一类苯并吡喃-4-酮取代的萘酰亚胺-多胺缀合物及其制备方法和用图_2

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l化04?1.4甜20: C 63.85%,H 5.:M%,N 5.73%;found C 63.90%,H 5.51%,N 5.48%.
[0044] 实施例2
[0045] 6-(2-4H-1-苯并化喃-4-酬)-{2-[3-(3-氨基丙基)-氨基丙基]IH-苯并异哇嘟-1, 3(2H)-酬}二盐酸盐(18b)的制备:
[0046]
[0047] 除第(8)步中用3a代替N,N-二甲基乙二胺,滴加 2血4M肥1乙醇(V4M細|:V雄=1:2) 溶液外,其它合成及提纯方法同实施例1。产率:86%,1hNMR(400MHz,化0) S: 8.15~8.26(m, 3H,Ar-H);7.82(d,lH,J = 8.Wz,Ar-H);7.63~7.67(m,lH,Ar-H);7.51~7.56(m,2H,Ar-H);7.29(t,J = 7.7細z,lH,Ar-H),7.12(d,J = 4.2細z,lH,Ar-H);6.26(s,lH,Ar-H);4.18 (t,J = 6.9細z,2H,lXN-C出);3.21~3.26(m,4H,2XN-CH2);3.15(t,J = 7.82Hz,2H,lXN-C出);2.12~2.20(m,4H,2X畑2);ESI-MSm/z:456.2[M+l-2HCl^.Anal.calcdfor C2讯27CI2化04* 1.85此0:C 57.73%,H 5.51%,N 7.48%;found C 57.64%,H 5.50%,N 7.42%.
[004引实施例3
[00例 6-(2-4H-1-苯并化喃-4-酬)-{2-[3-(4-氨基下基)-氨基丙基]IH-苯并异哇嘟-1, 3(2H)-酬}二盐酸盐(18c)的制备:
[(K)加]
[0051 ]除第(8)步中用3b代替N,N-二甲基乙二胺,滴加2血4M肥I乙醇溶液(V4M細|:V雄= 1:2)外,其它合成及提纯方法同实施例1。产率:86 %,白色固体Ih NMR(400MHz,化0) S: 7.74 ~7.78(m,3H,Ar-H);7.42(t,lH,J = 3.70Hz,Ar-H);7.26~7.29(m,2H,Ar-H);7.05(s,2H, Ar-H);6.74(t,J = 4.0細z,lH,Ar-H),5.64(d,lH,J = 4.6細z,Ar-H);3.98(t,J = 6.7細z, 2H,lXN-CH2);3.16~3.22(m,4H,2XN-CH2);3.10(t,2H,J = 7.12HzlXN-CH2);2.06(t, 2H,J = 7.02Hz I X 畑2); 1.78-1.89(4H,2X 畑2) .ESI-MI m/z:470.21[M+H-2HCir .Anal.calcd for C2姐29CI2化04*1.6H20:C 58.87%,H 5.68%,N 7.36%;found C 58.97%,H 5.57%,N 7.45%.
[0化2] 实施例4
[0053] 6-(2-4H-1-苯并化喃-4-酬)-{2-[(4-下基)-氨基下基]IH-苯并异哇嘟-1,3(2H)- 酬}二盐酸盐(18(1)的制备:
[0化4]
[00对除第(8)步中用化合物7代替N,N-二甲基乙二胺,滴加 1.OmL 4M HCl乙醇溶液 (V4M細I: V雄=1:2)外,其它合成及提纯方法同实施例1。产率:86%,白色固体1hNMR(400MHz, D20)S:7.77~7.86(m,3H,Ar-H);7.46(d,lH,J = 7.28Hz,Ar-H);7.35(t,2H,J = 7.84Hz,Ar-H);7.16(d,J = 6.7細z,lH,Ar-H);7.07(t,lH,J = 7.44Hz,Ar-H);6.84(d,J = 7.72Hz,lH, Ar-H);5.83(s,lH,Ar-H);3.89(t,J = 8.0Hz,lXN-CH2);3.06~3.13(m,4H,2XN-CH2);1.75 ~1.79(m,2H,lXOl2);1.65~1.73(m,4H,2Xai2);1.39~1.45(m,2H,lxai2);0.95(t,3H, J = 7.36Hz,1XCH3).ESI-MI m/z:469.2[M+H-3HCl] + .Anal.calcd for C2讯29CI1 化〇4. 0.6出0:C 67.53%,H 5.90%,N 5.43%;found C 67.36%,H 5.90%,N 5.49%.
[0056] 实施例5
[0057] 6-(2-4H-1-苯并化喃-4-酬)-{2-[4-(4-氨基下基)-氨基下基]IH-苯并异哇嘟-1, 3(2H)-酬}二盐酸盐(18e)的制备:
[0化引
[0化9]除第(8)步中用化合物3d代替N,N-二甲基乙二胺,滴加2mL 4M HCl乙醇溶液 (V4M細I: V雄=1:2)外,其它合成及提纯方法同实施例1。产率:86%,白色固体iHNMR(400MHz, D2〇)S:7.68~7.76(m,3H,Ar-H);7.37(d,lH,J = 8.0Hz,Ar-H);7.20~7.30(m,2H,Ar-H); 6.98-7.06(m,2H,Ar-H);6.73(d,J = 8.0Hz,lH,Ar-H),5.71(s,lH,Ar-H);3.83(t,2H,J = 6.0Hz,lXN-(M2);3.04~3.12(m,6H,3XN-CH2);;1.76-1.78(m,6H,3Xai2);1.63-1.65(m, 2H,1XCH2KESI-MI m/z:484.2[M+H-2HCl] + .Anal.calcd for C29曲 1CI2化04 * 3.35H20:C 56.47%,H 6.16%,N 6.81%;found C 56.86%,H 6.24%,N 6.43%.
[0060] 实施例6
[0061] 6-(2-4H-1-苯并化喃-4-酬)-{2-[3-(3-(3-氨基丙基)氨基丙基)-氨基丙基]-胺} IH-苯并异哇嘟-1,3(2扣-酬}^盐酸盐(18f)的制备:
[0062]
[0063] 除第(8)步中用化合物5a代替N,N-二甲基乙二胺,滴加 3mL 4M HCl乙醇溶液 (V4M細I: V雄=1:2)外,其它合成及提纯方法同实施例1。产率:86 %,Ih醒R(400MHz,化0)S : 7.98~8.06(m,3H,Ar-H);7.65(d,lH,J = 7.68Hz,Ar-H);7.51(t,lHJ = 7.92Hz,Ar-H); 7.41-7.45(m,lH,Ar-H);7.31(d,J = 7.72Hz,lH,Ar-H),7.19(t,lH,J = 7.細z,Ar-H);6.95 (d,lH,J = 8.32Hz,Ar-H);6.00(s,lH,Ar-H);4.10(t,2H,J = 6.68Hz,lXN-CH2);3.21~ 3.27(m,8H,4XN-CH2);3.14(t,2H,J = 7.86Hz,lXN-CH2);2.09-2.25(m,6H,3XCH2).ESI-MI m/z:513.25[M+H-3HCir.Anal.calcd for C30出5CI3N4O4 ?!.0&0:0 56.30%,H 5.83%,N 8.75%;found C 56.03%,H 5.84%,N 8.88%.
[0064] 实施例7
[00化]6-(2-4H-i-苯并化喃-4-酬)-{2-[(3-赃嗦基)-丙基]IH-苯并异哇嘟-1,3(2H)-酬}二盐酸盐(1始)的制备:
[0066]
[0067]除第(8)步中用化合物IOa代替N,N-二甲基乙二胺,滴加1.5mL 4M HCl乙醇溶液 (V4M細|:V己醇=1:2)外,其它合成及提纯方法同实施例1。产率:86%,白色固体Ih應R (400MHz,D2〇)S:7.61~7.85(m,3H,Ar-H);7.29(d,J = 5.16Hz,lH,Ar-H);7.17~7.19(m, 2H,Ar-H);6.96(s,lH,Ar-H);6.64(d,J = 6.32Hz,lH,Ar-H),6.84~6.87(m,lH,Ar-H);5.55 (s,lH,Ar-H);3.71~3.82(t,J=10Hz,5XN-CH2);3.40(t,J = 8.2Hz,lH,lXN-CH2);1.87~ 1.88(m,2H,l XCH2) ; 1.63~1.65(m,2H, I X畑2) .ESI-MI m/z:468.19[M+H-2HCir .Anal.calcd for C2姐27CI2化04*3.0H20:C 56.57%,H 5.60%,N 7.07%;found C 56.65%,H 5.:34%,N 7.03%.
[006引实施例8
[00例 6-(2-4H-1-苯并化喃-4-酬)-{2-[(4-赃嗦基)-下基]IH-苯并异哇嘟-1,3(2H)-酬}-二盐酸盐(1化)的制备:
[0070]
[0071] 除第(8)步中用化合物IOb代替N,N-二甲基乙二胺,滴加 I.5mL 4M HCl乙醇溶液 (V4M細I: V雄=1:2)外,其它合成及提纯方法同实施例1。产率:86%,白色固体1hNMR(400MHz, D20)S:7.61~7.65(m,3H,Ar-H);7.29(d,lH,J = 5.1細z,Ar-H);7.18~7.20(m,2H,Ar-H); 6.96(s,2H,Ar-H);6.64(d J = 6.32Hz,lH,Ar-H),5.55(s,lH,Ar-H);3.70-3.82(m,8H,4X N-CH2);3.39(t J = 8.2Hz,2H,lXN-(M2);1.86-1.88(m,2H,lxai2);1.63-1.65(m,2H,lX CH2KESI-MIm/z:482.2[M+H-2肥l]+.Anal.calcdforC2姐29Cl2化04?3.0出0:C 57.24%, H 5.80%,N 6.91%;found C 57.53%,H 5.64%,N 6.95%.
[0072] 实施例9
[0073] 6-(2-4H-1-苯并化喃-4-酬)-{2-[(3-吗嘟基)-丙基]IH-苯并异哇嘟-1,3(2H)-酬}盐酸盐(18i)的制备:
[0074]
[0075] 除第(8)步中用化合物12代替N,N-二甲基乙二胺外,其它合成及提纯方法同实施 例 1。产率:86%,白色固体Ih NMR(400MHz,D2〇)S:7.85(d,J = 7.56Hz,2H,Ar-H);7.78(d,lH, J = 7.12Hz,Ar-H);7.49(d,J = 7.16Hz,lH,Ar-H);7.37~7.40(m,lH,Ar-H);7.31(t,lH,J = 7.82Hz,Ar-H);7.11~7.18(m,2H,Ar-H);6.87(d,J = 8.28Hz,lH,Ar-H);5.66(s,lH,Ar-H); 4.19(t J = 5.82Hz,lXN-CH2);4.04(t J = 6.68Hz,lXN-CH2);3.92(t,2H
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