6623-89-8Relevant articles and documents
Imino isatin derivatives; synthesis, in silico molecular dynamic study over monoamine oxidase B, ADME prediction, and in vitro cytotoxicity evaluation
Ahmadi, Samaneh,Azizian, Homa,Azizian, Javad
, p. 1090 - 1103 (2021)
The monoamine oxidase B (MAO-B) depicts an attractive drug target for the development of neuro protective agents toward the treatment of neurodegenerative diseases. The current study involved synthesis, in silico and cytotoxic evaluation of N1-alkylated-5-substituted 3-imino isatin derivatives with the proposed MAO-B inhibitory activities. The In silico molecular modeling investigation was performed through the induced fit docking, molecular mechanics-generalized born surface area, and molecular dynamic method in order to uncover the binding mode interaction and their proposed impact on the active site environment and flexibility. The synthesized compounds were characterized by spectroscopic methods. Compound 3-Imino-1-pentyl indolin-2-one (3h) with the highest free binding energy adopts an extended conformation spanning from the flavin ring location to the entrance of the substrate cavity. In this way, Ile199 adopts the “open” conformation so the two separate cavities of MAO-B active site fused and formed a single-space, which abled the compound extending to the MAO-B entrance cavity space. From consideration of the data presented in this paper, we reveal that longer N1-alkylated-3-imino isatin derivative could be proposed as inhibitor that would occupy both cavities of the MAO-B active site. Furthermore, the mentioned derivatives provided acceptable drug profiling based on in silico ADME calculation and MTT cytotoxicity test evaluation.
Nukleophile Reaktionen an 2-Phenylindolenin-3-onen
Adam, Jean-Marie,Winkler, Tammo
, p. 2186 - 2191 (1984)
Nucleophilic reagents such as 4-nitrophenylhydrazine, malonic acid derivatives, and hydrogen peroxide react with 2-phenylindolenin-3-ones giving, in the first step, addition products to the N=C(2) bond.This addition can be reversible, but in most cases ne
An environmentally benign approach for the synthesis of 3,3′-pyrrolidonyl spirooxindole derivatives via a cascade Knoevenagel-Michael-cyclization multicomponent reaction
Yu, Chengbin,Lyu, Hairong,Cai, Yan,Miao, Xinyu,Miao, Zhiwei
, p. 18857 - 18862 (2013)
A series of 3,3′-pyrrolidonyl spirooxindole derivatives have been synthesized in good yields from the cascade Knoevenagel-Michael-cyclization multicomponent reaction of isatin, malononitrile and α-isothiocyanato imide in the presence of a catalytic amount
Synthesis of novel 2-oxospiro[indoline-3,4′-[1,3]dithiine]-5′-carbonitrile derivatives by new spiro[indoline-3,4′-[1,3]dithiine]?Cu(NO3)2 supported on Fe3O4?gly?CE MNPs as efficient catalyst and evaluation of biological activity
Akhgar, Mohammadreza,Ghazanfari, Dadkhoda,Moghaddam-Manesh, Mohammadreza,Sheikhhosseini, Enayatollah
, (2020)
New spiro[indoline-3,4′-[1,3]dithiine]?Cu(NO3)2 supported on Fe3O4?gly?CE magnetic nanoparticle were synthesized and used as efficient and recyclable catalyst in the synthesis of 2-oxospiro[indoline-3,4′-[1,3]dithiine]-5′-carbonitrile derivatives. The structure of magnetic nanoparticles were confirmed using energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA), infrared spectroscopy (FT-IR) and inductively coupled plasma optical emission spectroscopy (ICP-OES). Subsequently, antibacterial and antifungal activities in terms of inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration and antioxidant activity against the DPPH free radical of the derivatives were investigated. The results revealed acceptable biological effects of the synthetic derivatives and a significant relationship between their structure and biological activity were observed.
Four-Component Reaction Access to Nitrile-Substituted All-Carbon Quaternary Centers
Bian, Qiang,Guo, Lin-Jie,Hu, Xin,Wang, Ge,Wang, Zheng-Lin,Xu, Da-Zhen,Xu, Yi-Ze
, p. 66 - 75 (2021/12/27)
A four-component reaction strategy for access to acyclic nitrile-substituted all-carbon quaternary centers is disclosed. In the presence of a DABCO-based ionic liquid catalyst, the reactions proceed smoothly with a wide range of substrates efficiently to deliver nitrile-substituted all-carbon quaternary centers under mild reaction conditions. This protocol is further demonstrated as an efficient method for the construction of contiguous all-carbon quaternary centers. All the reactions are easily operated in a green manner, producing water as the only byproduct. Some of the products show excellent activity against specific fungi.
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
