Synthesis, X‐ray crystal structure and biological activities of α‐phenoxyl‐1,2,3‐thiadiazoleacetamide

Abstract

The annelation of 1,2,3-thiadiazole rings was accomplished by the reaction of N-acylhydrazone 2a bearing an adjacent α α-methyl with thionyl chloride to give α-chloro-N-methyl-1,2,3-thiadiazole-4-acetamide 4 and was demonstrated by the X-ray crystal structure of its derivative 5a. A novel series of α-substituted phenoxy-N-methyl-1,2,3-thiadiazole-4-acetamide 5 were synthesized through the reaction of the compound 4 and phenols. The results of bioassays show that the title compounds exhibit good anti-HBV activities. The crystal of compound 5a, N-methyl-α α-2-bromophenyl-1,2,3-thiadiazole-4-acetamide, has been prepared and determined by X-ray diffraction.

4-{2-[(4-Methoxyphenyl)sulfanyl]-2-(1,2,3-thiadiazol-4-yl)acetyl}morpholine

“…Compound (I) was prepared according to the reported precedure of Zhao et al (2003), using -chloro-1,2,3-thiadiazole-4-acetylmorpholine (4 mmol), 4-methoxybenzenethiol (4 mmol), potassium carbonate (5 mmol) and acetonitrile (15 ml) (1.07 g, 76% yield). Colourless single crystals suitable for X-ray diffraction analysis were obtained by recrystallization from methanol.…”

Synthesis and antiviral activity against tobacco mosaic virus and 3D-QSAR of α-substituted-1,2,3-thiadiazoleacetamides

“…8 The N-acylhydrazone, which was easily prepared from commercially available N-methyl-a-chloroacetoacetamide and ethyl carbazate in ethanol, was cyclized with three equivalents of thionyl chloride at room temperature to form a-chloro-N-methyl-1,2,3-thiadiazole-4-acetamide (1) in accord with the Hurd-Mori reaction conditions. The compound (1) reacted with substituted phenols, substituted benzenethiols or mercapto heterocyclic compounds in the presence of inorganic base to yield a-substituted phenoxy(phensulfydryl)-N-methyl-1,2,3-thiadiazole-4-acetamide (2)(3)(4)(5)9 10-13 10 ) as shown in Schemes 1-3.…”

“…By controlling reaction temperature, compounds (4, 5) could be easily oxidized by hydrogen peroxide to afford sulfoxide (6, 7 11 ) or sulfone (8, 9 12 ). And sulfone (8,9) was readily obtained by the reaction of compound 4 and compound 5 with hydrogen peroxide, respectively. Table 1 summarizes the antiviral screening results of the studied compounds.…”

Design, synthesis and biological activities of novel 1,2,3-thiadiazole derivatives containing oxime ether

“…In the previous paper, we had reported some 1,2,3thiadiazoleacetamides exhibited better anti-tobacco mosaic virus (anti-TMV) activity, plant growth-regulating activity and showed some anti-hepatitis B virus (anti-HBV) activity. [9][10][11][12] Considering the oxime ethers are very important active compounds, many of them are used as insecticide, fungicide, herbicide and so on, and oxime ether group is often used in new pesticide discovery because of their high biological activites and their good environmental profiles. 13 In order to search for novel 1,2,3-thiadiazole derivatives which have high activities, we report here our synthesise a series of novel 2-methoxyimino-1,2,3-thiadiazole-5-acetamides 6.…”