1-取代芐基-3(或5)-(5-羥甲基-2-呋喃基)-5(或3)-苯基吡唑之合成及其生理活性; Synthesis and Biological activities of 1-Substituted Benzyl-3(or5)-(5-hydroxymethyl-2-furyl)-5(or3)- phenylpyrazoles

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Title:	1-取代芐基-3(或5)-(5-羥甲基-2-呋喃基)-5(或3)-苯基吡唑之合成及其生理活性;Synthesis and Biological activities of 1-Substituted Benzyl-3(or5)-(5-hydroxymethyl-2-furyl)-5(or3)- phenylpyrazoles
Authors:	湯先佑;Hsien-Yu Tang
Contributors:	中國醫藥大學：藥物化學研究所碩士班
Keywords:	吡;唑;抗血小板;pyrazole;YC-1;antiplatelet
Date:	2006-07-21
Issue Date:	2009-08-13 09:37:27 (UTC+8)
Abstract:	在持續尋找新型的抗血小板藥物中，1-Benzyl-3-(5-hydroxymethyl -2-furyl)-5-phenylpyrazole (7b)被選擇作為先導化合物。著者以methyl 2-furoate (1)當作起始原料，與氯化氫、paraformaldehyde形成methyl 5-chloromethyl-2-furoate (2)，接著和hexamethylenetetramine形成銨鹽並水解形成methyl 5-formyl-2-furomate (3)。化合物3和acetophenone在鹼的存在下反應生成1-phenyl-3-(5-carboxy-2-furyl)-2-propene-1-one (4)，續以聯胺環化後，可得化合物3(or 5)-(5-ethoxycarbonyl-2-furyl)-5(or 3)-phenylpyrazole (5)。化合物5和不同取代之芐基氯進行取代反應，可得一系列1-取代芐基-3(or 5)-(5-ethoxycarbonyl -2-furyl)-5(or 3)-phenylpyrazole (6a及6b)，將6b還原後即得標的化合物7b。著者並經由一維、二維核磁共振圖譜完成其位置異構物之解析。已提供測試之化合物對於部分腫瘤細胞之抑制作用並不明顯，抗血小板活性則尚在測試當中。 As a part of our continuing search for potential aniplatelet agent, 1-Benzyl-3-(5-hydroxymethyl -2-furyl)-5-phenylpyrazole (7b) was chosen as the lead compund. The starting material was methyl 2-furoate(1), which was introduced by hydrogen chloride and paraformadehyde to prepare methyl 5-chloromethyl-2-furoate (2). The compound 2 was successively reacted with hexamethelentetramine, then hydrolysis the formed salt, and methyl 5-formyl-2-furomate (3) was yield. Compound 4 was obtained from compound 3, which reacted with acetophenone in alkaline. And then compound 4 was proceeded cyclization with hydrazine hydrate to yield 3(or 5)-(5-ethoxy carbonyl-2-furyl)-5(or 3)-phenylpyrazole (5). Compound 5 was reacted successively with various kind of benzyl chlordie, and a series of 1-substituted benzyl-3(or 5)-(5-ethoxycarbonyl -2-furyl)-5(or 3)-phenylpyrazoles (6) was prepared. The reduction of compound 6 eventually brings the target compound. We also completed the identification of positional isomers by exploiting the 1D and 2D NMR spectra. The inhibition of some tumor cell of tested compound was not significant, and activities of antiplatelet were still in progress.
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