thiosulfuric acid S-(2-amino-5-diethylamino-3-methylphenyl) ester | 94582-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: thiosulfuric acid S-(2-amino-5-diethylamino-3-methylphenyl) ester
• 英文别名: 2-amino-3-methyl-5-diethylaminophenylthiosulphonic acid；Thiosulfuric acid S-(2-amino-5-diethylamino-3-methyl-phenyl)ester；2-amino-5-(diethylamino)-1-methyl-3-sulfosulfanylbenzene
• CAS: 94582-84-0
• 化学式: C₁₁H₁₈N₂O₃S₂
• 分子量: 290.408
• InChiKey: KKQVJOVVPDRISR-UHFFFAOYSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  thiosulfuric acid S-(2-amino-5-diethylamino-3-methylphenyl) ester 、 1,6-二羟基萘 在 potassium dichromate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以68%的产率得到9-diethylamino-2-hydroxy-11-methyl-benzo[a]phenoxazin-5-one
  参考文献：
  名称：

  Probing lipid- and drug-binding domains with fluorescent dyes

  摘要：

  A series of 2- and 3-OH Nile red dyes was prepared in order to generate water-soluble probes that could be used to probe lipid binding to proteins. Various substitutions in positions 243-, 6-, and 7-shifted wavelengths while maintaining the environmental sensitivity of Nile red. In order to increase the solubility of the dyes in aqueous solutions, we attached butyric acid groups to the 2- or 3-OH position. In addition., phenothiazine dyes, which exhibited particularly long excitation properties, were synthesized and tested for the first time. All dyes showed Stoke's shifts of 70-100 nm and changes in excitation and emission of over 100 nm, depending on the hydrophobicity of the environment. Binding studies with bovine serum albumin and the non-specific lipid transfer protein SCP2 revealed emission changes of more than 30 nm upon binding to the protein and a five-fold increase in emission intensity. Titration of the dye-loaded proteins with various lipids or drugs replaced the dye and thereby reversed the shift in wavelength intensity. This allowed us to estimate the lipid binding affinity of the investigated proteins. For SCP2, isothermal calorimetry (ITC) data verified the titration experiments. NMR titration experiments of SCP2 with Nile red 2-O-butyric acid (1a) revealed that the dye is bound within the lipid binding pocket and competes with lipid ligands for this binding site. These results give valuable insight into lipid and drug transport by proteins outside and inside cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.080

文献信息

• Phenothiazinium photosensitisers IX. Tetra- and pentacyclic derivatives as photoantimicrobial agents
  作者：Mark Wainwright、Katie Meegan、Ciara Loughran

  DOI：10.1016/j.dyepig.2011.02.001

  日期：2011.10

  Methylene blue derivatives, synthesised as novel photosensitising agents are usually simple auxochromic variations on the lead compound. The current paper represents the initial report on the synthesis and biological testing of a new class of phenothiazinium derivatives, having either one or two tetrahydropyridine rings fused to the phenothiazinium chromophore. The derivatives exhibited extended absorption

  作为新型光敏剂合成的亚甲蓝衍生物通常是铅化合物上的简单的变色变体。目前的论文代表了有关新的一类吩噻嗪鎓衍生物的合成和生物学测试的初步报告，该衍生物具有一个或两个与噻吩噻嗪鎓发色团稠合的四氢吡啶环。与亚甲基蓝相比，这些衍生物表现出扩展的吸收波长，增加的两亲特性和更大的光抗菌作用，甚至比二甲基亚甲基蓝更有效。这类光敏剂的高活性建议将其用于局部和血液产品净化中的感染控制。
• Fluorescent compounds for monitoring protein-lipid binding
  申请人：EUROPÄISCHES LABORATORIUM FÜR MOLEKULARBIOLOGIE (EMBL)

  公开号：EP1595872A1

  公开（公告）日：2005-11-16

  The invention refers to compounds according to formula I wherein R1 is independently in position 2', 3', or both of the A ring of the compound and is hydroxyl, linear or branched -O-alkyl with 1-12, preferably 3-8, more preferably 4 carbon atoms, -O-carboxylic acid with 1-12, preferably 3-8, more preferably 4 carbon atoms, -O-aromatic compound, linear or branched -O-(CH2)m-CH(NH2)-COOH with m = 1-6, preferably m= 2-4, or any combination thereof, R2 and R3 independently are F, Cl, Br, I, H, CN, -CH=CH-alkyl, -C≡C-alkyl, or an aromatic compound, X is O or S, R4 is in position 8', 10', or 11' of the D ring of the compound and is H or (CH2)n-CH3 with n = 0-6, COOH, CN, or halogen R5 and R6 independently are ethyl-, methyl-, H, or -(CH2)3 connected to position 8 or 10 of the D ring of the fluorescent dye, except compounds according to formula I wherein R1 is 2' or 3' - hydroxyl or 2' -O-(CH2)5-COOH, R2, R3, and R4 are H, X is O, and R5 and R6 are ethyl. The invention further refers to the use of the compounds according to formula I as environmentally sensitive fluorescent dyes. They particularly lend themselves to measure the binding of ligands to lipid binding sites of proteins. They can also be used in an assay for performing this measurement.

  该发明涉及到符合以下式I的化合物，其中R1独立地位于化合物的A环的2'、3'或两者位置，且为羟基、线性或支链的-O-烷基（具有1-12，优选3-8，更优选4个碳原子）、-O-羧酸（具有1-12，优选3-8，更优选4个碳原子）、-O-芳香化合物、线性或支链的-O-(CH2)m-CH(NH2)-COOH（其中m = 1-6，优选m= 2-4），或者以上任意组合；R2和R3独立地为F、Cl、Br、I、H、CN、-CH=CH-烷基、-C≡C-烷基，或芳香化合物；X为O或S；R4位于化合物的D环的8'、10'或11'位置，为H或( )n-CH3（其中n = 0-6）、COOH、CN或卤素；R5和R6独立地为乙基基、甲基基、H，或-( )3连接到荧光染料的D环的8或10位置，除了符合式I的化合物，其中R1为2'或3'-羟基或2'-O-( )5-COOH，R2、R3和R4为H，X为O，R5和R6为乙基。该发明还涉及将符合式I的化合物用作对环境敏感的荧光染料。它们特别适用于测量配体与蛋白质的脂质结合位点的结合。它们也可用于进行此测量的分析。
• Fluorescent Method And Compounds To Monitor Protein-Lipid Binding
  申请人：Schultz Carsten

  公开号：US20080038840A1

  公开（公告）日：2008-02-14

  The invention refers to compounds according to formula (I), wherein R 1 is independently in position 2′, 3′, or in both positions of the A ring and is hydroxyl, linear or branched -0-alkyl, wherein the alkyl group has 1-12 carbon atoms, preferably 3-8, more preferably 4 carbon —O-(alkyl)COOH wherein the alkyl group has 1-12 carbon atoms, preferably 3-8, more preferably 4 carbon atoms, —O-(aryl)COOH, -0-aryl, linear or branched —O—(CH 2 ) m —CH(NH 2 )—COOH with m=1-6, preferably m=2-4, or any combination thereof; R 4 is in position 8′, 10′, or 11′ of the D ring of the compound and is H or (CH 2 ) n —CH 3 with n=0-6, COOH, CN, or halogen, R 5 and R 6 independently are ethyl-, methyl-, H, or —(CH 2 ) 3 connected to position 8 or 10 of the D ring, and wherein provided that X is O, R 2 is F, Cl, Br, I, H, CN, —CH═CH-alkyl, —C═—C-alkyl, aryl and R 3 is F, Cl, Br, I, CN, —CH═CH-alkyl, —C═C-alkyl, aryl an provided that X is S, R 2 and R 3 independently are F, Cl, Br, I, H, CN, —CH═CH-alkyl, —C═C-alkyl, aryl. The invention further refers to the use of the compounds according to formula (I), wherein R 1 , R 4 , R 5 and R 6 are defined as aforementioned and wherein R 2 and R 3 independently are F, Cl, Br, I, H, CN, —CH═CH-alkyl, —C═—C-alkyl, or aryl, and wherein X is O or S, as environmentally sensitive fluorescent dyes, particularly in an assay for identifying proteinlipid interactions.

  该发明涉及公式（I）的化合物，其中R1独立于A环的2'、3'位置或两个位置，并且为羟基，线性或支链状-0-烷基，其中烷基具有1-12个碳原子，优选3-8个，更优选4个碳-O-（烷基）COOH，其中烷基具有1-12个碳原子，优选3-8个，更优选4个碳原子，-O-（芳基）COOH，-0-芳基，线性或支链状-O-（CH2）m-CH（NH2）-COOH，其中m = 1-6，优选m = 2-4或任何组合；R4在化合物的D环的8'、10'或11'位置，并且为H或（ ）n-CH3，其中n = 0-6，COOH，CN或卤素，R5和R6独立地为乙基，甲基，H或-（ ）3连接到D环的8或10位置，其中如果X为O，则R2为F，Cl，Br，I，H，CN，-CH═CH-烷基，-C═-C-烷基，芳基，而R3为F，Cl，Br，I，CN，-CH═CH-烷基，-C═C-烷基，芳基，如果X为S，则R2和R3独立地为F，Cl，Br，I，H，CN，-CH═CH-烷基，-C═C-烷基，芳基。该发明还涉及公式（I）的化合物的用途，其中R1、R4、R5和R6如上所述，并且R2和R3独立地为F，Cl，Br，I，H，CN，-CH═CH-烷基，-C═-C-烷基或芳基，而X为O或S，作为环境敏感荧光染料，特别是在识别蛋白质脂质相互作用的分析中。
• [EN] COMPOUNDS METHOD AND USE<br/>[FR] COMPOSÉS, PROCÉDÉ ET UTILISATION
  申请人：PHARMALUCIA LTD

  公开号：WO2009047534A2

  公开（公告）日：2009-04-16

  The present invention relates to compounds of Formula 4 and to antimicrobial compounds and antimicrobial compositions based on the compounds of Formula 4: wherein: X comprises sulphur or selenium; Y comprises a pharmaceutically acceptable anion; R1 and R9 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkoxyl, optionally substituted amine or halogen; and R3a, R3b, R7a and R7b are each independently H or optionally substituted alkyl with the proviso that at least one of R3a or R3b and/or R7a or R7b together with the nitrogen atoms to which they are attached form an optionally substituted, optionally saturated 6 or 7-membered ring with R2 or R4 and/or R6 or R8 respectively; and R2, R4, R6, and R8 are each independently, hydrogen, optionally substituted alkyl, optionally substituted alkoxyl, or halogen, so long as at least one of R2, R4, R6 or R8 together with the atoms to which they are attached form an optionally substituted, optionally saturated 6 or 7-membered ring with R3a or R3b and/or R7b or R7a respectively; and with the proviso that the compounds are not of Formula 3a or 3b.