Synthesis, Crystal Structures of S- and N- Benzyl Derivatives Of 5-phenyl-1,3,4-oxadiazol-2-thione

Benzylation reaction is carried out 5-phenyl-1,3,4-oxadiazol-2-thione with benzyl chloride in acetone and HMPA. In the acetone was obtained exclusively S-benzyl derivative and in the case of HMPA - isomeric mixture of S- and N-benzyl derivatives were obtained, individually isolated, characterized, and their structure was proved by spectral methods. By slow evaporation of solvents at room temperature were obtained two polymorphic crystals of 5-phenyl-1,3,4-oxadiazol-2-thione from acetone 1 and ethanol 2. Crystals of 2-benzylthio-5-phenyl-1,3,4-oxadiazole 3 and 3-benzyl-5-phenyl-1,3,4-oxadiazol-2-thione 4 obtained in similar conditions have structures without the inclusion of solvent molecules

N-(5-Benzylsulfanyl-1,3,4-thiadiazol-2-yl)-2-(piperidin-1-yl)acetamide

The title compound, C16H20N4OS2, was synthesized by the reaction of 2-benzylsulfanyl-5-chloroacetamido-1,3,4-thiadiazole and piperidine in a 1:2 ratio. The planes of the acetamide and 1,3,4-thiadiazole units are twisted by 10.8 (4)°. The thiadiazole S atom and the acetamide O atom are syn-oriented due to a hypervalent S...O interaction of 2.628 (4) Å. In the crystal, molecules form centrosymmetric dimers via N—H...N hydrogen bonds. These dimers are further connected by C—H...O interactions into (100) layers

Highly Selective Synthesis and Fungicidal Activity of the Novel 2-Alkylthio-5-Amino-1,3,4-Thiadiazoles

ABSTRACT Selective alkylation of 5-amino-1,3,4-thiadiazole-2-thione with alkyl (C2-C9) halides have been studied and exclusively S-alkyl derivatives were obtained in excellent yields. It was found that the alkylation products in the presence of amino group or a nitrogen atom in position 3 are not observed. Reaction conditions, structure and fungicidal activity of the synthesized compounds have been investigated. It was found that the obtained S-alkyl derivatives have weak activity against Xanthomonas malvacearum bacteria

FREE-RADICAL OXIDATION ACTIVITY IN PATIENTS WITH ACUTE MYOCARDIAL INFARCTION WITHOUT Q WAVE TREATED WITH EPROSARTAN OR ENALAPRIL ADDITIONALLY TO THE BASIC THERAPY

Aim. To compare effects of eprosartan and enalapril on free-radical oxidation in patients with acute myocardial infarction (AMI) without Q wave.Material and methods. 50 patients (aged 52,8±3,3 y.o.) with AMI without Q were involved into the study. Patients were randomized on 2 groups. The first group consisted of 24 patients (51,1±2,4 y.o.) which received basic therapy and enalapril (10 mg daily). The second group consisted of 26 patients (53,1±3,0 y.o.) which received basic therapy and eprosartan (600 mg daily). Basic therapy included anticoagulants, antiplatelets, beta-blockers, nitrates and statins. Intensity of free-radical oxidation was evaluated by change of serum malonic dialdehyde (MDD) concentration. Functional activity of serum enzymes of antioxidatic system (AOS) was evaluated by rate of reaction of superoxide dismutase (SOD) and catalase (CT).Results. The intensity of free-radical oxidation increased in patients with AMI without Q: high level of MDD and peroxinitrite (ONOO-). Besides activity of AOS enzymes (SOD and CT) decreased. Eprosartan reduced intensity of peroxide oxidation more prominently in comparison with enalapril. Both drugs preserved low activity of SOD and CT.Conclusion. Eprosartan was significantly more effective than enalapril in reduction of serum free-radical oxidation in patients with AMI without Q wave during 10 days after hospital admission.</p

FREE-RADICAL OXIDATION ACTIVITY IN PATIENTS WITH ACUTE MYOCARDIAL INFARCTION WITHOUT Q WAVE TREATED WITH EPROSARTAN OR ENALAPRIL ADDITIONALLY TO THE BASIC THERAPY

Aim. To compare effects of eprosartan and enalapril on free-radical oxidation in patients with acute myocardial infarction (AMI) without Q wave.Material and methods. 50 patients (aged 52,8±3,3 y.o.) with AMI without Q were involved into the study. Patients were randomized on 2 groups. The first group consisted of 24 patients (51,1±2,4 y.o.) which received basic therapy and enalapril (10 mg daily). The second group consisted of 26 patients (53,1±3,0 y.o.) which received basic therapy and eprosartan (600 mg daily). Basic therapy included anticoagulants, antiplatelets, beta-blockers, nitrates and statins. Intensity of free-radical oxidation was evaluated by change of serum malonic dialdehyde (MDD) concentration. Functional activity of serum enzymes of antioxidatic system (AOS) was evaluated by rate of reaction of superoxide dismutase (SOD) and catalase (CT).Results. The intensity of free-radical oxidation increased in patients with AMI without Q: high level of MDD and peroxinitrite (ONOO-). Besides activity of AOS enzymes (SOD and CT) decreased. Eprosartan reduced intensity of peroxide oxidation more prominently in comparison with enalapril. Both drugs preserved low activity of SOD and CT.Conclusion. Eprosartan was significantly more effective than enalapril in reduction of serum free-radical oxidation in patients with AMI without Q wave during 10 days after hospital admission

Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole

The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C17H17N3OS (I), and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C17H15ClFN3OS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C–H...π interactions are observed between neighboring molecules. Hirshfeld surface analysis indicates that H...H and H...C/C...H interactions make the most important contributions to the crystal packing