“Click Chemistry”在一些氨基酸、甾体和山楂酸衍生物合成中的应用
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摘要
1、通过L-保护丝氨酸3-位羟基的叠氮基取代,成功地获得了系列3-位叠氮基修饰的保护L-丝氨酸衍生物；并从L-丝氨酸出发,经氨基保护、炔丙醚化、羧基保护,顺利合成了系列含3-位O-炔基的L-保护丝氨酸衍生物。
2、利用"Click"反应,以3-位叠氮化和炔基化修饰的L-保护丝氨酸为原料成功地高效合成了十种三氮唑环交联的L-氨基酸衍生物24-33。这些交联L-氨基酸衍生物有可能作为潜在的蛋白质交联剂和金属核素标记配体。
3、以保护赖氨酸为原料利用ImSO2N3试剂以70%的收率获得了化合物15；并分别从L-酪氨酸和对硝基苯丙氨酸出发,成功合成了叠氮基和端基炔修饰的保护苯丙氨酸。这些工作为后续的荧光氨基酸的合成提供了基础。
1、通过对anthracene、fluorescein、benzothiadiazole、dansyl、NBD和coumarin等荧光团进行叠氮化或炔基化修饰,然后与含有叠氮基或端基炔的保护氨基酸发生“Click”反应,成功合成了10种对称双取代(47、53-54、65-66、70-72、74-75)和16种单取代的(56-58、76-79、84-87、90、93-94、100-101)荧光氨基酸衍生物；采用分步‘'Click"反应的策略,通过对"Click"反应条件的优化,成功获得了非对称的荧光氨基酸衍生物69、73。
2、研究了56、76-79、84、92等化合物的稳定态荧光性质,结果表明：除荧光黄衍生物外,新合成的荧光氨基酸衍生物的荧光性质都与其原始发光团类似,都拥有较大的Stokes位移和高的量子产率；所有荧光氨基酸衍生物的荧光发射情况都受溶剂极性的影响,其中化合物56、84、92,特别是水溶性化合物77随溶剂极性增加有明显的红移趋势；特别有价值的是,所有新型荧光氨基酸衍生物的发射波长都在可见光区域。
3、考察了部分化合物的荧光寿命,发现苯并噻二唑取代的氨基酸衍生物76-79在DMSO和H2O的混合溶剂中的荧光寿命都超过14 ns,显著高于色氨酸的3 ns。结合其稳定态荧光性质,化合物76-79有可能作为非常有前景的蛋白质荧光探针材料。
4、研究了溶剂和pH对7-羟基香豆素氨基酸衍生物100和101荧光性质的影响。研究表明,pH值的变化通过7-位羟基的质子交换平衡强烈影响化合物100的荧光性质,因而化合物100有可能作为pH敏感的荧光氨基酸,探测细胞腔隙的pH值变化。
5、化合物70、73-75、77是令人非常感兴趣的水溶性荧光氨基酸衍生物,我们选取化合物74,重点考察了其水溶液与不同金属离子(Cu2+、Mg2+、Ni2+、Co2+、Mn2+、Zn2+、Cd2+、Fe2+、Pb2+、Hg2+)配位后荧光吸收的变化情况,发现Hg2+和Cu2+对该化合物的荧光吸收有显著的淬灭作用,因而有可能在荧光传感器方面有重要应用前景。
1、发展了以AlMe3作为甲基化试剂,通过1,6-共轭加成立体选择性合成C-3位或C-7位α-甲基甾体化合物的方法；合成了12个甲基取代的甾体化合物(105、110、114、115、116、120、128、135、144、145、148、149),其中120、128、135、148为新化合物,化合物120和148的结构通过X-单晶衍射得到确认。
2、对所得化合物进行了抗肿瘤活性筛选,发现化合物114和144对人胃癌细胞MGC-803具有很好的抑制活性,其IC50值分别为1.00±0.02μM和1.04±0.03μM；化合物135亦有良好的抑制活性,其IC50值为4.71±0.01μM。
3、利用"Click"反应对化合物114、128、144、148、149进行糖苷化得到相应的6个新型糖缀合物155-160。初步对比考察了其对人胃癌细胞MGC-803的抑制活性,化合物159表现出优于未糖苷化甾体149的抑制活性,而其余糖缀合物相对于母体化合物抑制活性降低。
以提高山楂酸水溶性,即提高山楂酸的成药性和生物利用度为目的,利用"Click"反应将氨基酸、莽草酸、葡萄糖和麦芽糖等水溶性基团引入山楂酸的C-28位,合成了系列山楂酸衍生物,主要结果如下：
1、在山楂酸C-28位成功引入端炔基,再与叠氮基修饰的L-保护丝氨酸发生经"Click"反应、脱保护,合成了三氮唑环交联的L-丝氨酸-山楂酸衍生物。
2、设计、合成了含叠氮基的莽草酸衍生物,再通过与端炔基修饰山楂酸的"Click"反应、脱保护,顺利得到了三氮唑环交联的莽草酸-山楂酸衍生物。
4、合成了含叠氮基的单糖衍生物和二糖衍生物,与含端炔基修饰山楂酸发生"Click"反应后,经脱乙酰基保护得山楂酸糖缀合物。对所得山楂酸衍生物的药理活性研究正在进行中。
This dissertation is mainly focused on the synthesis of some novel derivatives of amino acid, steroid and Maslinic acid via "Click Chemistry", and includes four parts:
(1) A series of azide-functionalized L-serine derivatives were prepared by azide substitution of C3-OH of the protected L-serine. Meanwhile, some protected L-serine derivatives with O-alkynyl at C-3 position were also synthesized with L-serine as the raw material.
(2) Ten triazole crosslinking L-amino acid derivatives 24-33, which could be used as potential protein crosslinkers, metal labels, were synthesized via click reaction of 3-azide and alkyne protected L-serine as raw material.
(3) 6-aminohexanoic acid functionalized with 6-azide was prepared with a yield of 70% with protected L-lysine as the starting material and ImSO2N3 as a reagent. L-phenylalanine derivatives with azide and alkynyl groups were also synthesized with L-tyrosine and p-nitrophenylalanine as raw materials.
(1) Ten fluorescent symmetrical bis-amino acids and sixteen mono-substituted amino acid derivatives were successfully prepared with click chemistry, by introducing different fluorophores (fluorescein, dansyl, NBD, coumarin and benzothiadiazole) into the side chain of serine, lysine and phenylalanine. Furthermore, asymmetrical fluorescent bis-amino acid derivatives were synthesized via step by step of click reaction.
(2) The general spectroscopic properties of 56、76-79、84、92 indicated that, except for the fluorescein derivatives, spectroscopic properties of the newly synthesized fluorophores in EtOH and DMSO were similar to the native molecules which exhibited large Stokes shifts and high quantum yields. Fluorescent emission of the different compounds was affected by solvent polarity. Compound 77, which is water-soluble, was characterized by a significant red shift in water compared to DMSO (λmaxF=500 and 475 nm, respectively). Importantly, all amino acid derivatives emit fluorescence in the visible region of the spectrum.
(3) The fluorescence lifetime of the benzothiadiazole substituted amino acid derivatives (76-79) in DMSO-H2O was exceeding 14 ns which is much higher than that of tryptophan, about 3 ns. Thus, compounds 76-79 are potential fluorescence probes for studying protein dynamics or molecular interactions.
(4) Insight into the fluorescence properties of coumarin derivatives 100 and 101 showed that the property of 7-hydroxy coumarin-substituted amino ester 100 was very sensitive to the pH value which made this molecule a suitable pH-sensitive amino acid to probe local pH in cell compartments.
(5) Compounds 70,73-75, and 77 are interesting water soluble fluorescent amino acid derivatives. We chose 74 as a model compound to get insight into the binding properties towards metal ions (Cu2+、Mg2+、Ni2+、Co2+、Mn2+、Zn2+、Cd2+、Fe2+、Pb2+、Hg2+), and found that Hg2+ and Cu2+ could significantly quenched the fluorescent intensity, which can be used as fluorescent chemical sensor.
(1) A selective method has been developed for synthesis of a-methylated steroids at C-3 and C-7 positions via 1,6-conjugate addition with AlMe3 as the methylating reagent. 12 compounds were prepared and four of them are new compounds. The structures of 120 and 148 were confirmed by X-ray single crystal diffraction.
(2) The methylated steroids were tested against human gastric cancer cell line MGC-803 for their in vitro cytotoxicity, by using the SRB assay method in a dose dependent way. Compounds 114 and 144 showed the most significant cytotoxic effects, with IC50 about 1μM, and compound 135 also displayed nice inhibitory potency with IC50 about 4.7μM.
(3) Six glycoconjugates of their correspondingα-methylated compounds were synthesized via click reaction, and glycoconjugate 159 showed higher cytotoxic effects on human gastric cancer cell line MGC-803 than the parent steroid 149.
In order to improve the water solubility of maslinic acid which can increase the possibility of medicine and bioavailability, introducing water soluble groups (amino acids, shikimic acid, glucose and maltose) to C-28 position of MA by click reaction is a better choice.
(1) Triazole crosslinking MA derivatives were prepared by introducing terminal alkynyl group at C-28 position, click reaction with azide-functionalized L-serine, and deprotection.
(2) Design, synthesis of shikimic acid derivatives modified with azide. Triazole crosslinking shikimic acid-MA derivative was successfully obtained by click reaction with alkyne-functionalized MA at C-28 position and then deprotection.
(3) Click reaction of MA functionalized with alkyne and azide of glucose or maltose, then deprotection of the acetyl group gave the target glycoconjugate of MA.
The determination of the bioactivities of these MA derivatives is still under way.
2、利用"Click"反应,以3-位叠氮化和炔基化修饰的L-保护丝氨酸为原料成功地高效合成了十种三氮唑环交联的L-氨基酸衍生物24-33。这些交联L-氨基酸衍生物有可能作为潜在的蛋白质交联剂和金属核素标记配体。
3、以保护赖氨酸为原料利用ImSO2N3试剂以70%的收率获得了化合物15；并分别从L-酪氨酸和对硝基苯丙氨酸出发,成功合成了叠氮基和端基炔修饰的保护苯丙氨酸。这些工作为后续的荧光氨基酸的合成提供了基础。
1、通过对anthracene、fluorescein、benzothiadiazole、dansyl、NBD和coumarin等荧光团进行叠氮化或炔基化修饰,然后与含有叠氮基或端基炔的保护氨基酸发生“Click”反应,成功合成了10种对称双取代(47、53-54、65-66、70-72、74-75)和16种单取代的(56-58、76-79、84-87、90、93-94、100-101)荧光氨基酸衍生物；采用分步‘'Click"反应的策略,通过对"Click"反应条件的优化,成功获得了非对称的荧光氨基酸衍生物69、73。
2、研究了56、76-79、84、92等化合物的稳定态荧光性质,结果表明：除荧光黄衍生物外,新合成的荧光氨基酸衍生物的荧光性质都与其原始发光团类似,都拥有较大的Stokes位移和高的量子产率；所有荧光氨基酸衍生物的荧光发射情况都受溶剂极性的影响,其中化合物56、84、92,特别是水溶性化合物77随溶剂极性增加有明显的红移趋势；特别有价值的是,所有新型荧光氨基酸衍生物的发射波长都在可见光区域。
3、考察了部分化合物的荧光寿命,发现苯并噻二唑取代的氨基酸衍生物76-79在DMSO和H2O的混合溶剂中的荧光寿命都超过14 ns,显著高于色氨酸的3 ns。结合其稳定态荧光性质,化合物76-79有可能作为非常有前景的蛋白质荧光探针材料。
4、研究了溶剂和pH对7-羟基香豆素氨基酸衍生物100和101荧光性质的影响。研究表明,pH值的变化通过7-位羟基的质子交换平衡强烈影响化合物100的荧光性质,因而化合物100有可能作为pH敏感的荧光氨基酸,探测细胞腔隙的pH值变化。
5、化合物70、73-75、77是令人非常感兴趣的水溶性荧光氨基酸衍生物,我们选取化合物74,重点考察了其水溶液与不同金属离子(Cu2+、Mg2+、Ni2+、Co2+、Mn2+、Zn2+、Cd2+、Fe2+、Pb2+、Hg2+)配位后荧光吸收的变化情况,发现Hg2+和Cu2+对该化合物的荧光吸收有显著的淬灭作用,因而有可能在荧光传感器方面有重要应用前景。
1、发展了以AlMe3作为甲基化试剂,通过1,6-共轭加成立体选择性合成C-3位或C-7位α-甲基甾体化合物的方法；合成了12个甲基取代的甾体化合物(105、110、114、115、116、120、128、135、144、145、148、149),其中120、128、135、148为新化合物,化合物120和148的结构通过X-单晶衍射得到确认。
2、对所得化合物进行了抗肿瘤活性筛选,发现化合物114和144对人胃癌细胞MGC-803具有很好的抑制活性,其IC50值分别为1.00±0.02μM和1.04±0.03μM；化合物135亦有良好的抑制活性,其IC50值为4.71±0.01μM。
3、利用"Click"反应对化合物114、128、144、148、149进行糖苷化得到相应的6个新型糖缀合物155-160。初步对比考察了其对人胃癌细胞MGC-803的抑制活性,化合物159表现出优于未糖苷化甾体149的抑制活性,而其余糖缀合物相对于母体化合物抑制活性降低。
以提高山楂酸水溶性,即提高山楂酸的成药性和生物利用度为目的,利用"Click"反应将氨基酸、莽草酸、葡萄糖和麦芽糖等水溶性基团引入山楂酸的C-28位,合成了系列山楂酸衍生物,主要结果如下：
1、在山楂酸C-28位成功引入端炔基,再与叠氮基修饰的L-保护丝氨酸发生经"Click"反应、脱保护,合成了三氮唑环交联的L-丝氨酸-山楂酸衍生物。
2、设计、合成了含叠氮基的莽草酸衍生物,再通过与端炔基修饰山楂酸的"Click"反应、脱保护,顺利得到了三氮唑环交联的莽草酸-山楂酸衍生物。
4、合成了含叠氮基的单糖衍生物和二糖衍生物,与含端炔基修饰山楂酸发生"Click"反应后,经脱乙酰基保护得山楂酸糖缀合物。对所得山楂酸衍生物的药理活性研究正在进行中。
This dissertation is mainly focused on the synthesis of some novel derivatives of amino acid, steroid and Maslinic acid via "Click Chemistry", and includes four parts:
(1) A series of azide-functionalized L-serine derivatives were prepared by azide substitution of C3-OH of the protected L-serine. Meanwhile, some protected L-serine derivatives with O-alkynyl at C-3 position were also synthesized with L-serine as the raw material.
(2) Ten triazole crosslinking L-amino acid derivatives 24-33, which could be used as potential protein crosslinkers, metal labels, were synthesized via click reaction of 3-azide and alkyne protected L-serine as raw material.
(3) 6-aminohexanoic acid functionalized with 6-azide was prepared with a yield of 70% with protected L-lysine as the starting material and ImSO2N3 as a reagent. L-phenylalanine derivatives with azide and alkynyl groups were also synthesized with L-tyrosine and p-nitrophenylalanine as raw materials.
(1) Ten fluorescent symmetrical bis-amino acids and sixteen mono-substituted amino acid derivatives were successfully prepared with click chemistry, by introducing different fluorophores (fluorescein, dansyl, NBD, coumarin and benzothiadiazole) into the side chain of serine, lysine and phenylalanine. Furthermore, asymmetrical fluorescent bis-amino acid derivatives were synthesized via step by step of click reaction.
(2) The general spectroscopic properties of 56、76-79、84、92 indicated that, except for the fluorescein derivatives, spectroscopic properties of the newly synthesized fluorophores in EtOH and DMSO were similar to the native molecules which exhibited large Stokes shifts and high quantum yields. Fluorescent emission of the different compounds was affected by solvent polarity. Compound 77, which is water-soluble, was characterized by a significant red shift in water compared to DMSO (λmaxF=500 and 475 nm, respectively). Importantly, all amino acid derivatives emit fluorescence in the visible region of the spectrum.
(3) The fluorescence lifetime of the benzothiadiazole substituted amino acid derivatives (76-79) in DMSO-H2O was exceeding 14 ns which is much higher than that of tryptophan, about 3 ns. Thus, compounds 76-79 are potential fluorescence probes for studying protein dynamics or molecular interactions.
(4) Insight into the fluorescence properties of coumarin derivatives 100 and 101 showed that the property of 7-hydroxy coumarin-substituted amino ester 100 was very sensitive to the pH value which made this molecule a suitable pH-sensitive amino acid to probe local pH in cell compartments.
(5) Compounds 70,73-75, and 77 are interesting water soluble fluorescent amino acid derivatives. We chose 74 as a model compound to get insight into the binding properties towards metal ions (Cu2+、Mg2+、Ni2+、Co2+、Mn2+、Zn2+、Cd2+、Fe2+、Pb2+、Hg2+), and found that Hg2+ and Cu2+ could significantly quenched the fluorescent intensity, which can be used as fluorescent chemical sensor.
(1) A selective method has been developed for synthesis of a-methylated steroids at C-3 and C-7 positions via 1,6-conjugate addition with AlMe3 as the methylating reagent. 12 compounds were prepared and four of them are new compounds. The structures of 120 and 148 were confirmed by X-ray single crystal diffraction.
(2) The methylated steroids were tested against human gastric cancer cell line MGC-803 for their in vitro cytotoxicity, by using the SRB assay method in a dose dependent way. Compounds 114 and 144 showed the most significant cytotoxic effects, with IC50 about 1μM, and compound 135 also displayed nice inhibitory potency with IC50 about 4.7μM.
(3) Six glycoconjugates of their correspondingα-methylated compounds were synthesized via click reaction, and glycoconjugate 159 showed higher cytotoxic effects on human gastric cancer cell line MGC-803 than the parent steroid 149.
In order to improve the water solubility of maslinic acid which can increase the possibility of medicine and bioavailability, introducing water soluble groups (amino acids, shikimic acid, glucose and maltose) to C-28 position of MA by click reaction is a better choice.
(1) Triazole crosslinking MA derivatives were prepared by introducing terminal alkynyl group at C-28 position, click reaction with azide-functionalized L-serine, and deprotection.
(2) Design, synthesis of shikimic acid derivatives modified with azide. Triazole crosslinking shikimic acid-MA derivative was successfully obtained by click reaction with alkyne-functionalized MA at C-28 position and then deprotection.
(3) Click reaction of MA functionalized with alkyne and azide of glucose or maltose, then deprotection of the acetyl group gave the target glycoconjugate of MA.
The determination of the bioactivities of these MA derivatives is still under way.
引文
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