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 PDFInfo
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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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：
其中：
或
Description
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：
其中：
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。
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：
其中：
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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