380335-36-4Relevant articles and documents
Solubility and thermodynamic analysis of N′-(1-(N-(methyl) benzylaminomethyl)-2-oxoindolin-3-ylidene)-2-(benzyloxy) benzohydrazide in different neat solvents at different temperatures
Shakeel, Faiyaz,Haq, Nazrul,Radwan, Awwad A.,Alanazi, Fars K.,Alsarra, Ibrahim A.
, p. 108 - 112 (2016)
The present study was undertaken to determine the solubilities of newly synthesized anticancer compound N′-(1-(N-(methyl) benzylaminomethyl)-2-oxoindolin-3-ylidene)-2-(benzyloxy) benzohydrazide (NMBOBB) in nine different neat solvents including water, isopropanol (IPA), ethanol, ethylene glycol (EG), 1.2-propanediol (PG), 1-butanol, 2-butanol, polyethylene glycol-400 (PEG-400) and Transcutol (diethylene glycol monoethyl ether) at T = 298.15 K to 318.15 K and p = 0.1 MPa. Experimental solubility data of NMBOBB was fitted with Apelblat and ideal models. The mole fraction solubility of NMBOBB was recorded highest in PEG-400 (1.14 × 10- 2 at T = 318.15 K) followed by Transcutol (7.14 × 10- 3 at T = 318.15 K), 2-butanol (1.45 × 10- 3 at T = 318.15 K), 1-butanol (1.38 × 10- 3 at T = 318.15 K), ethanol (9.69 × 10- 4 at T = 318.15 K), PG (9.52 × 10- 4 at T = 318.15 K), IPA (9.41 × 10- 4 at T = 318.15 K), EG (8.09 × 10- 4 at T = 318.15 K) and water (3.00 × 10- 6 at T = 318.15 K). The highest solubility of NMBOBB in PEG-400 was possible due to lower polarity and higher molar mass of PEG-400. The dissolution behavior of NMBOBB was observed as an endothermic, spontaneous and an entropy-driven due to positive values of standard enthalpies, Gibbs free energies and entropies in all nine neat solvents investigated. The results of this work would be helpful in purification, recrystallization and dosage form design of NMBOBB.
Target β-catenin/CD44/Nanog axis in colon cancer cells by certain N′-(2-oxoindolin-3-ylidene)-2-(benzyloxy)benzohydrazides
Radwan, Awwad A.,Al-Mohanna,Alanazi, Fares K.,Manogaran,Al-Dhfyan, Abdullah
, p. 1664 - 1670 (2016/12/22)
Cell surface molecule CD44 plays a major role in regulation of cancer stem cells CSCs on both phenotypic and functional level, however chemical inhibition approach of CD44 to targets CSCs is poorly studied. Herein, we report the discovery of certain N′-(2-oxoindolin-3-ylidene)-2-(benzyloxy)benzohydrazides as a novel inhibitor of CD44. Molecular docking study showed interference of the scaffold of these compounds with β-catenin/TCF-4 complex, building a direct relationship between CD44 inhibition and observed well-fitted binding domain. Compound 11a, most potent member elicits inhibition effect on TCF/LEF reporter activity conformed the involvement of Wnt pathway inhibition as a mechanism of action. Furthermore, the treatment by the mentioned compound leads to inhibition of embryonic transcriptional factor Nanog but not Sox2 or Oct-4 suggested specific targeted effect. Moreover, the cytotoxicity and cell cycle effect of this series seems to be dependent on CD44 expression.
Recyclable CuO nanoparticles-catalyzed synthesis of novel-2,5-disubstituted 1,3,4-oxadiazoles as antiproliferative, antibacterial, and antifungal agents
Murty,Penthala, Raju,Buddana, Sudheer Kumar,Prakasham,Das, Pompi,Polepalli, Sowjanya,Jain,Bojja, Sreedhar
, p. 4579 - 4594 (2016/02/20)
A series of new 2,5-disubstituted 1,3,4-oxadiazoles have been conveniently synthesized through an oxidative C-O coupling by direct C-H bond activation of N-aroyl-N-arylidinehydrazines using a catalytic quantity of CuO nanoparticles. Twenty compounds have been synthesized in good to excellent yields (75-90 %). All the synthesized compounds were evaluated for their in vitro antiproliferative, antibacterial, and antifungal activity. Compounds 8d and 10d are more promising antiproliferative agents with IC50 value of 3.66 and 3.89 μM in MCF-7 cell line, and compounds 8a and 10a were showed more potent antifungal activity than standard drug.
A Novel Series of 2,5-Disubstituted 1,3,4-oxadiazoles: Synthesis and SAR Study for their Anticonvulsant Activity
Rajak, Harish,Singour, Pradeep,Kharya, Murli Dhar,Mishra, Pradeep
experimental part, p. 152 - 158 (2012/01/06)
In search for a better anticonvulsant drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-oxadiazoles as anticonvulsant pharmacophore, a series of novel substituted semicarbazones were designed, synthesized, and evaluated for their anticonvulsant activity. The chemical structures of the synthesized molecules were confirmed by elemental and spectral (IR, 1H NMR, 13C NMR and MS) analysis. The anticonvulsant activities of the compounds were investigated using maximal electroshock seizure and subcutaneous pentylenetetrazole (scPTZ) models. Efforts were also made to establish structure-activity relationships among synthesized compounds. The results of the present study validated that the pharmacophore model with four binding sites is essential for anticonvulsant activity.
Synthesis and anticonvulsant activity of new 2-substituted-5-(2- benzyloxyphenyl)-1,3,4-oxadiazoles
Zarghi, Afshin,Tabatabai, Sayyed A.,Faizi, Mehrdad,Ahadian, Avideh,Navabi, Parisa,Zanganeh, Vahideh,Shafiee, Abbas
, p. 1863 - 1865 (2007/10/03)
A series of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles have been synthesized and evaluated as anticonvulsant agents. Compound 4b shows considerable anticonvulsant activity both in PTZ and MES models. It seems this effect is mediated through benzodiazepine receptors mechanism.
