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A novel series of 2,5-disubstituted 1,3,4-thiadiazoles as potential anticonvulsant agent 被引量:1

A novel series of 2,5-disubstituted 1,3,4-thiadiazoles as potential anticonvulsant agent
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摘要 In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l,3,4-thiadiazol-2-yl}carba- mothioyl)-2/3/4-substitutedbenzamide were designed, synthesized and evaluated for their anticonvulsant activity. The findings of the present studies confirmed that the pharmacophore model with four binding sites is crucial for anticonvulsant activity. Structure-activity relationships among synthesized compounds were also established. In pursuit for better antiepileptic drug and the importance of semicarbazones and 2,5-disubstituted 1,3,4-thiadiazoles as anticonvulsant pharmacophore, a series of novel N-({5-[(6-methyl-l-benzofuran-3-yl)methyl]-l,3,4-thiadiazol-2-yl}carba- mothioyl)-2/3/4-substitutedbenzamide were designed, synthesized and evaluated for their anticonvulsant activity. The findings of the present studies confirmed that the pharmacophore model with four binding sites is crucial for anticonvulsant activity. Structure-activity relationships among synthesized compounds were also established.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第10期1149-1152,共4页 中国化学快报(英文版)
关键词 1 3 4-Thiadiazoles SEMICARBAZONES Anticonvulsant activity 1,3,4-Thiadiazoles Semicarbazones Anticonvulsant activity
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  • 10Compound 7(d):mp (℃) 218-220; yield 62%; IR (cm-1) (KBr) 3035.3 (aromatic C-H str),1601.3 and 1502.7 (aromatic C-C str),746.8 (C-S of 1,3,4-thiadiazole nucleus),1644.1 (C=N of 1,3,4-thiadiazole nucleus),1684.2 (C=O str of amide),3436.6 (N-H str of amide),1612.4 (C=N group),833.6 (para-disubstituted C-H def),722.8 (C-Cl str),2894.8 (Alkane C-H str),1092.5 (C=S str); 13C NMR (75 MHz,DMSO-d6,TMS):δ 140.3 (C-2'),115.8 (C-3'),126.4 (C-4'),154.1 (C-5'),112.5 (C-6'),133.6 (C-7'),123.8 (C-8'),121.6 (C-9'),164.3 (C-2),156.4 (C-5),177.5 (NHCSNHNCO),168.9 (NHCSNHNCO),128.8 (C-2''' and C-6'''),129.2 (C-3''' & C-5'''),137.3 (C-4'''),131.6 (C-1'''),21.2 (CH3),24.4''' (CH2 connecting benzofuran & thiadiazole ring); 1H NMR (300 MHz,DMSO-d6,TMS):δ 7.5-7.9 (m,4H,ArH),2.3 (s,3H,CH3),4.2 (s,2H,CH2),6.9-7.4 (m,4H,benzofuran protons),6.5 (s,1 H,NHCSNHCO),9.3 (s,1H,NHCSNHCO); ESI-MS (methanol) m/z 443.9 ([M+H] +).Compound 7(g):mp (℃) 263-265; yield 65%; IR (cm-1) (KBr) 3040.6 (aromatic C-H str),1602.5 and 1503.8 (aromatic C-C str),.

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