CN104926774B - 刺芒柄花素席夫碱类衍生物及其合成方法与应用 - Google Patents
刺芒柄花素席夫碱类衍生物及其合成方法与应用 Download PDFInfo
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Abstract
本发明属于化学制药技术领域,具体涉及刺芒柄花素席夫碱类衍生物及其在肿瘤抑制方面的应用。通过合成手段获得相应化合物,体外抗肿瘤的活性研究表明,这类刺芒柄花素席夫碱类衍生物对肿瘤细胞株有很强的抑制活性。
Description
一:技术领域
本发明属于化学制药技术领域,具体涉及刺芒柄花素席夫碱类衍生物的制备及其在肿瘤抑制方面的应用。
二:背景技术
刺芒柄花素(Formononetin)为豆科植物红车轴草的花序及带花枝叶,是一类具有显著地抗癌活性的天然产物,为一类异黄酮化合物,对于预防乳腺癌、前列腺癌、结肠癌,改善骨质疏松和改善妇女更年期症状等有一定的作用。
虽然天然产物刺芒柄花素具有显著的抗肿瘤和抗病毒活性,但是与其他异黄酮类化合物相比,其抗肿瘤活性较弱,在应用过程中受到很大限制。很多研究对天然产物刺芒柄花素的结构进行改造,以求获得具有更好抗癌效果的衍生物,如胡昆等人设计合成了一系列刺芒柄花素氮芥类衍生物,并经活性试验证实其比刺芒柄花素具有更好的抗癌活性。
席夫碱(Schiff base)主要是指含有亚胺或甲亚胺特性基团(-RC=N-)的一类有机化合物,通常席夫碱是由胺和活性羰基缩合而成。席夫碱类化合物及其金属配合物在医学、催化、分析化学、腐蚀以及光致变色领域的重要应用。尤其是在医学领域,席夫碱具有抑菌、杀菌、抗肿瘤、抗病毒的生物活性。正因为席夫碱类化合物具有如此多的优点与应用,因此席夫碱类化合物的药理学和生理学活性,近年来一直是引人注目的研究对象。
本研究设计合成了一系列刺芒柄花素席夫碱类衍生物,以期获得活性较好、选择性较高的新型抗肿瘤药物。研究以刺芒柄花素为母体,经过简单的3步反应,设计合成了22种未见文献报道的刺芒柄花素席夫碱类衍生物。
三:发明内容
本发明需要解决的问题是提供一类刺芒柄花素席夫碱类衍生物的制备及其在肿瘤抑制方面的应用。
本发明的刺芒柄花素席夫碱类衍生物是通过刺芒柄花素与相应苯甲醛半合成得到新颖的结构活性功能化合物。
本发明的席夫碱类化合物结构式如式I所示:
四:附图说明
图1表示刺芒柄花素席夫碱类衍生物对肿瘤细胞Hela的抑制活性
图2表示刺芒柄花素席夫碱类衍生物对肿瘤细胞MCF-7的抑制活性
图3表示刺芒柄花素席夫碱类衍生物对肿瘤细胞HCT-116的抑制活性
图4表示刺芒柄花素席夫碱类衍生物对肿瘤细胞A549的抑制活性
图5表示化合物11对肿瘤细胞MCF-7凋亡的影响
五:具体实施方式
实例一:刺芒柄花素席夫碱类衍生物的制备
在加热条件下,于100mL圆底烧瓶中以丙酮为溶剂将刺芒柄花素做成酯;然后在乙醇回流条件下,与水合肼发生取代反应生成中间产物,最后再与一系列不同取代的苯甲醛在冰乙酸催化下反应,经TLC检测反应完全后过滤得到相应的刺芒柄花素席夫碱类衍生物。
相应化合物的理化数据如下:
化合物1:Yield:75%,Mp:250.5-252.3℃;1H NMR(300MHz,DMSO)δ11.60(d,J=7.3Hz,1H,-CH=N),8.10(t,J=60.3Hz,1H,Ar-H),7.90-7.62(m,3H,N-NH,Ar-H),7.44(d,J=3.6Hz,3H,Ar-H),7.27-7.11(m,2H,Ar-H),7.03(t,J=8.6Hz,1H,Ar-H),6.85(d,J=8.1Hz,2H,Ar-H),6.60-6.24(m,2H,Ar-H),4.87(d,J=142.4Hz,2H,-O-CH2-),3.72(s,3H,-OCH3).
化合物2:Yield 62%,Mp:202.3-203.7℃;1H NMR(300MHz,DMSO)δ11.52(d,J=6.4Hz,1H,-CH=N),8.12(d,J=92.9Hz,1H,Ar-H),7.74(s,1H,N-NH),7.58(d,J=7.8Hz,2H,Ar-H),7.35-7.10(m,4H,Ar-H),7.01(t,J=8.6Hz,1H,Ar-H),6.84(d,J=7.6Hz,2H,Ar-H),6.45(dd,J=28.6,17.3Hz,2H,Ar-H),4.84(d,J=141.7Hz,2H,-O-CH2-),3.71(s,3H,-OCH3),2.32(s,3H,-CH3).
化合物3:Yield 75%;Mp:216.2-217.9℃;1H NMR(300MHz,DMSO)δ11.82(d,J=20.7Hz,1H,-CH=N),8.58(d,J=103.2Hz,1H,Ar-H),8.00(m,2H,Ar-H),7.78(s,1H,N-NH),7.57-7.37(m,2H,Ar-H),7.21(dd,J=7.0,1.4Hz,2H,Ar-H),7.09-6.95(m,1H,Ar-H),6.86(d,J=8.5Hz,2H,Ar-H),6.59-6.31(m,2H,Ar-H),4.83(d,J=141.9Hz,2H,-O-CH2-),3.73(s,3H,-OCH3).
化合物4:Yield 59%;Mp:213.8-215.2℃;1H NMR(300MHz,DMSO)δ11.67(s,1H,-CH=N),8.16(d,J=95.8Hz,1H,Ar-H),7.74(dd,J=8.5,4.8Hz,2H,Ar-H),7.51(dd,J=8.4,5.0Hz,2H,Ar-H),7.21(d,J=8.6Hz,2H,Ar-H),6.93(dd,J=47.9,7.5Hz,3H,Ar-H),6.59-6.27(m,2H,Ar-H),4.85(d,J=141.8Hz,2H,-O-CH2-),3.72(s,3H,-OCH3).
化合物5:Yield 63%;Mp:245.7-247.1℃;1H NMR(300MHz,DMSO)δ11.71(s,1H,-CH=N),8.40(d,J=109.5Hz,1H,Ar-H),7.91(dt,J=15.0,7.6Hz,1H,Ar-H),7.76(s,1H,N-NH),7.55-7.39(m,1H,Ar-H),7.35-7.22(m,2H,Ar-H),7.21-7.13(m,2H,Ar-H),7.02(t,J=9.1Hz,1H,Ar-H),6.84(d,J=8.0Hz,2H,Ar-H),6.62-6.22(m,2H,Ar-H),4.88(d,J=144.4Hz,2H,-O-CH2-),3.71(s,3H,-OCH3).
化合物6:Yield 73%;Mp:220.1-223.9℃;1H NMR(300MHz,DMSO)δ11.69(s,1H,-CH=N),8.08(t,J=62.7Hz,1H,Ar-H),7.72(s,1H,N-NH),7.63-7.37(m,3H,Ar-H),7.31-7.11(m,3H,Ar-H),7.08-6.92(m,1H,Ar-H),6.84(d,J=7.9Hz,2H,Ar-H),6.46(t,J=21.5Hz,2H,Ar-H),4.87(d,J=144.2Hz,2H,-O-CH2-),3.71(s,3H,-OCH3).
化合物7:Yield 67%;Mp:261.9-263.5℃;1H NMR(300MHz,DMSO)δ11.60(s,1H,-CH=N),8.16(d,J=96.5Hz,1H,Ar-H),7.89(s,1H,N-NH),7.75(dt,J=10.2,5.3Hz,2H,Ar-H),7.25(ddd,J=21.7,13.2,6.1Hz,4H,Ar-H),7.00(s,1H,Ar-H),6.83(s,2H,Ar-H),6.50(d,J=16.2Hz,2H,Ar-H),4.85(d,J=142.2Hz,2H,-O-CH2-),3.70(s,3H,-OCH3).
化合物8:Yield 82%;Mp:214.2-215.7℃;1H NMR(300MHz,DMSO)δ11.89(d,J=20.9Hz,1H,-CH=N),8.58(d,J=107.9Hz,1H,Ar-H),8.04-7.87(m,1H,Ar-H),7.86-7.59(m,2H,N-NH,Ar-H),7.43(td,J=7.9,4.1Hz,1H,Ar-H),7.19(d,J=8.4Hz,2H,Ar-H),7.07-6.94(m,1H,Ar-H),6.84(d,J=8.2Hz,2H,Ar-H),6.46(t,J=23.2Hz,2H,Ar-H),4.88(d,J=141.5Hz,2H,-O-CH2-),3.71(s,3H,-OCH3).
化合物9:Yield 74%;Mp:238.5-239.8℃;1H NMR(300MHz,DMSO)δ11.70(s,1H,-CH=N),8.13(d,J=99.7Hz,1H,Ar-H),7.90-7.64(m,2H,N-NH,Ar-H),7.64-7.40(m,2H,Ar-H),7.19(d,J=8.6Hz,2H,Ar-H),7.01(t,J=8.6Hz,1H,Ar-H),6.84(d,J=7.0Hz,2H,Ar-H),6.45(t,J=20.6Hz,2H,Ar-H),4.86(d,J=145.7Hz,2H,-O-CH2-),3.71(s,3H,-OCH3).
化合物10:Yield 86%;Mp:198.2-199.6℃;1H NMR(300MHz,DMSO)δ11.52(d,J=11.9Hz,1H,-CH=N),8.13(d,J=94.3Hz,1H,Ar-H),7.75(s,1H,N-NH),7.61(d,J=8.2Hz,2H,Ar-H),7.30(dd,J=8.0,5.1Hz,2H,Ar-H),7.19(dd,J=8.8,2.5Hz,2H,Ar-H),7.02(t,J=8.6Hz,1H,Ar-H),6.84(d,J=8.1Hz,2H,Ar-H),6.56-6.30(m,2H,Ar-H),4.84(d,J=140.1Hz,2H,-O-CH2-),3.71(s,3H,-OCH3),2.90(dt,J=13.6,6.8Hz,1H,-CH(CH3)2),1.20(dd,J=6.9,1.8Hz,6H,-CH(CH3)2).
化合物11:Yield 68%;Mp:176.7-178.2℃;1H NMR(300MHz,DMSO)δ11.79(s,1H,-CH=N),8.24(d,J=96.7Hz,1H,Ar-H),7.92(d,J=8.1Hz,2H,Ar-H),7.78(t,J=7.2Hz,3H,N-NH,Ar-H),7.19(dd,J=8.7,2.1Hz,2H,Ar-H),7.02(t,J=8.7Hz,1H,Ar-H),6.84(d,J=8.3Hz,2H,Ar-H),6.61-6.29(m,2H,Ar-H),4.89(d,J=142.9Hz,2H,-O-CH2-),3.71(s,3H,-OCH3).
化合物12:Yield 86%;Mp:218.9-220.5℃;1H NMR(400MHz,DMSO)δ11.62(d,J=17.4Hz,1H,-CH=N),8.52(d,J=130.0Hz,1H,Ar-H),7.84(ddd,J=16.7,7.7,1.5Hz,2H,N-NH,Ar-H),7.47-7.34(m,1H,Ar-H),7.21(dd,J=8.8,2.4Hz,2H,Ar-H),7.09(t,J=9.1Hz,1H,Ar-H),7.02(dt,J=10.7,8.2Hz,2H,Ar-H),6.86(d,J=8.0Hz,2H,Ar-H),6.60-6.27(m,2H,Ar-H),4.86(d,J=193.8Hz,2H,-O-CH2-),3.86(d,J=3.2Hz,3H,-OCH3),3.72(s,3H,-OCH3).
化合物13:Yield 75%;Mp:193.5-194.9℃;1H NMR(400MHz,DMSO)δ11.52(s,1H,-CH=N),8.11(d,J=122.4Hz,1H,Ar-H),7.75-7.56(m,2H,Ar-H),7.21(d,J=7.5Hz,2H,Ar-H),7.01(dd,J=8.7,6.8Hz,3H,Ar-H),6.85(s,2H),6.63-6.22(m,2H,Ar-H),4.85(d,J=188.9Hz,2H,-O-CH2-),3.80(d,J=2.8Hz,3H,-OCH3),3.72(s,3H,-OCH3).
化合物14:Yield 73%;Mp:203.1-204.8℃;1H NMR(300MHz,DMSO)δ11.90(d,J=35.0Hz,1H,-CH=N),8.53(d,J=103.8Hz,1H,Ar-H),8.19(dd,J=16.1,7.6Hz,1H,Ar-H),7.69(d,J=46.9Hz,4H,N-NH,Ar-H),7.19(d,J=7.3Hz,2H,Ar-H),7.09-6.91(m,1H,Ar-H),6.84(d,J=7.5Hz,2H,Ar-H),6.62-6.22(m,2H,Ar-H),4.89(d,J=145.3Hz,2H,-O-CH2-),3.70(s,3H,-OCH3).
化合物15:Yield 63%;Mp:140.7-142.1℃;1H NMR(400MHz,DMSO)δ11.52(d,J=20.7Hz,1H,-CH=N),8.09(d,J=123.9Hz,1H,Ar-H),7.73(s,1H,Ar-H),7.32(dd,J=9.1,1.6Hz,1H,Ar-H),7.21(dd,J=8.4,2.6Hz,3H,Ar-H),7.03(dd,J=16.7,8.3Hz,2H,Ar-H),6.86(d,J=6.8Hz,2H,Ar-H),6.59-6.31(m,2H,Ar-H),4.87(d,J=199.7Hz,2H,-O-CH2-),3.81(dd,J=8.5,6.6Hz,6H,-OCH3),3.72(s,3H,-OCH3).
化合物16:Yield 77%;Mp:181.6-183.1℃;1H NMR(300MHz,DMSO)δ11.86(s,1H,-CH=N),8.39(d,J=81.0Hz,1H,Ar-H),7.78(d,J=73.6Hz,1H,N-NH),7.55(d,J=7.9Hz,2H,Ar-H),7.48-7.35(m,1H,Ar-H),7.18(d,J=8.0Hz,2H,Ar-H),6.91(d,J=49.6Hz,3H,Ar-H),6.50(d,J=29.2Hz,2H,Ar-H),4.83(d,J=110.0Hz,2H,-O-CH2-),3.70(s,3H,-OCH3).
化合物17:Yield 82%;Mp:224.2-225.9℃;1H NMR(300MHz,DMSO)δ11.69(s,1H,-CH=N),8.12(d,J=94.3Hz,1H,Ar-H),7.90(d,J=9.7Hz,1H,Ar-H),7.69(d,J=7.7Hz,1H,Ar-H),7.59(d,.J=6.6Hz,1H,Ar-H),7.39(dd,J=14.5,6.7Hz,1H,Ar-H),7.19(d,J=8.4Hz,2H,Ar-H),6.99(d,J=8.1Hz,1H,Ar-H),6.84(s,2H,Ar-H),6.56-6.22(m,2H,Ar-H),4.87(d,J=146.3Hz,2H,-O-CH2-),3.70(s,3H,-OCH3).
化合物18:Yield 78%;Mp:231.8-233.1℃;1H NMR(400MHz,DMSO)δ11.76(s,1H,-CH=N),8.16(d,J=125.6Hz,1H,Ar-H),7.94(s,1H,N-NH),7.85-7.72(m,1H,Ar-H),7.68(d,J=3.2Hz,1H,Ar-H),7.48(dd,J=13.8,7.9Hz,2H,Ar-H),7.21(s,2H,Ar-H),7.04(s,1H,Ar-H),6.87(d,J=22.1Hz,2H,Ar-H),6.58-6.27(m,2H,Ar-H),4.90(d,J=195.9Hz,2H,-O-CH2-),3.71(s,3H,-OCH3).
化合物19:Yield 82%;Mp:294.1-295.7℃;1H NMR(400MHz,DMSO)δ11.59(s,1H,-CH=N),8.08(d,J=123.6Hz,1H,Ar-H),7.68(s,1H,N-NH),7.28-6.95(m,6H,Ar-H),6.83(d,J=8.1Hz,3H,Ar-H),6.52(d,J=25.9Hz,2H,Ar-H),4.86(d.J=185.1Hz,2H,-O-CH2-),3.72(s,3H,-OCH3).
化合物20:Yield 69%;Mp:182.4-183.9℃;1H NMR(300MHz,DMSO)δ11.46(d,,J=8.5Hz,1H,-CH=N),8.09(d,J=93.7Hz,1H,Ar-H),7.80(d,J=8.4Hz,1H,N-NH),7.63(d,J=8.3Hz,2H,Ar-H),7.38(ddd,J=19.5,13.1,6.8Hz,5H.Ar-H),7.19(d,J=8.0Hz,2H,Ar-H),7.05(dd,J=15.8,7.5Hz,3H,Ar-H),6.85(s,2H,Ar-H),6.58-6.22(m,2H,Ar-H),5.14(s,2H,Ph-CH2),4.83(d,J=140.8Hz,2H,-O-CH2-),3.70(s,3H,-OCH3).
化合物21:Yield 82%;Mp:248.3-249.7℃;1H NMR(300MHz,DMSO)δ11.38(d,J=8.6Hz,1H,-CH=N),9.89(d,J=81.5Hz,2H,-OH),8.04(d,J=91.3Hz,1H,Ar-H),7.76(s,1H,N-NH),7.51(d,J=8.4Hz,2H,Ar-H),7.19(dd,J=8.8,2.6Hz,2H,Ar-H),7.01(t,J=8.5Hz,1H,Ar-H),6.89-6.73(m,4H,Ar-H),6.54-6.25(m,2H,Ar-H),4.81(d,J=139.8Hz,2H,-O-CH2-),3.70(s,3H,-OCH3).
化合物22:Yield 69%;Mp:247.6-249.2℃;1H NMR(300MHz,DMSO)δ11.23(d,J=5.6Hz,1H,-CH=N),8.14-7.78(m,1H,Ar-H),7.75(s,1H,N-NH),7.34(d,J=8.5Hz,2H,Ar-H),7.17(dt,J=14.1,7.0Hz,2H,Ar-H),7.00(t,J=8.3Hz,1H,Ar-H),6.82(t,J=10.8Hz,2H,Ar-H),6.56(d,J=8.0Hz,2H,Ar-H),6.47-6.28(m,2H,Ar-H),5.61(d,J=9.2Hz,2H,-NH2),4.78(d,J=139.3Hz,2H,-O-CH2-),3.70(s,3H,-OCH3).
实例二:式I刺芒柄花素席夫碱类衍生物活性研究
我们对式I类刺芒柄花素席夫碱类衍生物进行了抗肿瘤活性研究,选取肿瘤细胞Hela、MCF-7、A549、为检测细胞,以MTT比色法为检测方法,酶标仪以570nm条件下测其吸光度并计算OD值。
IC50值计算方法如式所示:
细胞抑制率(%)=(对照组OD值-实验组OD值)/对照组OD值×100%
结果表明,刺芒柄花素席夫碱类衍生物在抗肿瘤方面具有一定的潜力。相应结果见附图1、2、3、4。
细胞活性结果表明,化合物11的活性明显优于其他衍生物,分别对Hela、MCF-7、HCT-116、A549细胞株的IC50值为7.35μM、2.32μM、9.45μM、16.8μM。
实例三:化合物11对肿瘤细胞MCF-7凋亡的影响
我们对活性较好的化合物11进行了其对MCF-7细胞株凋亡的影响进行了研究。结果表明,化合物11能够促进MCF-7细胞株的凋亡,并呈现了浓度、时间依赖性。相应结果见附图5。
本发明所述刺芒柄花素席夫碱类衍生物可制备成抗肿瘤药物。
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