CN108727329B - N-羟乙基甲酰胺基取代二苯并呫吨及其应用 - Google Patents
N-羟乙基甲酰胺基取代二苯并呫吨及其应用 Download PDFInfo
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Abstract
Description
技术领域:
本发明涉及药物化学技术领域,具体涉及一种N-羟乙基甲酰胺基取代二苯并呫吨及其应用。
背景技术:
恶性肿瘤是一种严重威胁人类健康的常见病和多发病,因恶性肿瘤引起的死亡率在所有疾病中占第二位,仅次于心脑血管疾病。肿瘤的治疗,尤其是恶性肿瘤的治疗在很大程度上以化学治疗为主。20世纪末,紫杉醇的发现及以其为母核的一系列品种的开发,为癌症的临床化学治疗带来了新的希望。然而,随着紫杉醇类药物应用的推广,其耐药性问题也逐渐显现,所以抗肿瘤新药的开发需求依然非常迫切。苯并呫吨化合物属于二苯并吡喃或氧杂蒽类芳杂环化合物,研究表明该类化合物具有抗病毒、抗细菌、抗炎等广泛的药理作用,有报道称呫吨类化合物还可以作为光敏剂应用于光动力治疗。因此,近年来越来越多的化学和药物研究者对苯并呫吨化合物类的进行广泛研究。
发明内容:
本发明的目的是提供一种N-羟乙基甲酰胺基取代二苯并呫吨及其应用。
本发明是通过以下技术方案予以实现的:
结构如式Ⅰ所示的N-羟乙基甲酰胺基取代二苯并呫吨:
其中R1选自H或CONH(CH2)2OH,R2选自CONH(CH2)2OH,R选自CH3、CH2CH3、(CH2)2CH3、CH(CH3)2、(CH2)3CH3中的任一种。
所述N-羟乙基甲酰胺基取代二苯并呫吨的制备方法,反应方程式如下:
包括以下步骤:先在反应容器内用醇溶剂溶解催化剂CuCl2·2H2O,然后再用醇溶剂稀释乙醇胺后加入反应容器,最后加入底物,控制底物、催化剂和乙醇胺的摩尔比为1:4:4,若发现底物溶解性差,可加适量1,4-二氧六环助溶使得底物刚好溶解,升温至50℃,搅拌反应,TLC跟踪原料至反应完全后,用空气吹干大部分溶剂,然后加入水和5wt%氨水破坏铜胺络合物,过滤,沉淀即为产物。
本发明还保护所述N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肿瘤药物中的应用。
本发明N-羟乙基甲酰胺基取代二苯并呫吨在制备抗***药物中的应用。
本发明N-羟乙基甲酰胺基取代二苯并呫吨在制备抗***癌药物中的应用。
本发明N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肺癌药物中的应用。
本发明N-羟乙基甲酰胺基取代二苯并呫吨在制备抗胃癌药物中的应用。
本发明的有益效果如下:
1)本发明的新型的化合物具有较高的抗肿瘤活性,在制备抗肿瘤药物中具有较好的前景。
2)制备方法简单,反应条件温和,速度快,收率高。
具体实施方式:
以下是对本发明的进一步说明,而不是对本发明的限制。
当所述N-羟乙基甲酰胺基取代二苯并呫吨为双(N-羟乙基甲酰胺基)取代二苯并[a,kl]呫吨时,反应方程式为:
当所述N-羟乙基甲酰胺基取代二苯并呫吨为单(N-羟乙基甲酰胺基)取代二苯并[a,kl]呫吨时,反应方程式为:
先在反应容器内用醇溶剂溶解催化剂CuCl2·2H2O,然后再用醇溶剂稀释乙醇胺后加入反应容器,最后加入底物,控制底物、催化剂和乙醇胺的摩尔比为1:4:4,若发现底物溶解性差,可加适量1,4-二氧六环助溶使得底物刚好溶解,升温至50℃,搅拌反应,TLC跟踪原料至反应完全后,用空气吹干大部分溶剂,然后加入大量水和适量的5wt%氨水破坏铜胺络合物,过滤,沉淀即为产物。
实施例1:1-氧代-5,11-二(N-羟乙基甲酰胺基)-13c-甲氧基-1,13c-二氢-二苯并[a,kl]-呫吨(化合物1)
产物结构式为:
醇溶剂为甲醇,反应时间为8h,产物为黄色固体,收率为56.5%。1H-NMR(500MHz,DMSO-d6)δ:8.691(t,J=5.5Hz,1H),8.593(t,J=5.5Hz,1H),8.560(s,1H),8.276(d,J=9Hz,1H),8.091(d,J=9Hz,1H),7.934(dd,J=9Hz1.5Hz,,1H),7.881(s,1H),7.849(d,J=1.5Hz,1H),7.628(d,J=8Hz,1H),7.583(d,J=10.5Hz,1H),6.488(d,J=10Hz,1H),4.786(t,J=5.5Hz,2H),3.695-3.647(m,4H),3.531-3.479m,4H),2.824(s,3H).13C-NMR(125MHz,DMSO-d6)δ:197.57,166.58,165.06,152.61,151.72,139.82,138.18,134.20,133.65,131.32,130.44,128.26,127.77,126.76,124.55,123.95,118.49,117.86,115.43,107.50,75.36,60.28,60.04,51.78,42.82,42.72.IR(KBr,cm-1)ν:3363.7,2927.4,1694.9,1635.7,1547.5,1383.3,1309.4,1238.7,1205.2,1039.6.HRMS:489.16563([M+H]+,C27H25N2O7).
实施例2:1‐氧代‐5,11‐二(N‐羟乙基甲酰胺基)‐13c‐乙氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物2)
产物结构式为:
醇溶剂为乙醇,反应时间为11h,产物为黄色固体,收率为51.9%。
1H-NMR(500MHz,DMSO-d6)δ:8.766(t,J=5.5Hz,1H),8.687(t,J=5.5Hz,1H),8.560(s,1H),8.270(d,J=9Hz,1H),8.126(d,J=9Hz,1H),7.935(dd,J=9Hz2Hz,,1H),7.876(s,1H),7.838(s,1H),7.620(t,J=9Hz,2H),6.496(d,J=10Hz,1H),4.871(t,J=5.5Hz,2H),3.677-3.628(m,4H),3.515-3.437(m,4H),2.983-2.952(m,1H),2.882-2.850(m,1H),0.927(t,J=7Hz,3H).13C-NMR(125MHz,DMSO-d6)δ:197.55,166.60,165.09,152.31,151.40,139.76,138.07,134.28,133.68,133.54,131.25,130.44,128.25,127.82,126.76,124.41,123.84,118.59,118.46,115.42,108.33,74.97,60.28,60.04,42.82,42.72,15.69.IR(KBr,cm-1)ν:3377.5,2922.7,1706.8,1637.9,1543.7,1383.1,1306.7,1235.2,1052.1.HRMS:503.18128([M+H]+,C28H27N2O7).
实施例3:1‐氧代‐5,11‐二(N‐羟乙基甲酰胺基)‐13c‐正丙氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物3)
产物结构式为:
醇溶剂为正丙醇,还加了1,4‐二氧六环助溶,反应时间为19h,产物为褐色固体,收率为61.4%。
1H-NMR(500MHz,DMSO-d6)δ:8.693(t,J=5.5Hz,1H),8.598(t,J=5.5Hz,1H),8.460(s,1H),8.169(d,J=9Hz,1H),8.018(d,J=9Hz,1H),7.829(dd,J=9.5Hz1.5Hz,,1H),7.775(s,1H),7.741(s,1H),7.526(d,J=6Hz,1H),7.506(d,J=7Hz,1H),6.409(d,J=10Hz,1H),4.781(t,J=5Hz,2H),3.539(q,J=6Hz,4H),3.400-3.360(m,4H),2.769-2.726(m,1H),2.693-2.652(m,1H),1.258-1.203(m,2H),0.553(t,J=7.5Hz,3H).13C-NMR(125MHz,DMSO-d6)δ:197.57,166.60,165.08,152.26,151.46,139.70,138.05,134.26,133.74,133.53,131.24,130.42,128.25,127.87,126.88,124.38,123.79,118.53,118.47,115.39,108.29,74.86,66.23,60.21,60.03,42.82,42.72,22.80,11.04.IR(KBr,cm-1)ν:3355.4,2931.0,1707.0,1641.1,1543.5,1382.6,1305.9,1236.1,1053.4,812.5.HRMS:517.19693([M+H]+,C29H29N2O7).
实施例4:1‐氧代‐5,11‐二(N‐羟乙基甲酰胺基)‐13c‐异丙氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物4)
产物结构式为:
醇溶剂为异丙醇,还加了还加1,4-二氧六环助溶,反应时间为32h,产物为砖红色固体,收率为55.9%。1H-NMR(500MHz,DMSO-d6)δ:8.615(t,J=5.5Hz,1H),8.502(t,J=5.5Hz,1H),8.444(d,J=1.5Hz,1H),8.160(d,J=9Hz,1H),8.014(d,J=9Hz,1H),7.827(dd,J=9.5Hz,2Hz,1H),7.753(d,J=5Hz,1H),7.517(d,J=9Hz,1H),7.463(d,J=10Hz,1H),6.400(d,J=10Hz,1H),4.694(t,J=2.5Hz,2H),3.570(t,J=5Hz,4H),3.415-3.362(m,4H),1.245(s,1H),0.642(d,J=6Hz,3H),0.476(d,J=6.5Hz,3H).13C-NMR(125MHz,DMSO-d6)δ:197.66,166.59,165.04,152.04,151.24,139.23,138.04,134.43,134.14,133.54,131.15,130.44,128.71,128.21,127.13,124.01,123.54,119.01,118.50,115.61,109.37,74.77,68.11,60.26,60.02,42.84,42.72,23.86.IR(KBr,cm-1)ν:3380.2,2922.4,1707.3,1642.2,1545.0,1382.7,1306.5,1236.2,1054.0,1004.4.HRMS:517.19693([M+H]+,C29H29N2O7).
实施例5:1‐氧代‐5,11‐二(N‐羟乙基甲酰胺基)‐13c‐正丁氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物5)
产物结构式为:
醇溶剂为正丁醇,还加了1,4‐二氧六环助溶,反应时间为48h,产物为黄色固体,收率为58.2%。1H-NMR(500MHz,DMSO-d6)δ:8.489(s,1H),8.388(s,1H),8.342(s,1H),8.047(d,J=9Hz,1H),7.915(d,J=9Hz,1H),7.718(d,J=8.5Hz,1H),7.656(s,1H),7.624(s,1H),7.397(t,J=10Hz,2H),6.285(d,J=9.5Hz,1H),4.576(s,2H),3.455(t,J=6Hz,5H),3.278(dd,J=14.5Hz,6Hz,5H),2.707-2.680(m,1H),2.637-2.597(m,1H),1.117-1.074(m,2H),0.934-0.920(m,2H),0.431(t,J=7Hz,3H).13C-NMR(125MHz,Acetone-d6)δ:197.57,166.60,165.08,152.26,151.48,139.67,138.06,134.26,133.74,133.52,131.23,130.41,128.24,127.83,126.88,124.36,123.78,118.52,118.46,115.38,108.29,74.86,63.98,60.28,60.04,42.83,42.73,31.45,19.04,13.65.IR(KBr,cm-1)ν:3368.9,2930.8,2870.4,1706.9,1638.2,1545.8,1382.9,1305.5,1068.9,1053.7,814.8.HRMS:531.21258([M+H]+,C30H31N2O7).
实施例6:1‐氧代‐11‐(N‐羟乙基甲酰胺基)‐13c‐甲氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物6)
产物结构式为:
醇溶剂为甲醇,反应时间为8h,产物为黄色固体,收率为70.6%。
1H-NMR(500MHz,Acetone-d6)δ:8.533(d,J=2Hz,1H),8.200(dd,J=9Hz,4Hz,2H),7.952(dd,J=9Hz,2Hz,1H),7.940(s,1H),7.612(t,J=8Hz,1H),7.535(d,J=9Hz,1H),7.466(d,J=10Hz,1H),7.355(d,J=7Hz,1H),7.295(dd,J=8.5Hz,1Hz,1H),6.331(d,J=10Hz,1H),4.042(t,J=5.5Hz,1H),3.827(q,J=6Hz,2H),3.682-3.641(m,2H),2.878(s,3H).13C-NMR(125MHz,Acetone-d6)δ:197.11,166.74,152.57,152.13,139.21,134.59,133.63,132.85,131.40,131.07,130.41,127.99,127.62,125.95,124.62,123.70,118.00,116.35,115.71,107.94,75.45,61.13,50.86,42.76.IR(KBr,cm-1)ν:3421.3,2931.7,1701.8,1637.6,1541.6,1456.0,1268.2,1056.1,811.0.HRMS:402.13360([M+H]+,C24H20NO5).
实施例7:1‐氧代‐11‐(N‐羟乙基甲酰胺基)‐13c‐乙氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物7)
产物结构式为:
醇溶剂为乙醇,反应时间为7h,产物为黄色固体,收率为32.9%。
1H-NMR(500MHz,Acetone-d6)δ:8.417(s,1H),8.159(d,J=9Hz,1H),8.058(d,J=9Hz,1H),7.852(dd,J=9Hz,1.5Hz,1H),7.481(t,J=7.5Hz,1H),7.403(dd,J=9Hz,2.5Hz,1H),7.331(dd,J=10Hz,2.5Hz,1H),7.226(d,J=7Hz,1H),7.160(d,J=8Hz,1H),6.220(dd,J=10Hz,3Hz,1H),3.743-3.7115(m,2H),3.566(t,J=5.5Hz,2H),2.958-2.930(m,1H),2.860-2.829(m,1H),0.864(t,J=7Hz,3H).13C-NMR(125MHz,Acetone-d6)δ:197.12,166.80,166.73,152.27,151.81,139.16,134.67,133.66,132.73,131.25,131.00,130.41,128.08,127.61,125.94,124.50,123.58,117.98,116.41,116.34,108.77,75.05,61.00,59.77,42.73,42.61,14.79.IR(KBr,cm-1)ν:3421.4,2928.6,1707.0,1637.9,1541.8,1455.6,1387.9,1267.8,1052.7,810.8.HRMS:416.14925([M+H]+,C25H22NO5).
实施例8:1‐氧代‐11‐(N‐羟乙基甲酰胺基)‐13c‐正丙氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物8)
产物结构式为:
醇溶剂为正丙醇,还加了1,4‐二氧六环助溶,反应时间为8h,产物为黄色固体,收率为36.3%。1H-NMR(500MHz,Acetone-d6)δ:8.551(d,J=2Hz,1H),8.286(d,J=9Hz,1H),8.206(d,J=9Hz,1H),7.980(dd,J=9Hz,1.5Hz,1H),7.931(s,1H),7.626(t,J=8Hz,1H),7.511(d,J=9Hz,1H),7.478(d,J=10Hz,1H),7.369(d,J=7Hz,1H),7.305(d,J=8.5Hz,1H),6.369(d,J=9.5Hz,1H),3.859(q,J=6Hz,2H),3.689(q,J=6Hz,2H),2.989-2.964(m,1H),2.918-2.877(m,1H),1.459-1.376(m,2H),0.739(t,J=7Hz,3H).13C-NMR(125MHz,Acetone-d6)δ:197.10,166.74,151.88,139.12,134.64,133.72,132.71,131.27,131.02,130.39,128.12,127.59,126.06,124.47,123.57,118.00,116.40,116.29,108.73,74.94,65.82,61.13,61.00,42.76,22.71,10.14.IR(KBr,cm-1)ν:3432.7,2934.1,2874.2,1706.8,1637.8,1543.7,1456.0,1388.8,1267.8,1068.0,808.6.HRMS:430.16490([M+H]+,C26H24NO5).
实施例9:1‐氧代‐11‐(N‐羟乙基甲酰胺基)‐13c‐异丙氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物9)
产物结构式为:
醇溶剂为异丙醇,还加了1,4‐二氧六环助溶,反应时间为22h,产物为砖红色固体,收率为52.8%。1H-NMR(500MHz,Acetone-d6)δ:8.556(d,J=1.5Hz,1H),8.260(d,J=9Hz,1H),8.215(d,J=9Hz,1H),8.036(s,1H),7.987(dd,J=9Hz,1.5Hz,1H),7.644(dd,J=8.5Hz,1.5Hz,1H),7.565(d,J=9Hz,1H),7.470(d,J=10Hz,1H),7.378(d,J=7Hz,1H),7.335(dd,J=8.5Hz,1Hz,1H),6.381(d,J=10Hz,1H),4.144(t,J=5.5Hz,1H),3.849(q,J=5.5Hz,2H),3.703-3.662(m,2H),3.575-3.526(m,1H),0.792(d,J=6Hz,3H),0.628(d,J=6Hz,3H).13C-NMR(125MHz,Acetone-d6)δ:197.19,166.77,151.98,151.66,138.65,134.82,134.13,132.72,131.31,130.94,130.42,128.99,127.53,126.33,124.24,123.21,118.03,116.80,116.56,109.86,74.87,67.69,61.14,42.76,23.07,22.94.IR(KBr,cm-1)ν:3394.3,1707.4,1638.0,1542.2,1455.8,1381.5,1301.2,1267.9,810.5.HRMS:430.16490([M+H]+,C26H24NO5).
实施例10:1‐氧代‐11‐(N‐羟乙基甲酰胺基)‐13c‐正丁氧基‐1,13c‐二氢‐二苯并[a,kl]‐呫吨(化合物10)
产物结构式为:
醇溶剂为正丁醇,还加了1,4‐二氧六环助溶,反应时间为48h,产物为黄色固体,收率为43.6%。1H-NMR(500MHz,Acetone-d6)δ:8.355(d,J=1.5Hz,1H),8.060(d,J=9Hz,1H),8.003(d,J=9Hz,1H),7.852(s,1H),7.782(dd,J=9.5Hz,2Hz,1H),7.423(t,J=7.5Hz,1H),7.347(d,J=9Hz,1H),7.287(d,J=10.5Hz,1H),7.173(d,J=7Hz,1H),7.104(d,J=8.5Hz,1H),6.166(d,J=10Hz,1H),3.635(t,J=6Hz,2H),3.468(q,J=5.5Hz,2H),2.795-2.767(m,1H),2.715-2.686(m,1H),1.201-1.142(m,2H),1.036-0.995(m,2H),0.488(t,J=7Hz,3H).13C-NMR(125MHz,Acetone-d6)δ:197.14,166.75,152.23,151.87,139.15,134.64,133.71,132.73,131.29,130.98,130.38,128.08,127.61,126.05,124.50,123.58,118.01,116.38,116.30,108.69,74.92,63.59,61.12,42.76,31.48,18.91,12.79.IR(KBr,cm-1)ν:3421.7,2930.1,2870.0,1704.1,1637.0,1550.1,1455.6,1381.4,1268.4,1069.1,1032.6,808.9.HRMS:444.18055([M+H]+,C27H26NO5).
实施例11:活性测试
采用MTT实验对实施例1-10得到的化合物体外抑制肿瘤细胞生长进行检测,分别选取人***细胞株HeLa、人***癌细胞PC3、人肺癌细胞A549、人胃癌细胞株SGC-7901进行了筛选。具体方法为:将处于对数生长期的各肿瘤细胞株按8×104个/孔的细胞量接种至96孔板中,放置于培养箱中孵育24h,更换培养液后加入浓度梯度的各药物,使药物终浓度为10-6-10-4mol/L,每组设置3个平行复孔,且设置培养液空白对照孔。然后在培养箱中孵育48h,各孔都加入不含血清的培养基90μL和浓度为5mg/mL的MTT溶液10μL,然后在培养箱中培养4h,加入100μL DMSO微量振荡器中震荡15min后,采用酶标仪490nm处测定吸光度值。按下式计算细胞成活率:细胞成活率(%)=(实验组)/空白组)×100%。将各组药物的浓度与所对应的细胞成活率绘制出细胞生长曲线,从图中读出当细胞成活率为50%时所对应的化合物浓度,该浓度即为IC50值。结果参见表1.
表1
Claims (6)
2.权利要求1所述N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肿瘤药物中的应用。
3.根据权利要求2所述N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肿瘤药物中的应用,其特征在于,N-羟乙基甲酰胺基取代二苯并呫吨在制备抗***药物中的应用,所述N-羟乙基甲酰胺基取代二苯并呫吨选自:化合物1-3或化合物5-10。
4.根据权利要求2所述N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肿瘤药物中的应用,其特征在于,N-羟乙基甲酰胺基取代二苯并呫吨在制备抗***癌药物中的应用。
5.根据权利要求2所述N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肿瘤药物中的应用,其特征在于,N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肺癌药物中的应用。
6.根据权利要求2所述N-羟乙基甲酰胺基取代二苯并呫吨在制备抗肿瘤药物中的应用,其特征在于,N-羟乙基甲酰胺基取代二苯并呫吨在制备抗胃癌药物中的应用。
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