CN110590765A - 2-噻唑甲醛-糠醛席夫碱的结构、制备和用途 - Google Patents
2-噻唑甲醛-糠醛席夫碱的结构、制备和用途 Download PDFInfo
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Abstract
本发明涉及有机合成、光学材料和药物化学等领域，具体是一种化合物晶体的结构、制备方法及部分性质；该化合物外观呈黄色条块状晶体，熔点为97.0‑99.9℃，分子式C9H7N3OS,化学名为：2‑((E)‑(((E)‑呋喃‑2‑基亚甲基)亚肼基)甲基)噻唑；该化合物结构详见说明书，具有一定的荧光性质及抗癌活性。
Description
技术领域
本发明涉及有机合成、光学材料和药物化学等领域，使用较简单的方法一步合成目标产物，其优点在于化合物结构的新颖性、简单易行的合成方法、较高的纯度以及产率。
背景技术
目前，随着现代科学技术的不断进步，人们对荧光的研究越来越多，对其荧光性质的研究也越来越深入。荧光物质在染料、有机颜料、光学增白剂、光氧化剂、涂料、化学及生化标记分析、太阳能捕集器、防伪标记、药物示踪及激光等领域得到了更为广泛的应用。其中有机荧光材料主要用于当今热门的技术，如荧光探针、荧光分析等，更是光学电子器件，DNA诊断、光化学传感器、激光染料、有机电致发光器件不可或缺的材料。
席夫碱主要是指含有亚胺或甲亚胺特征基团(-RC＝N-)的一类有机化合物，通常席夫碱是由胺和活性羰基缩合而成。席夫碱类化合物及其金属配合物主要在医药学、催化、分析化学、腐蚀以及光致变色领域有重要应用。在医学领域，席夫碱具有抑菌、杀菌、抗肿瘤、抗病毒的生物活性；在催化领域，席夫碱的钴、镍和钯的配合物已经作为催化剂使用；在分析化学领域，席夫碱作为良好配体，可以用来鉴别、鉴定金属离子和定量分析金属离子的含量；在腐蚀领域，某些芳香族的席夫碱经常作为铜的缓蚀剂；在光致变色领域，某些含有特征基团的席夫碱也具有独特的应用。
发明内容
本发明的内容是合成一种可用作荧光材料及抗癌药物的化合物，其化合物外观呈黄色条块状晶体，熔点为：97.0-99.9℃，分子式C9H7N3OS,化学名为：2-((E)-(((E)-呋喃-2-基亚甲基)亚肼基)甲基)噻唑，结构如下：
1、结构鉴定:
元素分析表明这种化合物具有的分子式为C9H7N3OS，分子量205.24；元素分析结果(％)：实验值:C,52.69，H,3.49，N,20.49，S,15.66；计算值：C52.67，H,3.44，N,20.47，S,15.62；单晶结构分析表明，其结晶属于正交晶系，空间群为Pca21，Z＝4.有关的1HNMR谱见附图1；附图2、附图3分别是该化合物的热椭球晶体结构图和晶体结构堆积图。
2、合成方法。
方法一，其特征在于：以(E)-2-(亚肼基)噻唑和糠醛为原料，在合适的有机溶剂中一步完成。步骤如下：
1)将(E)-2-(亚肼基)噻唑全部溶于合适的有机溶剂后，按照一定的物质的量之比加入糠醛，在一定温度下搅拌或研磨反应几小时即可完成。
2)过滤，待滤液自然挥发，析出的黄色条块状晶体即为目标产物；若采用固相反应，则反应完毕用合适的有机溶剂重结晶即可得目标产物晶体。
方法二，其特征在于：以(E)-2-(亚肼基)噻唑和糠醛为原料，在合适的有机溶剂中一步完成，步骤如下：
1)将糠醛全部溶于合适的有机溶剂后，按照一定的物质的量之比加入(E)-2-(亚肼基)噻唑，在一定温度下搅拌或研磨反应几小时即可完成。
2)过滤，待滤液自然挥发，析出的黄色条块状晶体即为目标产物；若采用固相反应，则反应完毕用合适的有机溶剂重结晶即可得目标产物晶体。
以上两种方法的区别在于反应物加料顺序不同，但反应物的摩尔比均介于1:4与4:1之间。
以上两种方法中的有机溶剂(包括反应用溶剂和重结晶用溶剂)选自：甲醇、乙醇、乙腈、二氯甲烷、氯仿、四氢呋喃、丙酮等，反应时也可以不用有机溶剂，原料之间直接反应(即固相反应)。
优选的,所述反应温度为常温或加热回流，反应方法为搅拌或研磨。
优选的，所述反应时间选自：1－10h。
本发明的有益效果是：能够以比较简单的步骤和反应物合成比较复杂的功能分子材料。
3、紫外和荧光性质
化合物在230.0nm、265nm和342.0nm附近有三个强吸收峰，紫外光谱见附图4；在375.0-450.0nm范围有很强的荧光发射峰，荧光光谱见附图5；这表明该化合物有较好的荧光性质。
4、体外抗肿瘤活性：
将处于对数期生长的A549肺癌细胞，A375人类恶性黑色素瘤细胞和HeLa宫颈癌细胞，分别用0.25％胰酶消化细胞，使其成为单细胞，用含10％胎牛血清的F12K培养液制成浓度为1.25×107个/L的单细胞悬液，将细胞接种于96孔培养板中，每孔200μL(每孔2.5×103个细胞)。将96孔细胞培养板置于CO2培养箱中，在37℃，5％CO2条件下，培养48h。
当孔内细胞长满(90％满即可)时，按实验分组加入不同剂量的本席夫碱溶液(200μL/孔)，使待测化合物的终浓度分别为25μM、50μM、100μM、200μM、400μM、800μM，每组设3个复孔，培养96h。
各个孔中分别加入20μL浓度为0.5g/L的MTT，继续培养4h，使MTT还原为甲瓒(Formazan)。吸出全部上清液后，每孔加入200μL的DMSO，震摇15min，使甲瓒充分溶解后，运用酶联免疫检测仪测定490nm处的吸光度(OD值)。然后按照下式进行计算：
细胞抑制率％＝(对照组OD值-实验组OD值)/对照组OD值×100％
测试结果表明，该席夫碱对A549肺癌细胞，A375人类恶性黑色素瘤细胞和HeLa宫颈癌细胞的IC50(药物的半数抑制浓度)分别为780、550、760μmol/L，表明该化合物对这三种癌细胞有微弱的抑制效果。
具体实施方式
为了更好的理解本发明内容，下面通过一个具体实施例进一步说明本发明的技术方案：
实施例1
称取0.1270g(约1mmol)(E)-2-(亚肼基)噻唑溶于50ml乙腈中，将溶液放入烧瓶内，放在恒温加热磁力搅拌器上搅拌，用移液枪吸取166μL(约2mmol)糠醛加入溶液中，加热回流搅拌反应2小时。溶液逐渐变为黄棕色，反应结束后，过滤，滤液静置，自然挥发；烧杯底部析出条块状黄色晶体，即为目标产物，产率约为87％。
附图说明
附图1是2-((E)-(((E)-呋喃-2-基亚甲基)亚肼基)甲基)噻唑的1HNMR谱图(DMSO-D6)。
附图2是2-((E)-(((E)-呋喃-2-基亚甲基)亚肼基)甲基)噻唑的晶体结构图。
附图3是2-((E)-(((E)-呋喃-2-基亚甲基)亚肼基)甲基)噻唑的晶体结构堆积图。
附图4是2-((E)-(((E)-呋喃-2-基亚甲基)亚肼基)甲基)噻唑的紫外光谱图(10- 5mol/L,CH2CL2)。
附图5是2-((E)-(((E)-呋喃-2-基亚甲基)亚肼基)甲基)噻唑的荧光光谱图(10- 5mol/L,CH2CL2)。
Claims (4)
1.一种化合物，外观呈黄色条状晶体，熔点为：97.0-99.9℃，分子式C9H7N3OS,化学名为：2-((E)-(((E)-呋喃-2-基亚甲基)亚肼基)甲基)噻唑，结构如下：
其结晶属于正交晶系，空间群为Pca21， Z＝4。
2.如权利要求1中所述的化合物的合成方法，其特征在于：以(E)-2-(亚肼基)噻唑和糠醛为原料，反应温度为常温或加热至回流,在甲醇/乙醇/乙腈/二氯甲烷/氯仿/四氢呋喃/丙酮等有机溶剂中反应，步骤如下：
1)将(E)-2-(亚肼基)噻唑全部溶于有机溶剂后，按1:4-4:1物质的量之比加入糠醛，在一定温度下搅拌或研磨反应1－10h即可完成；若采用固相反应，则可以不用有机溶剂；
2)过滤，待滤液自然挥发，析出的橙色块状晶体即为目标产物；若采用固相反应，则可用甲醇/乙醇/乙腈/二氯甲烷/氯仿/四氢呋喃/丙酮等有机溶剂重结晶，可得目标产物晶体。
3.如权利要求1所述化合物晶体在染料、有机颜料、光学增白剂、光氧化剂、涂料、化学及生化标记分析、太阳能捕集器、防伪标记、药物示踪、荧光探针、荧光分析、光学电子器件、光化学传感器、激光染料、有机电致发光器件等领域的用途，该用途基于其荧光性质。
4.如权利要求1中所述化合物晶体或其他药物学上可接受的盐在制备治疗肿瘤药物中的应用，其特征在于：所述肿瘤为肺癌、恶性黑色素瘤和宫颈癌。
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