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克拉霉素的合成新方法 总被引:5,自引:0,他引:5
以醚化剂1-乙氧基环己烯和硅烷化试剂1,1,1,3,3,3-六甲基二硅氨烷为保护试剂, 采用醚化-硅烷化保护法制备了克拉霉素. 以红霉素A肟为原料计算, 经肟羟基醚化、2',4"-OH硅烷化、6-OH选择性甲基化、脱保护至克拉霉素, 四步反应总收率为49.5%. 相似文献
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克拉霉素在不同条件下水解,分别生成3-羟基克拉霉素(2)和3-羟基-8,9,10,11-二脱水-9,12-半缩酮克拉霉素(3),用乙酸酐保护2的C(2')-OH得到2'-乙酰基-3-羟基克拉霉素(4),用Ⅳ-氯代琥珀酰亚胺(NCS)氧化4的C(3)-OH合成了2'-乙酰基-3-氧代克拉霉素(5),采用MS,IR,1H NMR,13C NMR等对这些化合物进行了表征.用X射线单晶衍射法测定了化合物2和5的晶体结构,其均属于正交晶系,P212121空间群.化合物2的晶胞参数a=1.3657(3)nm,6=1.4783(3)nm,c=1.6510(3)nm,Z=4,V=3.3332(12)am3,Dc=1.175 g/cm3,F(000)=1288,μ=0.087mm-1;化合物5的晶胞参数a=1.5124(3)nm,b=1.5247(3)nm,c=1.5288(3)nm,Z=4,V=3.5254(12)nm3,Dc=1.187g/cm3,F(000)=1368.0,μ=0.088 mm-1. 相似文献
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克拉霉素在不同条件下水解,分别生成3-羟基克拉霉素(2)和3-羟基-8,9,10,11-二脱水-9,12-半缩酮克拉霉素(3),用乙酸酐保护2的C(2’)-OH得到2’-乙酰基-3-羟基克拉霉素(4),用N-氯代琥珀酰亚胺(NCS)氧化4的C(3)-OH合成了2’-乙酰基-3-氧代克拉霉素(5),采用MS,IR,^1H NMR,^13C NMR等对这些化合物进行了表征.用X射线单晶衍射法测定了化合物2和5的晶体结构,其均属于正交晶系,P212121空间群.化合物2的晶胞参数a=1.3657(3)nm,b=1.4783(3)nm,c=1.6510(3)nm,Z=4,V=3.3332(12)nm^3,Dc=1.175g/cm^3,F(000)=1288,/t=0.087mm^-1;化合物5的晶胞参数a=1.5124(3)nm,b=1.5247(3)nm,c=1.5288(3)nm,Z=4,V=3.5254(12)nm^3,Dc=1.187g/cm^3,F(000)=1368.0,μ=0.088mm^-1. 相似文献
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克拉霉素在不同条件下水解, 分别生成3-羟基克拉霉素(2)和3-羟基-8,9,10,11-二脱水-9,12-半缩酮克拉霉素(3), 用乙酸酐保护2的C(2’)-OH得到2′-乙酰基-3-羟基克拉霉素(4), 用N-氯代琥珀酰亚胺(NCS)氧化4的C(3)—OH合成了2’-乙酰基-3-氧代克拉霉素(5), 采用MS, IR, 1H NMR, 13C NMR等对这些化合物进行了表征. 用X射线单晶衍射法测定了化合物2和5的晶体结构, 其均属于正交晶系, P212121 空间群. 化合物2的晶胞参数a=1.3657(3) nm, b=1.4783(3) nm, c=1.6510(3) nm, Z=4, V=3.3332(12) nm3, Dc=1.175 g/cm3, F(000)=1288, μ=0.087 mm-1; 化合物5的晶胞参数 a=1.5124(3) nm, b=1.5247(3) nm, c=1.5288(3) nm, Z=4, V=3.5254(12) nm3, Dc=1.187 g/cm3, F(000)=1368.0, μ=0.088 mm-1. 相似文献
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克拉霉素的电化学反应机理研究与应用 总被引:1,自引:0,他引:1
应用线性扫描伏安法、循环伏安法、常规脉冲伏安法等电化学手段并结合紫外吸收光谱研究了药物克拉霉素(clarithromycin, CAM)在pH 1.8~9.2 Britton-Robinson缓冲溶液和0.05 mol•L-1 NaOH溶液中的电化学行为. 在所研究的pH范围, CAM分别产生P1, P2, P3, P4四个还原波, 其中P1, P2, P4三个波均为其药效活性基团C-9位羰基的还原所产生. 实验结果表明: 在pH 1.8~5.7的B-R缓冲溶液条件下所获得的P1波为两电子不可逆弱吸附还原波; 在6.0<pH<9.2的B-R缓冲溶液中, CAM产生P2和P3两个波, 其中P2为两电子不可逆还原波, P3为催化氢波. 在0.05 mol• L-1 NaOH溶液中, CAM产生的P4波是一个单电子的不可逆吸附还原波. 根据P4波的峰电流iP与CAM浓度的线性关系, 建立了CAM含量测定的新方法. 相似文献
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Chao-Yue Chen Jian-Guo Sun Fei-Yan Liu Kwok-Pui Fung Ping Wu Zhi-Zhen Huang 《Tetrahedron》2012,68(12):2598-2606
A novel route for the efficient synthesis of a target psoralen moiety, 4,4′-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photo-induced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. 相似文献
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G. N. Nugumanova S. V. Bukharov R. G. Tagasheva M. V. Kurapova V. V. Syakaev N. A. Mukmeneva P. A. Gurevich A. R. Burilov 《Russian Journal of Organic Chemistry》2007,43(12):1797-1803
Reactions of 3,5-di-tert-butyl-4-hydroxybenzyl acetate with indole and its derivatives gave a series of sterically hindered phenolic compounds having various functional groups. The products are potentially capable of inhibiting radical chain oxidation processes according to different mechanisms. 相似文献
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To improve the specificity of nitrogen mustards towards tumor cells, glucose-nitrogen mustard, fructose-nitrogen mustard, and lactose-nitrogen mustard were prepared as three novel glycosylated nitrogen mustard derivatives by esterification of bis(2-chloroethyl)carbamic chloride (BCC) with glucose, fructose, and lactose, respectively. BCC was synthesized from bis(2-chloroethyl)amine hydrochloride and triphosgene. The topic products were characterized by infrared (IR) and mass spectrometry (MS), and their interaction with bovine serum albumin was investigated by measuring fluorescence spectra in tris(hydroxymethyl)aminomethane hydrochloride (Tris–HCl) buffer solution at physiological conditions. 相似文献
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Apparently homogenous glycoproteins can be synthesised in good yield by a combination of site directed mutagenesis, a highly flexible but selective chemical derivatisation and efficient purification through the use of glycosyl thiosulfonates such as 2-((biotinoyl)-amino)-ethyl methanethiosulfonate. 相似文献
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Zhitao Li George Ngojeh Paul DeWitt Zhi Zheng Min Chen Brendan Lainhart Vincent Li Peter Felpo 《Tetrahedron letters》2008,49(51):7243-7245
Flavonols are an important class of natural products isolated from plants. Some glycosylated flavonols showed very interesting biological activities. A library of flavonols has been made through Algar-Flynn-Oyamada reaction from 2′-hydroxyacetophenones and benzaldehydes. Glycosylation of these flavonols with various glycosyl donors affords a library of glycosylated flavonols. These compounds are potentially useful pharmacologically active compounds and will be studied for biological activities. 相似文献
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以三聚氯氰(TCT)、2,4-二羟基二苯甲酮(UV-0)、双丙酮葡萄糖为原料,经三步反应合成一种具有反应性基团的水溶性紫外吸收剂3-(2-(2-羟基苯基苯甲酮-4-氧基)-4-氯-1,3,5-三嗪-6-氧基)-1,2-异丙叉-α-D-葡萄糖(UV-DTM),产物的结构经IR、NMR和MS表征。探讨了每一步反应的条件对反应产率的影响。合成3-(4,6-二氯-1,3,5-三嗪-2-氧基)-1,2,5,6-双异丙叉-α-D-葡萄糖(DTDT)的优化反应条件为:n(三聚氯氰)∶n(双丙酮葡萄糖)∶n(Na OH)=0.9∶1∶1.7,在丙酮和水的混合体系中0℃下反应8h,产率73%。合成3-(2-(2-羟基苯基苯甲酮-4-氧基)-4-氯-1,3,5-三嗪-6-氧基)-1,2,5,6双异丙叉-α-D-葡萄糖(UV-DT)的优化条件为:n(DTDT)∶n(UV-0)∶n(Na OH)=1∶1.1∶1,在丙酮和水的混合体系中30℃下反应2h,产率74%。合成UV-DTM的优化条件为:每1mmol UV-DT与0.5m L盐酸(36%)在THF体系中25℃下反应5h,产率74%。UV-DTM的紫外吸收性能在240~400 nm内表现良好,水溶性得到大幅改善。 相似文献
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Fahmi NE Dedkova L Wang B Golovine S Hecht SM 《Journal of the American Chemical Society》2007,129(12):3586-3597
Glycosylation of proteins can have a dramatic effect on their physical, chemical, and biological properties. Analogues of dihydrofolate reductase and firefly luciferase containing glycosylated amino acids at single, predetermined sites have been elaborated. Misacylated suppressor tRNAs activated with glycosylated serine and tyrosine derivatives were used for suppression of the nonsense codons in a cell-free protein biosynthesizing system, thereby permitting the preparation of the desired glycosylated proteins. In this fashion, it was possible to obtain proteins containing both mono- and diglycosylated amino acids, including glycosylated serine and tyrosine moieties. For the modified firefly luciferases, the effect of these substitutions on the wavelength of the light emitted by firefly luciferase was investigated. The maximum wavelength for mutants containing peracetylated glycosylated serine derivatives at position 284 showed a red shift in the emission spectra. For mutants containing glycosylated tyrosines, the red shift was observed only when the carbohydrate moiety was fully deacetylated. 相似文献