.,Shah, Syed J. A.,Khan, Khalid M.,Alharthy, Rima D.,Furtmann, Norbert,Bajorath, Jürgen,Tahir, Muhammad N.,Iqbal, Jamshed
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p. 1115 - 1120
(2015/10/28)
-
- Metal free one-pot synthesis of α-ketoamides from terminal alkenes
-
A practical approach towards the synthesis of α-ketoamides from readily available terminal alkenes (styrenes) has been developed. Use of inexpensive I2/2-iodoxybenzoic acid (IBX) in dimethyl sulphoxide (DMSO) as an oxidant under metal free one-pot conditions makes this methodology versatile.
- Dutta, Sayan,Kotha, Surya Srinivas,Sekar, Govindasamy
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p. 47265 - 47269
(2015/06/16)
-
- PYRIDOPYRAZINES AS ANTICANCER AGENTS
-
The present invention relates to pyridopyrazine derivatives and solvates, hydrates and pharmaceutically acceptable salts thereof, the use of them in the prevention and/or the treatment of cancer diseases, as well as pharmaceutical compositions containing at least one of them as pharmaceutically active agent(s) together with pharmaceutically acceptable carrier, excipient and/or diluents, especially for the prevention and/or treatment of cancer diseases.˙
- -
-
Page/Page column 13
(2014/07/22)
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- Synthesis of 3-(3-aryl-pyrrolidin-1-yl)-5-aryl-1,2,4-triazines that have antibacterial activity and also inhibit inorganic pyrophosphatase
-
Inorganic pyrophosphatases are potential targets for the development of novel antibacterial agents. A pyrophosphatase-coupled high-throughput screening assay intended to detect o-succinyl benzoic acid coenzyme A (OSB CoA) synthetase inhibitors led to the unexpected discovery of a new series of novel inorganic pyrophosphatase inhibitors. Lead optimization studies resulted in a series of 3-(3-aryl-pyrrolidin-1-yl)-5-aryl-1,2,4-triazine derivatives that were prepared by an efficient synthetic pathway. One of the tetracyclic triazine analogues 22h displayed promising antibiotic activity against a wide variety of drug-resistant Staphylococcus aureus strains, as well as activity versus Mycobacterium tuberculosis and Bacillus anthracis, at a concentration that was not cytotoxic to mammalian cells.
- Lv, Wei,Banerjee, Biplab,Molland, Katrina L.,Seleem, Mohamed N.,Ghafoor, Adil,Hamed, Maha I.,Wan, Baojie,Franzblau, Scott G.,Mesecar, Andrew D.,Cushman, Mark
-
p. 406 - 418
(2014/01/17)
-
- Metal-free oxidative amidation of 2-oxoaldehydes: A facile access to α-ketoamides
-
A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a central feature of reaction wherein C1-oxygen atom of α-ketoamides is finally derived from DMSO.
- Mupparapu, Nagaraju,Khan, Shahnawaz,Battula, Satyanarayana,Kushwaha, Manoj,Gupta, Ajai Prakash,Ahmed, Qazi Naveed,Vishwakarma, Ram A.
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supporting information
p. 1152 - 1155
(2014/03/21)
-
- Remote activation of the nucleophilicity of isatin
-
The concept of the remote activation of reactivity was first applied in asymmetric organocatalysis. An isatin 3-phenylimine derivative acts as a donor in the thiourea catalyzed asymmetric addition to unsaturated 1,4-ketoesters, affording aza-Michael adducts in high enantiomeric purity and yield.
- Zari, Sergei,Kudrjashova, Marina,Pehk, Tonis,Lopp, Margus,Kanger, Tonis
-
supporting information
p. 1740 - 1743
(2014/04/17)
-
- A convenient and mild synthesis of new 2-aryl-3-hydroxy-6,7-dihydro-1H- indol-4(5H)-ones via a one-pot, three-component reaction in water
-
A simple and convenient synthesis of 2-aryl-3-hydroxy-6,7-dihydro-1H-indol- 4(5H)-ones is achieved in high yields via the one-pot, three-component reaction of arylglyoxals, 1,3-cyclohexanedione, and ammonium acetate in water under reflux conditions.
- Khalafy, Jabbar,Etivand, Nasser,Dilmaghani, Shadi,Ezzati, Mahnaz,Marjani, Ahmad Poursattar
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p. 3781 - 3783
(2014/07/07)
-
- Iodine-mediated oxidative annulation for one-pot synthesis of pyrazines and quinoxalines using a multipathway coupled domino strategy
-
An efficient iodine-mediated oxidative annulation of aryl acetylenes-arylethenes-aromatic ketones with 1,2-diamines for the synthesis of pyrazines and regioselective synthesis of quinoxalines is presented. A multipathway coupled domino approach has been developed for the one-pot synthesis of 1,4-diazines with high functional group compatibility.
- Viswanadham, K. K. Durga Rao,Prathap Reddy, Muktapuram,Sathyanarayana, Pochampalli,Ravi, Owk,Kant, Ruchir,Bathula, Surendar Reddy
-
supporting information
p. 13517 - 13520
(2015/01/09)
-
- Quinoxaline derivatives: Novel and selective butyrylcholinesterase inhibitors
-
Alzheimer's disease (AD) is a progressive brain disorder which occurs due to lower levels of acetylcholine (ACh) neurotransmitters, and results in a gradual decline in memory and other cognitive processes. Acetycholinesterase (AChE) and butyrylcholinesterase (BChE) are considered to be primary regulators of the ACh levels in the brain. Evidence shows that AChE activity decreases in AD, while activity of BChE does not change or even elevate in advanced AD, which suggests a key involvement of BChE in ACh hydrolysis during AD symptoms. Therefore, inhibiting the activity of BChE may be an effective way to control AD associated disorders. In this regard, a series of quinoxaline derivatives 1-17 was synthesized and biologically evaluated against cholinesterases (AChE and BChE) and as well as against achymotrypsin and urease. The compounds 1-17 were found to be selective inhibitors for BChE, as no activity was found against other enzymes. Among the series, compounds 6 (IC50 = 7.7 ± 1.0μM) and 7 (IC50 = 9.7 ± 0.9 μM) were found to be the most active inhibitors against BChE. Their IC50 values are comparable to the standard, galantamine (IC50 = 6.6 ± 0.38 μM). Their considerable BChE inhibitory activity makes them selective candidates for the development of BChE inhibitors. Structure-activity relationship (SAR) of this new class of selective BChE inhibitors has been discussed.
- Zeb, Aurang,Hameed, Abdul,Khan, Latifullah,Khan, Imran,Dalvandi, Kourosh,Choudhary, M. Iqbal,Basha, Fatima Z.
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p. 724 - 729
(2015/04/14)
-
- [1,2,4]TRIAZOLO[4,3-B][1,2,4]TRIAZINE COMPOUND, PREPARATION METHOD AND USE THEREOF
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The present invention relates to a structurally novel [1,2,4]triazolo[4,3-b][1,2,4]triazine compounds represented by formula (I) or formula (II), pharmaceutically acceptable salts thereof, prodrugs thereof, hydrates or solvates thereof, and also relates to a preparation method of the compounds, a pharmaceutical composition comprising a therapeutically effective amount of the compounds, as well as the use thereof as protein tyrosine kinase inhibitors, particularly as c-Met inhibitors, in the preparation of medicaments for the prevention and/or treatment of diseases associated with c-Met abnormality.
- -
-
Paragraph 0313; 0314; 0315
(2013/11/05)
-
- Design and synthesis of 2-acylbenzothiazoles via in situ cross-trapping strategy from benzothiazoles with aryl ketones
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An I2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.
- Gao, Qinghe,Wu, Xia,Jia, Fengcheng,Liu, Meicai,Zhu, Yanping,Cai, Qun,Wu, Anxin
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p. 2792 - 2797
(2013/04/24)
-
- Oxidation of aryl and heteroaryl methyl ketone to aryl and heteroarylglyoxals by using CuCl2-DMSO
-
The oxidation of aryl methyl ketone and heteroaryl methyl ketone to arylglyoxals and heteroaryl glyoxal respectively has been carried out by using the cheap and easily available, non toxic, Lewis acid CuCl2 in DMSO solvent at 70-80°C within 1-2 hr. The reaction can be performed in air without loss of variety of oxidisable fuctional group like phenolic OH, hetroaryl ring, aryl substituted methyl, halo, nitro group, etc.
- Lokhande, Pradeep D.,Waghmare, Smita R.,Gaikwad, Harsh,Hankare
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p. 300 - 305
(2013/05/08)
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- I2-promoted direct one-pot synthesis of 2-aryl-3-(pyridine-2- ylamino)imidazo[1,2-a]pyridines from aromatic ketones and 2-aminopyridines
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An I2-promoted one-pot protocol was proposed for the synthesis of 2-aryl-3-(pyridine-2-ylamino)imidazo[1,2-a]pyridines from aromatic ketones and 2-aminopyridines. The present reaction proceeded well in the presence of I2 in DMSO, and it avoided the requirement of any metal, base, and ligand.
- Fei, Zhuan,Zhu, Yan-Ping,Liu, Mei-Cai,Jia, Feng-Cheng,Wu, An-Xin
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supporting information
p. 1222 - 1226
(2013/03/14)
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- A simple three-component synthesis of 3-amino-5-arylpyridazine-4- carbonitriles
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New 3-amino-5-arylpyridazine-4-carbonitriles have been synthesized by a one-pot three-component reaction of malononitrile with arylglyoxals in the presence of hydrazine hydrate at room temperature in water and ethanol.
- Khalafy,Rimaz,Farajzadeh,Ezzati
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p. 179 - 182
(2013/07/26)
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- An efficient one-pot protocol for regioselective synthesis of 3-aryl-6,8-dialkyl-7-thioxo-7,8-dihydropyrimido[4,5-c ] pyridazine-5(6 H)-ones
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A series of 3-aryl-6,8-dialkyl-7-thioxo-7,8-dihydropyrimido[4,5-c] pyridazine-5(6H)-one derivatives have been regioselectively synthesized via the one-pot three-component reaction of 1,3-dimethylthiobarbituric acid and 1,3-diethylthiobarbituric acid with various arylglyoxals in the presence of hydrazinium dihydrochloride in warm ethanol. These new substituted pyrimidopyridazines may be potential monoamine oxidase inhibitors.
- Khalafy, Jabbar,Rimaz, Mehdi,Rabiei, Hossein,Panahi, Leila
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p. 395 - 406
(2013/09/23)
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- Synthesis and characterization of a 4-nitrophenyl functionalized NHC ligand and its palladium(II) complex
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The synthesis and characterization of a novel pyridine coordinated dichloridopalladium(II) NHC complex is described. This compound possesses a saturated NHC ligand that is substituted with a para-nitrophenyl function in the 4-position of the NHC backbone.
- Rajabi, Fatemeh,Trampert, Jens,Sun, Yu,Busch, Mark,Br?se, Stefan,Thiel, Werner R.
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p. 101 - 107
(2013/10/01)
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- Kinetics of the reaction of arylethanediylidene-bis-dithiocarbazonoate Ni complexes with morpholine in benzene: Substituent and temperature effects
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[1-Arylethanediylidene-bis(methyl dithiocarbazonoate) NN′SS′ (-2)]Ni(II) complexes were prepared by condensation of arylglyoxals with methyl dithiocarbazoate to give the corresponding hydrazonoates. The chelation of nickel(II) with these hydrazonoates gave square planar Ni complexes. The k 3 values for the substitution of -SCH3 close to the aryl group with morpholine (Mo) in benzene were found to increase steadily (20-35°C) followed by a sudden drop after 35°C. A continuous decrease in k3 values was observed by further elevation in the temperature. The Arrhenius plot showed a convex curve at the whole temperatures 20-55°C, and negative ΔH# values for the reactions were obtained at 40-55°C. The Hammett plots at the temperature ranges 20-35° and 40-55°C exhibited good straight lines with ρ values of 1.44-0.73 and 1.18-1.25, respectively. The proposed mechanism is a nucleophilic aromatic substitution-like, in which the rate-determining step is the proton transfer process in the temperature range 20-35°C whereas the mechanism in the range 40-55°C passes through the attack of Mo on the carbon carrying the SCH 3 group followed by the addition of the second Mo molecule on Ni to form an intermediate, which undergoes elimination of Mo and CH3SH to give a monosubstitution complex.
- Shehata, Aziza K.,Fathalla, Magda F.,Header, Heba M. A.,Hamed, Ezzat A.
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experimental part
p. 27 - 40
(2012/02/05)
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- Microwave-assisted selenium dioxide oxidation of aryl methyl ketones to aryl glyoxals
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We report an improved procedure for the synthesis of phenyl glyoxal and a series of para-substituted aryl glyoxals by microwave-assisted selenium dioxide oxidation. The reaction time has been reduced from several hours to three minutes for activated aryl methyl ketone substrates and 18 min for deactivated substrates, with all reactions affording quantitative conversion into the corresponding aryl glyoxals.
- Young, Ryan M.,Davies-Coleman, Michael T.
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experimental part
p. 4036 - 4038
(2011/08/09)
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- Arylglyoxals: A novel and efficient reagent for the oxidation of thiols to homodisulfides
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The stoichiometric oxidation of thiols to their corresponding homodisulfides by arylglyoxals has been described. The process has several advantages: high yields, short reaction times, simple experimental and work-up procedures. Figure Presented.
- Mosslemin, Mohammad Hossein,Anary-Abbasinejad, Mohammad,Movahhed, Abolfazl Eshghi,Hassanabadi, Alireza,Ghoroghchian, Saeedeh
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body text
p. 111 - 115
(2012/01/06)
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- One-pot synthesis of enantiomerically pure 1, 2-diols: Asymmetric reduction of aromatic α-oxoaldehydes catalysed by Candida parapsilosis ATCC 7330
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A facile and simple one-pot method was developed to produce a series of optically active (S)-1-phenyl-1,2-ethanediols with good yields (up to 70%) and high enantiomeric excess (>99%) via asymmetric reduction of various substituted aromatic α-oxoaldehydes using Candida parapsilosis ATCC 7330.
- Mahajabeen, Pula,Chadha, Anju
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experimental part
p. 2156 - 2160
(2012/05/04)
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- A regiospecific One-Pot, Three component synthesis of 4-Aryl-6,8- dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones as New potential monoamine oxidase inhibitors
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A series of new 4-aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)- diones have been synthesized via three component reaction of 1,3-dimethylbarbituric acid with arylglyoxals in the presence of hydrazinium dihydrochloride in ethanol. All of these derivatives may act as potential monoamine oxidase inhibitors.
- Khalafy, Jabbar,Rimaz, Mehdi,Panahi, Leila,Rabiei, Hossein
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scheme or table
p. 2428 - 2432
(2012/06/01)
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- Gas-phase pyrolysis of N-alkoxyphthalimides to functionally substituted aldehydes: Kinetic and mechanistic study
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Flash vacuum Pyrolysis (FVP) of primary N-alkoxyphthalimides at 400-500 C° and 0.02 Torr gave functionally substituted aldehydes. A mechanism of this pyrolytic transformation was proposed based on the kinetic data and product analysis. ARKAT USA, Inc.
- Al-Etaibi, Alya M.,Al-Awadi, Nouria A.,Ibrahim, Maher R.,Ibrahim, Yehia A.
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experimental part
p. 149 - 162
(2010/12/25)
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- New heteroaromatic aminations on 5-aryl-1,2,4-triazines and 1,2,4,5-tetrazines by palladium catalysis
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The efficient and original palladium-catalyzed amination of 5-Aryl-1,2,4-triazines and 1,2,4,5-tetrazines is reported. This Buchwald-Hartwig type reaction leads to the formation of aminated heterocycles via methylsulfur release. The reaction is optimized and a wide range of amines is used to determine the scope and limitations of this methodology.
- Pellegatti, Laurent,Vedrenne, Emeline,Leger, Jean-Michel,Jarry, Christian,Routier, Sylvain
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experimental part
p. 4383 - 4389
(2010/07/05)
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- A simple one-pot, three component synthesis of 3-arylpyrimido[4,5-c] pyridazine-5,7(6h,8h)-diones and their sulfur analogues as potential monoamine oxidase inhibitors
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Several new 3-arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and 3-aryl-5-oxo-7-thioxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-ones have been synthesized by a three-component reaction of barbituric acid or thiobarbituric acid with arylglyoxals in the presence of a catalytic amount of pyridine and hydrazine hydrate at room temperature in water.
- Rimaz, Mehdi,Khalafy, Jabbar,Pesyan, Nader Noroozi,Prager, Rolf H.
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scheme or table
p. 507 - 510
(2010/07/15)
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- INHIBITORS OF HEPATITIS C VIRUS REPLICATION
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The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.
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Page/Page column 74
(2010/11/04)
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- Design, synthesis and conformational analysis of turn inducer cyclopropane scaffolds: microwave assisted amidation of unactivated esters on catalytic solid support to obtain γ-turn mimic scaffolds
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Novel constrained 1-aroyl-cyclopropane-2,3-cis-dicarboxylic acid bis-[(2-hydroxy-ethyl)-amides] (17a-e) with varied torsional angles have been synthesized in high yield from unactivated esters of 1-aroyl-2,3-cis-diethoxycarbonylcyclopropanes (15a-e) on a catalytic solid support with reduced reaction times by using the monomode-microwave irradiation; 15a-e were obtained by diastereoselective ethoxycarbonylmethylene transfer from a sulfur ylide to ethyl β-aroylacrylates (10a-e). Torsional angles and interatomic distance measurements on the energy minimized structures of the obtained molecules (17a-e, DFT, B3LYP/6-31G* level) have established these molecules as valuable γ-turn mimic scaffolds.
- Bhella, Surinderjit Singh,Elango, Munusamy,Ishar, Mohan Paul S.
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experimental part
p. 240 - 246
(2009/04/06)
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- Synthesis and anti-protozoal activity of C2-substituted polyazamacrocycles
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A focused library of C2-substituted-1,4,7,10-tetraazacyclododecanes was synthesised and the compounds were tested for their ability to kill trypanosome and malaria parasites. Several compounds showed significant in vitro activity and were selectively active against the parasites over human embryonic kidney cells used as a counter screen.
- Reid, Caroline M.,Ebikeme, Charles,Barrett, Michael P.,Patzewitz, Eva-Maria,Mueller, Sylke,Robins, David J.,Sutherland, Andrew
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p. 2455 - 2458
(2008/09/21)
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- Microwave assisted synthesis of 1,5-disubstituted hydantoins and thiohydantoins in solvent-free conditions
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1,5-Disubstituted hydantoins/thiohydantoins 3a-p have been synthesized in 81-95% yield by a microwave-promoted solvent-free condensation of arylglyoxals 1 and phenylurea/thiourea 2 using PPE as a reaction mediator. This method can be extended towards the parallel synthesis of 3. The workup is simple and involves treatment with ice-cold water.
- Paul,Gupta,Gupta,Loupy
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- Structure-activity relationships for analogues of the phenazine-based dual topoisomerase I/II inhibitor XR11576
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As part of a programme to identify further analogues of the dual topo I/II inhibitor XR11576, we describe here the syntheses and SAR studies of various 'minimal' and 3,4-benzofused phenazine chromophores of the phenazine template of XR11576.
- Wang, Shouming,Miller, Warren,Milton, John,Vicker, Nigel,Stewart, Alistair,Charlton, Peter,Mistry, Prakash,Hardick, David,Denny, William A.
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p. 415 - 418
(2007/10/03)
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