75629-62-8Relevant academic research and scientific papers
Theoretical, electrochemical and computational inspection for anti-corrosion activity of triazepine derivatives on mild steel in HCl medium
Paul, Priya Kumari,Mehta, Raj Kumar,Yadav, Mahendra,Obot
, (2021/11/24)
The two triazepine derivatives, 2-amino-9-(1H-indol-3-yl)-4-(4-methoxyphenyl)-7-oxo-1,7-dihydropyrido[1,2-b][1,2,4]triazepine-3,8,10-tricarbonitrile [AITT] and ethyl 2-amino-8,10-dicyano-9-(2-hydroxy-3-methoxyphenyl)-4-(4-methoxyphenyl)-7-oxo-1,7-dihydrop
A Simplistic Approach for Preparation of Alkylidenemalononitrile Derivatives: Characterization, In silico Studies, Quantum Chemical Evaluation, Molecular Docking, and In vitro Biological Activity Evaluation
Ahmad, Rumana,Azad, Iqbal,Kamal, Azhar,Khan, Abdul Rahman,Khan, Tahmeena,Nasibullah, Malik
, (2020/11/24)
A new and efficient green grinding-based catalyst free Knoevenagel condensation of aldehydes/ketones and malononitrile for the rapid preparation of twelve malononitrile derivatives (C1-C12) is proposed. Characterization of the derivatives was done by sup
Ammonium chloride catalyzed Knoevenagel condensation in PEG-400 as ecofriendly solvent
Waghmare, Smita R.
, p. 849 - 855 (2021/09/28)
A simple and selective green methodology has been successfully developed for Knoevenagel condensation in polyethylene glycol-400 using 10 mol % ammonium chloride as catalyst. The method is applicable to a wide range of aromatic, heteroaromatic and α,β-unsaturated aldehydes. The reactions have been found to be clean and free from the formation of the Michael adduct.
Simple, stepwise and alternative syntheses of indolyl triazoles via huisgen, s 1, 3-dipolar cycloaddition reaction
Ganga Reddy, G.,Venkata Ramana Reddy, Ch.
, p. 187 - 194 (2021/03/19)
A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol-3-yl)me thylene)malononitrile derivatives were synthesized by the 1,3-dipolar cycloaddition reaction (click reaction) of 2-((1-(prop-2-yn-1-yl)-1H-indol-3-yl)methylene)malononitrile with different aryl azides in the presence of sodium ascorbate and copper sulphate in good yields. The advantages of this method are efficient, clean, high yields, easy workup procedures, and shorter reaction time. These reactions are very facile, giving products by simple processing that does not require purification by column chromatography. Spectroscopic methods confirmed all the newly synthesized compounds.
Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents
Silva, Daniel,Mendes, Eduarda,Summers, Eleanor J.,Neca, Ana,Jacinto, Ana C.,Reis, Telma,Agostinho, Paula,Bolea, Irene,Jimeno, M. Luisa,Mateus, M. Luisa,Oliveira-Campos, Ana M. F.,Unzeta, Mercedes,Marco-Contelles, José,Majekova, Magdalena,Ramsay, Rona R.,Carreiras, M. Carmo
, p. 215 - 231 (2019/09/03)
Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.
Triazole-Pyridine Dicarbonitrile Targets Phosphodiesterase 4 to Induce Cytotoxicity in Lung Carcinoma Cells
Keerthy, Hosadurga K.,Mohan, Surender,Basappa,Bharathkumar, Hanumantharayappa,Rangappa, Shobith,Svensson, Fredrick,Bender, Andreas,Mohan, Chakrabhavi Dhananjaya,Rangappa, Kanchugarakoppal S.,Bhatnagar, Rakesh
, (2019/09/06)
Phosphodiesterase 4 (PDE4) is a key enzyme involved in the hydrolysis of cyclic adenosine monophosphate (cAMP) and widely expressed in several types of cancers. The inhibition of PDE4 results in an increased concentration of intracellular cAMP levels that imparts the anti-inflammatory response in the target cells. In the present report, two series of triazolo-pyridine dicarbonitriles and substituted dihydropyridine dicarbonitriles were synthesized using green protocol (TBAB in refluxed water). We next evaluated the title compounds for their cytotoxicity towards lung cancer (A549) cells and identified 7′-[4-(methylsulfonyl)phenyl]-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5h) and 7′-(1-methyl-1H-imidazol-2-yl)-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5j) as lead analogs with the IC50 values of 15.2 and 24.1 μm, respectively. Furthermore, all the new compounds were tested for PDE4 inhibitory activity and 5j showed relatively good inhibitory activity towards PDE4 with inhibition of 50.9 % at 10 μm. In silico analysis demonstrated the favorable interaction of the title compounds with the target enzyme. Taken together, the present study introduces a new scaffold for the development of novel PDE4 inhibitors to fight against inflammatory diseases.
Knoevenagel Reactions of Indole-3-carbaldehyde. Synthesis of 3-Substituted Indole Derivatives
Dyachenko,Matusov,Dyachenko,Nenajdenko
, p. 1777 - 1784 (2019/03/26)
The Knoevenagel condensations of 1H-indole-3-carbaldehyde with various CH acids gave a number of substituted 3-(1H-indol-3-yl)acrylonitriles and acrylamides which were alkylated to afford the corresponding N-alkyl derivatives. The latter were used as Michael acceptors in the synthesis of 4H-pyran, pyridine, 5,6,7,8-tetrahydroquinoline, and [1,3]thiazolo[3,2-a]pyridine derivatives containing an indole fragment.
New quinoline- and isoquinoline-based multicomponent methods for the synthesis of 1,1(3,3)-dicyanotetrahydrobenzoindolizines
Sanin,Zubarev,Rudenko, A. Yu.,Rodinovskaya,Batuev,Shestopalov
, p. 297 - 303 (2018/05/15)
Convenient multicomponent methods for the synthesis of benzannulated dihydroindolizines based on quinoline or isoquinoline, malononitrile, aromatic aldehydes and α-halomethylcarbonyl compounds were developed. Several alternative protocols of using the reactants were studied, starting with separate generation of two most probable intermediates and ending with the four-component condensation of all reactants. The scope of applicability of these methods was found, depending on the initial compounds used. The reaction is highly stereoselective with predominant formation of one of the possible isomers.
Calcium ferrite, an efficient catalyst for knoevenagel condensation(A green approach)
Pippal, Parveen,Singh, Prabal Pratap
, p. 1736 - 1743 (2017/10/27)
Calcium ferrite NPs catalyst have been used as a cheaper and highly efficient catalyst for Knoevenagel condensation of active methylene substrate with various carbonyl compounds affording condensed products in excellent yields in shorter reaction time. Th
Porous hierarchical magnesium oxide-based heterogeneous catalyst for the Knoevenagel condensation
Deilami,Sayyahi
, p. 1085 - 1086 (2017/06/29)
Herein, an operationally facile and efficient Knoevenagel reaction catalyzed by porous hierarchical MgO/Mg(OH)2 is presented. Condensation of various aldehydes with malononitrile proceeds under mild conditions and gives the target products with
