- N-Functionalised heterocyclic dicarbene complexes of silver: Synthesis and structural studies
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A range of new diimidazolium salts, held together by an alkyl unit and bearing alcohol pendant arms on their nitrogen, was synthesized. A short modular reaction pathway leads to the N-heterocyclic carbene (NHC) precursors, differing by the flexibility of
- Jean-Baptiste dit Dominique, Fran?ois,Gornitzka, Heinz,Hemmert, Catherine
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- Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes
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The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.
- Barrios-Rivera, Jonathan,Xu, Yingjian,Clarkson, Guy J.,Wills, Martin
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supporting information
(2021/12/02)
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- Design, synthesis and biological evaluation of imidazole and triazole-based carbamates as novel aromatase inhibitors
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In the search for novel aromatase inhibitors, a series of triazole and imidazole-based carbamate derivatives were designed and synthesized. Final compounds were thus evaluated against human aromatase by in vitro kinetic experiments in a fluorimetric assay in comparison with letrozole. The effect of most active derivatives 13a and 15c was then evaluated in vitro on the human breast cancer cell line MCF7 by MTT assay, cytotoxicity assay (LDH release) and cell cycle analysis, revealing a dose-dependent inhibition profile of cell viability and low micromolar IC50 values. In addition, docking simulations were also carried out to elucidate at a molecular level of detail the binding modes adopted to target human aromatase.
- Ammazzalorso, Alessandra,Gallorini, Marialucia,Fantacuzzi, Marialuigia,Gambacorta, Nicola,De Filippis, Barbara,Giampietro, Letizia,Maccallini, Cristina,Nicolotti, Orazio,Cataldi, Amelia,Amoroso, Rosa
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- Synthesis, in vitro antifungal evaluation and docking studies of novel derivatives of imidazoles and benzimidazoles
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A series of imidazole and benzimidazole derivatives was designed and prepared in good yields via convenient and efficient two steps synthetic route using readily available starting materials. The structures of the synthesized compounds and their intermedi
- Shojaei, Pegah,Mokhtari, Babak,Ghorbanpoor, Masoud
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p. 1359 - 1367
(2019/07/03)
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- Diaryl-containing imidazole compound and preparation method and medical application thereof
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The invention discloses a diaryl-containing imidazole compound. The invention further discloses application of the diaryl-containing imidazole compound to preparation of drugs for preventing or treating Alzheimer's disease. The inventor screens butyrylcholine esterase and IDO1 as carriers for inhibiting the activity to evaluate the effect of the diaryl imidazole compound to treat Alzheimer's disease, and finds that the diaryl imidazole compound has good in vitro activity, and can be further developed as a precursor substance for performing the Alzheimer's disease resistant effect by inhibitingthe activity of cholinesterase. (The formula is shown in the description).
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Paragraph 0192; 0197; 0198
(2019/02/21)
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- New azole derivatives showing antimicrobial effects and their mechanism of antifungal activity by molecular modeling studies
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Azole antifungals are potent inhibitors of fungal lanosterol 14α demethylase (CYP51) and have been used for eradication of systemic candidiasis clinically. Herein we report the design, synthesis, and biological evaluation of a series of 1-phenyl/1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethanol esters. Many of these derivatives showed fungal growth inhibition at very low concentrations. Minimal inhibition concentration (MIC) value of 15 was 0.125?μg/mL against Candida albicans. Additionally, some of our compounds, such as 19 (MIC: 0.25?μg/mL), were potent against resistant C.?glabrata, a fungal strain less susceptible to some first-line antifungal drugs. We confirmed their antifungal efficacy by antibiofilm test and their safety against human monocytes by cytotoxicity assay. To rationalize their mechanism of action, we performed computational analysis utilizing molecular docking and dynamics simulations on the C.?albicans and C.?glabrata CYP51 (CACYP51 and CGCYP51) homology models we built. Leu130 and T131 emerged as possible key residues for inhibition of CGCYP51 by 19.
- Do?an, ?nci Selin,Sara?, Selma,Sari, Suat,Kart, Didem,E?siz G?khan, ?ebnem,Vural, ?mran,Dalkara, Sevim
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p. 124 - 138
(2017/03/02)
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- A comparative study of hydroxyl- and carboxylate-functionalized imidazolium and benzimidazolium salts as precursors for N-heterocyclic carbene ligands
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The preparation of imidazolium and benzimidazolium salts with hydroxyl or carboxylate functions has been achieved using straightforward synthetic pathways. These salts in combination with palladium(II) acetate give active catalytic systems for Suzuki reac
- Allegue, Andrs,Albert-Soriano, Mara,Pastor, Isidro M.
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p. 524 - 532
(2015/09/01)
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- Ultrasound-assisted regioselective ring opening of epoxides with nitrogen heterocycles using pyrrolidonium and imidazolium-based acidic ionic liquids
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Imidazolium and N-methyl-2-pyrrolidonium ionic liquids under ultrasound irradiation were developed as a green and expeditious approach for C-alkylation and N-alkylation of the nitrogen heterocycles including indoles and imidazoles with aliphatic and aroma
- Zakeri, Masoumeh,Nasef, Mohamed Mahmoud,Abouzari-Lotf, Ebrahim,Haghi, Hoda
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p. 10097 - 10108
(2016/01/12)
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- Highly efficient and green chemical synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds using nanocrystalline ZSM-5 catalysts
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A solvent free protocol is developed for the synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds. Imidazolyl alcohols were synthesized by the ring opening of epoxides with imidazoles and N-imidazolyl functionalized β-amino compounds were synthesized by the hydroamination reaction of imidazoles and activated olefins. These reactions were catalyzed by a variety of crystalline heterogeneous catalysts such as Al/Zr substituted nanocrystalline ZSM-5 (M-Nano-ZSM-5), conventional M-ZSM-5 (where M = Zr, Al), and Zr substituted amorphous mesoporous catalysts (Zr-SBA-15 and Zr-KIT-6). Among these catalysts, nanocrystalline Zr-Nano-ZSM-5 exhibited the highest activity and regioselectivity. Structure activity relationship is explained based on the catalytic activity, acidity measurements, reactivity of reactants (imidazoles/epoxides/methyl acrylate), competitive adsorption, nature, and type of catalysts. Zr-Nano-ZSM-5 exhibited exceptionally high catalytic activity compared to the catalysts reported in the literature for the synthesis of imidazolyl alcohols and other imidazole derivatives.
- Kore, Rajkumar,Satpati, Biswarup,Srivastava, Rajendra
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- Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors
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Indoleamine 2,3-dioxygenase 1 (IDO1) is a key regulator of immune responses and therefore an important therapeutic target for the treatment of diseases that involve pathological immune escape, such as cancer. Here, we describe a robust and sensitive high-throughput screen (HTS) for IDO1 inhibitors using the Prestwick Chemical Library of 1200 FDA-approved drugs and the Maybridge HitFinder Collection of 14,000 small molecules. Of the 60 hits selected for follow-up studies, 14 displayed IC50 values below 20 μM under the secondary assay conditions, and 4 showed an activity in cellular tests. In view of the high attrition rate we used both experimental and computational techniques to identify and to characterize compounds inhibiting IDO1 through unspecific inhibition mechanisms such as chemical reactivity, redox cycling, or aggregation. One specific IDO1 inhibitor scaffold, the imidazole antifungal agents, was chosen for rational structure-based lead optimization, which led to more soluble and smaller compounds with micromolar activity.
- R?hrig, Ute F.,Majjigapu, Somi Reddy,Chambon, Marc,Bron, Sylvian,Pilotte, Luc,Colau, Didier,Van Den Eynde, Beno?t J.,Turcatti, Gerardo,Vogel, Pierre,Zoete, Vincent,Michielin, Olivier
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p. 284 - 301
(2014/08/05)
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- Silver(I) N-heterocyclic carbene complexes: Synthesis, characterization and antibacterial activity
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Five new silver complexes having bidentate N-heterocyclic carbene ligands were synthesized and characterized by elemental analysis, IR, NMR and mass spectroscopic methods. Four of the ligands used are neutral, having an alcohol group on alkyl substituent
- Napoli, Mariagrazia,Saturnino, Carmela,Cianciulli, Elena Immacolata,Varcamonti, Mario,Zanfardino, Anna,Tommonaro, Giuseppina,Longo, Pasquale
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- Direct hydrosilylation of tertiary amides to amines by an in situ formed iron/N-heterocyclic carbene catalyst
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Tertiary amides were efficiently reduced to their corresponding tertiary amines in high isolated yields by using the commercially available and inexpensive polymeric silane polymethylhydrosiloxane (PMHS) as the reducing agent. The reaction is efficiently catalyzed by an in situ generated iron/N-heterocyclic carbene complex (1 mol-%) obtained from iron(II) acetate and 1-(2-hydroxy-2-phenylethyl)-3-methylimidazolium triflate ([PhHEMIM][OTF]). A catalytic amount of lithium chloride (1 mol-%) present in the reaction mixture significantly reduced the reaction time and increased the chemoselectivity of the reduction process. Tertiary amides are reduced to their corresponding tertiary amines in high isolated yields by using the polymeric silane polymethylhydrosiloxane (PMHS) in the presence of an in situ generated iron/N-heterocyclic carbene complex (1 mol-%), generated from iron(II) acetate and 1-(2-hydroxy-2-phenylethyl)-3-methylimidazolium triflate ([PhHEMIM][OTF]), and a catalytic amount of lithium chloride (1 mol-%). Copyright
- Volkov, Alexey,Buitrago, Elina,Adolfsson, Hans
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supporting information
p. 2066 - 2070
(2013/05/09)
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- Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)- 1-phenylethanol derivatives
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A new series of aromatic ester and carbamate derivatives of 2-(1H-imidazol-1-yl)-1-phenylethanol were synthesized and evaluated for their antifungal activity towards Candida albicans and non-albicans Candida species strains. The aromatic biphenyl ester derivatives 6a-c were more active than the reference compound fluconazole. 6c possesses a MIC mean values of 1.7 ± 1.4 μg mL-1 vs C. albicans and 1.9 ± 2.0 μg mL -1 vs non-albicans Candida species strains. The racemic mixtures of 6a, b were purified to afford the pure enantiomers. The (-) isomers were up to 500 times more active than (+) isomers. (-)-6a and (-)-6b were thirty and ninety times more active than fluconazole towards C. krusei strain respectively. The racemates of 6a-c showed low cytotoxicity against human monocytic cell line (U937) with 6a demonstrating a CC50 greater than 128 μg mL -1.
- De Vita, Daniela,Scipione, Luigi,Tortorella, Silvano,Mellini, Paolo,Di Rienzo, Barbara,Simonetti, Giovanna,D'Auria, Felicia Diodata,Panella, Simona,Cirilli, Roberto,Di Santo, Roberto,Palamara, Anna Teresa
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p. 334 - 342
(2012/04/10)
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- Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents
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A series of aryloxy alkyl/aryl alkyl imidazoles were synthesized and evaluated in vitro as antileishmanials against Leishmania donovani. All the 19 compounds exhibited 94-100% inhibition at 10 μg/mL against promastigotes and 12 compounds exhibited high in
- Bhandari, Kalpana,Srinivas, Nagarapu,Marrapu, Vijay K.,Verma, Aditya,Srivastava, Saumya,Gupta, Suman
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scheme or table
p. 291 - 293
(2010/04/05)
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- Y(NO3)3·6H2O catalyzed regioselective ring opening of epoxides with aliphatic, aromatic, and heteroaromatic amines
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Yttrium nitrate hexahydrate [Y(NO3)3·6H2O] was found to be an efficient catalyst for selective ring opening of epoxides with aliphatic, aromatic, and heteroaromatic amines at room temperature under solvent-free conditions. The system tolerated a variety of hindered and functionalized epoxides/amines and afforded the desired β-amino alcohols at low catalyst concentration.
- Bhanushali, Mayur J.,Nandurkar, Nitin S.,Bhor, Malhari D.,Bhanage, Bhalchandra M.
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p. 3672 - 3676
(2008/09/19)
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- Regioselectivity in a highly efficient, microwave-assisted epoxide aminolysis
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We have developed a microwave-assisted aminolysis of epoxides as an efficient method for synthesizing a number of β-amino alcohols. In most cases, including in reactions of amines with a trisubstituted epoxide, only one equivalent of amine is required to
- Desai, Hinal,D'Souza, Brendan R.,Foether, Devin,Johnson, Benjamin F.,Lindsay, Harriet A.
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p. 902 - 910
(2008/01/06)
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- Solvent-free direct regioselective ring opening of epoxides with imidazoles
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The reaction of different epoxides with commercially available imidazole at 60 °C leads to the formation of the corresponding 1-(β-hydroxyalkyl)imidazoles in a regioselective manner. When the reaction is applied to a chiral epoxide [(R)-styrene oxide], th
- Torregrosa, Rosario,Pastor, Isidro M.,Yus, Miguel
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p. 469 - 473
(2007/10/03)
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- Fluoroboric acid adsorbed on silica gel catalyzed regioselective ring opening of epoxides with nitrogen heterocycles
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Aryl epoxides can be opened in a regioselective and efficient manner with nitrogen heterocycles such as indoles, pyrroles and imidazoles in the presence of a catalytic amount of HBF4-SiO2 under mild conditions to afford the correspon
- Bandgar,Patil, Abasaheb V.
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p. 173 - 176
(2007/10/03)
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- The "reverse-tethered" ruthenium (II) catalyst for asymmetric transfer hydrogenation: Further applications
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The attachment of a tethering group from the basic nitrogen atom to the arene ligand of a ruthenium(II) catalyst greatly improves its ability to catalyze asymmetric transfer hydrogenation (ATH) reactions. In this paper, we describe further applications of this versatile system to an extended substrate range.
- Morris, David J.,Hayes, Aidan M.,Wills, Martin
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p. 7035 - 7044
(2007/10/03)
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- Synthesis and Biological activity of kappa opioid receptor agonists. Part 2: Preparation of 3-aryl-2-pyridone analogues generated by solution- and solid-phase parallel synthesis methods
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New analogues of the previously described 3-aryl pyridone KOR agonists have been synthesised by parallel synthetic methods, both in solution- and with solid-phase chemistry, making use of the well known and versatile Mitsunobu, Suzuki and Buchwald reactions. Opioid receptor binding data for the compounds produced is reported.
- Semple, Graeme,Andersson, Britt-Marie,Chhajlani, Vijay,Georgsson, Jennie,Johansson, Magnus J.,Rosenquist, Asa,Swanson, Lars
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p. 1141 - 1145
(2007/10/03)
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- Bicyclic inhibitors of protein farnesyl transferase
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PCT No. PCT/US98/03025 Sec. 371 Date Aug. 2, 1999 Sec. 102(e) Date Aug. 2, 1999 PCT Filed Feb. 11, 1998 PCT Pub. No. WO98/34921 PCT Pub. Date Aug. 13, 1998The present invention provides compounds of Formula (I). The present invention also provides a metho
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- A new series of miconazole analogs: Synthesis and in vitro antifungal and antimycobacterial activities
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The synthesis and antimicrobial activity of new miconazole analogs are reported. All compounds showed good antimycobacterial activity; some of them were also active against some strains of Candida albicans and Candida sp.. Of the synthesized compounds, two showed good activity both against some strains of Mycobacterium and some strains of Candida. Structure-activity relationships are discussed.
- Fioravanti, Rossella,Biava, Mariangela,Porretta, Giulio Cesare,Lampis, Giorgio,Deidda, Delia,Pompei, Raffaello
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p. 162 - 175
(2007/10/03)
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- High-pressure organic chemistry. 19. High-pressure-promoted, silica gel-catalyzed reaction of epoxides with nitrogen heterocycles
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The reaction of epoxides with nitrogen heterocycles such as indoles, pyrroles, imidazoles, and pyrazoles was studied under both high-pressure and silica gel-catalyzed conditions. Whereas it has been reported that the treatment of indole with styrene oxide
- Kotsuki, Hiyoshizo,Hayashida, Katsunori,Shimanouchi, Tomoyasu,Nishizawa, Hitoshi
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p. 984 - 990
(2007/10/03)
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- Research on antibacterial and antifungal agents. X. Synthesis and antimicrobial activities of 1-phenyl-2-(1H-azol-1-yl) ethane derivatives. Anticonvulsant activity of 1-(4-methylphenyl)-2-(1H-imidazol-1-yl) ethanol.
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The synthesis and antimicrobial activity of new phenylazolylethane derivatives are reported.Antimicrobial data in comparison with those obtained with miconazole, fluconazole, enilconazole, imazalil sulfate, pipemidic acid and minocycline showed that tested compounds generally possessed poor or weak activity.Toxicity and anticonvulsant activity of 1-(4-methylphenyl)-2-(1H-imidazol-1-yl)ethanol and structural likeness to Denzimol were also tested.The obtained results showed interesting anticonvulsant activity but only on the supraspinal region. azoles / antifungal / anticonvulsant agent
- Porretta, G. C.,Fioravanti, R.,Biava, M.,Cirilli, R.,Simonetti, N.,et al.
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p. 749 - 760
(2007/10/02)
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