CN101367761B - 6,7-取代-2,2,4-三甲基-四氢喹啉-1-羧酸芳基酰胺、合成方法及用途 - Google Patents
6,7-取代-2,2,4-三甲基-四氢喹啉-1-羧酸芳基酰胺、合成方法及用途 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及一种有机化合物6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺、简便合成方法和用途。
背景技术
6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺有可能是一类潜在的抑制细胞程序性坏死活性的先导化合物结构,可发展为有用的药物,其结构式如下:
但目标化合物的合成方法经SciFinder***及其他文献检索,未发现有文献报导。
文献中有6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺的报道([1]Cliffe,W.H.J.Chem.Soc.19331327.):用2,2,4-三甲基-二氢喹啉与芳基异氰酸酯在干***中回流4小时反应得到。由于此反应使用了***回流的条件,扩大反应时存在一定的危险性,所以人们还希望获得更为温和的反应,同时获得6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺一类有用的药物。
发明内容
本发明的目的是提供一种6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物。
本发明的目的还提供一种上述6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺简便合成方法。
本发明的另一目的是提供一种上6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺的用途。
本发明的6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物具有如下结构式:
其中R1=氢、C1-4的直链烷基或C1-4的烷氧基;R2=氢或C1-4的直链烷基;R3=氢、单取代或双取代的C1-4的烷基、C1-4的烷氧基、卤素、乙酰基或硝基等。
本发明的方法是在室温(rt)下,在6,7-取代-2,2,4-三甲基四氢(或二氢)喹啉(1)和芳基异氰酸酯的有机溶剂(solvent)中,每摩尔6,7-取代-2,2,4-三甲基四氢(或二氢)喹啉(1)加入0.05-0.2摩尔的4—二甲胺基吡啶(DMAP)作为催化剂反应1-5小时即生成目标产物6,7-取代-2,2,4-三甲基四氢(或二氢)喹啉-1-羧酸芳基酰胺(2)。反应式如下:
方法一
其中R1和R2如前所述;---为单键或无键。当---为单键时,反应式系由6,7-取代-2,2,4-三甲基二氢喹啉(1)和芳基异氰酸酯反应生成产物6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺;当---为无键时,系由6,7-取代-2,2,4-三甲基四氢喹啉(1)和芳基异氰酸酯反应生成产物6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺。
所述溶剂为常用有机溶剂,如丙酮、***、四氢呋喃、二氯甲烷或甲苯等,推荐为二氯甲烷;
所述6,7-取代-2,2,4-三甲基四氢(二氢)喹啉和异氰酸酯的摩尔比例为1:1~3,推荐为1:2。
采用本发明的方法合成了15个化合物6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺(2)典型结果见表1。
序号 | 化合物 | 取代基(R1) | 取代基(R2) | 产率(%) |
1 | 2a | 6-Me | 4-OMe | 58 |
2 | 2b | 6-Me | 4-F | 77 |
3 | 2c | 6-Me | 4-Cl | 84 |
4 | 2d | 6-Me | 2-OMe | 93 |
5 | 2e | 6-Me | 2,4-Cl2 | 67 |
6 | 2f | 6-Me | 3-F | 80 |
7 | 2g | 6,7-Me2 | 4-Cl | 65 |
8 | 2h | 6,7-Me2 | 4-OMe | 65 |
9 | 2i | 6,7-Me2 | 2,4-Cl2 | 79 |
10 | 2j | 6-F | 4-OMe | 85 |
11 | 2k | 6-H | 4-Cl | 80 |
12 | 21 | 6-H | 4-Me | 70 |
13 | 2m | 6-H | 4-NO2 | 90 |
14 | 2n | 6-H | 4-OMe | 78 |
15 | 2o | 6-OMe | 4-H | 75 |
本发明的实验方法反应条件温和,反应时间短,产率较高,对于2,2,4-三甲基二氢喹啉底物可通过方法二制备。其中,6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺通过Pd/C氢化反应获得6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺,在室温和氢气下,用Pd/C催化剂催化6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺反应1~5小时获得6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺;所述的6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺和Pd/C催化剂的摩尔比为1:0.05-1:0.2。
方法二
本发明的化合物可以用于制备抗细胞程序性坏死的药物,可以用于治疗中风、癌症的药物。例如本发明的下述结构式的2a和2c
对N-(对甲氧苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺和N-(对氯苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺化合物测定结果,它们的抗细胞程序性坏死的活性(necroptosis)分别为EC50=1.40μM和1.36μM。
具体实施方式
下述实施例将有助于进一步理解本发明,但不能限制本发明的内容.
实施例1 6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物的制备
一般试验操作:
在干燥25mL的单口瓶中,1mmol四氢喹啉底物1的5mL二氯甲烷溶液中依次加入2mmol异氰酸苯酯和6mg4—二甲胺基吡啶(DMAP)。体系在氮气保护下室温搅拌反应1小时结束,体系中有少量固体产生。在旋转蒸发仪上除去溶剂,残余物加入15mL无水***,振荡过滤,固体用5mL无水***洗。合并的滤液在旋转蒸发仪上除去溶剂后快速柱层析纯化(淋洗剂:二氯甲烷/石油醚=1:1)
N-(对甲氧苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺(2a)
产率58%,白色固体,m.p.115-116℃
1H NMR(300MHz CDCl3):δ1.33(m,4H),1.57(s,3H),1.65(s,3H),1.87(dd,1H,J1=3.0Hz,J2=12.9Hz),2.34(s,3H),2.73-2.79(m,1H),3.77(s,3H),6.99(brs,1H,-NH-),6.82(d,2H,J=8.7Hz),6.94-6.97(m,1H),7.02(d,2H,J=8.7Hz),7.24-7.27(m,2H);ESIMS:393([M+MeOH+Na]+),361([M+Na]+),339([M+H]+),190;
元素分析理论值C21H26N2O2:C,74.53;H,7.74;N,8.28.实测值:C,74.09;H,7.68;N,8.15.
N-(对氟苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺(2b)
产率77%
1H NMR(300MHz CDCl3):δ1.31-1.35(m,4H),1.58(s,3H),1.66(s,3H),1.88(dd,1H,J1=2.7Hz,J2=12.9Hz),2.35(s,3H),2.73-2.79(m,1H),6.99(brs,1H,-NH-),6.93-7.02(m,5H),7.26-7.31(m,2H);
ESIMS:381([M+MeOH+Na]+),349([M+Na]+),327([M+H]+),190;
IR(KBr,cm-1):3293,2956,2928,1656,1510,1499,1314,1211,833,808;
元素分析理论值C20H23N2O:C,73.59;H,7.10;N,8.58.实测值:C,73.63;H,7.32;N,8.56.
N-(对氯苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺(2c)
产率84%,白色固体,m.p.144-145℃
1HNMR(300MHz CDCl3):δ1.31-1.35(m,4H),1.56(s,3H),1.66(s,3H),1.88(dd,1H,J1=2.7Hz,J2=12.9Hz),2.34(s,3H),2.73-2.79(m,1H),6.59(brs,1H,-NH-),6.98-7.02(m,3H),7.20-7.30(m,4H);
ESIMS:397([M+MeOH+Na]+),365([M+Na]+),343([M+H]+),190;
IR(KBr,cm-1):3280,2966,2930,1681,1654,1520,1492,1314,1240,1098,830,808;
元素分析理论值C20H23ClN2O:C,70.06;H,6.76;N,8.17.实测值:C,69.77;H,6.60;N,7.87.
N-(邻甲氧苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺(2d)
产率93%,
1HNMR(300MHz CDCl3):δ1.33-1.35(m,4H),1.58(s,3H),1.68(s,3H),1.87(dd,1H,J1=2.7Hz,J2=12.9Hz),2.34(s,3H),2.76-2.82(m,1H),3.67(s,3H),6.77-6.80(m,1H),6.91-6.96(m,3H),6.98(m,1H),7.07-7.10(m,1H),7.40(brs,1H,-NH-),8.22-8.26(m,1H);
ESIMS:361([M+Na]+),339([M+H]+);
IR(KBr,cm-1):3417,2962,2932,1683,1601,1518,1459,1305,1029,822,806;
元素分析理论值C21H26N2O2:C,74.53;H,7.74;N,8.28.实测值:C,74.60;H,7.83;N,8.20.
N-(2,4-二氯苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺(2e)
产率67%,
1H NMR(300MHz CDCl3):δ1.22-1.26(m,4H),1.48(s,3H),1.61(s,3H),1.79(dd,1H,J1=2.7Hz,J2=12.9Hz),2.26(s,3H),2.68-2.74(m,1H),3.78(s,3H),6.87-6.90(m,1H),6.94(s,1H,-NH-),7.01(d,1H,J=7.5Hz),7.11(dd,1H,J1=2.4Hz,J2=8.7Hz),7.16-7.19(m,2H),8.24(d,1H,J=9.0Hz);
13C NMR(400MHz CDCl3):δ17.1,21.1,26.1,28.5,28.8,52.2,58.3,120.9,122.4,123.7,124.4,127.0,127.6,128.4,134.0,134.6,135.8,140.1,153.8
EIMS:378(12.60),377(3.21),376(M+,17.10),189(18.90),174(100,base),159(16.09),160(61.13),142(16.80);
HRMS(EI):理论值C20H22N2OCl2:376.1109;实测值:376.1106;
IR(KBr,cm-1):3403,2964,2929,1687,1508,1307,1246,1223,810.
实施例2 6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺化合物的制备:
方法同实施例1,仅用相应的二氢喹啉底物代替四氢喹啉底物,反应产物和分析结果如下:
N-(邻氟苯基)-2,2,4,6-四甲基-3,4-二氢喹啉-1(2H))-酰胺(2f)
1H NMR(DMSO-d6,300MHz)δ:9.15(s,1H),
6.73-7.30(m,8H),2.62-2.78(m,1H),2.27(s,3H),1.93(dd,J=3.9,12.9Hz,1H),1.46(d,J=8.4Hz,1H),1.21-1.36(m,4H);
MS(EI)m/z(%):326(M+,91),327(22),311(8),189(11),174(100),160(45);
IR(KBr)v:3428,3339,2964,2931,1685,1616,1600,1524,1492,1439,1309;
HRMS(MALDI)理论值C20H24NO2F+(M+H+):327.1867,实测值327.1881
N-(对氯苯基)-2,2,4,6,7-五甲基-3,4-二氢喹啉-1(2H))-酰胺(2g)
产率65%,白色固体,m.p.151-152℃
1H NMR(300MHz CDCl3):δ1.30-1.34(m,4H),1.56(s,3H),1.65(s,3H),1.87(dd,1H,J1=3.0Hz,J2=12.9Hz),2.18(s,3H),2.26(s,3H),2.72-2.77(m,1H),6.62(brs,1H,-NH-),6.88(s,1H),6.97(s,1H),7.22(d,2H,J=8.7Hz),7.29(d,2H,J=8.7Hz);
EIMS:357([M]+,1.46),356(4.45),203(22.54),188(100,base),189(15.03),174(23.52),153(23.42);
IR(KBr,cm-1):3290,2964,2928,1682,1654,1525,1492,1396,1313,1239,830;
元素分析理论值C21H25ClN2O:C,70.67;H,7.06;N,7.85.实测值:C,70.65;H,7.09;N,7.82.
N-(对甲氧基苯基)-2,2,4,6,7-五甲基-3,4-二氢喹啉-1(2H))-酰胺(2h)
产率65%,白色固体,m.p.130-131℃
1HNMR(300MHz CDCl3):δ1.31-1.33(m,4H),1.57(s,3H),1.64(s,3H),1.86(dd,1H,J1=3.0Hz,J2=12.9Hz),2.19(s,3H),2.25(s,3H),2.72-2.77(m,1H),3.78(s,3H),6.55(brs,1H,-NH-),6.83(d,2H,J=9.0Hz),6.94(d,2H,J=8.7Hz),7.25(s,1H),7.27(s,1H);
EIMS:352([M]+,33.12),203(27.40),188(100,base),189(15.10),174(27.00),149(25.80),134(14.33);
IR(KBr,cm-1):3308,2931,1677,1657,1532,1510,1248,1238,838;
元素分析理论值C22H28N2O2:C,74.97;H,8.01;N,7.95.实测值:C,75.25;H,8.00;N,7.86.
N-(2,4-二氯苯基)-2,2,4,6,7-五甲基-3,4-二氢喹啉-1(2H))-酰胺(2i)
产率79%,白色固体,m.p.128-129℃
1H NMR(300MHz CDCl3):δ1.29-1.33(m,4H),1.57(s,3H),1.70(s,3H),1.86(dd,1H,J1=2.7Hz,J2=12.9Hz),2.19,(s,3H),2.26(s,3H),2.73-2.81(m,1H),6.97(s,1H),7.01(s,1H),7.21(dd,1H,J1=2.7Hz,J2=8.7Hz),7.26-7.28(m,1H),7.40(brs,1H,-NH-),8.35(d,1H,J=9.0Hz);
EIMS:392([M+H]+,12.42),391(M+,6.95),390(20.20),189(20.12),188(100,base),174(74.37),172(17.52),156(16.34),41(13.53),
IR(KBr,cm-1):3403,2958,2921,1685,1574,1507,1314,1304,1245,1230,811;Anal.Caled for C21H24Cl2N2O:C,64.45;H,6.18;N,7.16.实测值:C,64.36;H,6.25;N,6.91.
N-(对甲氧基苯基)-6-氟-2,2,4-三甲基-3,4-二氢喹啉-1(2H))-酰胺(2j)
1H NMR(300MHz CDCl3):δ1.32-1.34(m,4H),1.56(s,3H),1.66(s,3H),1.86(d,1H,J2=13.2Hz),2.73-2.84(m,1H),3.77(s,3H),6.40(s,1H),6.83(d,2H,J=8.7Hz),6.87-6.94(m,2H),7.06-7.11(m,1H),7.24(d,2H,J=8.7Hz).
N-(对氯苯基)-2,2,4,-三甲基-3,4-二氢喹啉-1(2H))-酰胺(2k)
1H NMR(DMSO-d6,300MHz)δ:9.34(s,1H),7.47
(d,J=7.2Hz,2H),7.39(d,J=9.3Hz,2H),7.20(d,J=7.5Hz,1H),7.06(t,J=7.8Hz,1H),6.95(d,J=7.5Hz,1H),2.65-2.84(m,1H),1.93(dd,J=3.9,12.9Hz,1H),1.43(s,6H),1.23-1.39(m,4H);
MS(EI)m/z:328(14),330(5),160(100),146(98);
IR(KBr)v:3420,2956,2873,1689,1590,1516,1494,1484,1313cm-1;
HRMS(MA1DI)理论值C19H22N2OCl+(M+H+):329.1415,实测值:329.1441.
N-(对甲苯基)-2,2,4,-三甲基-3,4-二氢喹啉-1(2H))-酰胺(2l)
1H NMR(DMSO-d6,300MHz)δ:9.20(s,1H),6.72-7.35(m,8H),3.32(s,3H),2.75-2.83(m,1H),2.22(s,3H),1.88(dd,J=4.5,10.2Hz,1H),1.40(d,J=4.2Hz,6H),1.21-1.32(m,4H);
ESIMS m/z:309(M+H+).
N-(对硝基苯基)-2,2,4-三甲基-3,4-二氢喹啉-1(2H))-酰胺(2m)
1H NMR(DMSO-d6,300MHz)δ:9.17(s,1H),6.74-7.32(m,8H),2.68-2.82(m,1H),223(s,3H),1.90(dd,J=4.5,12.9Hz,1H),1.40(d,J=3.0Hz,1H),1.29(d,J=6.6Hz,3H),1.06-1.21(m,1H).
N-(对甲氧基苯基)-2,2,4-三甲基-3,4-二氢喹啉-1(2H))-酰胺(2n)
1H NMR(CDCl3300MHz)δ1.34-1.37(m,4H),1.59(s,3H),1.66(s,3H),1.90(dd,1H,J1=3.0Hz,J2=12.9Hz),2.74-2.87(m,1H),3.78(s,3H),6.53(brs,1H,-NH-),6.82(s,1H,),6.85(s,1H),7.04-7.10(m,1H),7.14-7.17(m,2H),7.21-7.28(m,3H);
ESIMS:325([M+H]+),347([M+Na]+);
IR(KBr cm-1):3283,2966,2928,1682,1654,1513,1237,1034;
元素分析理论值C20H24N2O2:C,74.04;H,7.46;N,8.64.实测值:C,74.15;H,7.57;N,8.51.
N-苯基-6-甲氧基-2,2,4-三甲基-3,4-二氢喹啉-1(2H))-酰胺(2o)
1H NMR(CDCl3300MHz)δ1.29-1.33(m,4H),1.56(s,3H),1.67(s,3H),1.87(dd,1H,J1=3.0Hz,J2=12.6Hz),2.71-2.84(m,1H),3.80(s,3H),6.57(brs,1H,-NH-),6.82(s,1H,),6.70(dd,1H,J1=3.3Hz,J2=9.0Hz),6.78(d,1H,J=2.1Hz),6.97-7.02(m,1H),67.07(d,1H,J=5.7Hz)7.22-7.34(m,4H);
ESIMS:325([M+H]+);347([M+Na]+);
IR(KBr cm-1):3340,2962,1735,1684,1521,1438,1235,1046;
元素分析理论值C20H24N2O2:C,74.04;H,7.46;N,8.64.实测值:C,73.92;H,7.42;N,8.51.
实施例3从6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺化合物制备6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物
一般实验操作:在干燥25mL单口瓶中,加入1mmol6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺化合物2,20mg10%钯碳和10mL无水甲醇。体系在氢气氛围中室温下搅拌反应3小时结束,通过硅藻土滤去钯碳,2mL无水甲醇清洗。滤液浓缩后在旋转蒸发仪上除去溶剂,粗产品通过快速柱层析进一步纯化(淋洗剂二氯甲烷:石油醚=1:2)得6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物3。
Claims (4)
2.一种如权利要求1所述的6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物的制备方法,其特征是采用如下步骤(1)或(2)方法:
(1),在室温下和有机溶剂中,在6,7-取代-2,2,4-三甲基四氢(或二氢)喹啉(1)和芳基异氰酸酯在4-二甲胺基吡啶催化剂催化反应1-5小时,生成产物6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺;所述的6,7-取代-2,2,4-三甲基四氢(二氢)喹啉,异氰酸酯和4-二甲胺基吡啶摩尔比1∶1~3∶0.05~0.2;
(2),在室温下和有机溶剂中,在6,7-取代-2,2,4-三甲基二氢喹啉和芳基异氰酸酯在4-二甲胺基吡啶催化剂催化反应1-5小时,生成产物6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺;所述的6,7-取代-2,2,4-三甲基二氢喹啉,异氰酸酯和4-二甲胺基吡啶摩尔比1∶1~3∶0.05~0.2;
在室温和氢气下,用Pd/C催化剂催化上述的6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺反应1~5小时获得6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺;所述的6,7-取代-2,2,4-三甲基二氢喹啉-1-羧酸芳基酰胺和Pd/C催化剂的摩尔比为1∶0.05-0.2。
3.如权利要求2所述的6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物的制备方法,其特征是所述的有机溶剂是丙酮、***、四氢呋喃、二氯甲烷或甲苯。
4.一种如权利要求1所述的6,7-取代-2,2,4-三甲基四氢喹啉-1-羧酸芳基酰胺化合物用于制备抗细胞程序性坏死的药物。
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