82522-52-9Relevant academic research and scientific papers
Multistate/multifunctional molecular-level systems: Light and pH switching between the various forms of a synthetic flavylium salt
Pina, Fernando,Roque, Ana,Melo, Maria Joao,Maestri, Mauro,Belladelli, Livia,Balzani, Vincenzo
, p. 1184 - 1191 (1998)
The photochromic properties of the 4'-hydroxyflavylium ion (AH+) have been investigated in aqueous solution. This system can be interconverted between as many as ten different forms by light excitation and/or pH changes. In neutral or moderately acidic solution the thermodynamically stable form of this compound is trans-2,4'-dihydroxychalcone (Ct). Light excitation of Ct in acidic or neutral solution gives rise to cis-chalcone Cc (Φ=0.04 at 365 nm), which undergoes slow equilibration with three other forms, namely hemiacetal B, flavylium cation AH+, and quinoidal base A. The relative amounts of the photoproducts depend on pH. At pH +. In neutral and moderately acidic solutions, the four photoproducts revert back to Ct by a slow thermal reaction (k = 4.0 x 10-5 s-1, half-life 27 hours at 25°C, pH = 3), whose rate can be accelerated by increasing the temperature (k= 1.8 x 10-2 s-1 at 75°C, pH=3), and by exploiting the photochemical conversion of Cc to Ct (Φ > 0.16 at 313 nm). At pH + is the thermodynamically stable form of the system. A pH jump from 1 to 12 causes the complete conversion of AH+ to the Cc2- dianion. This species is relatively stable (half-life 400 hours at pH 12 and 25°C). Its thermal and photochemical reactions (Φ = 0.17 at 313 nm) lead to Ct2-, which is the thermodynamically stable form of the system in basic solution. Ct2- does not undergo any photochemical reaction. All the observed processes are fully reversible and accompanied by large changes in the absorption and emission spectra. The flavylium salt investigated represents a multistate/multifunctional molecular-level system. It has properties required by optical memory devices with multiple storage in two different memory levels and nondestructive readout capacity through a write - lock - read - unlock - erase cycle. Its light- and/or pH-induced transformations can be taken as a basis for simple logic operations and create an intricate network of chemical processes. The photochromic properties of the 4′-hydroxyflavylium ion (AH+) have been investigated in aqueous solution. This system has been interconverted between several forms by light excitation and/or pH changes. Different processes have been observed which are accompanied by large changes in the absorption and emission spectra.
Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies
Bhoi, Manoj N.,Borad, Mayuri A.,Jethava, Divya J.,Pandya, Himanshu A.,Patel, Chirag N.,Patel, Hitesh D.
, (2020/07/21)
In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.
Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones
Cáceres-Castillo, David,Carballo, Rubén M.,Graniel-Sabido, Manlio,Mena-Rejón, Gonzalo J.,Mirón-López, Gumersindo,Moo-Puc, Rosa E.,Quijano-Qui?ones, Ramiro
, (2020/01/08)
A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five co
Facile One-Pot Synthesis Methodology for Nitrogen-Containing Heterocyclic Derivatives of 3,5-Disubstituted 4,5-Dihydro-1H-Pyrazole, Their Biological Evaluation and Molecular Docking Studies
Upadhyay, Savita,Tripathi, Avinash C.,Paliwal, Sarvesh,Saraf, Shailendra K.
, p. 564 - 575 (2017/11/10)
A series of 2-pyrazoline derivatives (PS-1 to PS-16) were synthesized by reacting different aromatic/heteroaromatic aldehydes and ketones, in a two-step reaction through Claisen – Schmidt condensation, followed by cyclization of the resulting chalcones wi
Antiradical and reductant activities of anthocyanidins and anthocyanins, structure-activity relationship and synthesis
Ali, Hussein M.,Almagribi, Wafaa,Al-Rashidi, Mona N.
, p. 1275 - 1282 (2015/09/21)
Eight anthocyanidins, seven anthocyanins and two synthesized 4′-hydroxy flavyliums were examined as hydrogen donors to DPPH, ABTS and hydroxyl radicals, and as electron donors in the FRAP assay. Most compounds gave better activities than trolox and catech
Synthesis, in Vitro, and in Vivo Biological Evaluation and Molecular Docking Analysis of Novel 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one Derivatives as Anti-breast Cancer Agents
Dube, Pritam N.,Waghmare, Madhuri N.,Mokale, Santosh N.
, p. 608 - 617 (2016/03/19)
The analogs of coumarin-chalcones have been reported to exhibit antineoplastic, anti-allergic, antihepatoprotective, and estrogenic activity. Herein, we have reported 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one derivatives as a new class of compounds that exhibit selectivity for ER-α binding along with antiproliferative and cytotoxic activity on human breast cancer cell line. The active compounds which show prominent activity against estrogen receptor-alpha-positive (ER+) human breast cancer cell lines MCF-7 and Zr-75-1 are subjected to in vivo screening. The Glide XP docking was performed for designed scaffold to optimize its structural requirement for ER-α inhibition.
Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison
Karki, Radha,Park, Chanmi,Jun, Kyu-Yeon,Kadayat, Tara Man,Lee, Eung-Seok,Kwon, Youngjoo
, p. 360 - 378 (2015/03/18)
Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen-Schmidt condensation reaction and modified Kr?hnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups
Synthesis and biological activity of 2,4-di- p -phenolyl-6- 2 -furanyl-pyridine as a potent topoisomerase II poison
Karki, Radha,Park, Chanmi,Jun, Kyu-Yeon,Kadayat, Tara Man,Lee, Eung-Seok,Kwon, Youngjoo
, p. 360 - 378 (2015/02/19)
Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen-Schmidt condensation reaction and modified Kr?hnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups
ZrCl4-catalysed synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridine derivatives
Liu, Meilin,Yin, Guodong
, p. 236 - 266 (2015/06/02)
In the presence of a catalytic amount of zirconium(IV) chloride, an efficient synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridines has been developed by the reaction 2-hydroxychalcones with 3-methyl-1-phenyl-1H-pyrazol-5-amine in refluxing ethanol. All these novel compounds have been characterised by 1H NMR, 13C NMR, HRMS, IR spectra and X-ray crystallographic analysis.
Discovery of dihydroxylated 2,4-diphenyl-6-thiophen-2-yl-pyridine as a non-intercalative DNA-binding topoisomerase II-specific catalytic inhibitor
Jun, Kyu-Yeon,Kwon, Hanbyeol,Park, So-Eun,Lee, Eunyoung,Karki, Radha,Thapa, Pritam,Lee, Jun-Ho,Lee, Eung-Seok,Kwon, Youngjoo
, p. 428 - 438 (2014/05/20)
We describe our rationale for designing specific catalytic inhibitors of topoisomerase II (topo II) over topoisomerase I (topo I). Based on 3D-QSAR studies of previously published dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives, 9 novel dihydroxyl
