Murat Koca

Synthesis, Reactivity and Biological Activity of Novel Bisbenzofuran-2-yl-Methanone Derivatives

Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested against five different microorganisms and some of them were found to be active against some of the species studied.

Studies on the Synthesis and Reactivity of Novel Benzofuran-2-yl-[3-Methyl-3-Phenylcyclobutyl] Methanones and their Antimicrobial Activity

Preparation in excellent yields of cyclobutyl benzofuran-2-yl- and naphthofuran-2-yl-ketones, the corresponding ketoximes and thiosemicarbazones, ether derivatives of the ketoximes and thiazoles derived from the thiosemicarbazones are described. Two of the synthesized compounds have been tested against eight different microorganisms and found to be active against some of the species studied.

Investigation of Antioxidant Vitamins (A, E, C) and Lipid Peroxidation Levels in Rats Injected N-(1,3-Benzothiazol-2-yl)- N-(4,5-dihydro-1H-imidazol-2-yl) amine

The present study examined the influence of synthetic N-(1,3-benzothiazol-2-yl)-N-(4,5-dihydro-1H-imidazol-2-yl) amine (2-Amdz) on levels of vitamins A, E and C and malondialdehyde (MDA) in rats. A total of 30 rats, divided into two groups, were used in the study. The control group was given only a subcutaneous injection of 250 µL 75% ethanol, every other day. The other group of rats was administered a subcutaneous injection of 2-Amdz (25 mg kg-1, dissolved in 250 µL of 75% ethanol). Injections were continued for 16 days. After the application of 2-Amdz for 16 days, the serum levels of vitamins A, E and C and malondialdehyde (MDA) were determined by HPLC. The serum vitamin A, E, and C levels decreased significantly compared to controls (p<0.05) whereas serum MDA levels were higher than control levels (p<0.005). As a result, it can be suggested that 2-Amdz induced a severe stress and more importantly, increased the amount of free radicals and significantly decreased the levels of serum antioxidant vitamins.

(Benzo­furan-2-yl)(3-methyl-3-phenyl­cyclo­butyl)­methanone

The structure of the title compound, C20H18O2, consists of a dimeric arrangement of benzofuran molecules around an inversion centre, linked via C-H...O hydrogen bonds. There are also C-H...pi ring interactions. All these interactions result in the formation of infinite chains parallel to the [100] axis. The cyclobutane ring is puckered, with a dihedral angle of 29.03 (13) degrees between the two three-atom planes.

1,3-Dibenzoylimidazolidine-2-thione and 1,3-dibenzoyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione.

The title compounds, 1,3-dibenzoylimidazolidine-2-thione, C17H14N2O2S, (I), and 1,3-dibenzoyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione, C18H16N2O2S, (II), were obtained from the reactions of imidazolidine-2-thione and 1,4,5,6-tetrahydropyrimidine-2-thiol, respectively, with benzoyl chloride. Compounds (I) and (II) contain, respectively, imidazolidinethione [C=S = 1.6509 (14) A] and pyrimidinethione [C=S = 1.6918 (19) A] moieties bonded to two benzoyl rings. The molecules of (I) exhibit C2 symmetry, the C=S bond lying along the twofold rotation axis, while the molecules of (II) have mirror symmetry (Cs). The imidazolidine ring in (I) is essentially planar, while the pyrimidine ring in (II) adopts a boat conformation. Molecules of (I) are linked by weak intermolecular C-H...O interactions, while molecules of (II) are held together by van der Waals interactions.

C—H⋯O, C—H⋯π and π–π inter­actions in three benzofuran-2-yl ketone derivatives

The molecules of 2-benzoyl-l-benzofuran, C 15 H 10 O 2 , (I), interact through double C-H...O hydrogen bonds, forming dimers that are further linked by C-H...O, C-H...π and π-π interactions, resulting in a three-dimensional supramolecular network. The dihedral angle between the benzoyl and benzofuran fragments in (I) is 46.15 (3)°. The molecules of bis(5-bromo-1-benzofuran-2-yl) ketone, C 17 H 8 Br 2 O 3 , (II), exhibit C 2 symmetry, with the carbony] group (C=O) lying along the twofold rotation axis. and are linked by a combination of C-H...O and C-H...π interactions and Br...Br contacts to form sheets. The stability of the molecular packing in 3-mesityl-3-methylcyclobutyl 3-methylnaphtho[1,2-b]furan-2-yl ketone, C 28 H 28 O 2 , (III), arises from C-H...π and 7r-7r stacking interactions. The fused naphthofuran moiety in (III) is essentially planar and makes a dihedral angle of 81.61 (3)° with the mean plane of the trimethylbenzene ring.