| 第 51 卷第 3 期 |  | Vol. 51 No. 3 | | 2021 年 6 月 | Jun 2021 |
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所屬欄目：醫藥及中間體
4-甲基-N1-（3-苯基丙基）-1，2-苯二胺的合成及抗腫瘤活性研究 |
| 姜曉曄，王 璇，黎七雄
（武漢城市學(xué)院 醫學(xué)部，湖北 武漢 430083） |
| 摘 要：以4-甲基-2-硝基苯胺（4）為原料，在氫化鈉催化下，與1-溴-3-苯基丙烷（3）反應制得4-甲基-2-硝基-N-（3-苯基丙基）-苯胺（2），2 的硝基經(jīng)鐵粉還原得到化合物4-甲基-N1-（3-苯基丙基）-1，2-苯二胺（1），產(chǎn)品結構經(jīng)核磁共振氫譜表征確證，同時(shí)優(yōu)化了反應條件。在第一步反應中，氫化鈉為催化劑，甲苯為溶劑，n（4-甲基-2-硝基苯胺）∶n（氫化鈉）=1∶2，70 ℃反應24 h；在還原反應中，鐵粉與氯化銨為還原劑，n（鐵粉）∶n（氯化銨）=1∶2，n（4-甲基-2-硝基-N-（3-苯基丙基）-苯胺）∶n（鐵粉）=1∶2。優(yōu)化條件下產(chǎn)物總收率為59.7%。此外，初步的生物活性測試表明，4-甲基-N1-（3-苯基丙基）-1，2-苯二胺（1）對MCF-7、MDA-MB-231、HepG2、PC-3和A549均有明顯的抑制活性，尤其是對MDA-MB-231展現出了最強的抑制活性，其IC50=（7.9±0.9） μmol·L-1。 |
| 關(guān)鍵詞：4-甲基-N1-（3-苯基丙基）-1，2-苯二胺；合成；反應條件；抗腫瘤活性 |
| 中圖分類(lèi)號：TQ463 文獻標識碼：A 文章編號：1009-9212（2021）03-0022-05 |
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| Synthesis and Anti-tumor Activity Evaluation of 4-Methyl-N1-(3-phenyl-propyl)-benzene-1,2-diamine |
| JIANG Xiao-ye, WANG Xuan, LI Qi-xiong
(School of Medicine, Wuhan Institute of City, Wuhan 430083, China) |
| Abstract：4-Methyl-2-nitroaniline was used as raw material, which reacted with 1-bromo-3-phenylpropane (3) to obtained 4-methyl-2-nitro-N-(3-phenyl-propyl)-aniline (2) under the catalysis of sodium hydride. The nitro group of 3 was reduced by iron powder toproduce the compound 4-methyl-N1-(3-phenyl-propyl)-benzene-1,2-diamine (1). The structure of the product 4 was confirmed by 1H NMR. Meanwhile, the reaction conditions were optimized: in the first step reaction, sodium hydride as catalyst, toluene as solvent, n(4-methyl-2-nitroaniline)∶n(sodium hydride)=1∶2, reaction at 70 ℃ for 24 h; in the reduction reaction: iron powder and ammonium chloride as reducing agent, n(iron powder)∶n(ammonium chloride)=1∶2, n(4-methyl-2-nitro-N-(3-phenyl propyl)-anilin∶n(ironpowder)=1∶2. Under optimal conditions, the total of 4-methyl-N1-(3-phenyl-propyl)-benzene-1,2-diamine(1) was 59.7%. Moreover, the preliminary biological results showed that 4-methyl-N1-(3-phenyl-propyl)-benzene-1,2-diamine (1) showed obvious antiproliferative effect on MCF-7, MDA-MB-231, HepG2, PC-3and A549 cell lines, especially to MDA-MB-231, which showed strong inhibitory effect with the IC50 value was (7.9±0.9) μmol·L-1. |
| Key words：4-methyl-N1-(3-phenyl-propyl)-benzene-1,2-diamine; synthesis; reaction conditions; anti-tumor activity |
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作者簡(jiǎn)介：姜曉曄（1987—），女，湖北武漢人，碩士，研究方向：藥物合成反應（E-mail：511811879@qq.com）。
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收稿日期：2021-06-01
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