- Synthesis, characterization, and antibacterial activity of dibenzildithiocarbamate derivates and Ni(II)–Cu(II) coordination compounds
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In this work, the study of the synthesis methodology to obtain dibenzylamine derivates as intermediates for the formation of dithicarbamate ligands (DTC) and its coordination compounds was conducted. Four molecules derived from dibenzylamine were synthesized by two methodologies: classical (reflux) and microwave. From these amines, Four dithiocarbamate ligands (DTC): dibenzyldithiocarbamate, N-benzyl-1-(4-methoxyphenyl)dithiocarbamate, N-benzyl-1-(4-chlorophenyl)dithiocarbamate, and N-benzyl-1-(3-nitrophenyl)dithiocarbamate, and eight coordination complexes with general formula [M(DTC)2]nH2O (M= Cu(II) and Ni(II)) were obtained. All the compounds were characterized using different spectroscopic and thermal techniques such as Fourier-transform infrared spectroscopy (FT-IR), ultraviolet–visible spectroscopy (UV–VIS), proton and carbon-13 nuclear magnetic resonance (1H and 13C NMR), thermogravimetric analysis–differential scanning calorimetry (TGA-DSC). Additionally, it was possible to characterize two new crystalline phases of salts through single-crystal X-ray diffraction: dibenzyl ammonium nitrate and N-benzyl-1-(3-nitrophenyl)ammonium chloride. Additionally, microbial inhibition tests were conducted using the dibenzildithiocarbamate derivates. All DTC compounds showed important activity against Pseudomonas aeruginosa and Staphylococcus aureus but less sensitivity against Escherichia coli and Mycobacterium smegmatis. Among the coordination compounds, only [Cu(N-benzyl-1-(3-nitrophenyl)dithiocarbamate)2] presented a moderate activity against M. smegmatis mc2 155.
- Amaya-Flórez, Andres,Aranaga, Carlos,D'Vries, Richard F.,Ellena, Javier,Flórez-López, Edwin,Macías, Mario,Pastrana-Dávila, Andrea
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- Ru Nanoparticles-Loaded Covalent Organic Framework for Solvent-Free One-Pot Tandem Reactions in Air
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Condensation of benzene-1,3,5-tricarbohydrazide with benzene-1,4-dicarboxaldehyde generated a new covalent organic framework, COF-ASB (1), in which the organic units are held together via hydrazone linkage to form porous frameworks. COF-ASB (1) is highly crystalline and displays good chemical and thermal stability and is permanently porous. In addition, 1 can be an ideal support to load Ru nanoparticles (Ru NPs) to generate Ru@COF-ASB (2). The obtained composite material is able to highly promote one-pot tandem synthesis of imine products from benzyl alcohols and corresponding amines under solvent-free conditions in air.
- Chen, Gong-Jun,Li, Xiao-Bo,Zhao, Chen-Chen,Ma, Hui-Chao,Kan, Jing-Lan,Xin, Yu-Bin,Chen, Cheng-Xia,Dong, Yu-Bin
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supporting information
p. 2678 - 2685
(2018/03/13)
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- Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites
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A group III metabotropic glutamate (mGlu) receptor agonist (PCEP) was identified by virtual HTS. This orthosteric ligand is composed by an l-AP4-derived fragment that mimics glutamate and a chain that binds into a neighboring pocket, offering possibilities to improve affinity and selectivity. Herein we describe a series of derivatives where the distal chain is replaced by an aromatic or heteroaromatic group. Potent agonists were identified, including some with a mGlu4 subtype preference, e.g., 17m (LSP1-2111) and 16g (LSP4-2022). Molecular modeling suggests that aromatic functional groups may bind at either one of the two chloride regulatory sites. These agonists may thus be considered as particular bitopic/dualsteric ligands. 17m was shown to reduce GABAergic synaptic transmission at striatopallidal synapses. We now demonstrate its inhibitory effect at glutamatergic parallel fiber-Purkinje cell synapses in the cerebellar cortex. Although these ligands have physicochemical properties that are markedly different from typical CNS drugs, they hold significant therapeutic potential.
- Selvam, Chelliah,Lemasson, Isabelle A.,Brabet, Isabelle,Oueslati, Nadia,Karaman, Berin,Cabaye, Alexandre,Tora, Amélie S.,Commare, Bruno,Courtiol, Tiphanie,Cesarini, Sara,McCort-Tranchepain, Isabelle,Rigault, Delphine,Mony, Laetitia,Bessiron, Thomas,McLean, Heather,Leroux, Frédéric R.,Colobert, Fran?oise,Daniel, Hervé,Goupil-Lamy, Anne,Bertrand, Hugues-Olivier,Goudet, Cyril,Pin, Jean-Philippe,Acher, Francine C.
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supporting information
p. 1969 - 1989
(2018/03/21)
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- Monocyclic β-lactam and unexpected oxazinone formation: synthesis, crystal structure, docking studies and antibacterial evaluation
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Novel monocyclic β-lactam derivatives bearing aryl, phenyl and heterocyclic rings were synthesized as possible antibacterial agents. Cyclization of imines (3h, 3t) with phenylacetic acid in the presence of phosphoryl chloride and triethyl amine did not afford the expected β-lactams. Instead, highly substituted 1,3-oxazin-4-ones (4h, 4t) were isolated as the only product and confirmed by single crystal X-ray analysis of 4t. The results of antibacterial activity showed that compound 4l exhibited considerable antibacterial activity with MIC and MBC values of 62.5 μg/mL against Klebsiella pneumoniae. Cytotoxicity assay on Chinese Hamster Ovary (CHO) cell line revealed non-cytotoxic behavior of compounds 4d, 4h, 4k and 4l up to 200 μg/mL conc. Molecular docking was performed for compound 4l with penicillin binding protein-5 to identify the nature of interactions. The results of both in silico and in vitro evaluation provide the basis for compound 4l to be carried as a potential lead molecule in the drug discovery pipeline against bacterial infections.
- Aneja, Babita,Irfan, Mohammad,Hassan, Md. Imtaiyaz,Prakash, Amresh,Yadava, Umesh,Daniliuc, Constantin G.,Zafaryab, Md.,Rizvi, M. Moshahid A.,Azam, Amir,Abid, Mohammad
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p. 834 - 852
(2016/07/07)
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- Selectively catalytic epoxidation of α-pinene with dry air over the composite catalysts of Co-MOR(L) with Schiff-base ligands
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Twelve bi-/tridentate Schiff-base ligands (L1-L12) have been designed, synthesized and coordinated with ion-exchanged Co-MOR (Mordenite) forming a series of Co-MOR(L) composite catalysts, for which various analyzes and characterizations are conducted. Selectively catalytic epoxidation of α-pinene with dry air over Co-MOR(L) catalysts has been carried out, where uses TBHP in small amounts as the initiator. Among these Co-MOR(L) catalysts, Co-MOR(L8) exhibits the best activity for the titled reaction to obtain 85.8 mol% conversion and 90.8% selectivity of epoxide. Some factors such as the structure of ligands, the oxidants, the solvents, the catalyst amount, the reaction temperature and time play important roles in controlling the epoxidation. The recyclable stability of the Co-MOR(L8) catalyst is confirmed. The studies on the electrochemical behaviors of Co species in Co-MOR(L8) reveal the importance of reversible change between Co oxidation states for the epoxidation.
- Lu,Lei,Wei,Ma,Zhang,Hu,Zhou,Xia
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- Direct synthesis of imines via solid state reactions of carbamates with aldehydes
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Various solid carbamates were prepared from the reactions of liquid amines with carbon dioxide in an autoclave and these carbamates were used as stable, efficient alternatives for toxic liquid amines. Solid-state grinding of carbamates and aldehydes, using a mortar and pestle, produced imines as the sole products in greater than 97% yields. Complete conversions were generally accomplished within a day at 25 °C without using solvents or additives. Reaction rates were drastically enhanced upon increasing the reaction temperature. In contrast, reactions of aldehydes with liquid amines in the presence of solvent or in neat conditions afforded imines in moderate yields along with by-products.
- Lee, Byeongno,Lee, Kyu Hyung,Lim, Byung Wook,Cho, Jaeheung,Nam, Wonwoo,Hur, Nam Hwi
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supporting information
p. 389 - 394
(2013/05/08)
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- Chitosan: A highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions
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Commercial chitosan-without any post-modification with active Bronsted or Lewis acid centers-was found to be a highly efficient renewable and recoverable bio-polymer catalyst for the rapid and convenient synthesis of α-amino nitriles or imines from aromatic aldehydes and amines under mild reaction conditions at room temperature in high to quantitative yields. The α-amino nitrile derivatives were prepared through the Strecker reaction using trimethylsilyl cyanide (TMSCN) and catalyzed by chitosan as a heterogeneous bifunctional organocatalyst.
- Dekamin, Mohammad G.,Azimoshan, Mojtaba,Ramezani, Leila
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supporting information
p. 811 - 820
(2013/04/10)
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- Generation of azomethine imine and metal-free formal 1,3-dipolar cycloaddition of imine with PhIO: Reaction, scope, and synthesis
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Generation of azomethine imine and its scope in regioselective 1,3-dipolar cycloaddition (DC) of imine with PhIO toward highly substituted Δ2-1,2,4-triazoline, 1,2,4-triazole, and their fused, chiral, and sugar-based analogues are demonstrated. The Royal Society of Chemistry.
- Maiti, Dilip K.,Chatterjee, Nirbhik,Pandit, Palash,Hota, Sandip K.
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supporting information; experimental part
p. 2022 - 2024
(2010/09/10)
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- Preparation of benzolactams by Pd(OAC)2-catalyzed direct aromatic carbonylation
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We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary ω-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines. Copyright
- Orito, Kazuhiko,Horibata, Akiyoshi,Nakamura, Takatoshi,Ushito, Harumi,Nagasaki, Hideo,Yuguchi, Motoki,Yamashita, Satoshi,Tokuda, Masao
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p. 14342 - 14343
(2007/10/03)
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- The cleavage of 1-amino-2'-nitrobenzylphosphonates in a basic medium. Formation of the 3-amino-2,1-benzisoxazole derivatives
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Treatment of 1-amino-2'-nitrobenzylphosphonic acids with aqueous sodium hydroxide caused a C-P bond cleavage, with formation of 3-amino-2,1-benzisoxazole derivatives (3). The leaving phosphorus moiety was identified here as phosphoric acid. In the case of basic hydrolysis of corresponding esters, new cyclic phosphorus compounds (derivatives of benzoxazaphosphorin-3,1,2 P(v)-one-2) were obtained. The cyclic products were formed as a result of the subsequent reaction of anthranil derivatives with leaving phosphorus fragment, presumably metaphosphate, These benzoxazaphosphorins (cormpounds 4) were converted by means of aqueous hydrochloric acid to 3-amino-2,1-benzisoxazole derivatives.
- Boduszek, Bogdan,Halama, Agnieszka,Zon, Jerzy
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p. 11399 - 11410
(2007/10/03)
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