Bilge Çakir

Synthesis and anticonvulsant activity of some (2/4-substituted)benzaldehyde (2-oxobenzothiazolin-3-yl)acetohydrazones

Fifteen new (2/4-substituted)benzaldehyde (2-oxobenzothiazolin-3-yl)acetohydrazones were synthesized and their structures were elucidated by NMR and elemental analysis. Their anticonvulsant activity was tested by a pentylenetetrazole induced seizure test. Compounds 4e and 4h were found to be the most promising among the others.

The in vitro effects of new non-steroidal antiinflammatory compounds on antioxidant system of human erythrocytes.

It has been reported by our group that some benzoxazolone and benzothiazolone derivatives showed significant antinociceptive and anti-inflammatory activity [DOGRUER et al. 1997]. It has been speculated that nonsteroidal anti-inflammatory drugs (NSAIDs) can act as the free radical scavengers and possess antioxidant activity. It is also well documented that oxidative stress can play an important role in the side effects of many xenobiotics including NSAIDs. Therefore, in the present study, the effects of six of the above mentioned benzoxazolone and benzothiazolone derivatives bearing 2-pyridylaminocarbonylmetyl moiety at the position 3 (I) on the antioxidant system-related parameters of human erythrocytes have been investigated. Diclofenac and nimesulid were also tested in the same systems as the control, because they are commonly used as NSAIDs. Our results showed that these compounds made significant changes in the antioxidant system of human erythrocyte.

Synthesis and antinociceptive activity of some 3-substituted benzothiazolone derivatives

Thirteen 3-substituted benzothiazolone derivatives have been synthesized. Their chemical structures have been elucidated by IR and NMR spectral data and by elemental analyses. Among these compounds, 1-¿3-[2(3H)-benzothiazolon-3-yl[propanoyl]morpholine (5b); 1-¿3-[2(3H)-benzothiazolon-3-yl[propanoyl]-4-benzylpiperidine++ + (5c); 1-¿3-[2(3H)-benzothiazolon-3-yl[-propanoyl]-4-phenylpiperazine (5d); 3-[3-(4-benzylpiperidine-1-yl)propyl]-2(3H)-benzothiazolone (5k); 3-[3-(4-benzylpiperazine-1-yl)propyl]-2(3H)-benzothiazolone (5I); 3-[3-(4-phenylpiperazine-1-yl)propyl]-2(3H)-benzothiazolone (5m) have been found to be significantly more active than the others.

The in vitro hepatic metabolism of 1-phenyl-2-(2-benzothiazolinone-3-yl)ethanone and their reduced derivatives

The in vitro hepatic microsomal metabolism of 1-phenyl-2-(2-benzothiazolinone-3-yl)ethanone (I) and (+/-)-1-Phenyl-2-(2-benzothiazolinone-3-yl)ethanol (II) was studied using both rat microsomal preparations and soluble fractions fortified with NADPH. These two substrates and their potential dealkylation metabolite 2-benzothiazolinone were synthesized and their structures were elucidated by spectral methods. The results showed that (I) was metabolised to (II), the corresponding alcohol by reduction. More alcohol metabolite was observed with microsomes than those obtained with the soluble fractions. No dealkylation of (I) was observed in the experiments using both microsomes and soluble fractions. (II) was metabolised to (I), the corresponding ketone by oxidation. However, compared to the metabolism of (I), more ketone metabolite was observed with soluble fractions than microsomes. (II) was also dealkylated to (III) with only soluble fractions but no dealkylated metabolites were found in the microsomes. In addition, a common unknown metabolite was observed with each substrates.

Superparamagnetic Iron Oxide Enhanced Magnetic Resonance Imaging in the Detection of Malignant Liver Lesions

Amac: Manyetik Rezonans (MR) goruntulemede kontrast madde olarak kullanilan superparamanyetik demir oksit (SPFeO) preparatinin malign karaciger kitlelerinin tanisindaki yerini arastirmaktir. Gerec ve Yontemler: Degisik tipte karaciger kitleleri bulunan 20 olguya 1 Tesla cihaz ile MR inceleme yapildi. Olgulara pre- ve post-kontrast T1- agirlikli FLASH (Fast Low Angle Shot) ve cift eko TSE (Turbo Spin Echo) T2-agirlikli sekanslar uygulandi. Lezyonlardan yapilan sinyal intensite ol- cumlerine gore “Tanimlayici istatistikler” yapildi. Bulgular: Onbir olguda metastaz, 4 olguda hemanjiom, 4 olguda HCC (Hepatoselluler Karsinom) ve 1 olguda ise birer adet hemanjiom ve metastaz bulundu. Sadece hemanjiom saptanan olgularda tum sekanslarda S/N oranlarinda anlamli degisim (p=0.043) saptanirken, cift eko TSE T2A sekansda sadece uzun TE’de SI degisimi (p=0.043) anlamli bulundu. Metastaz ve HCC olgularinda cift eko TSE T2A sekansda kisa TE’de diger sekanslara oranla C/N oranlarinda belirgin yuzde artis saptanirken, hemanjiom olgularinda ise kontrast sonrasinda ozellikle cift eko TSE T2A sekansda uzun TE’de C/N oranlarinda azalma belirlendi. Sonuc: Karacigerde gerek lezyon tespiti ve sayisinin belirlenmesi, gerekse benign (ozellikle hemanjiom), primer ya da metastatik malignite ayriminda SPFeO ile MR goruntuleme diger sekanslara ek bulgular saglayan noninvaziv bir radyolojik metod olarak kullanilabilir

Crystal structure of 4-(2-oxobenzothiazolin-3-yl)butanoic acid, C11H11NO3S

C11H11NO3S, triclinic, P1 (No. 2), a = 7.240(1) Å, b = 7.495(2) Å, c = 10.427(1) Å, = 83.89(1)°, = 85.74(1)°, = 71.16(1)°, V = 532.0 Å, Z = 2, Rgt(F) = 0.035, wRref(F) = 0.096, T = 293 K. Source of material For the synthesis, 10.0 mmol ethyl 4-(2-oxobenzothiazolin-3-yl)butanoate in concentrated hydrochloric acid (50 ml) was stirred at room temperature for 2 hours, then refluxed for 4 hours. The reaction mixture was cooled, poured into 100 g ice-water, and stirred for 1 hour. The precipitate was collected by filtration, washed with water, dried and crystallised from water. Discussion The benzene ring defined by C1–C2–C3–C4–C5–C6 atoms is planar. Torsion angles of C1–C2–C3–C4, C6–C5–C4–C3 and C1–C6–C5–C4 are 0.4(3)°, 0.1(3)° and 0.3(3)°, respectively. The thiazolon ring defined by C1–C6–N–C7–S atoms is planar. Torsion angles of C7–S–C1–C6 and C6–N–C7–S are 0.6(1)° and 1.2(2)°, respectively. The dihedral angle between these two planes is 0.99(8)° implying that they are co-planar. The torsion angles of C7–N–C6–C5, N–C6–C1–C2, C7–S–C1–C2 and S2–C1–C2–C3 are 178.8(2)°, 179.2(2)°, –178.6(2)° and 179.1(2)°, respectively. O1 and C8 atoms are also at this plane. Torsion angles of C6–N–C7–O1, C1–S–C7–O1, C8–N–C6–C1 and C8–N–C7–O1 are –179.0(2)°, 179.2(2)°, –179.0(2)° and –0.7(3)°, respectively. C9 atom lies below 1.351(3) Å from thiazolon plane. Torsion angles of C7–N–C8–C9, C6–N–C8–C9 and N–C8–C9–C10 are 103.8(2)°, –78.0(2)° and –68.5(2)°, respectively. The bond lengths and angles in the 4-(2-oxobenzothiazolin-3-yl)butanoic acid are all in accord with similar structures in the literature [1-3]. The bond lengths of C—C are between 1.378(3) Å – 1.522(3) Å. The bond lengths of C7=O1, C11—O2 and C11=O3 are 1.214(2) Å, 1.262(2) Å and 1.263(2) Å, respectively. The bond lengths of C7—S and C1—S are 1.782(2) Å and 1.743(2) Å, respectively. The bond lengths of C6—N, C7—N and C8—N are 1.395(2) Å, 1.368(2) Å and 1.464(2) Å, respectively. Z. Kristallogr. NCS 218 (2003) 175–176 175

Synthesis and Analgesic Activity of 1‐(1‐Piperidinyl)methyl‐2‐(4‐substituted styryl)‐5‐chlorobenzimidazole Derivatives

Seven 1-(1-piperidinyl)methyl-2-(4-substituted styryl)-5-chlorobenzimidazole derivatives were synthesized by the reaction of 2-(p-substituted styryl)-5-chlorobenzimidazoles with formaldehyde and piperidine in methanol. Analgesic activity of the 1-(1-piperidinyl)-methyl-2-(4-substituted styryl)-5-chlorobenzimidazole derivatives was investigated by the modified Koster test in mice. No obvious relationships between analgesic activity and the nature of the substituent on the styryl group was found.