CN110903288B - 咪唑并氮杂菲啶类化合物及制备方法和应用 - Google Patents
咪唑并氮杂菲啶类化合物及制备方法和应用 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 7
- -1 imidazophenanthridine compound Chemical class 0.000 claims abstract description 15
- DKQIZRNNADMWTR-ZHACJKMWSA-N (e)-3-(2-aminophenyl)-1-phenylprop-2-en-1-one Chemical class NC1=CC=CC=C1\C=C\C(=O)C1=CC=CC=C1 DKQIZRNNADMWTR-ZHACJKMWSA-N 0.000 claims abstract description 8
- PJXKDAHSYZDMOY-UHFFFAOYSA-N 2-iminoacetaldehyde Chemical class N=CC=O PJXKDAHSYZDMOY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000799 fluorescence microscopy Methods 0.000 claims abstract description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 100
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 18
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- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明提供一种咪唑并氮杂菲啶类化合物及制备方法和应用。在室温酸性条件下，取代的2‑氨基查尔酮与氨基烯酮反应合成。本发明提供的制备方法具有反应条件温和，操作简单，无需金属催化剂，原料易得，能同时引入多个取代基等优点，底物适用范围广。本发明制备的咪唑并氮杂菲啶类化合物具有一定的光学特性，可作为潜在的荧光分子，作为荧光团在荧光成像中应用。其结构通式如下：
Description
技术领域
本发明属化合物合成方法，主要涉及咪唑并氮杂菲啶类化合物及其制备方法和应用。
背景技术
三环平面基团可以嵌入DNA堆积碱基之间，其平面基团与螺旋的轴线垂直并通过范德华力与上下碱基作用，导致与DNA结合的染料呈现荧光，因此以菲啶为基础的荧光团可以用于DNA的检测。
目前主要以C-H键活化策略，通过金属催化合成构建菲啶母核(Chem-Eur.J.2013,19,10487-10491).
上述方法需要金属催化且收率较低,底物多样性不高。因此提供一种条件温和，反应高效的合成方法成为需要。
发明内容
本发明的目的是提供一种咪唑并氮杂菲啶类化合物，结构通式为：
其中：
R1为氢、甲基、氨基、三氟甲基、萘基、噻吩基、卤素，所述卤素选用氯、溴；
R2为取代的苯基、吡啶基、呋喃基、噻吩基或萘基，其中苯基上的取代基选用氢、甲基、氯。
本发明作为一种新的咪唑并氮杂菲啶类化合物，其结构选自如下任意一种：
4,11-二苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例1)
11-苯基-4-(对甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例2)
4-(4-氯苯基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例3)
11-苯基-4-(间甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例4)
11-苯基-4-(吡啶-3-基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例5)
4-苯基-11-(对-甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例6)
11-(4-氯苯基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例7)
11-(3-溴苯基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例8)
4-(萘-2-基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例9)
4-(3-氯苯基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例10)
11-苯基-4-(吡啶-4-基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例11)
4-(4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉-11-基)苯胺(实施例12)
4-(呋喃-2-基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例13)
11-(4-溴苯基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例14)
11-(萘-2-基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例15)
11-苯基-4-(噻吩-2-基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例16)
4-苯基-11-(4-(三氟甲基)苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例17)
11-(4-氯苯基)-4-(对甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉(实施例18)。
本发明的另一个目的是提供所述的咪唑并氮杂菲啶类化合物的制备方法，通过以下步骤实现：
将2-氨基查尔酮和氨基烯酮溶解在醋酸中，于室温条件下反应，反应时间为24小时，所得到的反应液加NaOH(1M)中和并萃取过柱，即得目标化合物。其中2-氨基查尔酮和氨基烯酮的摩尔比为1.2:1。
所述的2-氨基查尔酮的结构式为：
其中R1的取代基选用氢、甲基、氨基、三氟甲基、萘基、噻吩基、卤素，所述卤素选用氯、溴。
所述的氨基烯酮类化合物的结构式为：
其中R2为取代的苯基、吡啶基、呋喃基、噻吩基或萘基，其中苯基上的取代基选用氢、甲基、氯。
本发明的再一个目的是提供所述的咪唑并氮杂菲啶类化合物作为荧光团在荧光成像中应用。
本发明提供的合成方法，是以2-氨基查尔酮和氨基烯酮类化合物为起始原料，通过醋酸室温的温和条件提供一种咪唑并氮杂菲啶类化合物及其制备方法，反应条件温和，无需金属催化剂，反应高效，所用的反应原料易得，多种底物结构均可耐受该反应条件，适用范围广，为合成咪唑并氮杂菲啶类化合物提供了一种简单易行的方法。此外，本发明的所述的咪唑并氮杂菲啶类化合物及合成方法未见文献报道。发明制备的咪唑并氮杂菲啶类化合物具有一定的光学特性，可作为潜在的荧光分子，作为荧光团在荧光成像中应用。本发明为咪唑并氮杂菲啶类化合物的合成提供新的手段。
附图说明
图1是化合物的荧光光谱图。
具体实施方式
本发明将通过实施例和附图作进一步的说明。
实施例1 4,11-二苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮(0.6mmol,133.8mg)和2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮(0.5mmol,94mg)加入1mL的冰醋酸中，加料完毕后，室温反应24h，点板观察。反应结束，向反应液中加入NaOH(1M)中和后萃取过柱得黄色固体。
Yellow solid,m.p.>250℃,1H NMR(500MHz,CDCl3)δ8.40(d,J＝8.0Hz,1H),8.24(d,J＝8.5Hz,1H),7.98–7.93(m,1H),7.80–7.72(m,5H),7.65–7.59(m,6H),4.64–4.57(m,2H),4.22–4.15(m,2H).13C NMR(125MHz,CDCl3)δ159.3,156.3,149.4,147.3,142.9,142.3,135.5,130.9,130.3,129.9,129.2,129.0,128.1,127.9,126.6,123.3,121.8,111.5,98.3,53.0,49.1.HRMS(ESI):m/z calcd for(C26H20N3+H)+:374.1657；found:374.1660。
实施例2 11-苯基-4-(对甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成2-(咪唑烷-2-亚基)-1-(对甲苯基)乙-1-酮，得到黄色固体。
Yelbow solid,m.p.234.1-235℃，1H NMR(500MHz,Chloroform-d)δ8.16(d,J＝8.5Hz,1H),8.11(d,J＝8.0Hz,1H),7.72(m,1H),7.60(d,J＝8.0Hz,2H),7.55(m,2H),7.53–7.50(m,3H),7.24(d,J＝7.5Hz,2H),6.62(s,1H),3.87–3.76(m,4H),2.42(s,3H).13C NMR(125MHz,DMSO)δ158.6,154.9,149.7,146.6,142.4,139.6,136.5,135.1,130.9,129.7,129.3,129.0,128.7,128.0,127.6,126.6,124.3,121.3,110.8,96.8,52.9,48.2,21.0.HRMS(ESI):m/z calcd for(C27H22N3+H)+:388.1814；found:388.1822。
实施例3 4-(4-氯苯基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成1-(4-氯苯基)-2-(咪唑烷-2-亚基)乙-1-酮，得到黄色固体。
Yellow solid,m.p.>250℃,1H NMR(500MHz,CDCl3)δ8.69(s,2H),8.15(m,2H),7.77(s,1H),7.62–7.48(m,8H),6.62(s,1H),3.80(s,4H).13C NMR(125MHz,CDCl3)δ156.9,155.8,150.4,149.9,149.3,147.4,143.0,135.6,131.1,130.5,130.0,129.0,127.9,127.2,127.1,124.0,123.4,122.2,111.5,97.8,53.4,49.1.HRMS(ESI):m/z calcd for(C26H19ClN3+H)+:408.1268；found:408.1270。
实施例4 11-苯基-4-(间甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成2-(咪唑烷-2-亚基)-1-(间甲苯基)乙-1-酮，得到黄色固体。
Yellow solid,m.p.>250℃,1H NMR(500MHz,CDCl3)δ8.30(d,J＝8.5Hz,1H),8.17(d,J＝8.5Hz,1H),7.85(t,J＝8.0Hz,1H),7.68–7.59(m,3H),7.54(m,3H),7.44–7.36(m,3H),7.33(m,1H),7.04(s,1H),4.15(m,2H),3.94(m,2H),2.23(s,3H).13C NMR(125MHz,CDCl3)δ159.7,156.1,149.5,147.7,142.7,142.7,135.9,135.6,131.2,130.6,130.2,130.1,129.2,128.4,128.2,127.7，127.1,126.1,123.7,122.1,112.6,98.9,53.2,49.3,20.2.HRMS(ESI):m/z calcd for(C27H22N3+H)+:388.1814；found:388.1805。
实施例5 11-苯基-4-(吡啶-3-基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将(2-硝基乙烯基)苯换成1-硝基-3-(2-硝基乙烯基)苯，得到黄色固体。
Yellow solid,m.p.139.2-143.1℃,1H NMR(500MHz,CDCl3)δ8.19(d,J＝8.0Hz,1H),8.11(d,J＝8.5Hz,1H),7.76(t,J＝7.0Hz,1H),7.66(s,1H),7.61–7.54(m,4H),7.55–7.49(m,3H),7.40–7.35(m,2H),6.65(s,1H),3.84(s,4H).13C NMR(125MHz,CDCl3)δ157.7,156.0,149.6,147.2,143.9,142.9,135.5,133.5,130.9,130.3,129.9,129.4,128.9,128.2,127.8,127.4,126.8,123.3,121.9,111.4,98.1,77.2,53.2,49.0.HRMS(ESI):m/zcalcd for(C25H19N4+H)+:375.1610；found:375.1618。
实施例6 4-苯基-11-(对-甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(对甲苯基)丙-2-烯-1-酮，得到黄色固体。
Yellow solid,m.p.>250℃,1H NMR(500MHz,CDCl3)δ8.28(m,1H),8.16(d,J＝8.0Hz,1H),7.85(t,J＝7.5Hz,1H),7.78(d,J＝7.5Hz,1H),7.68(m,3H),7.56–7.49(m,4H),7.36(d,J＝6.5Hz,2H),7.09(d,J＝7.5Hz,1H),4.34-4.23(m,2H),4.08–3.97(m,2H),2.46(s,3H).13C NMR(125MHz,CDCl3)δ158.38,156.33,148.80,147.19,143.57,141.03,140.36,132.25,130.56,129.94,129.37,129.34,129.16,128.85,128.27,127.68,123.60,121.21,103.12,49.97,48.84,21.58.HRMS(ESI):m/z calcd for(C27H22N3+H)+:388.1814；found:388.1811。
实施例7 11-(4-氯苯基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(4-氯苯基)丙-2-烯-1-酮，得到黄色固体。
Yellow solid,m.p.164.7-167.3℃,1H NMR(500MHz,CDCl3)δ8.18(d,J＝8.0Hz,1H),8.13(d,J＝8.0Hz,1H),7.78–7.74(m,1H),7.68–7.66(m,2H),7.59–7.55(m,1H),7.54–7.48(m,4H),7.48–7.41(m,4H),6.66(s,1H),3.85–3.79(m,4H).13C NMR(125MHz,CDCl3)δ159.3,156.1,148.2,147.4,142.7,142.2,141.3,136.1,133.9,131.0,130.4,129.3,129.2,129.1,128.2,127.9,126.8,123.3,121.8,98.7,53.1,48.9.HRMS(ESI):m/z calcdfor(C26H19ClN3+H)+:408.1268；found:408.1258。
实施例8 11-(3-溴苯基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(3-溴苯基)丙-2-烯-1-酮，得到黄色固体。
Yellow solid,m.p.221.4-222.1℃.1H NMR(500MHz,CDCl3)δ8.19(d,J＝8.0Hz,1H),8.13(d,J＝8.5Hz,1H),7.77(t,J＝7.5Hz,1H),7.73(s,1H),7.69-7.63(m,3H),7.57(t,J＝7.5Hz,1H),7.51(d,J＝8.0Hz,1H),7.73-7.47(m,4H),6.66(s,1H),3.83(s,4H).13CNMR(125MHz,CDCl3)δ159.4,156.2,147.9,147.5,142.7,142.3,137.6,133.1,131.1,131.0,130.7,130.5,129.2,128.3,128.1,126.9,126.7,123.4,123.2,121.9,112.0,98.8,53.3,49.2.HRMS(ESI):m/z calcd for(C26H19BrN3+H)+:452.0762；found:452.0763。
实施例9 4-(萘-2-基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成2-(咪唑烷-2-亚基)-1-(萘-2-基)乙-1-酮，得到黄色固体。
Yellow solid,m.p.231.6-232.7℃.1H NMR(500MHz,CDCl3)δ8.22(d,J＝7.5Hz,1H),8.15(d,J＝8.0Hz,1H),7.92–7.71(m,6H),7.61-7.56(m,3H),7.60-7.52(m,3H),7.48-7.41(m,2H),6.71(s,1H),3.82–3.69(m,4H).13C NMR(125MHz,CDCl3)δ159.2,156.2,149.5,147.6,143.0,140.0,135.7,133.6,133.5,130.9,130.5,129.9,129.0,128.9,128.1,127.9,127.9,127.7,126.8,126.7,126.1,125.6,123.4,121.9,98.3,77.2,53.1,49.1.HRMS(ESI):m/z calcd for(C30H22N3+H)+:424.1814；found:424.1814。
实施例10 4-(3-氯苯基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成1-(3-氯苯基)-2-(咪唑烷-2-亚基)乙-1-酮，得到黄色固体。
Yellow solid,m.p.169.8-178.3℃.1H NMR(500MHz,CDCl3)δ8.18(d,J＝8.5Hz,1H),8.10(d,J＝8.0Hz,1H),7.75(t,J＝7.5Hz,1H),7.66(s,1H),7.60–7.50(m,7H),7.36(d,J＝4.5Hz,2H),6.63(s,1H),3.83(s,4H).13C NMR(125MHz,CDCl3)δ157.9,156.1,149.7,147.4,144.0,143.0,135.7,133.5,130.9,130.4,129.9,129.5,129.1,129.0,128.2,127.9,127.5,126.9,123.4,121.9,111.5,98.1,53.3,49.1.HRMS(ESI):m/z calcd for(C26H19ClN3+H)+:408.1268；found:408.1276。
实施例11 11-苯基-4-(吡啶-4-基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成2-(咪唑烷-2-亚基)-1-(吡啶-4-基)乙-1-酮，得到黄色固体。
Yellow solid,m.p.243.4-244.4℃.1H NMR(500MHz,CDCl3)δ8.69(s,2H),8.19(d,J＝7.5Hz,1H),8.11(d,J＝8.0Hz,1H),7.81–7.73(m,1H),7.61-7.51(m,8H),6.64(s,1H),3.81(s,4H).13C NMR(125MHz,CDCl3)δ156.9,155.8,150.3,149.9,149.3,147.4,143.0,135.5,131.1,130.5,129.9,129.0,127.9,127.2,123.9,123.4,122.2,111.4,97.9,77.2,53.3,49.1.HRMS(ESI):m/z calcd for(C25H19N4+H)+:375.1610；found:375.1618。
实施例12 4-(4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉-11-基)苯胺
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(4-氨基苯基)丙-2-烯-1-酮，得到黄色固体。
Yellow solid,m.p.148.6-151.2℃,1H NMR(500MHz,DMSO-d6)δ8.50(d,J＝8.5Hz,1H),7.91(d,J＝8.5Hz,1H),7.79(t,J＝7.0Hz,1H),7.61–7.58(m,1H),7.54-7.50(m,2H),7.41–7.34(m,5H),6.84(s,1H),6.68(d,J＝8.5Hz,2H),5.66(s,2H),3.94(d,J＝10.5Hz,2H),3.61(t,J＝10.5Hz,2H).13C NMR(125MHz,DMSO)δ158.4,155.4,150.7,150.6,146.5,142.8,142.1,131.5,131.0,129.2,129.0,127.6,127.2,126.6,124.3,121.1,113.3,109.2,96.6,65.0,51.9,48.6.HRMS(ESI):m/z calcd for(C26H20N4+H)+:389.1761；found:389.1763。
实施例13 4-(呋喃-2-基)-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成1-(呋喃-3-基)-2-(咪唑烷-2-亚基)乙-1-酮，得到黄色固体。
Yellow solid,m.p.169.3-170.9℃.1H NMR(500MHz,CDCl3)δ8.16(d,J＝8.5Hz,1H),8.12(d,J＝8.5Hz,1H),7.76(t,J＝7.5Hz,1H),7.60(s,1H),7.58-7.50(m,6H),7.08(d,J＝3.0Hz,1H),6.62-6.58(s,1H),6.59(s,1H),4.01(m,2H),3.91(m,2H).13C NMR(126MHz,CDCl3)δ155.8,153.6,149.5,148.5,147.5,143.1,135.4,131.1,130.5,130.0,129.1,127.9,127.1,123.4,122.0,111.7,111.6,111.3,98.7,52.9,49.3,29.8.HRMS(ESI):m/z calcd for(C24H18N3O+H)+:364.1450；found:364.1449。
实施例14 11-(4-溴苯基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(4-溴苯基)丙-2-烯-1-酮，得到黄色固体。
Yellow solid,m.p.129.4-132.3℃.1H NMR(500MHz,CDCl3)δ8.17(d,J＝8.0Hz,1H),8.13(d,J＝8.5Hz,1H),7.78–7.74(m,1H),7.68–7.65(m,4H),7.58-7.54(m,1H),7.47-7.40(m,5H),6.64(s,1H),3.86–3.77(m,4H).13C NMR(125MHz,CDCl3)δ159.25,156.10,148.17,147.44,42.68,142.05,134.32,132.84,132.29,131.03,130.46,129.53,129.12,128.24,127.95,126.81,123.25,121.68,111.56,98.89,52.73,49.16.HRMS(ESI):m/zcalcd for(C26H19BrN3+H)+:452.0762；found:452.0760。
实施例15 11-(萘-2-基)-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(萘-2-基)丙-2-烯-1-酮，得到黄色固体。
Yellow solid,m.p.227.9-229.9℃,1H NMR(500MHz,CDCl3)δ8.29(d,J＝8.0Hz,1H),8.16(d,J＝8.5Hz,2H),8.04–7.92(m,3H),7.82(t,J＝7.5Hz,1H),7.76–7.68(m,3H),7.66–7.59(m,3H),7.53-7.46(m,3H),7.09(s,1H),4.14(t,J＝10.0Hz,2H),3.94(t,J＝10.0Hz,2H).13C NMR(125MHz,CDCl3)δ159.2,156.4,149.4,147.4,143.0,142.,133.7,133.1,131.2,130.4,129.2,128.9,128.6,128.4,128.1,128.0,127.7,127.6,127.4,127.3,126.9,125.0,123.4,121.7,99.6,52.4,49.4..HRMS(ESI):m/z calcd for(C30H22N3+H)+:424.1808；found:424.1803。
实施例16 11-苯基-4-(噻吩-2-基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成2-(咪唑烷-2-亚基)-1-(噻吩-2-基)乙-1-酮，得到黄色固体。
Yellow solid,m.p.181.5-183.2℃,1H NMR(500MHz,CDCl3)δ8.13(d,J＝8.0Hz,1H),8.06(d,J＝8.5Hz,1H),7.77(d,J＝3.5Hz,1H),7.72(t,J＝7.5Hz,1H),7.58–7.55(m,2H),7.54-7.49(m,4H),7.43(d,J＝5.0Hz,1H),7.12–7.09(m,1H),6.62(s,1H),3.95(t,J＝9.0Hz,2H),3.85(t,J＝9.0Hz,2H).13C NMR(125MHz,DMSO)δ154.8,151.01,149.5,146.3,143.4,143.0,134.5,131.5,130.2,130.0,129.3,129.0,128.8,128.1,128.0,127.0,127.0,124.5,121.0,98.5,51.3,48.6.HRMS(ESI):m/z calcd for(C24H18N3S+H)+:380.1221；found:380.1225。
实施例17 4-苯基-11-(4-(三氟甲基)苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(4-(三氟甲基)苯基)丙-2-烯-1-酮，得到黄色固体。
Yellow solid,m.p.136.8-139.2℃,1H NMR(500MHz,CDCl3)δ8.18(d,J＝8.5Hz,1H),8.14(d,J＝8.0Hz,1H),7.84–7.75(m,3H),7.72(d,J＝7.5Hz,2H),7.67(d,J＝6.5Hz,2H),7.58(t,J＝7.5Hz,1H),7.49-7.39(m,3H),6.71(s,1H),3.84(s,4H).13C NMR(125MHz,CDCl3)δ158.5,156.2,147.3,147.0,143.1,140.6,137.6,132.2,130.6,129.9,129.2,128.9,128.7,127.7,126.28,126.3,124.8,123.4,121.2,109.8,102.8,49.7,29.8.HRMS(ESI):m/z calcd for(C27H19F3N3+H)+:442.1531；found:442.1533。
实施例18 11-(4-氯苯基)-4-(对甲苯基)-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉
合成步骤同实施例1，只是将3-(2-氨基苯基)-1-苯基丙-2-烯-1-酮换成3-(2-氨基苯基)-1-(4-氯苯基)丙-2-烯-1-酮，将2-(咪唑烷-2-亚基)-1-苯基乙烷-1-酮换成2-(咪唑烷-2-亚基)-1-(对甲苯基)乙-1-酮得到黄色固体。
Yellow solid,>250℃,1H NMR(500MHz,CDCl3)δ8.16(d,J＝8.5Hz,1H),8.09(d,J＝8.5Hz,1H),7.76–7.71(m,1H),7.63(d,J＝8.0Hz,2H),7.57–7.52(m,1H),7.44(d,J＝8.0Hz,2H),7.40(d,J＝8.0Hz,2H),7.32(d,J＝8.0Hz,2H),6.60(s,1H),3.82(s,4H),2.45(s,3H).13C NMR(125MHz,CDCl3)δ158.2,156.2,149.8,147.3,142.9,140.9,140.1,133.9,132.8,130.8,130.7,130.3,129.6,127.9,127.7,126.7,123.3,121.9,111.5,97.6,77.3,53.4,49.0,21.5.HRMS(ESI):m/z calcd for(C27H21ClN3+H)+:422.1424；found:442.1432。
实施例19化合物荧光性质测定
探针的吸收波长、激发波长与发射波长检测方法具体如下：
取约1mg的化合物粉末，以DMSO为溶剂，分别配成1mM的初始溶液，然后用无水乙醇稀释得到10μM的探针溶液，随后进行光学性质的检测，用Jascoo FP-6500型荧光光谱仪获取荧光发射光谱，得到探针的最大激发波长与发射波长，结果见表1和图1。
荧光光谱测定结果表明，本申请所合成的咪唑并氮杂菲啶化合物具有一定的荧光特性，发射波长在430-509nm,说明不同的取代基修饰可以影响分子的发射波长，本申请提供了一类全新的发光团，可用于荧光成像。
表1.化合物的荧光性质
| 实施例 | Compound | λ<sub>ex</sub>(nm) | λ<sub>em</sub>(nm) | △ν(cm<sup>-1</sup>) |
| 实施例1 | A-01 | 343 | 437 | 1594 |
| 实施例2 | A-02 | 342 | 436 | 1586 |
| 实施例4 | A-04 | 333 | 430 | 1476 |
| 实施例5 | A-05 | 343 | 456 | 1384 |
| 实施例6 | A-06 | 343 | 453 | 1412 |
| 实施例8 | A-08 | 343 | 443 | 1519 |
| 实施例9 | A-09 | 349 | 447 | 1591 |
| 实施例10 | A-11 | 343 | 455 | 1393 |
| 实施例11 | A-12 | 341 | 463 | 1294 |
| 实施例12 | A-13 | 363 | 509 | 1265 |
| 实施例13 | A-14 | 347 | 454 | 1472 |
Claims (4)
1.一种咪唑并氮杂菲啶类化合物，其特征在于，结构通式为：
其中：
R1为氢、甲基、氨基、三氟甲基、噻吩基、卤素，所述卤素选用氯、溴；
R2为取代的苯基、吡啶基、呋喃基、噻吩基，其中苯基上的取代基选用氢、甲基、氯。
2.依据权利要求1所述的一种咪唑并氮杂菲啶类化合物，其特征在于，选自下述化合物：
4,11-二苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉，
11-苯基-4-（对甲苯基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉，
4-（4-氯苯基）-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
11-苯基-4-（间甲基苯基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉，
11-苯基-4-（吡啶-3-基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7]喹啉，
4-苯基-11-（对甲基苯基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
11-（4-氯苯基）-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
11-（3-溴苯基）-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
4-（萘-2-基）-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
4-（3-氯苯基）-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
11-苯基-4-（吡啶-4-基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
4-（4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉-11-基）苯胺，
4-（呋喃-2-基）-11-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
11-（4-溴苯基）-4-苯基-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
11-苯基-4-（噻吩-2-基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
4-苯基-11-（4-（三氟甲基）苯基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉，
11-（4-氯苯基）-4-（对甲基苯基）-1,2-二氢苯并[f]咪唑并[2,1-α][2,7] 喹啉。
3.权利要求1所述的一种咪唑并氮杂菲啶化合物的制备方法，其特征在于，通过以下步骤实现：
将取代的2-氨基查尔酮和氨基烯酮溶解在醋酸中，于室温条件下反应，反应时间为24小时，所得到的反应液加NaOH中和并萃取过柱，得目标化合物，其中取代的2-氨基查尔酮和氨基烯酮的摩尔比为1.2:1；所述的取代的2-氨基查尔酮的结构式为：
其中R1的取代基选用氢、甲基、氨基、三氟甲基、噻吩基、卤素，所述卤素选用氯、溴；
所述的氨基烯酮类化合物的结构式为：
其中R2为取代的苯基、吡啶基、呋喃基、噻吩基，其中苯基上的取代基选用氢、甲基、氯。
4.根据权利要求1所述的一种咪唑并氮杂菲啶化合物作为荧光团在荧光成像中的应用。
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