73291-09-5Relevant articles and documents
Natural-product-inspired design and synthesis of two series of compounds active against Trypanosoma cruzi: Insights into structure–activity relationship, toxicity, and mechanism of action
Grand, Lucie,Popowycz, Florence,Schenkel, Eloir Paulo,Steindel, Mario,da Rosa, Rafael,Campos Bernardes, Lílian Sibelle,Dambrós, Bibiana Paula,H?ehr de Moraes, Milene,Jacolot, Ma?wenn
, (2021/11/30)
Chemical scaffolds of natural products have historically been sources of inspiration for the development of novel molecules of biological relevance, including hit and lead compounds. To identify new compounds active against Trypanosoma cruzi, we designed and synthesized 46 synthetic derivatives based on the structure of two classes of natural products: tetrahydrofuran lignans (Series 1) and oxazole alkaloids (Series 2). Compounds were screened in vitro using a cellular model of T. cruzi infection. In the first series of compounds, 11 derivatives of hit compound 5 (EC50 = 1.1 μM) were found to be active; the most potent (7, 8, and 13) had EC50 values of 5.1–34.2 μM. In the second series, 17 analogs were found active at 50 μM; the most potent compounds (47, 49, 59, and 63) showed EC50 values of 24.2–49.1 μM. Active compounds were assessed for selectivity, hemocompatibility, synergistic potential, effects on mitochondrial membrane potential, and inhibitory effect on trypanothione reductase. All active compounds showed low toxicity against uninfected THP-1 cells and human erythrocytes. The potency of compounds 5 and 8 increased steadily in combination with benznidazole, indicating a synergistic effect. Furthermore, compounds 8, 47, 49, 59, and 63 inhibited parasitic mitochondria in a dose-dependent manner. Although increased reactive oxygen species levels might lead to mitochondrial effects, the results indicate that the mechanism of action of the compounds is not dependent on trypanothione reductase inhibition. In silico calculation of chemical descriptors and principal component analysis showed that the active compounds share common chemical features with other trypanocidal molecules and are predicted to have a good ADMET profile. Overall, the results suggest that the compounds are important candidates to be further studied for their potential against T. cruzi.
Design, synthesis and study of antibacterial and antitubercular activity of quinoline hydrazone hybrids
Eswaran, Sumesh,Shruthi, T. G.,Subramanian, Sangeetha
, p. 137 - 147 (2020/11/12)
Emerging bacterial resistance is causing widespread problems for the treatment of various infections. Therefore, the search for antimicrobials is a never-ending task. Hydrazones and quinolines possess a wide variety of biological activities. Herewith, eleven quinoline hydrazone derivatives have been designed, synthesized, characterized and evaluated for their antibacterial activity and antitubercular potential against Mtb WT H37Rv. Compounds QH-02, QH-04 and QH-05 were found to be promising compounds with an MIC value of 4 μg/mL against Mtb WT H37Rv. Compounds QH-02, QH-04, QH-05, and QH-11 were also found to be active against bacterial strains including Acinetobacter baumanii, Escherichia coli and Staphylococcus aureus. Further, we have carried out experiments to confirm the cytotoxicity of the active compounds and found them to be non-toxic.
COMPOUND HAVING ALKENYL GROUP AT BOTH TERMINALS, LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY ELEMENT
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Paragraph 0154, (2017/05/16)
PROBLEM TO BE SOLVED: To provide a liquid crystalline compound satisfying at least one of demands for physical properties such as high stability to heat or light, a high clearing point (or a high maximum temperature), low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large dielectric anisotropy, suitable elastic modulus and good compatibility with other liquid crystalline compounds, a liquid crystal composition comprising the above compound, and a liquid crystal display element containing the composition. SOLUTION: A compound represented by formula (1) is provided. In the formula, R1 and R2 each independently represent an alkenyl group having 2 to 10 carbon atoms, or the like; ring A1, ring A2 and ring A3 each independently represent 1,4-phenylene or 1-4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine; Z1 and Z2 each independently represent an alkylene having 1 to 4 carbon atoms, or the like and at least one of Z1 and Z2 may be a single bond; and a represents 1 or 2. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
Gold nanoparticles supported on magnesium oxide nanorods for oxidation of alcohols
Emayavaramban,Ganesh Babu,Karvembu,Kadirvelu,Dharmaraj
, p. 2517 - 2526 (2016/03/19)
Gold nanoparticles supported on magnesium oxide nanorods (Au-MgO) have been synthesised by a solution based chemical reduction method. Au-MgO nanorods were found to be an efficient heterogeneous catalyst for oxidation of alcohols with hydrogen peroxide in aqueous medium at room temperature. To find out the best reaction conditions for oxidation, optimization of catalyst quantity, solvent, mole equivalence of hydrogen peroxide were carried out. The scope of the reaction was extended to several aromatic and aliphatic alcohols, product yields were quantified by gas chromatography (GC) and GC/mass spectroscopy. Heterogeneity and reusability tests were performed. The use of water as a solvent and hydrogen peroxide as co-catalyst at room temperature makes the reaction interesting from sustainable development point of view.
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents
Bailey, Christopher L.,Joh, Alexander Y.,Hurley, Zefan Q.,Anderson, Christopher L.,Singaram, Bakthan
, p. 3619 - 3628 (2016/05/24)
Dialkylboranes and aminoborohydrides are mild, selective reducing agents complementary to the commonly utilized amide reducing agents, such as lithium aluminum hydride (LiAlH4) and diisobutylaluminum hydride (DIBAL) reagents. Tertiary amides were reduced using 1 or 2 equiv of various dialkylboranes. The reduction of tertiary amides required 2 equiv of 9-borabicyclo[3.3.1]nonane (9-BBN) for complete reduction to give the corresponding tertiary amines. One equivalent of sterically hindered disiamylborane reacts with tertiary amides to afford the corresponding aldehydes. Aminoborohydrides are powerful and selective reducing agents for the reduction of tertiary amides. Lithium dimethylaminoborohydride and lithium diisopropylaminoborohydride are prepared from n-butyllithium and the corresponding amine-borane. Chloromagnesium dimethylaminoborohydride (ClMg+[H3B-NMe2]-, MgAB) is prepared by the reaction of dimethylamine-borane with methylmagnesium chloride. Solutions of aminoborohydride reduce aliphatic, aromatic, and heteroaromatic tertiary amides to give the corresponding alcohol, amine, or aldehyde depending on the steric requirement of the tertiary amide and the aminoborohydride used.
METHOD OF CONVERTING ALCOHOL TO HALIDE
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Page/Page column 51; 166; 170, (2017/01/02)
The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
Tsuji-Wacker Oxidation of Terminal Olefins using a Palladium-Carbon Nanotube Nanohybrid
Donck, Simon,Gravel, Edmond,Shah, Nimesh,Jawale, Dhanaji V.,Doris, Eric,Namboothiri, Irishi N. N.
, p. 2318 - 2322 (2015/08/11)
Palladium nanoparticles supported on carbon nanotubes were used in the Tsuji-Wacker oxidation. The palladium-based nanohybrid was found to be very active in combination with cuprous chloride for the selective oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions (room temperature, atmospheric pressure, low catalyst loading), as opposed to previously reported catalysts, and can be recycled without any loss in activity. Give it a whack: Palladium nanoparticles supported on carbon nanotubes are used in combination with cuprous chloride for the selective Tsuji-Wacker oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions and can be recycled without any loss in activity.
Aqueous oxidation of alcohols catalysed by recoverable iron oxide nanoparticles supported on aluminosilicates
Rajabi, Fatemeh,Pineda, Antonio,Naserian, Sareh,Balu, Alina Mariana,Luque, Rafael,Romero, Antonio A.
, p. 1232 - 1237 (2013/06/05)
Supported iron oxide nanoparticles on aluminosilicate catalysts were found to be efficient and easily recoverable materials in the aqueous selective oxidation of alcohols to their corresponding carbonyl compounds using hydrogen peroxide under both conventional and microwave heating. The protocol features an easy work-up, simplicity and the utilisation of mild reaction conditions as well as high selectivity toward aldehydes is highly advantageous compared to alternatively reported methodologies. The supported iron oxide nanoparticles could be easily recovered from the reaction mixture and reused several times without any loss in activity. ICP-MS results proved that there is no metal leaching observed, demonstrating the stability of the catalyst under the investigated conditions.
Electronic structure and catalytic aspects of [(trpy)(Cl)Ru(L)]n incorporating potential non-innocent ligands, L-: 9-Oxidophenalenone and trpy: 2,2′:6′,2″-terpyridine
Das, Amit,Ghosh, Tamal Kanti,Dutta Chowdhury, Abhishek,Mobin, Shaikh M.,Lahiri, Goutam Kumar
, p. 1130 - 1137 (2013/06/04)
The title complex [(trpy)(Cl)RuII(L)] (1) incorporating potential redox non-innocent ligands, L- = 9-oxidophenalenone and trpy = 2,2′:6′,2″-terpyridine has been structurally characterized. The crystal structure of 1 establishes the distorted octahedral arrangement, meridional coordinating mode of trpy and delocalized C-O bond distances of coordinated L-. Compound 1 displays two one-electron oxidations at E2980, 0.12 V (Ox1) and 1.32 V (Ox2) and one reduction, -1.58 V versus SCE. Predominantly ruthenium based first oxidation (Ox1) and L based second oxidation (Ox2) lead to the valence configurations of [(trpy)(Cl)Ru III(L-)]+ (1+) and [(trpy)(Cl)RuIII(L)]2+ (12+), respectively. The antiferromagnetic coupling of spins on Ru(III) (low-spin, t2g 5) and L develops a singlet (S = 0) ground state in 12+. The reduction, however, occurs at the trpy site. The electronic transitions in 1 and 1+ could be assigned based on the TD-DFT calculations. Interestingly, 1 has been established to be an efficient pre-catalyst for the oxidative cleavage of alkenes to carbonyl derivatives.
