One step synthesis of indirubins by reductive coupling of isatins with KBH4

One step synthesis of the natural product indirubin by reductive coupling of isatin with KBH₄ is described and a possible mechanism for the reaction is proposed. Eleven indirubin derivatives were obtained easily from the corresponding substituted isatin.     

超临界CO_2萃取板蓝根靛玉红的工艺优化研究

采用正交试验法,对板蓝根靛玉红超临界CO2萃取工艺进行优化。选用萃取温度、萃取压力、萃取时间作为正交试验的3个因素,每个因素选3个水平,以提取物中靛玉红的含量来确定最佳提取条件,并且在最佳条件下确定所加夹带剂的最佳剂量。结果表明最佳工艺为:萃取温度45℃、萃取压力35MPa、萃取时间3h,夹带剂为75%的乙醇200mL。最佳工艺条件下提取靛玉红的得率为4.95μg/g,为传统提取方法的1.6倍。     

Electrochemical monitoring of indigo preparation using Maya’s ancient procedures

The preparation of indigo from Indigofera suffruticosa following the procedures attributed to ancient Mayas was electrochemically monitored using the voltammetry-of-microparticles approach. The mechanism formation of indigotin and indirubin from its precursors, indican and isatan, is discussed. Comparison of voltammetric profiles for differently prepared and commercial indigos and genuine Maya Blue samples suggests that the preparation procedure of indigo changed during the Late Classical Maya period. Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users.     

Structural and Antileukemic Studies ofIndirubin Derivatives

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Improved Synthesis of Indirubin Derivatives by Sequential Build‐Up of the Indoxyl Unit: First Preparation of Fluorescent Indirubins

Indirubin, present in extracts of Isatis tinctoria and some other plant species, has promising cytotoxicity against a variety of cell lines by inhibition of cyclin‐dependent kinases. Chemical synthesis of its derivatives relies on the combination of isatins and 2,3‐dihydro‐1H‐indol‐3‐one (‘indoxyl’) derivatives and usually yields indigo as well as other by‐products. Inspection of the hydrolysis of the long‐known condensation products of 2‐thioxothiazolidin‐4‐one with isatins gave useful hints for an improved synthesis of indirubins: this reaction does not yield quinoline derivatives but 2‐(2,3‐dihydro‐2‐oxo‐1H‐indol‐3‐ylidene)‐2‐sulfanyl acetic acids. By substitution of the sulfanyl group in this oxindoles with anilines and straightforward cyclization under Nazarov conditions, a broad variety of indirubins substituted in the indoxyl ring system are thus available, usually in very good purity and yield. Use of naphthylamines in this reaction sequence yields various fluorescent substances with λ_fl at ca. 630 nm.     

小波变换-人工神经网络用于反相高效液相色谱法同时测定靛蓝和靛玉红

提出了小波变换-人工神经网络(WT-ANN)和小波变换-稳健回归(WT-RR)两算法的数学模型,并应用于高效液相色谱法测定板蓝根、大青叶及中成药复方板蓝根颗粒中靛蓝及靛玉红的测定,从而避免了繁琐的分离,实现了被测组分的直接、同时测定。所用色谱柱为Extend C18(4.6 mm×250 mm,5μm),所用流动相为甲醇与水(95+5)的混合溶液。由测得的相对标准偏差(RSD)可知两算法均可用于试样中多组分的测定,但WT-ANN法(RSD<0.6%)稍优于WT-RR法(RSD<2.5%)。三种实样的分析应用中,回收率在98.8%~101.5%之间。此方法可作为工业生产中在线分析法。     

Design, synthesis and anti-proliferative studies of a novel series of indirubin derivatives

<正>A series of novel derivatives of indirubin were synthesized and evaluated for their anti-proliferative activity against human cancer cell lines of SGC7901,A549,HL-60,SK-BR-3 and HCT116.Most of the compounds displayed more potent activity than Sunitinib.In addition,the derivatives showed improved water solubility,which may be favorable to their pharmacokinetic performances.     

First synthesis of indirubin N-glycosides (red sugars)

The first indirubin N-glycosides were prepared by reaction of isatine N-glycosides with indoxyl acetate under basic conditions.     

微分脉冲伏安法测定靛玉红的研究

在含10 % (φ)丙酮的0.10mol/LNa2HPO4 底液中 ,可获得灵敏的靛玉红还原峰 ,峰电位为 -0.600V(vsAg/AgCl)。峰电流与靛玉红的浓度在3.8×10-8 ～2.6×10-6 mol/L范围内呈线性关系 ,检出限为2.1×10-9mol/L。该文还初步探讨了靛玉红的电化学行为。     

靛玉红类CDK1抑制剂的同源模建、分子对接及3D-QSAR研究

细胞周期蛋白依赖性激酶1的异常表达会导致G2期的停滞及多种肿瘤的发生,故CDK1近年来已成为一个理想的治疗靶点. 本文以细胞分裂调控蛋白2的同源体为模板,同源模建了CDK1的结构,并与靛玉红类小分子抑制剂进行分子对接. 分别运用三种叠合方法进行分子叠合,并在此基础上采用Sybyl 7.1中的比较分子场分析(CoMFA)模块及Discovery Studio 3.0中的三维定量构效关系(3D-QSAR)模块(以下简称为DS)分别建立了3D-QSAR模型. 其中,将分子对接叠合与公共骨架叠合联合运用的叠合方法所得3D-QSAR模型的评价参数是最佳的(CoMFA：q²=0.681,r²=0.909,r_pred.²=0.836; DS：q²=0.579,r²=0.971,r_pred.²=0.795,其中q²为交叉验证系数,r²为非交叉验证系数). 本文的研究结果在对靛玉红类小分子进行结构修饰设计出新的CDK1抑制剂方面,可提供重要的理论基础.