Synthesis,Antiproliferative, and Antiplatelet Activities of Oxime‐Containing 3,4‐Dihydroquinolin‐2(1H)‐One Derivatives

Some oxime‐containing 3,4‐dihydroquinolin‐2(1H)‐one derivatives were synthesized and evaluated for their antiplatelet and antiproliferative activities. These compounds were synthesized via alkylation of hydroxyl precursors followed by the reaction with NH₂OH. The preliminary assays indicated that (Z)‐7‐[2‐(4‐fluorophenyl)‐2‐(hydroxyimino)ethoxy]‐3,4‐dihydroquinolin‐2(1H)‐one (13c) is the most active against U46619 induced platelet aggregation with an IC₅₀ value of 3.51 μM. For the inhibition of AA‐induced aggregation, (E)‐6‐[2‐(hydroxyimino)propoxy]‐3,4‐dihydroquinolin‐2(1H)‐one (15 ) is the most potent with an IC₅₀ value of 1.85 μM. These oxime‐containing 3,4‐dihydroquinolin‐2(1H)‐one derivatives were inactive against thrombin induced platelet aggregation with an IC₅₀ value of greater than 26.78 μM. For the antiproliferative activity, most of these oxime‐containing 3,4‐dihydroquinolin‐2(1H)‐one derivatives were inactive while (Z)‐7‐[2‐(hydroxyimino)‐2‐(naphthalen‐2‐yl)ethoxy]‐3,4‐dihydroquinolin‐2(1H)‐one (13a) exhibited only marginal activities with GI₅₀ value of 7.63, 7.34 and 6.36 μM against the growth of NPC‐TW01, NCI‐H661, and Jurkat respectively.     

Metallo Phthalocyanines bearing 2‐Isopropyl‐6‐methylpyrimidin‐4‐yloxy Substituents: Synthesis,Characterization, Aggregation Behavior,Antioxidant and Antibacterial Activity,and Electronic Properties

A novel phthalonitrile derivative bearing 2‐isopropyl‐6‐methylpyrimidin‐4‐yloxy substituents at peripheral positions was synthesized by a nucleophilic substitution reaction. Metallophthalocyanines were obtained from the reaction of the novel phthalonitrile with metal Zn, Cu, Co, and Ni salts. The characterization of the compounds was performed using elemental analysis as well as UV/Vis, FT‐IR, and ¹H‐NMR spectroscopy. The aggregation behaviors of phthalocyanine complexes were also investigated. These metallophthalocyanines do not show any aggregation behavior between 10^–4–10^–6 M concentration range in THF. The antioxidant activities of the synthesized compounds were evaluated using three different tests: 2, 2‐diphenyl‐1‐picrylhydrazyl (DPPH) radical scavenging, metal chelating activity, and reducing power assays. All the compounds exhibited various antioxidant activities. In addition, antimicrobial activity of the compounds was tested over four gram positive and two gram negative bacteria. Moreover, the ground‐state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6‐31G(d, p) level in order to obtain information about the 3D arrangements and electronic structure.     

Synthesis,Characterization and Evaluation of Antimicrobial and Antituberculosis Activities of New N‐(Substituted‐thioureido)aminobicyclo Dicarboximide and 3,4‐Disubstituted 1,2,4‐Triazolino‐5‐thione

The novel N‐(substituted‐thioureido)aminobicyclo dicarboximide and 3,4‐disubstituted 1,2,4‐triazolino‐5‐thione were synthesized and their antimicrobial and antituberculosis activities were examined. Selected dicarboxylic acid anhydrides were used to obtain derivatives of thiosemicarbazide and dicarboximide. Dicarboximides were also cyclized in the presence of an alkaline solution giving 1,2,4‐triazolino‐5‐thione. The chemical structure of all compounds was confirmed by IR, ¹H NMR, ¹³C NMR, the X‐ray crystallography ( 6 , 11 ) and elemental analysis. Antimicrobial and antituberculosis activities of the derivatives were measured.     

Synthesis,antimicrobial, and antioxidant activities of new pyridyl‐ and thiazolyl‐bearing carbohydrazides

A series of novel substituted (E)‐N′‐benzylidene‐4‐methyl‐2‐(2‐propylpyridin‐4‐yl)thiazole‐5‐carbohydrazide derivatives ( 6a‐l ) have been synthesized by following the multistep synthetic route starting from prothionamide. The resulting compounds were characterized via ¹H, ¹³C NMR, and HRMS spectral data. The synthesized carbohydrazides were evaluated for their in vitro antimicrobial and antioxidant activities. Tested molecules have displayed moderate to good growth inhibition activity. Among the screened compounds, 6b , 6e , 6j, and 6k are found to be the more promising antimicrobial agents. A 2,2‐diphenyl‐1‐picrylhydrazyl assay was used to test the antioxidant activity of the carbohydrazides. The carbohydrazide derivatives 6b and 6i have shown better free‐radical scavenging ability than the other investigated compounds.     

Synthesis,characterization, anti‐inflammatory and analgesic activity of transition metal complexes of 3‐[1‐(2‐hydroxyphenyl) ethylideamino]‐2‐phenyl‐3,4‐dihydroquinazolin‐4(3H)‐one

A new quinazolinone derivative, 3‐[1‐(2‐hydroxyphenyl)ethylideamino]‐2‐phenyl‐3,4‐dihydroquinazolin‐4(3H)‐one ( LH ) was synthesized by the condensation of 2‐hydroxyacetophenone‐2‐aminobenzoylhydrazone and benzaldehyde. The cyclization to form 1,2‐dihydroquinazolinone was confirmed by IR, 1D and 2D HETCOR studies. Coordination compounds of Co(II), Ni(II), Cu(II) and Zn(II) of LH were synthesized and characterized using various physico‐chemical studies like stoichiometric, conductivity, magnetic moment measurements and spectral techniques such as IR, NMR, UV‐vis and EPR spectroscopy. The elemental analysis and thermal studies suggested a general stoichiometry [M(HEPDQ)Cl] for all the complexes. A four‐coordinate geometry was assigned to all the complexes. The complexes along with the parent ligand were screened for their anti‐inflammatory activity, using carrageenan‐induced rat paw edema, and for their analgesic activity by Eddy's hot plate method. The activity of the ligand was enhanced on complexation with metal ions. This enhanced activity was attributed to the increased lipophilic nature of the complexes. Notable anti‐inflammatory activity was observed for Ni(II), Cu(II) and Zn(II) complexes. The analgesic activity of the ligand was greater than the standard at 60 min. and at a 10 mg kg⁻¹ dose, whereas the activity of Ni(II) and Cu(II) complexes at 10 mg kg⁻¹ dose was comparable with the standard used. Copyright © 2011 John Wiley & Sons, Ltd.     

Synthesis and Antimicrobial Activities of Novel 2‐[substituted‐1H‐pyrazol‐4‐yl] Benzothiazoles,Benzoxazoles, and Benzimidazoles

In an endeavor to find a new class of antimicrobial agents, a series of novel substituted benzimidazole, benzoxazole, and benzothiazole derivatives 6 containing pyrazole moiety have been synthesized by reaction of 3‐aryl‐4‐formyl pyrazole 4 with substituted phenylenediamine or o‐aminophenol or o‐aminothiophenol 5 . Reaction of phenyl hydrazine or 2‐hydrazinopyridine 1 with substituted acetophenones 2 gave the corresponding hydrazones 3 , which on Vilsmeier–Haack reaction with POCl₃–DMF gave substituted 3‐aryl‐4‐formyl pyrazoles 4 . All final compounds 6a , 6b , 6c , 6d , 6e , 6f , 6g , 6h , 6i , 6j , 6k were evaluated for in vitro antibacterial activities against Escherichia coli and Staphylococcus aureus strains and in vitro antifungal activity against Candida albicans and Aspergillus niger strains by using serial dilution method. The antimicrobial activities were expressed as the minimum inhibitory concentration in µg/mL. The compound containing benzimidazole and benzoxazole moiety gave better antibacterial and antifungal activities than benzothiazole compounds.     

Di‐ and tri‐organotin derivatives of 3S,4S‐3‐[(R)‐1‐(tert‐butyl‐dimethylsilyloxy)ethyl]‐4‐[(R)‐1‐carboxyethyl]‐2‐azetidinone: synthesis,characterization and in vitro antitumour activity

Di‐n‐butyl‐, triphenyl and tri‐n‐butyltin derivatives of 3 S, 4 S ‐3‐[( R )‐1‐(tert‐butyldimethyl‐­<?tw=103.5%>silyloxy)ethyl‐4‐[( R )‐1‐carboxyethyl]‐2‐azetidi<?tw>‐­none were synthesized and characterized. Their antitumour activity was screened against seven tumoural cell lines of human origin. Copyright © 1999 John Wiley & Sons, Ltd.     

Synthesis,structure and biological activity studies of 2‐[(1H‐1,2,4‐triazol‐1‐yl)methyl]‐1‐aryl)‐3‐ferrocenyl prop‐2‐en‐1‐one derivatives

Fifteen new ferrocene derivatives containing 1H‐1,2,4‐triazole moiety were synthesized in various yields by the condensation of ferrocenecarboxaldehyde with 1‐aryl‐3‐(1H‐1,2,4‐triazo‐1‐yl)‐propen‐1‐ones in toluene. Their structures have been confirmed by ¹H NMR, IR, MS and elemental analysis. In addition, the crystal structure of 4l was determined. The antifungal and plant growth regulatory activities of the title compounds are discussed. Copyright © 2005 John Wiley & Sons, Ltd.