CN101235019B - 3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途 - Google Patents

3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途 Download PDF

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CN101235019B
CN101235019B CN2008100204342A CN200810020434A CN101235019B CN 101235019 B CN101235019 B CN 101235019B CN 2008100204342 A CN2008100204342 A CN 2008100204342A CN 200810020434 A CN200810020434 A CN 200810020434A CN 101235019 B CN101235019 B CN 101235019B
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徐锁平
朱海亮
宫海滨
吕鹏程
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Xuzhou Normal University
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Abstract

一种3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物,它具有如下结构通式:
Figure 200810020434.2_AB_0
其中:
Figure 200810020434.2_AB_1

Description

3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物及其制法和用途
技术领域
本发明涉及3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物的制法以及它们在制备抑菌药物中的应用。
技术背景
碘代水杨醛作为一种医药中间体,具有广泛的应用前景。以碘代水杨醛为原料与各类胺作用可生成含碘Schiff碱。这些Schiff碱可以还原成卞胺(氨卞类化合物具有很好的抗菌活性),也可以进一步与金属离子发生配位作用合成一系列配位化合物。由于其广泛的生物活性,Schiff碱的金属配合物已经被越来越多的用于工农业的各个方面。
本发明人在碘代水杨醛的制备方法的发明基础上,又合成了一系列的3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物,并对它们进行了几种常见菌类的抑制作用测试。
发明内容
本发明的目的在于以3,5-二碘水杨醛为先导物,按药物设计的一些基本原理合成一系列3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物,在深入研究构效关系的基础上,发现具有较高抗微生物活性的金属配合物,并提供3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物的制法。
本发明的技术方案如下:
一种3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物,它具有如下结构通式:
Figure S2008100204342D00011
其中:
Figure S2008100204342D00012
M=Zn、Cu、Ni、Co、Cd、Mn、Fe或Hg。
一种3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物的制备方法,将3,5-二碘水杨醛、4-(ω-氨基烷基)吗啉和金属盐以物质的量之比为1∶1∶1~2∶2∶1,在甲醇(或乙醇)中,室温下反应15-30分钟,静置2-5天,得到3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物。
Figure S2008100204342D00021
实验证明,3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物对枯草芽胞杆菌(B.subtilis),金黄葡萄球菌(S.aureus),粪肠球菌(S.faecalis),铜绿假单胞菌(P.aeruginosa),大肠杆菌(E.coli)和阴沟肠杆菌(E.cloacae)都有不同程度的抑制作用,因此它们有可能用于制备抗菌性药物。
具体实施方式
通过以下实施例进一步详细说明本发明,但应注意本发明的范围并不受这些实施例的任何限制。
实施例1:3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合锌(II)(1)
将3,5-二碘水杨醛(0.7477g)与4-(2-氨乙基)吗啉(0.3mL)溶于20mL甲醇置于100mL的烧杯中,在磁力搅拌下加入Zn(CH3COO)2·2H2O(0.2195g),在室温下搅拌15分钟,然后在室温下静置5天,出现大量黄色晶体。过滤得黄色晶体,并用甲醇洗涤三次,置于无水氯化钙干燥器内干燥后得黄色晶体3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合锌(II)0.7326g,产率:70%。Mp:249-250℃,ESI-MS:1036.11(C26H31O4N4I4Zn+,[M+H]+),UV(λnm):259;397,IR(cm-1,KBr):1630(s);1446(s);1218(s);1113(s);672(s)。
实施例2:3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合铜(II)(2)
将3,5-二碘水杨醛(0.7477g)与4-(2-氨乙基)吗啉(0.3mL)溶于20mL乙醇置于100mL的烧杯中,在磁力搅拌下加入Cu(CH3COO)2·H2O(0.1997g),在室温下搅拌20分钟,然后在室温下静置4天,出现大量墨绿色晶体。过滤得墨绿色晶体,并用乙醇洗涤三次,置于无水氯化钙干燥器内干燥后得墨绿色晶体3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合铜(II)0.7432g,产率:72%。Mp:221-223℃,ESI-MS:1034.26(C26H31O4N4I4Cu+,[M+H]+),UV(λnm):260;401,IR(cm-1,KBr):1628(s);1434(s);1220(s);1112(s);671(s)。
按以上实施例相似的方法,以3,5-二碘水杨醛和4-(2-氨乙基)吗啉为原料,与不同的金属盐反应,我们合成了表1所列的八种3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉的金属配合物1~8。
表1   几种3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉的金属配合物
  序号 金属盐 配合物 性状   产率(%)
  12345678   Zn(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCu(CH<sub>3</sub>COO)<sub>2</sub>·H<sub>2</sub>ONi(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OCo(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCd(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OMn(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OFeSO<sub>4</sub>·7H<sub>2</sub>OHg(CH<sub>3</sub>COO)<sub>2</sub>   (C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Zn(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cu(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Ni(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Co(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cd(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Mn(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Fe(C<sub>13</sub>H<sub>15</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Hg   黄色晶体,Mp:249-250℃墨绿色晶体,Mp:221-223℃淡绿色晶体,Mp:217-220℃浅棕色晶体,Mp:193-195℃黄色晶体,Mp:248-250℃黑色晶体,Mp:153-156℃黑色晶体,Mp:>300℃亮黄色晶体,Mp:192-194℃   7072666471656572
实施例3:3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合铜(II)(10)
将3,5-二碘水杨醛(1.125g)与4-(3-氨丙基)吗啉(0.45mL)溶于30mL乙醇置于100mL的烧杯中,在磁力搅拌下加入Cu(CH3COO)2·H2O(0.2996g),在室温下搅拌20分钟,然后在室温下静置5天,出现大量黄色晶体。过滤得黄色晶体,并用乙醇洗涤三次,置于无水氯化钙干燥器内干燥后得黄色晶体3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合铜(II)1.036g,产率:67%。Mp:170-172℃.,ESI-MS:1061.4,UV(λnm):263;379,IR(cm-1,KBr):1621(s);1443(s);1222(s);1109(s);672(s)。
实施例4:3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合汞(II)(16)
将3,5-二碘水杨醛(1.5g)与4-(3-氨丙基)吗啉(0.58mL)溶于40mL甲醇置于100mL的烧杯中,在磁力搅拌下加入Hg(CH3COO)2(0.637g),在室温下搅拌30分钟,然后在室温下静置3天,出现大量亮黄色晶体。过滤得亮黄色晶体,并用甲醇洗涤三次,置于无水氯化钙干燥器内干燥后得亮黄色晶体3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合汞(II)1.715g,产率:72%。Mp:183-185℃,ESI-MS:1198.01(C28H35O4N4I4Hg+,[M+H]+),UV(λnm):262;422,IR(cm-1,KBr):1607(s);1455(s);1215(s);1120(s);664(m)。
按以上实施例相似的方法,以3,5-二碘水杨醛和3-氨丙基吗啉为原料,与不同的金属盐反应,我们合成了表2所列的八种3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉的金属配合物9~16。
表2  几种3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉的金属配合物
  序号 金属盐 配合物 性状   产率(%)
  910111213141516  Zn(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCu(CH<sub>3</sub>COO)<sub>2</sub>·H<sub>2</sub>ONi(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OCo(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OCd(CH<sub>3</sub>COO)<sub>2</sub>·2H<sub>2</sub>OMn(CH<sub>3</sub>COO)<sub>2</sub>·4H<sub>2</sub>OFeSO<sub>4</sub>·7H<sub>2</sub>OHg(CH<sub>3</sub>COO)<sub>2</sub>  (C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Zn(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cu(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Ni(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Co(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Cd(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Mn(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Fe(C<sub>14</sub>H<sub>17</sub>O<sub>2</sub>N<sub>2</sub>I<sub>2</sub>)<sub>2</sub>Hg   黄色晶体,Mp:165-167℃墨绿色晶体,Mp:170-172℃黄绿色晶体,Mp:251-253℃棕色晶体,Mp:230-232℃黄色晶体,Mp:254-256℃黑色晶体,Mp:145-148℃褐色晶体,Mp:198-201℃亮黄色晶体,Mp:183-185℃   6267666070626472
实施例5:3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物对枯草芽胞杆菌(B.subtilis),金黄葡萄球菌(S.aureus),粪肠球菌(S.faecalis),铜绿假单胞菌(P.aeruginosa),大肠杆菌(E.coli)和阴沟肠杆菌(E.cloacae)的作用
方法:MTT法。取培养的枯草芽胞杆菌(B.subtilis),金黄葡萄球菌(S.aureus),粪肠球菌(S.faecalis),铜绿假单胞菌(P.aeruginosa),大肠杆菌(E.coli)和阴沟肠杆菌(E.cloacae)的菌株,分别稀释成2×104个/ml,分装于96孔板(0.2ml/孔)。设青霉素和卡那霉素作参比对照组,DMSO对照组及16个不同浓度的受测化合物,每孔10μl。各组设3个平行孔,置37℃恒温培养箱中培养24h,打入MTT液(2mg/ml)5μl/孔,再培养4h。取出培养板,加入SDS 100μl/孔,再培养12h,在570nm波长下,用美国生产的BioRad 550型酶标仪测出OD值,按下列公式计算出细菌生长抑制率(最小半数抑制浓度,MICs)。
生长抑制率=(1-用药组平均OD值/对照组平均OD值)×100%
MICs越小,此化合物的抗菌性越好,结果见表3。
结果表明:3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物对枯草芽胞杆菌(B.subtilis),金黄葡萄球菌(S.aureus),粪肠球菌(S.faecalis),铜绿假单胞菌(P.aeruginosa),大肠杆菌(E.coli)和阴沟肠杆菌(E.cloacae)都有不同程度的抑制作用。
表3    十六种3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉的金属配合物的抑菌活性测试结果
  配合物   最小半数抑制浓度MICs(μg/mL)
  革兰氏(染色)阳性(Gram positive)   革兰氏(染色)阴性(Gram negative)
  B.subtilis   S.aureus   S.faecalis   P.aeruginosa   E.coli   E.cloacae
  1   0.781   >50   1.562   3.125   0.781   12.5
  配合物   最小半数抑制浓度MICs(μg/mL)
  2   12.5   25   1.562   0.781   >50   0.781
  3   1.562   6.25   0.781   0.781   >50   1.56
  4   0.781   12.5   6.25   3.125   50   12.5
  5   0.781   12.5   12.5   0.781   0.781   1.562
  6   0.781   25   1.562   50   >50   6.25
  7   0.781   12.5   3.125   0.781   >50   12.5
  8   0.781   12.5   6.25   3.125   3.125   6.25
  9   6.25   >50   1.562   6.25   1.562   12.5
  10   25   >50   0.781   6.25   >50   6.25
  11   0.781   12.5   1.562   0.781   >50   6.25
  12   >50   12.5   1.562   6.25   50   0.781
  13   3.125   12.5   12.5   6.25   3.125   6.25
  14   3.125   50   3.125   12.5   50   6.25
  15   0.781   6.25   1.562   6.25   12.5   6.25
  16   1.562   6.25   1.562   3.125   3.125   1.562
  Penicillin   1.562   1.562   1.562   6.25   6.25   3.125
  Kanamycin   0.39   1.562   3.125   3.125   3.125   1.562
配合物1~16的熔点、质谱、紫外及红外光谱数据
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合锌(II)(1)
Mp:249-250℃,ESI-MS:1036.11(C26H31O4N4I4Zn+,[M+H]+),UV(λnm):259;397,IR(cm-1,KBr):1630(s);1446(s);1218(s);1113(s);672(s)。
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合铜(II)(2)
Mp:221-223℃,ESI-MS:1034.26(C26H31O4N4I4Cu+,[M+H]+),UV(λnm):260;401,IR(cm-1,KBr):1628(s);1434(s);1220(s);1112(s);671(s)。
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合镍(II)(3)
Mp:217-220℃,ESI-MS:1029.32(C26H31O4N4I4Ni+,[M+H]+),UV(λnm):263;404,IR(cm-1,KBr):1621(s);1445(s);1210(s);1113(s);671(s)。
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合钴(II)(4)
Mp:193-195℃,ESI-MS:1029.36(C26H31O4N4I4Co+,[M+H]+),UV(λnm):265;388,IR(cm-1,KBr):1617(s);1435(s);1223(s);1116(s);681(s)。
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合镉(II)(5)
Mp:248-250℃,ESI-MS:1083.04(C26H31O4N4I4Cd+,[M+H]+),UV(λnm):259;399,IR(cm-1,KBr):1618(s);1445(s);1218(s);1109(s);669(s)。
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合锰(II)(6)
Mp:153-156℃,ESI-MS:1025.47(C26H31O4N4I4Mn+,[M+H]+),UV(λnm):262;390,IR(cm-1,KBr):1610(s);1423(s);1220(s);1113(s);673(s)。
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合铁(II)(7)
Mp:>300℃,ESI-MS:1026.25(C26H31O4N4I4Fe+,[M+H]+),UV(λnm):260;427,IR(cm-1,KBr):1630(s);1437(s);1218(s);1113(s);674(s)。
3,5-二碘水杨醛缩-4-(2-氨乙基)吗啉合汞(II)(8)
Mp:192-194℃,ESI-MS:1171.12(C26H31O4N4I4Hg+,[M+H]+),UV(λnm):260;432,IR(cm-1,KBr):1603(s);1443(s);1215(s);1118(s);667(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合锌(II)(9)
Mp:165-167℃,ESI-MS:1064.02(C28H35O4N4I4Zn+,[M+H]+),UV(λnm):260;381,IR(cm-1,KBr):1622(s);1448(s);1221(s);1118(s);669(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合铜(II)(10)
Mp:170-172℃,ESI-MS:1062.16(C28H35O4N4I4Cu+,[M+H]+),UV(λnm):263;379,IR(cm-1,KBr):1621(s);1443(s);1222(s);1109(s);672(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合镍(II)(11)
Mp:251-253℃,ESI-MS:1057.12(C28H35O4N4I4Ni+,[M+H]+),UV(λnm):261;406,IR(cm-1,KBr):1618(s);1450(s);1224(s);1118(s);671(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合钴(II)(12)
Mp:230-232℃,ESI-MS:1057.31(C28H35O4N4I4Co+,[M+H]+),UV(λnm):262;404,IR(cm-1,KBr):1616(s);1445(s);1223(s);1118(s);669(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合镉(II)(13)
Mp:254-256℃,ESI-MS:1110.75(C28H35O4N4I4Cd+,[M+H]+),UV(λnm):260;431,IR(cm-1,KBr):1620(s);1448(s);1218(s);1120(s);667(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合锰(II)(14)
Mp:145-148℃,ESI-MS:1053.26(C28H35O4N4I4Mn+,[M+H]+),UV(λnm):260;430,IR(cm-1,KBr):1618(s);1438(s);1223(s);1101(s);678(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合铁(II)(15)
Mp:198-201℃,ESI-MS:1054.22(C28H35O4N4I4Fe+,[M+H]+),UV(λnm):262;429,IR(cm-1,KBr):1609(s);1431(s);1219(s);1114(s);678(s)。
3,5-二碘水杨醛缩-4-(3-氨丙基)吗啉合汞(II)(16)
Mp:183-185℃,ESI-MS:1198.01(C28H35O4N4I4Hg+,[M+H]+),UV(λnm):262;422,IR(cm-1,KBr):1607(s);1455(s);1215(s);1120(s);664(m)。

Claims (3)

1.一种3,5-二碘水杨醛缩4-(ω-氨基烷基)吗啉金属配合物,其特征是它具有如下结构通式:
Figure FSB00000067794400011
其中:
Figure FSB00000067794400012
M=Zn、Cu、Ni、Co、Cd、Mn、Fe或Hg。
2.一种权利要求1所述的3,5-二碘水杨醛缩4-(ω-氨基烷基)吗啉金属配合物的制备方法,其特征是:将3,5-二碘水杨醛、4-(ω-氨基烷基)吗啉和金属盐以物质的量之比为1∶1∶1~2∶2∶1,在甲醇或乙醇中,室温下反应15-30分钟,静置2-5天,得到3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物。
3.权利要求1所述的3,5-二碘水杨醛缩-4-(ω-氨基烷基)吗啉金属配合物在制备抗枯草芽胞杆菌、金黄葡萄球菌、粪肠球菌、铜绿假单胞菌、大肠杆菌或阴沟肠杆菌药物中的应用。
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