CN111793070B - 一类具有荧光特性[1,2,4]-三氮唑并环类化合物及其制备方法和用途 - Google Patents

一类具有荧光特性[1,2,4]-三氮唑并环类化合物及其制备方法和用途 Download PDF

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CN111793070B
CN111793070B CN202010601062.3A CN202010601062A CN111793070B CN 111793070 B CN111793070 B CN 111793070B CN 202010601062 A CN202010601062 A CN 202010601062A CN 111793070 B CN111793070 B CN 111793070B
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黄龙江
耿延汝
廉成锡
陈丽平
李秀芬
赵迎春
葛晓萍
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Abstract

本发明涉及杂环化合物领域,公开了一类[1,2,4]‑三氮唑并环类荧光分子的制备方法及用途,本发明公开的[1,2,4]‑三氮唑并环类杂环化合物的激发波长在200‑800nm之间;发射波长在400‑800nm之间,且细胞毒性低,生物相容性好,连接上不同的金属响应基团,能够选择性的检测对应的微量金属元素。本发明的荧光分子可用于环境、细胞及生物体中痕量金属的检测且在生物成像方面具有良好的应用前景。

Description

一类具有荧光特性[1,2,4]-三氮唑并环类化合物及其制备方 法和用途
技术领域
本发明涉及一类新型荧光分子的制备方法及用途,特别是一类[1,2,4]-三氮唑并环类荧光分子及其制备方法和用途。
背景技术
金属元素与生命体尤其是人体健康的关系已引起人们的广泛关注,至今已知人体内含有的微量元素有铁、锌、铜、锰、钴、钼、铬、钒、镍和锡等。它们都是人体中不可或缺的元素,以铁元素为例,铁元素是生物体中至关重要的,特别是Fe3+,它参与构成了生命体内多种酶和蛋白质,在多种生物的化学反应中起着至关重要的作用。人体Fe3+失衡会引起新陈代谢紊乱,对身体健康产生影响,进而导致贫血、肝肾损伤和心力衰竭等疾病;其它人体必需的微量金属元素同样在生命体的平衡、生长、发育以及代谢活动起着至关重要的作用。另外,非人体必需的重金属元素(如钯、钌、铑、汞等)一旦被生命体摄入,不仅影响其健康甚至危及生命。因此,快速准确的检测食物、饮用水、环境以及生命体内的微量金属元素对自然环境的保护、食品和饮用水安全以及生命科学都具有十分重要的意义。目前,检测微量金属元素的方法主要有分光光度法、原子光谱法、电化学法和质谱法等,这些分析方法通常具有良好的检测范围、灵敏度和重复性,但也存在检测限高、检测时间长、繁琐的样品制备过程、操作复杂、容易受其他离子干扰等缺点。因此,开发一种准确且简单快速地检测诸如Fe3+、钯等微量金属元素的方法是非常必要的,而有机小分子荧光探针就是其中有效的方法之一。常用于荧光检测的有机小分子结构包括香豆素类、萘酰亚胺类、菲咪唑类、苯并噻唑类、罗丹明类、氟硼吡咯类等,这些分子大都具有荧光强度高,检测限低、响应快等特征;但这些分子在生物相容性、金属离子检测的专一性等方面尚有不足,尤其是对铁离子的检测,以上常用的有机荧光探针分子大部分无法有效的区分Fe3+和Fe2+,因此,本发明提供一类新型[1,2,4]-三氮唑类杂环化合物荧光分子及其在金属检测方面的应用,在该荧光分子结构中引入不同的金属响应基团,可以用于不同微量金属元素的检测,尤其在铁离子检测方面,该荧光分子能专一性的识别Fe3+,而不识别Fe2+
发明内容
有鉴于此,本发明提供一类新型的[1,2,4]-三氮唑并环类杂环化合物荧光分子并将其应用于微量金属元素的检测。
为了实现上述目的,本发明采用以下技术方案:
一类[1,2,4]-三氮唑并环类荧光分子探针,所述[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物的通式(I)和[1,2,4]-三氮唑并喹(唑)啉类杂环化合物通式(II)如下所示:
Figure GDA0003693070250000021
其中,R1为氨基、(烷基或酰基)取代氨基,烷基、烷氧基;所述烷氧基为-OCH2CH=CH2或-OCOOCH2CH=CH2;对于三价铁离子的检测,R1优选为酰基取代的氨基,对于钯检测,R1优选为OCOOCH2CH=CH2
R2是烷氧基,苯氧基,烷基,烯基,炔基,环烷基,卤代烷基芳基或杂芳基;每个所述烷基,环烷基,卤代烷基,芳基和杂芳基是未取代或任选一个可取代位置独立取代,各自独立的取代为卤素,氰基,烷氧基,烷基,卤代烷基,卤代烷氧基,芳基,杂芳基,杂环基,环烷基或酰胺基;所述卤代烷基,卤代烷氧基中卤素取代基为氟、氯、溴或碘。作为优选:R2取代基为甲氧基,苯氧基和苯基。
R3是芳基,单环芳基,并环芳基,稠环芳基;所述单环芳基为(取代)苯基,(取代)杂环芳基;所述并环芳基为(取代)苯并呋喃、(取代)苯并噻吩、(取代)苯并咪唑,(取代)苯并噻唑;所述稠环芳基为(取代)萘基,(取代)蒽基或(取代)菲基。其中单环芳基以苯环,噻吩环作为优选;并环芳基以苯并噻吩或苯并噻唑作为优选;稠环芳基以蒽基和菲基作为优选。
本发明还提供了[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式(I)的制备方法如图,
Figure GDA0003693070250000022
具体包括以下步骤:
(1)[1,2,4]-三氮唑并[1,5-a]嘧啶酮类杂环化合物1的制备方法参考中国专利(CN201611115587.6),将其溶于合适的溶剂中,加入三卤化物,得到7-卤代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2。
(2)7-卤代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2溶于溶剂中,加入芳基硼酸,有机碱或者无机碱和催化剂,得到取代的7-芳基取代-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式(I)。
(3)当R1为氨基或氨基的衍生物时,起始原料中的R1为硝基,通式(I)中的硝基经过还原后衍生化得到通式(I)荧光分子。
本发明还提供了[1,2,4]-三氮唑并喹(唑)啉类杂环化合物通式(II)的制备方法如图,
Figure GDA0003693070250000031
具体包括以下步骤:
(1)取代的2-氨基苯甲酸3经酯化和肼解得到取代的2-氨基酰肼类衍生物4。
(2)将取代的2-氨基酰肼类衍生物溶于合适溶剂中,加入硫氰酸铵,所得混合物加热至一定温度反应,得到化合物5。
(3)将化合物5溶于溶剂中,加入芳香酰氯,加热反应得到取代的[1,2,4]-三氮唑并喹(唑)啉酮类杂环化合物6。
(5)将[1,2,4]-三氮唑并喹(唑)啉酮类杂环化合物6与三卤氧磷反应得到7-卤代-[1,2,4]-三氮唑并喹(唑)啉类杂环化合物7。
(6)将7-溴代-[1,2,4]-三氮唑并喹(唑)啉类杂环化合物7与芳基硼酸衍生物偶联反应得到通式(Π)所示[1,2,4]-三氮唑并喹(唑)啉类杂环化合物目标分子。
(7)如果通式(II)中R1是氨基或取代的氨基衍生物,则起始原料中R1为硝基,化合物7经偶联后还原再衍生化得到通式(II)。
本发明提供了一类[1,2,4]-三氮唑并环类荧光分子,即[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物通式(I)和[1,2,4]-三氮唑并喹(唑)啉类杂环化合物通式(II)荧光分子,该类荧光分子的激发波长在200-800nm之间;发射波长在400-800nm之间,可用于环境中微量及痕量金属的检测,由于该类化合物细胞毒性低,生物相容性好,因而可用于细胞及生物体内微量金属的检测并在生物成像方面具有良好的应用前景。
附图说明:
图1是荧光探针化合物I-36对Fe3+的选择性荧光发射光谱在450nm处的柱状图
图2是金属阳离子对荧光探针化合物I-36检测Fe3+的干扰图。
图3是荧光探针化合物I-49与不同浓度的Pd0响应后的光谱变化图。
图4是荧光探针化合物I-49对Pd0的选择性荧光发射光谱在440nm处的柱状图。
图5是荧光探针化合物I-36检测Hela细胞中对Fe3+离子的激光共聚焦成像图。
具体实施方式
本发明公开了一类[1,2,4]-三氮唑并环类杂环化合物其制备方法及用途,通式(Ⅰ,Ⅱ)表示的化合物是在本发明中所合成的化合物,通式(Ⅰ,Ⅱ)的激发波长200-800nm之间;发射波长在400-800nm之间,且细胞毒性低,生物相容性好的事实是由本发明首次公开的。
通式(I)表示的化合物所制备的部分化合物结构实例及其激发波长(λex)和发射波长(λem)如下:
Figure GDA0003693070250000041
Figure GDA0003693070250000042
Figure GDA0003693070250000051
Figure GDA0003693070250000061
Figure GDA0003693070250000071
Figure GDA0003693070250000081
通式(Ⅱ)表示的化合物所制备的部分化合物结构实例及其激发波长(λex)和发射波长(λem)如下:
Figure GDA0003693070250000082
Figure GDA0003693070250000083
Figure GDA0003693070250000091
Figure GDA0003693070250000101
实施例1下面结合附图和实施例对本发明作更加详细的描述,应当理解,此处所描述的优选实施例仅用于说明和解释本发明,并不用于限定本发明。
Figure GDA0003693070250000111
化合物I-36a(1mmol)溶于15mL乙腈中,加入三溴氧磷(4mmol),加热至回流并在该温度下反应5-6小时(TLC跟踪反应),反应完毕后,减压浓缩去除溶剂,所得残留物经二氯甲烷萃取,取有机相溶液,减压浓缩去除溶剂得化合物I-36b纯品,收率为75%。
(2)化合物I-36c的制备
化合物I-36b(0.5mmol)溶于15mL 1,4-二氧六环中,加入苯硼酸(0.6mmol),然后加入碳酸钾(1mmol)和四三苯基膦钯(0.05mmol),无水无氧条件下,回流反应12小时(TLC跟踪反应),反应完毕后,减压浓缩去除溶剂,所得残留物经二氯甲烷萃取,取有机相溶液,减压浓缩去除溶剂得化合物I-36c,收率为80%。
(3)化合物I-36d的制备
化合物I-36c(0.5mmol)溶于10mL甲醇中,加入催化量雷尼镍,常温下氢化反应1-2小时(TLC跟踪反应),反应完毕后,过滤,滤液减压浓缩去除溶剂,得到化合物I-36d。
(4)化合物I-36e的制备
化合物I-36d(0.5mmol)溶于10mL二氯甲烷中,加入苯甲酰氯(0.5mmol),然后加入4-二甲氨基吡啶(0.5mmol),所得混合物常温反应1-2小时(TLC跟踪反应),反应完毕后,加入水,分出有机相,有机相经无水硫酸钠干燥后减压浓缩去除溶剂得化合物I-36e粗品,粗品经柱层析纯化得纯品。1H-NMR:(CD3OD,500MHz):δ8.22(t,J=8.6Hz,4H),8.11(s,1H),7.95(d,J=8.6Hz 2H),7.84-7.79(m,4H),7.69-7.63(m,3H),7.50(t,J=7.3Hz,1H),7.42(t,J=7.4Hz,2H),6.99(d,J=8.7Hz,2H),3.75(s,3H).13C-NMR:(CD3OD,125MHz):δ53.67(2C),108.15,113.53(2C),115.50,118.98(2C),126.30(2C),127.18(2C),127.73(2C),127.90(2C),128.31,128.90(2C),130.75(2C),131.47(2C),131.19,142.45,148.08,149.98,155.90,162.53,162.75,166.17.HRMS(ESI+)m/z calcd for C31H23N5O2(M+H)+498.1930,found 498.1928.
以下为探针分子的应用实例,分别以检测铁和钯为例说明:
实施例2荧光分子I-36对Fe3+离子的检测
2.1检测限的测定
向1×10-5μmol/L的I-36溶液中,分别加入0、20、40、60、80、100、120、140、160μmol/L的Fe3+离子,检测荧光强度的变化。440nm处的荧光强度不断降低,直至荧光消失,可计算出其检测限为0.8×10-6mol/L。
2.2荧光分子探针I-36对Fe3+离子的选择性
向1×10-5μmol/L的I-36溶液中,分别加入160μmol/L的三价铁离子、二价铁离子、锂离子、镁离子、铝离子、钙离子、锌离子、铜离子、镍离子、锰离子,快速检测荧光强度的变化。测试结果如图1所示,该探针与其他离子几乎没有响应,三价铁离子导致明显的荧光淬灭,该荧光分子突出的特性是对三价铁离子响应而二价铁离子不响应。
2.3荧光分子I-36检测Fe3+离子的抗干扰性
向1×10-5μmol/L的I-36溶液中,分别加入160μmol/L的二价铁离子、锂离子、镁离子、铝离子、钙离子、锌离子、铜离子、镍离子、锰离子后再加入相同浓度的三价铁离子,检测荧光强度的变化。测试结果如图2所示,该探针对Fe3+的响应中,不受其他金属离子的干扰,显示了荧光探针化合物检测Fe3+的优越性。
2.4荧光分子探针I-36的细胞成像
荧光化合物I-36在Hela细胞中的荧光成像研究如图5所示,发现该荧光分子可很好的在细胞内成像。
实施例3荧光分子I-49对金属钯的检测
采用类似的手段,如图3和图4,荧光探针化合物I-49对金属钯具有良好的选择性,检测限同样低至微摩尔级别。
实施例4部分代表性化合物的细胞毒性
以Hela细胞为例,其在10μg/mL 20μg/mL 30μg/mL浓度下的细胞存活率如下表所示:
Figure GDA0003693070250000121
Figure GDA0003693070250000131

Claims (3)

1.一类具有荧光特性[1,2,4]-三氮唑并环类化合物,其特征在于,所述[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物的通式(I)如下所示:
Figure FDA0003681314580000011
其中,R1
Figure FDA0003681314580000012
R2为p-OCH3、o-OCH3或m-OCH3
R3
Figure FDA0003681314580000013
2.根据权利要求1所述的化合物的应用,其特征在于,所述应用是所述通式(I)所示化合物用于环境、细胞及生物体中痕量金属Fe3+及钯的检测。
3.根据权利要求1所述的化合物的制备方法,其特征在于,所述通式(I)所示的化合物的制备方法如下:
Figure FDA0003681314580000014
(1)[1,2,4]-三氮唑并[1,5-a]嘧啶酮类杂环化合物2的制备方法如下,将化合物1溶于合适的溶剂中,加入三卤氧磷,得到7-Br-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2;
(2)7-Br-[1,2,4]-三氮唑并[1,5-a]嘧啶类杂环化合物2溶于溶剂中,加入芳基硼酸,然后加入有机碱或者无机碱,加入催化剂,得到5-硝基取代苯基-7-芳基-[1,2,4]-三氮唑并[1,5-a]嘧啶;
(3)步骤(2)制备得到化合物经硝基还原后再衍生化得到通式(I)所示的荧光分子。
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