2491-36-3Relevant academic research and scientific papers
3-Imidazolyl-substituted flavans as potential antifungal agents: Synthesis, stereochemical properties, and antifungal activity
Emami, Saeed,Foroumadi, Alireza
, p. 541 - 545 (2009)
A new series of 3-imidazolyl-substituted flavan derivatives being equipped with a N-(phenethyl)-azole scaffold as the common pharmacophore of azole antifungals, were synthesized. The stereochemical and conformational properties of compounds were also characterized by 1H-NMR data. The results of the antifungal evaluation of trans-3-imidazolyl-substituted flavan-4-ones and (Z)-trans-3-imidazolyl-substituted flavan-4-one oximes in comparison with the reference drug fluconazole indicated that most target compounds possessed significant in-vitro antifungal activities against the tested fungi, comparable or superior to fluconazole.
Synthesis, characterization, reactivity, and catalytic studies of heterobimetallic vanadium(V) complexes containing hydrazone ligands
Borthakur, Rosmita,Dhanpat, Shobha A.,Kumar, Arvind,Kurbah, Sunshine D.,Lal, Ram A.,Syiemlieh, Ibanphylla
supporting information, (2020/10/21)
Six heterobimetallic alkali metal dioxidovanadium(V) coordination polymer complexes {[M6{VO(μ-O)}2(μ-OH)4(μ4-slox/nph)].n DMF}∞ where M = Na, K, and Cs; n = 1 for (1), 0 for (2)-(6) of two dihydrazone ligands, disalicylaldehydeoxaloyldihydrazone (H4slox) and bis(2-hydroxy-1-naphthaldehyde)oxaloyldihydrazone (H4nph) are reported. All the complexes have been characterized by various physicochemical techniques such as elemental analyses, molar conductance, IR, NMR, UV–vis, and cyclic voltammetry. The IR, 1HNMR, and 13CNMR spectral data suggest that the dihydrazones are coordinated through phenolate/naphtholate oxygen, enolate oxygen, and azine nitrogen atoms to the metal centres. The structure of complex {[Na6{VO(μ-O)}2(μ-OH)4(μ4-slox)].DMF}∞ (1) is also determined by single-crystal X-ray data, which revealed that the H4slox coordinated via all possible dative sites to metal centres as tetrabasic octadentate ligand. The vanadium metal centres adopted distorted square-pyramidal coordination geometries, and the sodium atoms are also in five coordination atmospheres. The electronic spectra of the complexes showed LMCT bands in addition to intra-ligand π → π* and n → π* transitions. As evident from the cyclic voltammetry, the complexes showed two metal-centred electron transfer reactions {[(VVVV(slox)2?/VVVIV(slox)3?] and [(VVVIV(slox)3?/VVVIV(slox)4?]}, in addition to the ligand centred electron transfer reactions. Further, bovine serum albumin (BSA interaction studies of the complexes {[Na6{VO(μ-O)}2(μ-OH)4(μ4-slox)].DMF}∞ (1) and [Na6{VO(μ-O)}2(μ-OH)4(μ4-nph)]∞ (4) revealed strong binding affinity. Moreover, the catalytic studies of the complexes (1) and (4) were found to be effective for the oxidation of alcohols into their corresponding aldehydes and ketones and bromination of some organic substrates in the presence of H2O2 as an oxidizing agent.
MeONH 2·hCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonylo-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones
Chang, Meng-Yang,Chen, Kuan-Ting
, p. 135 - 145 (2020/09/07)
A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH 2·HCl-mediated sequential methylenation/ conjugate addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.
Preparation method of neticonazole hydrochloride
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Paragraph 0075-0097; 0164-0175; 0187-0192, (2021/01/20)
The invention discloses a preparation method of neticonazole hydrochloride. The preparation method comprises the following steps: (1) taking a compound as shown in a formula III and bromopentane as reaction raw materials, reacting under an alkaline condition, extracting a product obtained by the reaction, reacting the extracted and separated organic product with hydrogen chloride to form a salt soas to obtain neticonazole hydrochloride; optionally (2) refining the obtained neticonazole hydrochloride. According to the method disclosed by the invention, the reaction conditions for preparing each intermediate, the intermediate post-treatment process and the neticonazole hydrochloride refining process are strictly controlled, so that the prepared neticonazole hydrochloride is high in purity,very low in residual solvent and impurity content, and excellent in stability.
One pot synthesis and pharmacological evaluation of aryl substituted imidazoles as potential atypical antipsychotics
Singh, Arshjyoti,Bali, Alka,Kumari, Pooja
, p. 338 - 354 (2021/06/17)
Background: Second generation or “atypical” antipsychotics demonstrate an improved therapeutic profile over conventional neuroleptics. These are effective in both positive and negative symptoms of the disease and have a lower propensity to induce adverse symptoms. Objective: The main objective of the research was in silico design and synthesis of potential atypical antipsychotics with combined antiserotonergic / antidopaminergic effect. Methods: A one pot synthesis of aryl substituted imidazole derivatives was carried out in green solvent PEG-400 and the prepared compounds were evaluated for atypical antipsychotic activity in animal models for dopaminergic and serotonergic antagonism. The compounds were designed based on their 3D similarity studies to standard drugs and in silico (docking studies) with respect to 5-HT2A and D2 receptors. Results: Results from the docking studies with respect to 5-HT2A and D2 receptors suggested a potential atypical antipsychotic profile for the test compounds. Theoretical ADME profiling of the compounds based on selected physicochemical parameters suggested an excellent compliance with Lipinski’s rules. The potential of these compounds to penetrate the blood brain barrier (log BB) was computed through an online software program and the values obtained for the compounds suggested a good potential for brain permeation. Reversal of apomorphine induced mesh climbing be-haviour coupled with inactivity in the stereotypy assay indicates antidopaminergic effect and a potential atypical profile for the test compounds 1-5. Further, the activity of compounds in DOI assay indicated a 5-HT2 antagonistic profile (5-HT2 antagonism). Conclusion: Compound 5 emerged as important lead compound showing combined antidopa-minergic and antiserotonergic (5-HT2A) activity with a potential atypical antipsychotic profile.
Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones
González-Chávez, Marco Martín,González-Chávez, Rodolfo,Méndez, Francisco,Martínez, Roberto,Ni?o-Moreno, Perla Del Carmen,Ojeda-Fuentes, Luis Enrique,Richaud, Arlette,Zerme?o-Macías, María de los ángeles
, (2021/08/30)
The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.
C-H bond cleavage-enabled aerobic ring-opening reaction of: In situ formed 2-aminobenzofuran-3(2 H)-ones
Jiang, Zhihong,Lao, Chichou,Wang, Yingwei,Yang, Mingrong
supporting information, p. 9448 - 9459 (2021/11/17)
A C-H bond cleavage-enabled aerobic ring-opening reaction of 2-aminobenzofuran-3(2H)-ones formed in situ by hemiacetals with a variety of amines is reported. This simple one-pot reaction provides an alternative approach to obtain o-hydroxyaryl glyoxylamides in excellent yields of up to 97%. Alkylamines react with hemiacetals via a catalyst-free dehydration condensation to generate 2-aminobenzofuran-3(2H)-ones. The in situ formed semicyclic N,O-acetals undergo the same amine-initiated C-H bond hydroxylation in air under mild conditions to afford ring-opening products. Similarly, arylamines were investigated as substrates for a two-step tandem process involving a DPP-catalyzed condensation followed by a Et2NH-mediated C-H hydroxylation. Unlike the previously reported functionalization of N,O-acetals via a C-O or C-N cleavage, the aerobic oxidative C-H hydroxylation in this reaction, which is promoted by using stoichiometric amounts of alkylamines as both a Lewis base and a reductant at room temperature under atmospheric air, proceeds via α-carbonyl-stabilized carbanion intermediates from the C-H cleavage of N,O-acetals. This journal is
Bioinspired catalysis and bromoperoxidase like activity of a multistimuli-responsive supramolecular metallogel: Supramolecular assembly triggered by pi-pi stacking and hydrogen bonding interactions
Kurbah, Sunshine Dominic,Lal, Ram A.
, p. 5410 - 5418 (2020/04/17)
We report the synthesis and characterization of a new self-assembled VO2-L metallogel. Gel formation was investigated by dissolving VO2-L in various solvents and it was found that water/methanol (1?:?9 (v/v) ratio) induces gel formation. The single crystal X-ray structure of the VO2-L metallogel exhibits C-H?O and N-H?O hydrogen bonding interactions and pi-pi stacking. The VO2-L xerogel obtained after removing the solvents was found to exhibit outstanding performance in catalysis. Bromoperoxidase-like activity of the VO2-L metallogel was also reported. The present catalytic studies are simple and proceed under mild conditions.
Benzo[d]imidazo[2,1-b]thiazole-based fluorescent sensor for Zn2+ ion detection
Moradi, Seyed Ershad,Molavipordanjani, Sajjad,Hosseinimehr, Seyed Jalal,Emami, Saeed
, (2019/12/09)
In this study, we have synthesized and evaluated three benzo[d]imidazo[2,1-b]thiazole-based sensors (BIT-1, BIT-2 and BIT-3). Among them, BIT-3 namely 2-(benzo[d]imidazo[2,1-b]thiazol-2-yl)-5-methoxyphenol was introduced as a selective fluorescence chemosensor for Zn2+ ion detection. The presence of zinc ions enhanced fluorescence property of BIT-3 at 404 nm due to formation of a 1:1 complex between the chemosensor and the Zn2+ ion. Control experiments showed that the analogous ions do not have fluorescence enhancement effect and some of them even quench the fluorescence dramatically. The data obtained from UV–vis absorption analysis, fluorescence measurements and 1H NMR spectroscopy approved the interaction between BIT-3 and Zn2+ ion. The sensor probe BIT-3 exhibits a selective fluorescence enhancing property via a chelation-enhanced fluorescence (CHEF) upon addition of Zn2+. Thus, a selective fluorescent chemosensor BIT-3 establishes an important sensing platform for real-time monitoring of Zn2+ ion in aqueous environment.
PdCl2/CuCl2/Bi(OTf)3-promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o-Allylarylchromanones
Chang, Meng-Yang,Hsueh, Nai-Chen
supporting information, p. 5736 - 5750 (2020/12/01)
PdCl2/CuCl2/Bi(OTf)3-promoted intramolecular domino annulation of sulfonyl o-allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o-allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α-sulfonyl o-hydroxyacetophenones and o-allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one-pot ring closure via carbon-carbon (C?C) bond formation. (Figure presented.).
