5-(3-(3,4-dihydroxyphenethyl)thioureido)-2-(3-hydroxy-6-oxo-6H-xanthen-9-yl)benzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-(3-(3,4-dihydroxyphenethyl)thioureido)-2-(3-hydroxy-6-oxo-6H-xanthen-9-yl)benzoic acid
• 英文别名: 5-[2-(3,4-Dihydroxyphenyl)ethylcarbamothioylamino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid；5-[2-(3,4-dihydroxyphenyl)ethylcarbamothioylamino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₂₉H₂₂N₂O₇S
• 分子量: 542.569
• InChiKey: LPASOEPOBSTLLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Fluorescein isothiocyanate 、 盐酸多巴胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以55%的产率得到5-(3-(3,4-dihydroxyphenethyl)thioureido)-2-(3-hydroxy-6-oxo-6H-xanthen-9-yl)benzoic acid
  参考文献：
  名称：

  单/二羟基苯甲酸酯和苯酚吡啶鎓衍生物作为哺乳动物碳酸酐酶同工型I，II，VII，IX，XII和XIV的抑制剂

  摘要：

  以羟基/二羟基苯甲酸为先导，一系列4-羟基苯甲酸，2,4-，2,5-，2,6-，3,4-和3的甲基，乙基和异丙基酯获得了5-5-羟基苯甲酸和香豆酸，并研究了其对六种哺乳动物碳酸酐酶（CA，EC 4.2.1.1）同工型，即胞质CA I，II和VII以及跨膜CA IX的抑制作用， XII和XIV，其中许多是确定的药物靶标。从多巴胺中通过与异硫氰酸荧光素或与2,4,6-三取代的吡啶鎓盐反应，可以得到掺入苯酚/邻苯二酚基团的其他化合物。通过使用吡喃鎓盐，一些氨基酚也以类似的方式衍生化。与从中获得的先导化合物相比，这些化合物中的许多都显示出更高的抑制作用，对大多数研究过的CA同工型具有亚微摩尔范围内的功效。与苯磺酰胺相比，由于苯酚是一类研究较少的CA抑制剂（CAI），并且对它们的抑制机理了解得很少，因此此处设计的这类化合物可能有助于深入了解这些现象。

  DOI：

  10.1016/j.bmc.2012.05.019

文献信息

• Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV
  作者：Fabrizio Carta、Daniela Vullo、Alfonso Maresca、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2012.05.019

  日期：2013.3

  Using hydroxy-/dihydroxybenzoic acids as leads, a series of methyl, ethyl and iso-propyl esters of 4-hydroxy-benzoic acid, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acids and of coumaric acid, were obtained and investigated for the inhibition of six mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms, that is, the cytosolic CA I, II and VII, and the transmembrane CA IX, XII and XIV, many

  以羟基/二羟基苯甲酸为先导，一系列4-羟基苯甲酸，2,4-，2,5-，2,6-，3,4-和3的甲基，乙基和异丙基酯获得了5-5-羟基苯甲酸和香豆酸，并研究了其对六种哺乳动物碳酸酐酶（CA，EC 4.2.1.1）同工型，即胞质CA I，II和VII以及跨膜CA IX的抑制作用， XII和XIV，其中许多是确定的药物靶标。从多巴胺中通过与异硫氰酸荧光素或与2,4,6-三取代的吡啶鎓盐反应，可以得到掺入苯酚/邻苯二酚基团的其他化合物。通过使用吡喃鎓盐，一些氨基酚也以类似的方式衍生化。与从中获得的先导化合物相比，这些化合物中的许多都显示出更高的抑制作用，对大多数研究过的CA同工型具有亚微摩尔范围内的功效。与苯磺酰胺相比，由于苯酚是一类研究较少的CA抑制剂（CAI），并且对它们的抑制机理了解得很少，因此此处设计的这类化合物可能有助于深入了解这些现象。
• Toward live-cell imaging of dopamine neurotransmission with fluorescent neurotransmitter analogues
  作者：Hui-Jen Lin、Hsueh-Han Lu、Kuan-Miao Liu、Chi-Min Chau、You-Zung Hsieh、Yaw-Kuen Li、Ian Liau

  DOI：10.1039/c5cc03050a

  日期：——

  We report a novel ‘fluorescent dopamine’ that possesses essential features of natural dopamine.

  我们报道了一种新型的“荧光多巴胺”，它具有天然多巴胺的关键特征。
• DENDRIMER, DENDRIMER HAVING FUNCTIONAL GROUP AND ANTIBODY
  申请人：NATIONAL CHIAO TUNG UNIVERSITY

  公开号：US20160222173A1

  公开（公告）日：2016-08-04

  A dendrimer represented by formula (I): G0-G10 represent a generation 0-10 dendrimer; the dendrimer has a plurality of branches; each branch has a terminal group; and n is an integer of 4-4096.
• ANTIBODY
  申请人：NATIONAL CHIAO TUNG UNIVERSITY

  公开号：US20170342217A1

  公开（公告）日：2017-11-30

  An antibody includes a polyamidoamine (PAMAM) dendrimer and a first functional group. The polyamidoamine (PAMAM) dendrimer includes a plurality of branches and each of the branches has a phenylboronic acid (PBA) terminal group. The first functional group is bonded to at least one of the PBA terminal groups.
• Facile Method for Preparing Surface-Mounted Cucurbit[8]uril-Based Rotaxanes
  作者：Chi Hu、Yang Lan、Feng Tian、Kevin R. West、Oren A. Scherman

  DOI：10.1021/la5026125

  日期：2014.9.16

  Surface-immobilized rotaxanes are of practical interest for myriad applications including molecular rotors and analytical sensing. Herein, we present a facile method for the preparation of cucurbit[8]uril (CB[8])-based rotaxanes on gold (Au) surfaces threaded onto a viologen (MV2+) axle. The surface-bound CB[8] rotaxanes were characterized by contact angle measurements and optical microscopy. Direct imaging of the rotaxanes was accomplished by attaching either azobenzene-functionalized silica (Si-azo) colloids or fluorescein-labeled dopamine that were bound to the Au surface through a supramolecular heteroternary (1:1:1) complex with CB[8]. The surface density of CB[8] rotaxanes was examined based on their detection of dopamine. The calculated surface density is 4.8 x 10(13) molecules.cm(-2), which is only slightly lower than the theoretical value of 5.0 x 10(13) molecules.cm(-2). Surface-functionalized rotaxanes can be reversibly switched using external stimuli to bind electron-rich second guests for CB[8], including both small molecules such as dopamine and appropriately-functionalized colloidal particles. Such controlled reversibility gives rise to potential applications including selective sensing or reusable templates for preparing well-defined colloidal arrays. The formation of the surface-bound rotaxane structure is critical for successfully anchoring CB[8] host molecules onto Au substrates, yielding an interlocked architecture and preventing the dissociation of binary host-guest complex MV2+subset of CB[8]. The MV2+subset of CB[8] rotaxane structure thus effectively maintains the material density on the Au surface and dramatically enhances the stability of the functional surface.