- Synthesis, in vitro evaluation, and molecular docking studies of novel hydrazineylideneindolinone linked to phenoxymethyl-1,2,3-triazole derivatives as potential α-glucosidase inhibitors
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In this work, a novel series of hydrazineylideneindolinone linked to phenoxymethyl-1,2,3-triazole derivatives were designed, synthesized, and evaluated for their anti-α-glucosidase activity due to an urgent need to develop effective anti-diabetic agents.
- Shareghi-Boroujeni, Diba,Iraji, Aida,Mojtabavi, Somayeh,Faramarzi, Mohammad Ali,Akbarzadeh, Tahmineh,Saeedi, Mina
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- A series of isatin-hydrazones with cytotoxic activity and CDK2 kinase inhibitory activity: A potential type II ATP competitive inhibitor
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Isatin derivatives potentially act on various biological targets. In this article, a series of novel isatin-hydrazones were synthesized in excellent yields. Their cytotoxicity was tested against human breast adenocarcinoma (MCF7) and human ovary adenocarcinoma (A2780) cell lines using MTT assay. Compounds 4j (IC50 = 1.51 ± 0.09 μM) and 4k (IC50 = 3.56 ± 0.31) showed excellent activity against MCF7, whereas compound 4e showed considerable cytotoxicity against both tested cell lines, MCF7 (IC50 = 5.46 ± 0.71 μM) and A2780 (IC50 = 18.96± 2.52 μM), respectively. Structure-activity relationships (SARs) revealed that, halogen substituents at 2,6-position of the C-ring of isatin-hydrazones are the most potent derivatives. In-silico absorption, distribution, metabolism and excretion (ADME) results demonstrated recommended drug likeness properties. Compounds 4j (IC50 = 0.245 μM) and 4k (IC50 = 0.300 μM) exhibited good inhibitory activity against the cell cycle regulator CDK2 protein kinase compared to imatinib (IC50 = 0.131 μM). A molecular docking study of 4j and 4k confirmed both compounds as type II ATP competitive inhibitors that made interactions with ATP binding pocket residues, as well as lacking interactions with active state DFG motif residues.
- Abdalla, Ashraf N.,Al-Salem, Huda S.,Albalawi, Fatemah S.,Alkahtani, Hamad M.,Alqathama, Aljawharah,Arifuzzaman, Md,Issa, Iman S.,Motiur Rahman, A. F. M.
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- Synthesis, spectroscopic characterization, antibacterial and corrosion inhibitory activities of some 3d-metal complexes of [(2-pyrrole-2-carboxaldehyde)-3-isatin]bishydrazone
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A novel bishydrazone was synthesized by the condensation of isatin monohydrazone with pyrrole-2-carboxaldehyde, which formed a series of complexes with manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II). The ligand and the metal complexes were characterized on the basis of elemental analysis, molar conductance, magnetic moment, IR, UV-visible, 1H NMR, EPR and thermal analysis. Spectral studies revealed that the ligand acted as neutral bidentate, coordinating to the metal ion through the aldimine nitrogen and carbonyl oxygen atom of the isatin moiety. The low molar conductance values indicate that all complexes are non-electrolytes. Based on the spectral results and magnetic susceptibility measurements, suitable geometry was proposed for each metal complex. The EPR spectral data of copper(II) complex indicated that metal-ligand bond had considerable covalent character. The ligand and its nickel(II) complex were subjected to XRD studies. In vitro biological screening effects of the compounds were tested against the some selected bacteria by the agar disc diffusion method. The corrosion inhibitory activity of the ligand and its nickel(II) complex used in acid (H2SO4) media was examined by open circuit potential measurements.
- Swathy,Biju,Mohanan
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- A quick microwave preparation of isatin hydrazone schiff base conjugated organosilicon compounds: Exploration of their antibacterial, antifungal, and antioxidative potentials
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In the current study, five isatin hydrazone schiff base linked acetylinic scaffolds have been synthesized via condensation reaction of isatin hydrazone with aldehydic groups. In order to identify the structure characteristics of the prepared hydrazone derivatives, IR, 1H and 13C NMR spectroscopy, elemental analysis and X- ray crystallography were carried out. The antibacterial and antifungal activity of the derivatives against six bacterial strains (S. aureus, S. Pyogenes, E.coli, V. cholera, L. monocytogens and H.influenza) and seven fungal strains (C. glabrata,C. parapsilosis, C. krusei, C. albicans, C. tropicalis, C. keyfer, and C. neoformans) have been evaluated. All the compounds showed potent antibacterial activity with IC50 ≈ 7.81 μM against H. influenza while the activity against fungal strains was less. Compounds a and c also had IC50 ≈ 7.81 μM against S. Pyogens. Furthermore, the results of total antioxidant activity of hydrazone derivatives, expressed in terms of the ascorbic acid (mM) equivalents per mg of sample, indicates their superior bioactivity. These studies suggested that the istain hydrazone functionalized acetylenic derivatives could be an ideal biomaterial for antibacterial, antifungal and antioxidant applications. Besides this, these derivatives were transformed into isatin hydrazone appended 1,2,3 triazole based organotriethoxysilanes and their reaction conditions were optimised
- Espinosa-Ruíz, Cristóbal,Esteban, María Angeles,Kalra, Pooja,Mohit,Pawan,Sanchita,Sharma, Geetika,Singh, Akshpreet,Singh, Gurjaspreet
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- Colorimetric ‘naked eye’ sensor for fluoride ion based on isatin hydrazones via hydrogen bond formation: Design, synthesis and characterization ascertained by Nuclear Magnetic Resonance, Ultraviolet–Visible, Computational and Electrochemical studies
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A new colorimetric sensor ‘R-IND’ based on isatin hydrazones have been designed and synthesized by simple Schiff base reaction. The anion sensing properties of R-IND were examined, characterized by common spectroscopic techniques such as Fourier Transform-Infrared (FT-IR), Ultraviolet–Visible (UV–Visible), Proton and Carbon Nuclear Magnetic Resonance (1H & 13C NMR), Electrospray Ionization Mass Spectroscopy (ESI-MS) and electrochemical studies. The sensor R-IND bearing ortho hydroxy group and amine group acting as binding sites. The sensor R-IND exhibited sensitive and selective sensing towards F? ion over the other competitive anions like Cl?, I?, Br?, H2PO4?, AcO?, CN–, NO3–, ClO4? and HSO4? in 100% Aetonitrile and 20% aqua Acetonitrile media. The bathochromic shift of 222 nm and 228 nm was observed in UV–Vis spectra with a color change from pale yellow to purple which is due to the complex formation between R-IND and F? ion through hydrogen bond formation. This was further accounted by 1H NMR titration. The Job's plot reveals 1:2 stoichiometry between the host-guest complex. Binding and association constants were found to be 1.72 × 109 M?1, 2.82 × 109 M?1 and 6.0 × 105 M?1, 2.0 × 106 M?1 in 100% ACN and 20% aqua ACN respectively. The detection limit of sensor R-IND was turned out to be 0.45 and 0.41 ppm for F? ion in organic and aqua organic medium which is lesser than World Health Organization (WHO) permission level (1 ppm). The characteristic potential difference of 1.069 V has been observed for R-IND+F? complex in the electrochemical study. Finally, economically viable paper-based colorimetric test strips of R-IND were developed to detect the F? ions in 100% aqueous solution.
- Gauthama, B. U.,Manjunatha, J. G.,Narayana, B.,Sarojini, B. K.,Suresh, N. K.
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- Synthesis and pharmacological screening of new isatin-3-[N2-(benzimidazol-1-acetyl)]hydrazone
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Twenty new isatin-3-[N2-(benzimidazol-1-acetyl)]hydrazones (IV) were synthesized from ten different isatin-3-[N2–(chloroacetyl)] hydrazones (III) by reacting with benzimidazole and 2-methyl benzimidazole. The intermediates were obtained from isatin hydrazones (II) on condensation with chloroacetyl chloride. These compounds were characterized by IR, 1H NMR and mass spectra. All the compounds were screened for antimicrobial, antioxidant and cytotoxic activity. Some of the new compounds showed promising antibacterial and antifungal activity.
- Chaithanya,Kasiviswanath,Prabhakara Chary
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- Molecular docking, DNA binding, thermal studies and antimicrobial activities of Schiff base complexes
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Metal(II) complexes of 3-[(2-hydroxy-3-methoxybenzylidene)hydrazo]-1,3-dihydroindol-2-one (HL) were prepared, their compositions and physicochemical properties were characterized on the basis of elemental analysis, molar conductivity,1H NMR, UV
- El-Sonbati,Diab,El-Bindary, Ashraf,Abou-Dobara,Seyam
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- A turn-on fluorescent sensor for highly selective recognition of Mg2+ based on new Schiff's base derivative
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A new senser Isatin-3-(7′-Methoxychromone-3′-methylidene) hydrazone based on chromone Schiff base was synthesized to detect Mg2+. The complexation behavior of chemosensor with different metal ions in ethanolic solution was studied on UV-vis absorption spectra and fluorescent spectra. Results showed that the chemosensor HL displayed a 70-fold fluorescence enhancement upon the addition of Mg2+ due to the photo-induced electron transfer (PET) effect. On the other hand, metal ions except Mg2+ did not cause significant change in either the absorption or the fluorescence spectrum of HL. In addition, HL showed a good selectivity to Mg2+ over other metal cations, especially Ca2+, which often responds together with Mg2+. Therefore, HL can act as an efficient sensor for magnesium ion.
- Wang, Guan-Qun,Qin, Jin-Can,Fan, Long,Li, Chao-Rui,Yang, Zheng-Yin
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- New method for the preparation of 3-diazo-1,3-dihydroindol-2-ones
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A new method for the preparation of diazo compounds of 2-indolinone series by oxidation of isatin hydrazones with polyhaloalkanes in the presence of copper salts in catalytic amounts was developed.
- Muzalevskiy,Balenkova,Shastin,Magerramov,Shikhaliev,Nenajdenko
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- Synthesis, Characterization, and Antibacterial Activity of Complexes of Hg(II) with Mixtures of 3-Hydrazonoindolin-2-one and Diphosphine, or Diimine Ligands
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Abstract: In the current study, six new tetrahedral Hg(II) complexes of 3-hydrazonoindolin-2-one (HZI) with diphosphines (dppm, dppe, dppp, dppb) or diimines (bipy, phen) ligands have been prepared and characterized by molar conductivity, IR, 1
- Irzoqi, A. A.,Jirjes, H. M.,Mensoor, M. K.,Salih, M. M.
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- New 2-oxoindolin phosphonates as novel agents to treat cancer: A green synthesis and molecular modeling
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The work reports the facile synthesis of novel α-aminophosphonate derivatives coupled with indole-2,3-dione moieties, namely the diethyl(substituted phenyl/heteroaryl) (2-(2-oxoindolin-3-ylidene)hydrazinyl)methylphosphonates derivatives 4(a–n). One-pot three component Kabachnik-Fields reactions were used to synthesize these derivatives. The reaction was carried out at room temperature by stirring in presence of ceric ammonium nitrate (CAN) as a green catalyst. The structures of the synthesized compounds were established by spectral studies. The synthesized derivatives 4(a–n) were evaluated for their in vitro anticancer activity against six human cancer cell lines by the SRB assay method. The cancer cell lines used in this research work are SK-MEL-2 (melanoma), MCF-7 (breast cancer), IMR-32 (neuroblastoma) MG-63 (human osteosarcoma), HT-29 (human colon cancer) and Hep-G2 (human hepatoma). All the synthesized derivatives inhibited the cell proliferation. Importantly, all the target compounds showed no cytotoxicity towards normal tissue cells (GI50 > 250 μM). A docking study was performed to predict the mode of action. Docking results indicate that the compounds have good binding with the enzyme tyrosine kinase as well as with microtubules, which makes them dual inhibitors. The result of in-silico bioavailability studies suggests that the compounds from the present series have good oral drug-like properties and are non-toxic in nature. In vivo acute oral toxicity study results indicate that the compounds can be considered safe, and therefore could be developed in the future as good anticancer agents or as leads for the design and synthesis of novel anticancer agents.
- Tiwari, Shailee V.,Sharif, Nawaz S.,Gajare, Rekha I.,Seijas Vazquez, Julio A.,Sangshetti, Jaiprakash N.,Damale, Manoj D.,Nikalje, Anna Pratima G.
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- New chromogenic bis(isatin hydrazonyl)calix[4]arenes for dual recognition of fluoride and silver ions
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New calixarene based dual chromogenic receptors bearing isatin hydrazone units have been synthesized and evaluated for their ion recognition potential. The synthesized molecular receptors can effectively and selectively recognize fluoride and silver ions through visible color changes and pronounced bathochromic shifts in their UV-visible spectra. NMR titration data further support the preliminary conclusions.
- Chawla, Har Mohindra,Gupta, Tanu
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- Synthesis, spectroscopic characterization, DFT calculations, and molecular docking studies of new unsymmetric bishydrazone derivatives
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Three new unsymmetric isatin bishydrazone compounds; Comp. I, II, III, were synthesized by the condensation of 3,5-dichloro-salicylaldehyde, 3-bromo-5-chloro-salicylaldehyde, and 3,5-dibromo-salicylaldehyde with isatin monohydrazone, respectively. The synthesized compounds were characterized by elemental analysis, 1H-NMR, FT-IR, UV-Vis spectroscopy, and mass spectrometry technique. For studied molecules, chemical parameters like frontier orbital energies, energy gap, electronegativity, chemical potential, chemical hardness, softness, electrophilicity, nucleophilicity, electrodonating power, electroaccepting power, polarizability, and dipole moment were calculated and discussed. Investigating the validity of well-known electronic structure principles like Maximum Hardness, Minimum Polarizability, and Minimum Electrophilicity Principles in the study, it was determined which compound is more stable compared to others. In recent days, a new software having PRIMorDIA name was developed to explore reactivity and electronic structure in large biomolecules by some of the authors of this paper. Molecular docking studies for these newly synthesized molecules were performed using PRIMorDIA software. Considering the intramolecular interactions, NBO analyzes of three bishydrazone derivatives were conducted to evaluate the chemical behavior.
- Er?a?, Ay?e,Grillo, Igor Barden,Kaya, Sava?,Kaya, Yeliz,Rocha, Gerd Bruno,Serdaro?lu, Goncagül
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- ISATIN DERIVATIVES
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Isatin derivatives having a chemical structure according to Formula I: where R represents a hydrogen or chloro group, or a pharmaceutically acceptable salt thereof have anticancer activities. The isatin derivatives have anticancer activities and may be synthesized and used in a pharmaceutical composition or otherwise to treat cancers in a subject diagnosed with, for example, at least one of leukemia, lung cancer, central nervous system (CNS) cancer, melanoma, ovarian cancer, renal cancer, prostate cancer, breast cancer or colon cancer.
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Paragraph 0008
(2021/07/24)
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- Novel thiomorpholine tethered isatin hydrazones as potential inhibitors of resistant Mycobacterium tuberculosis
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Novel chemotherapeutic agents against multidrug resistant-tuberculosis (MDR-TB) are urgently needed at this juncture to save the life of TB-infected patients. In this work, we have synthesized and characterized novel isatin hydrazones 4(a-o) and their thi
- Karunanidhi, Sivanandhan,Chandrasekaran, Balakumar,Karpoormath, Rajshekhar,Patel, Harun M.,Kayamba, Francis,Merugu, Srinivas Reddy,Kumar, Vishal,Dhawan, Sanjeev,Kushwaha, Babita,Mahlalela, Mavela Cleopus
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- Synthesis and evaluation of isatin derivatives as antifungal agents
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Various types of isatin derivatives were synthesized by reacting isatin with different reagents viz substituted acetophenones, sodium nitrate, hydroxylamine hydrochloride and hydrazine hydrate. Characterization of the synthesized compounds was done by using various spectral techniques such as IR,1HNMR,13CNMR, elemental analysis and mass spectrometry. Synthesized compounds were further evaluated for their antifungal activity against Helminthosporium oryzae, Rhizoctonia solani and Fusarium moniliforme using poison food technique. 3-(2-Oxo-2-phenylethylidene) indolin-2-one showed significant mycelium inhibition against all tested rice fungi.
- Dawar, Monika,Kaur, Komalpreet,Rani, Ritu,Utreja, Divya
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p. 199 - 205
(2020/02/29)
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- Pharmacophore modeling and 3D-QSAR study of indole and isatin derivatives as antiamyloidogenic agents targeting Alzheimer’s disease
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Thirty-six novel indole-containing compounds, mainly 3-(2-phenylhydrazono) isatins and structurally related 1H-indole-3-carbaldehyde derivatives, were synthesized and assayed as inhibitors of beta amyloid (Aβ) aggregation, a hallmark of pathophysiology of Alzheimer’s disease. The newly synthesized molecules spanned their IC50 values from sub- to two-digit micromolar range, bearing further information into structure-activity relationships. Some of the new compounds showed interesting multitarget activity, by inhibiting monoamine oxidases A and B. A cell-based assay in tau overexpressing bacterial cells disclosed a promising additional activity of some derivatives against tau aggregation. The accumulated data of either about ninety published and thirty-six newly synthesized molecules were used to generate a pharmacophore hypothesis of antiamyloidogenic activity exerted in a wide range of potencies, satisfactorily discriminating the ‘active’ compounds from the ‘inactive’ (poorly active) ones. An atom-based 3D-QSAR model was also derived for about 80% of ‘active’ compounds, i.e., those achieving finite IC50 values lower than 100 μM. The 3D-QSAR model (encompassing 4 PLS factors), featuring acceptable predictive statistics either in the training set (n = 45, q2 = 0.596) and in the external test set (n = 14, r2ext = 0.695), usefully complemented the pharmacophore model by identifying the physicochemical features mainly correlated with the Aβ anti-aggregating potency of the indole and isatin derivatives studied herein.
- Purgatorio, Rosa,Gambacorta, Nicola,Catto, Marco,de Candia, Modesto,Pisani, Leonardo,Espargaró, Alba,Sabaté, Raimon,Cellamare, Saverio,Nicolotti, Orazio,Altomare, Cosimo D.
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- Synthesis and application of new reactive disperse dyes based on isatin derivatives and their antibacterial activity
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A NEW two reactive disperse dyes based on a hybrid structure of isatin and benzanthrone or anthraquinone via 1, 3, 5 triazine spacer were prepared. The prepared compounds were characterized by 1H-NMR, mass spectrometry and elemental analysis. The UV/vis absorption spectra and emission spectra were measured in N, N-dimethylformamide (DMF) solution at room temperature, the effects of substituent’s on the emission spectra of these compounds were interpreted. The dyeing application of the prepared dyes on wool and polyamide-6 fabrics at various concentrations of dye and different pH were investigated as well as the exhaustion and dye fixation were studied. The antibacterial activity of the prepared reactive disperse dyes were studied against different kind of bacteria such as Staphylococcus aureus (Gram-positive bacteria) and Escherichia coli (Gram-negative bacteria). The antibacterial affinity of the prepared dyes was exhibit a significant effect compared with selected antibiotics as reference standard. The fastness properties of the dyed fabrics were studied which showing excellent wash fastness, rubbing and perspiration fastness as well as high stability to light.
- El-Sedik, Mervat,Elmegied, Saadia Abd,Aysha, Tarek,Mahmoud, Safia A.
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p. 2253 - 2264
(2020/01/13)
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- Novel [(3-indolylmethylene)hydrazono]indolin-2-ones as apoptotic anti-proliferative agents: design, synthesis and in vitro biological evaluation
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On account of their significance as apoptosis inducing agents, merging indole and 3-hydrazinoindolin-2-one scaffolds is a logic tactic for designing pro-apoptotic agents. Consequently, 27 hybrids (6a–r, 9a–f and 11a–c) were synthesised and evaluated for their cytotoxicity against MCF-7, HepG-2 and HCT-116 cancer cell lines. SAR studies unravelled that N-propylindole derivatives were the most active compounds such as 6n (MCF-7; IC50=1.04 μM), which displayed a significant decrease of cell population in the G2/M phase and significant increase in the early and late apoptosis by 19-folds in Annexin-V-FTIC assay. Also, 6n increased the expression of caspase-3, caspase-9, cytochrome C and Bax and decreased the expression of Bcl-2. Moreover, compounds 6i, 6j, 6n and 6q generated ROS by significant increase in the level of SOD and depletion of the levels of CAT and GSH-Px in MCF-7.
- Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Ibrahim, Hany S.,Al-Ansary, Ghada H.,Ghabbour, Hazem A.,Elaasser, Mahmoud M.,Ahmed, Hanaa Y. A.,Safwat, Nesreen A.
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p. 686 - 700
(2018/04/02)
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- Solvent Effects: Syntheses of 3,3-Difluorooxindoles and 3-Fluorooxindoles from Hydrazonoindolin-2-one by Selectfluor
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Efficient syntheses of 3,3-difluorooxindoles and 3-fluorooxindoles via fluorination of hydrazonoindolin-2-one with Selectfluor are reported. Under different solvent conditions, this method produced 3,3-difluorooxindoles and 3-fluorooxindoles selectively. The broad substrate scope and mild reaction conditions make this transformation a valuable method in drug discovery and development.
- Yang, Qiong,Dai, Guo-Li,Yang, Yu-Ming,Luo, Zhuangzhu,Tang, Zhen-Yu
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p. 6762 - 6768
(2018/05/29)
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- Enantioselective Synthesis of Trifluoromethyl α,β-Unsaturated δ-Lactones via Vinylogous Aldol-Lactonization Cascade
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The novel vinylogous aldol-lactonization cascade of alkylidene oxindole with trifluoromethyl ketones is presented. The reaction, catalyzed by a bifunctional tertiary amine, provides an efficient application of the vinylogous reactivity of alkylidene oxindoles for the preparation of enantioenriched trifluoromethylated α,β-unsaturated δ-lactones.
- Crotti, Simone,Di Iorio, Nicola,Mazzanti, Andrea,Righi, Paolo,Bencivenni, Giorgio
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p. 12440 - 12448
(2018/10/09)
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- PHARMACEUTICAL COMPOUNDS
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A compound having the general formula (I) or (II), in which R, R1, R2 and R3 are as described herein, or a pharmaceutically acceptable salt thereof, is provided. An associated method for treating a mycobacterial infection is also provided.
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(2018/06/22)
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- Synthesis, in vitro α-glucosidase inhibitory activity and docking studies of novel chromone-isatin derivatives
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A novel series of chromone-isatin derivatives 6a–6p were designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS. These novel synthetic compounds were evaluated for inhibitory activity against yeast α-glucosidase enzyme. The results of biological test have shown that all tested compounds exhibited excellent to potent inhibitory activity in the range of IC50 = 3.18 ± 0.12–16.59 ± 0.17 μM as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 6j (IC50 = 3.18 ± 0.12 μM) with a hydroxyl group at the 7-position of chromone and a 4-bromobenzyl group at the N1-positions of isatin, was found to be the most active compound among the series. Furthermore, molecular docking study was performed to help understand binding interactions of the most active analogs with α-glucosidase enzyme. These results indicated that this class of compounds had potential for the development of anti-diabetic agents.
- Wang, Guangcheng,Chen, Ming,Qiu, Jie,Xie, Zhenzhen,Cao, Anbai
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p. 113 - 116
(2017/12/11)
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- New hydrazonoindolin-2-ones: Synthesis, exploration of the possible anti-proliferative mechanism of action and encapsulation into PLGA microspheres
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The synthesis and molecular characterization of new isatin-based hydrazonoindolin-2-ones 4a-o and 7a-e are reported. The in vitro anti-proliferative potential of the synthesized compounds 4a-o and 7a-e was examined against HT-29 (colon), ZR-75 (breast) and A549 (lung) human cancer cell lines. Compounds 7b, 7d and 7e were the most active congeners against the tested human cancer cell lines with average IC50 values of 4.77, 3.39 and 2.37 μM, respectively, as compared with the reference isatin-based drug, sunitinib, which exhibited an average IC50 value of 8.11 μM. Compound 7e was selected for further pharmacological evaluation in order to gain insight into its possible mechanism of action. It increased caspase 3/7 activity by 2.4- and 1.85-fold between 4 and 8 h of treatment, respectively, at 10 μM and it caused a decrease in the percentage of cells in the G1 phase of the cell cycle with a corresponding increase in the S-phase. In addition, compound 7e increased phosphorylated tyrosine (p-Tyr) levels nearly two-fold with an apparent IC50 value of 3.8 μM. The 7e-loaded PLGA microspheres were prepared using a modified emulsion-solvent diffusion method. The average encapsulation efficiency of the 7e-loaded PLGA microspheres was 85% ± 1.3. While, the in vitro release profile of the 7e-loaded microspheres was characterized by slow and continuous release of compound 7e during 21 days and the release curve was fitted to zero order kinetics. Incorporation of 7e into PLGA microspheres improved its in vitro anti-proliferative activity toward the human cancer cell line A549 after 120 h incubation period with an IC50 value less than 0.8 μM.
- Attia, Mohamed I.,Eldehna, Wagdy M.,Afifi, Samar A.,Keeton, Adam B.,Piazza, Gary A.,Abdel-Aziz, Hatem A.
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- Lewis acid-promoted direct synthesis of N-unsubstituted hydrazones via the reaction of hydrazine with acetophenone and isatin derivatives
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Hydrazones 2–22 were synthesized via the reaction of acetophenone with isatin derivatives and anhydrous hydrazine promoted by BF3 as a Lewis acid at 0°C. Structures of the synthesized hydrazones were determined on the basis of NMR and X-ray crystallograph
- El-Azab,Ghabbour,El-Husseiny,Maarouf,Mohamed,Abdel-Aziz
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p. 2837 - 2844
(2017/03/22)
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- Metronidazole-isatin type compound as well as preparation method and application thereof
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The invention discloses a metronidazole-isatin type compound as well as a preparation method and an application thereof. The compound has a structure represented by a formula (I) (shown in the specification). The preparation method comprises the following
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Paragraph 0012
(2016/10/09)
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- Design, synthesis, pharmacological evaluation and molecular docking studies of substituted oxadiazolyl-2-oxoindolinylidene propane hydrazide derivatives
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The manuscript describes design and synthesis of novel oxadiazolyl-2-oxoindolinylidene propane hydrazides as amide tethered hybrids of indole and oxadiazole and their evaluation for antiinflammatory and analgesic activity. The compounds were synthesized following five step reaction to yield fifteen derivatives as 3-(5-substituted-1,3,4-oxadiazol-2-yl)-N′-[2-oxo-1,2-dihydro-3Hindol-3-ylidene]propane hydrazides. The final derivatives 3-[5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]-N′-[2-oxo-1,2-dihydro-3H-indol-3-ylidene]propane hydrazide and 3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]-N′-[2-oxo-1,2-dihydro-3H-indol-3-ylidene]propane hydrazide were found to be highly promising molecules with severity index of 0.35 and 0.56, respectively, which is promising for an analgesic compound. The hydroxy and methyl substitution on phenyl ring system provided with active anti-inflammatory compounds having increase in reaction time of 84.11 and 83.17percent, respectively compared to standard drug at 85.84percent. Molecular docking studies exhibit comparable interaction with synthesized derivatives and standard drug having a dock score of -4.44 by the K-nearest neighbour genetic algorithm method.
- Kerzare, Deweshri,Chikhale, Rupesh,Bansode, Ratnadeep,Amnerkar, Nikhil,Karodia, Nazira,Paradkar, Anant,Khedekar, Pramod
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p. 1998 - 2010
(2016/11/03)
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- Application of SBA-Pr-SO3H in the green synthesis of isatinhydrazone derivatives: Characterization, UV-Vis investigation and computational studies
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An efficient and green synthesis is developed for the preparation of the arylidene isatinhydrazone derivatives 4a-m using a heterogeneous mesoporous acid catalyst of SBA-Pr-SO3H with a pore size of 6 nm under solvent free conditions. The hydrazones 4a-m were then analyzed by UV-Vis spectroscopy and the results were used for the calculation of the HOMO-LUMO band gap. In addition, the quantum chemical calculations were performed to provide an illustrative explanation for the obtained band gap; it is found that probably these molecules have a high tendency to donate electrons to the appropriate small-molecule acceptors with low energy and empty molecular orbital.
- Gholamzadeh, Parisa,Mohammadi Ziarani, Ghodsi,Badiei, Alireza
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p. 2935 - 2939
(2016/10/06)
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- Action of Hydrazines on 2-(2-Oxindolin-3-ylidene)malononitrile, (E,Z)-Ethyl 2-cyano-2-(2-oxindolin-3-ylidene)acetate and Isatin-β-thiosemicarbazone as a Source of Spiro Indoline-pyrazole Systems
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2-(2-Oxindolin-3-ylidene)malononitrile (1a) or (E,Z)-ethyl 2-cyano-2-(2-oxindolin-3-ylidene)acetate (1b) or isatin-β-thiosemicarbazone (1c) undergoes reactions with prototype hydrazine hydrate itself and some of its simple congeners to give hydrazone derivatives bearing indoline-2-one moiety (2). The hydrazone derivatives (2) when heated with acetyl acetone or ethyl acetoacetate in dry pyridine afforded the spiro indoline derivatives (3a, 3b). Also, cinnoline derivative (9) is obtained by action of hydrazine hydrate on the N-acetyl derivative of (6a). The structures of the newly synthesized compounds were evaluated by IR, 1H-NMR spectroscopy, mass spectra and elemental analyses.
- Youssef, Ahmed S. A.,Hemdan, Magdy M.,Emara, Samir A.,Kamel, Rabaa M.
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p. 1331 - 1336
(2015/10/06)
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- A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: Construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters
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A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.
- Gui, Yong-Yuan,Yang, Jian,Qi, Liang-Wen,Wang, Xiao,Tian, Fang,Li, Xiao-Nian,Peng, Lin,Wang, Li-Xin
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p. 6371 - 6379
(2015/06/08)
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- Hydrolysis and hydrazinolysis of isatin-based ald-and ketazines
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The hydrolysis of isatin aldazine 4a-d afforded the unexpected 3,3'-(hydrazine-1,2-diylidene)bis(indolin-2-one) (5) and 1,2-di(arylidene)hydrazines 6a-d through dual hydrolysis of 4a-d. A mechanism to explain the formation of 5 and 6a-d was proposed. In addition, the hydrazinolysis of 4a-d yielded 3-hydrazonoindolin-2-one (2) and 1,2-di(arylidene)hydrazines 6a-d instead of hydrazones 17a-d, while hydrazinolysis of isatin ketazine 5 gave the expected 3-hydrazonoindolin-2-one (2). These results indicated the ability of the title compounds for unusual hydrolysis and hydrazinolysis reactions.
- Ibrahim, Hany S.,Abdelhadi, Soha R.,Abdel-Aziz, Hatem A.
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- Microwave synthesis, characterization, and antimicrobial activity of some novel isatin derivatives
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Three series of isatin derivatives [3-hydrazino, 3-thiosemicarbazino, and 3-imino carboxylic acid derivatives] were synthesized employing microwave irradiation. The prepared compounds were characterized by FT-IR, NMR, elemental analysis, and X-ray crystal
- El-Faham, Ayman,Hozzein, Wael N.,Wadaan, Mohammad A. M.,Khattab, Sherine N.,Ghabbour, Hazem A.,Fun, Hoong-Kun,Siddiqui, Mohammed Rafiq
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- Synthesis, cytoprotective and anti-Tumor activities of Isatin Schiff bases
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A series of simple isatin Schiff bases were synthesized through the condensation reaction. These isatin Schiff bases were characterized by NMR and MS, and the structure was discussed. Then, the cytoprotective and anti-Tumor activities of these compounds were evaluated. The results show that several compounds show protection activity on the apoptosis of PC12 cells induced by H2O2, which are more effective than that of (±) α-Tocophreol (VE) and isatin. Besides, some compounds also show more potent anti-Tumor activity against A549 and P388 cell lines than that of isatin.
- Chen, Gang,Meng, Mei,Zhang, Yu,Hao, Xiaojiang,Wang, Ye,Mu, Shuzhen
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p. 802 - 805
(2015/11/18)
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- Design, synthesis and in Vitro antiproliferative activity of novel isatin-quinazoline hybrids
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Using a molecular hybridization approach, a new series of isatin-quinazoline hybrids 15a-o was designed and synthesized via two different synthetic routes. The target compounds 15a-o were prepared by the reaction of quinazoline hydrazines 12a-e with indoline-2,3-diones 13a-c or by treating 4-chloroquinazoline derivatives 11a-e with isatin hydrazones 14a-c. The in vitro anticancer activity of the newly synthesized hybrids was evaluated against the liver HepG2, breast MCF-7 and colon HT-29 cancer cell lines. A distinctive selective growth inhibitory effect was observed towards the HepG2 cancer cell line. Compounds 15b, 15g and 15l displayed the highest potency, with IC50 values ranging from 1.0 ± 0.2 to 2.4 ± 0.4 mM, and they were able to induce apoptosis in HepG2 cells, as evidenced by enhanced expression of the pro-apoptotic protein Bax and reduced expression of the anti-apoptotic protein Bcl-2, in addition to increased caspase-3 levels.
- Fares, Mohamed,Eldehna, Wagdy M.,Abou-Seri, Sahar M.,Abdel-Aziz, Hatem A.,Aly, Mohamed H.,Tolba, Mai F.
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p. 144 - 154
(2015/02/19)
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- Synthesis, biological activity, and docking study of novel isatin coupled thiazolidin-4-one derivatives as anticonvulsants
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A series of 2-(substituted-phenyl)-3-(2-oxoindolin-3-ylidene)amino)-thiazolidin-4-one derivatives were designed and synthesized under microwave irradiation, using an eco-friendly, efficient, microwave-assisted synthetic protocol that involves cyclocondensation of 3-substituted benzylidine-hydrazono-indolin-2-one 3a-j with thioglycolic acid in dimethyl formamide (DMF) as solvent and anhydrous zinc chloride as a catalyst, keeping in view the structural requirement of the pharmacophore. The intermediate compounds 3a-j were obtained by condensation of the hydrazone of indoline-2,3-dione with aromatic aldehydes. The synthesized derivatives were evaluated for CNS depressant activity and anticonvulsant activity in mice using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (sc-PTZ) induced seizure tests. All the derivatives showed good CNS depressant activity and showed protection in the MES test, indicative of their ability to inhibit the seizure spread. A histopathological study was performed to evaluate liver toxicity caused by the synthesized compounds. The compounds were nontoxic. A computational study was performed, in which log P values were calculated experimentally. Virtual screening was performed by molecular docking of the designed compounds into the ATP binding sites of the NMDA and AMPA receptors, to predict if these compounds have analogous binding modes.
- Nikalje, Anna P.,Ansari, Altamash,Bari, Sanjay,Ugale, Vinod
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p. 433 - 445
(2015/06/08)
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- Catalyst free, multicomponent-tandem synthesis of spirooxindole-indazolones and spirooxindole-pyrazolines: A glycerol mediated green approach
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The development of a versatile new one pot, catalyst free, multicomponent-tandem strategy for assembly of spirooxindole-indazolones and spirooxindole-pyrazolines is described. The reported protocol includes several advantages like environmental friendliness, cost effectiveness, high atom economy, short reaction times and high yields. The reported method is the first green synthesis of spirooxindole-indazolones and spirooxindole-pyrazolines. This journal is
- Singh, Swastika,Saquib, Mohammad,Singh, Shyam Babu,Singh, Mandavi,Singh, Jagdamba
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p. 45152 - 45157
(2015/06/02)
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- Synthesis leishmanicidal activities of bis-Schiff bases of isatins
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Twenty seven (27) derivatives of bis-Schiff bases of isatins 1-27 were studied for their leishmanicidal potential. Out of twenty seven (27) analogs, five exhibited varying degree of leishmanicidal activity with IC50 values 44.86 ± 0.66, 65.27 ±
- Khan, Momin,Khan, Khalid Mohammed,Rahim, Fazal,Samreen,Perveen, Shahnaz,Karim, Aneela,Imtiazuddin,Choudhary, Muhammad Iqbal
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p. 520 - 526
(2015/08/04)
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- Electrochemical reduction of isatin-monohydrazone on mercury electrode
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Electrochemical behaviour of isatin monohydrazone (IM) on a hanging mercury drop electrode in the Britton-Robinson (B-R) buffer solution of pH = 2.00 - 9.00 has been investigated using square-wave voltammetry (SWV) and cyclic voltammetry (CV) techniques. In the pH range of 2.00-5.00, the voltammogram of IM exhibited a single cathodic irreversible peak. When the pH value exceeds 5.00, a new cathodic irreversible peak was also seen. According to the voltammetric data, a plausible electrode reaction mechanism of IM was proposed. The first reduction peak of IM is resulted from the reduction of =N-NH- group with consumption of 2e-/2H+. Also, its second cathodic peak is formed by the participation of 2e-/2H+ for the reduction of -N=N- group on its tautomeric form.
- akir, Semiha,Bier, Ender,Arslan, Emine Yilmaz
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- Potassium N-iodo p-toluenesulfonamide (TsNIK, iodamine-T): A new reagent for the oxidation of hydrazones to diazo compounds
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A new reagent for the oxidation of hydrazones to diazo compounds is described. N-Iodo p-toluenesulfonamide (TsNIK, iodamine-T) allows the preparation of α-diazoesters, α-diazoamides, α-diazoketones and α-diazophosphonates in good yield and in high purity after a simple extractive work-up. α-Diazoesters were also obtained in high yield from the corresponding ketones through a one-pot process of hydrazone formation/oxidation. Diazo compounds: N-Iodo p-toluenesulfonamide (TsNIK, iodamine-T), readily prepared from p-toluenesulfonamide and iodine in aqueous KOH, is a new reagent for the oxidation of hydrazones to diazo compounds in good yields and high purity (see scheme).
- Nicolle, Simon M.,Moody, Christopher J.
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supporting information
p. 4420 - 4425
(2014/05/06)
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- An atypical easy reductive cleavage of the conjugated CC bond in 1,1′-disubstituted isoindigos under the action of aqueous hydrazine hydrate
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The reaction of diverse symmetrically-substituted isoindigo derivatives with 80% aqueous hydrazine hydrate is described. The influence of the structure of the substituent on either oxindole or isatin-3-hydrazone formation is discussed.
- Bogdanov, Andrei V.,Petrova, Alisa V.,Krivolapov, Dmitry B.,Mironov, Vladimir F.
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p. 6615 - 6618
(2015/01/16)
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- Synthesis, characterization, DNA interaction, thermal and in vitro biological activity investigation of some Ni(II)-Isatin bishydrazone complexes
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Complexes of the type [Ni (L) (H2O)] Cl2.nH 2O, where L = [(pyridine-2-carboxaldhyde)-3-isatin]-bishydrazone (cpish), [(2-acetyl pyridine)-3-isatin]-bishydrazone (apish) and [(2-benzoyl pyridine)-3-isatin]-bishydrazone (bp
- Rabia, Mostafa K.,Mohamad, Ahmad Desoky M.,Ismail, Nabawia M.,Mahmoud, Ali Abdo
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p. 1147 - 1163
(2014/08/05)
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- Acid-catalyzed aquation of ni(II)-hydrazone complexes: Kinetics and solvent effect
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Complexes of the type [Ni(L)(H2O)]Cl2·nH 2O, where L = 2-pyridyl-3-isatinbishydrazone ligands, have been synthesized and characterized on the bases of elemental analysis, molar conductance, IR, electronic spectra, and ther
- Mohamad, Ahmad Desoky M.,Rabia, Mostafa K.,Ismail, Nabawia M.,Mahmoud, Ali Abdo
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p. 451 - 461
(2014/07/08)
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- Analogue-based design, synthesis and biological evaluation of 3-substituted-(methylenehydrazono)indolin-2-ones as anticancer agents
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The docking studies on CDK2 and GSK-3β inspired us to synthesis a series of indoline-2,3-dione hydrazones 10a-l. Treatment of indoline-2,3-dione derivatives 7a-d with hydrazine gave 3-hydrazonoindolin-2-ones 8a-d which were reacted with the appropriate aldehydes 9a-c to yield 3-substituted- (methylenehydrazono)indolin-2-ones 10a-l. Compounds 10a-l showed a significant anticancer activity against human breast cell line MCF-7. Compounds 10c, f, i exhibited the highest activity almost the same of doxorubicin (IC50 = 6.10 μM) with IC50 = 7.75, 6.75, 6.25 μM, respectively.
- Dweedar, Haytham E.,Mahrous, Hoda,Ibrahim, Hany S.,Abdel-Aziz, Hatem A.
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p. 275 - 280
(2014/04/17)
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- Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agents
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A hybrid pharmacophore approach was adopted to design and synthesize new series of isatin-pyridine hybrids. All the newly prepared hybrids (5a-o, 8 and 11a-d) were in vitro evaluated for their anti-proliferative activity against three human cancer cell lines, namely HepG2 hepatocellular carcinoma, A549 lung cancer and MCF-7 breast cancer. Compound 8 emerged as the most active member against HepG2 cell line (ICinf50/inf = 2.5 ± 0.39 μM), with 2.7-fold increased activity than the reference drug, doxorubicin (ICinf50/inf = 6.9 ± 2.05 μM). Whilst, compound 11c was found to be the most potent counterpart against A549 and MCF-7 cell lines with ICinf50/inf values of 10.8 ± 1.15 and 6.3 ± 0.79, respectively. The weightiness of the utilization of non-cleavable linker, as the chalcone linker, and simplification of the first group, was explored via the SAR study. Furthermore, a QSAR model was built to explore the structural requirements controlling the cytotoxic activities. Notably, the predicted activities by the QSAR model were very close to those experimentally observed, hinting that this model could be safely applied for prediction of more efficacious hits comprising the same skeletal framework. Finally, a theoretical kinetic study was established to predict the ADME of the active hybrids.
- Eldehna, Wagdy M.,Altoukhy, Ayman,Mahrous, Hoda,Abdel-Aziz, Hatem A.
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p. 684 - 694
(2015/02/02)
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- Investigation of reactions between binucleophilic reagents with 2-(2-Oxindolin-3-ylidene)malononitrile derivatives
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Nucleophilic addition of hydrazines and thiosemicarbazide to the 2-(2-oxoindolin-3-ylidene) malononitrile derivatives 1, followed by elimination of malononitrile, lead to 3-(2-Arylhydrazono)indolin-2-ones and 1-(2-oxoindolin-3- ylidene)thiosemicarbzides r
- Seifi, Mohammad,Sheibani, Hassan
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p. 478 - 481
(2013/08/23)
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- Superoxide respiratory burst inhibitory activity of bis-schiff bases of Isatins
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Bis-Schiff bases 1-27 were synthesized and evaluated for their anti-inflammatory activity and possible cytotoxicity. Compounds 1-27 showed a varying degree of respiratory burst inhibitory activity with IC50 values between 242.97 - 652.12 μM. Co
- Khan, Khalid Mohammed,Khan, Momin,Ali, Muhammad,Qadir, Muhammad Irfan,Perveen, Shahnaz,Karim, Aneela,Choudhary, Muhammad Iqbal
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p. 987 - 993
(2013/07/26)
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- Synthesis, characterization, anti-fungi and anti-bacterial activity of new [(2-pyridyl)-3-isatin]-bishydrazone
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New [(pyridine-2-carboxaldhyde)-3-isatin]-bishydrazone (cpish), [(2-acetylpyridine)-3-isatin]-bishydrazone (apish), and [(2-benzoyl pyridine)-3-isatin]-bishydrazone (bpish) have been synthesized and characterized by the elemental analysis, IR, NMR and ele
- Rabia, Mostafa K.,Mohamad, Ahmad Desoky M.,Ismail, Nabawia M.,Mahmoud, Ali Abdo
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p. 2406 - 2412
(2014/03/21)
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- Synthesis and physico-chemical properties of some Ni(II) complexes with isatin-hydrazones
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New Ni(II) complexes with bioactive bishydrazones ligands based on (pyridine-2-carboxaldhyde)-3-isatin, (2-acetylpyridine)-3-isatin, and (2-benzoylpyridine)-3-isatin have been synthesized and characterized by elemental analysis, conductivity measurements,
- Rabia, Mostafa K.,Mohamad, Ahmad Desoky M.,Ismail, Nabawia M.,Mahmoud, Ali Abdo
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p. 2502 - 2509
(2014/03/21)
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- Ultrasound-assisted synthesis of azlactone and its reactions with nucleophiles
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4-(2-Oxoindolin-3-ylidene)-2-phenyl-5(4H)-oxazolone (azlactone) was synthesized as a mixture of E- and Z-isomers by ultrasound-assisted Erlenmeyer-Pl?chl reaction between isatin and N-benzoylglycine. Treatment of azlactone with nucleophiles causes opening of its oxazolone moiety.
- Paponov, Boris V.,Lvov, Sergey V.,Ichetovkina, Ekaterina V.,Panasenko, Ilya A.,Stepanian, Stepan G.
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p. 273 - 274
(2013/01/15)
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- Novel N, N'-Hydrazino-bis-isatin Derivatives with Selective Activity Against Multidrug-Resistant Cancer Cells
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The invention is directed to a compound of Formula (I), wherein R is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; R1 is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; X is selected from the group consisting of hydrogen atom or halogen atom; and Y is selected from the group consisting of hydrogen atom, halogen atom, C1-C4 alkyl group, nitro group, and —OCF3 group, as well as for its use in therapy, preferably for the treatment of cancer, and to a related pharmaceutical composition, the use of the compound for the manufacture of a medicament for the respective medical indication, and a method of synthesis of the compounds of the invention.
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Page/Page column 9
(2012/10/08)
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- Fluoradenes via palladium-catalyzed intramolecular arylation
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A novel approach towards 7b-aryl-indeno[1,2,3-jk]fluorene based on a nitrogen-containing core is reported. The acid-promoted Friedel-Crafts reaction of 9-(2-bromophenyl)-9-fluorenol with carbazole, triphenylamine or triindole afforded 9-(2-bromophenyl)fluorenyl-carbazole, -triphenylamine and -triindole derivatives, which were subsequently converted to 7b-aryl-fluoradenes via palladium-catalyzed intramolecular C-H direct arylation as a key step.
- Rong, Lingling,Liu, Qiancai,Shi, Yingbo,Tang, Jie
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supporting information; experimental part
p. 2155 - 2157
(2011/03/22)
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