N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine | 37034-22-3

• 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: N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine
• 英文别名: benzyl 3,4-dihydroxyphenethylcarbamate；N-(benzyloxycarbonyloxy)dopamine；N-benzyloxycarbonyldopamine；N-(carbobenzyloxy)dopamine；N-Carbobenzyloxy dopamine；(3,4-dihydroxy-phenethyl)-carbamic acid benzyl ester；benzyl N-[2-(3,4-dihydroxyphenyl)ethyl]carbamate
• CAS: 37034-22-3
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: XEVWDUMEFJXJOU-UHFFFAOYSA-N

物化性质

• 溶解度：
  DCM、乙醚

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine 在 potassium fluoride 、 N,N-硫酰二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以80%的产率得到N-(carbobenzyloxy)dopamine cyclic sulfate
  参考文献：
  名称：

  An Efficient Synthesis of Catechol Cyclic Sulfates

  摘要：

  A mild and efficient synthesis of catechol cyclic sulfates using N,N'-sulfuryldiimidazole and potassium fluoride is described.

  DOI：

  10.1080/00397919408010165
• 作为产物：
  描述：

  N-Carbobenzoxy-homovanillylamin 在 氧气 、 copper(II) perchlorate 、 维生素 C 作用下， 以 水 、 丙酮 为溶剂， 反应 43.0h， 以21%的产率得到N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine
  参考文献：
  名称：

  Aihara, Kazuhiro; Higuchi, Tsunehiko; Hirobe, Masaaki, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 2, p. 837 - 840

  摘要：

  DOI：

文献信息

• Synthesis of glycosyl derivatives as dopamine prodrugs: interaction with glucose carrier GLUT-1Electronic supplementary information (ESI) available: experimental details for the preparation of all derivatives and biological assays. See http://www.rsc.org/suppdata/ob/b2/b212066f/
  作者：Caridad Fernández、Ofelia Nieto、José Angel Fontenla、Emilia Rivas、María L. de Ceballos、Alfonso Fernández-Mayoralas

  DOI：10.1039/b212066f

  日期：2003.2.27

  Glucosyl dopamine (DA) derivatives may represent a new class of DA prodrugs that would interact with glucose transporter GLUT-1, present in the blood–brain barrier, and generate DA in the brain. Therefore, compounds bearing the sugar moiety linked to either the amino group or the catechol ring of DA through amide, ester, carbamate, peptide or glycosidic bonds were synthesized. The behavior of the compounds as prodrugs was monitored in different media and the affinity of the glycoconjugates for the glucose carrier GLUT-1 using human erythrocytes was also studied. Most of the compounds were markedly stable in buffer and plasma, and several compounds released DA when incubated with brain extracts and the rate was related to the bond linking DA with glucose. The new glucosyl conjugates substituted at the C-6 position of the sugar were more potent inhibitors of glucose transport when compared to C-1 and C-3 substituted derivatives. This work provides structure–activity information about the interaction of substituted glucose with the GLUT-1 transporter.

  葡萄糖多巴胺（DA）衍生物可能代表一类新型DA前药，它们与存在于血脑屏障中的葡萄糖转运体GLUT-1相互作用，并在脑内生成DA。因此，通过酰胺、酯、氨基甲酸酯、肽或糖苷键将糖部分连接到DA的氨基或儿茶酚环上的化合物被合成出来。监测了这些化合物在不同介质中的前药行为，并研究了糖 conjugate 对人体红细胞中葡萄糖载体GLUT-1的亲和力。大多数化合物在缓冲液和血浆中显著稳定，几种化合物在与脑提取物共孵育时释放DA，且速率与DA与葡萄糖之间的连接键相关。与C-1和C-3取代的衍生物相比，在糖的C-6位取代的新型葡萄糖 conjugate 对葡萄糖转运的抑制作用更强。这项工作提供了关于取代葡萄糖与GLUT-1转运体相互作用的结构-活性信息。
• Tri- and Tetravalent Photoactivable Cross-Linking Agents
  作者：Jacqueline Marchand-Brynaert、Alexandre Welle、François Billard

  DOI：10.1055/s-0031-1290444

  日期：2012.7

  Abstract A modular synthesis of photoactivable cross-linking agents is described, using an aromatic core, di- or triethyleneglycol spacers and photoaffinity labeling synthons that feature either perfluorophenyl azide or aryl(trifluoromethyl)diazirine motifs. Symmetrical and nonsymmetrical trivalent structures were obtained from phloroglucinol and dopamine, respectively. Symmetrical tetravalent structures

  摘要 描述了使用芳族核，二乙二醇或三乙二醇间隔基和具有全氟苯基叠氮化物或芳基（三氟甲基）二嗪基序的光亲和标记合成子的光活化交联剂的模块合成。分别从间苯三酚和多巴胺获得对称和不对称的三价结构。对称的四价结构是由于两种多巴胺衍生物与草酰氯的偶合。 描述了使用芳族核，二乙二醇或三乙二醇间隔基和具有全氟苯基叠氮化物或芳基（三氟甲基）二嗪基序的光亲和标记合成子的光活化交联剂的模块合成。分别从间苯三酚和多巴胺获得对称和不对称的三价结构。对称的四价结构是由于两种多巴胺衍生物与草酰氯的偶合。
• Gd‐DTPA‐Dopamine‐Bisphytanyl Amphiphile: Synthesis, Characterisation and Relaxation Parameters of the Nanoassemblies and Their Potential as MRI Contrast Agents
  作者：Abhishek Gupta、Scott A. Willis、Lynne J. Waddington、Tim Stait‐Gardner、Liliana de Campo、Dennis W. Hwang、Nigel Kirby、William S. Price、Minoo J. Moghaddam

  DOI：10.1002/chem.201501905

  日期：2015.9.28

  Here, a new amphiphilic magnetic resonance imaging (MRI) contrast agent, a GdIII‐chelated diethylenetriaminepentaacetic acid conjugated to two branched alkyl chains via a dopamine spacer, Gd‐DTPA‐dopamine‐bisphytanyl (Gd‐DTPA‐Dop‐Phy), which is readily capable of self‐assembling into liposomal nanoassemblies upon dispersion in an aqueous solution, is reported. In vitro relaxivities of the dispersions

  在这里，一种新的两亲磁共振成像（MRI）造影剂，一种Gd III螯合的二亚乙基三胺五乙酸通过多巴胺间隔物Gd-DTPA-多巴胺-双植烷酰基（Gd-DTPA-Dop-Phy）与两个分支烷基链共轭，据报道，当分散在水溶液中时，它很容易自组装成脂质体纳米组装体。发现分散体的体外弛豫度在0.47 T时要比市售造影剂Magnevist高得多，但在9.40 T时是可比的。可变温度17 O NMR横向弛豫测量的分析表明，纳米组件的水交换更快比以前报道的顺磁性脂质体要多。分子重新定向动力学由1探测使用经典的内部和外部球面松弛模型以及Lipari-Szabo“无模型”方法进行H NMRD谱分析。仅由Gd-DTPA-Dop-Phy两亲物制成的脂质体纳米组件中具有高有效载荷的Gd III离子，再加上缓慢的分子重新定向和快速的水交换，使得这种新型两亲物成为适合作为先进MRI造影剂进行研究的候选物。
• Preparation for endermism containing dopamine derivatives
  申请人：Sansho Co., Ltd.

  公开号：US05246949A1

  公开（公告）日：1993-09-21

  (A) a diacylated dopamine derivative represented by the formula (I): ##STR1## wherein R.sup.1 represents an alkyl group having 3 to 7 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, substituted or unsubstituted phenyl group or a substituted or unsubstituted nitrogen-containing heterocyclic group; and R.sup.2 represents a hydrogen atom or a lower alkyl group; or a salt thereof; and (B) one or more compounds selected from lactic acid esters, fatty acid monoglycerides and higher alcohols; optionally together with (C) an unsaturated fatty acid monohydric alcohol ester. This preparation has a sustained effect, a high skin permeability and a low skin irritativeness.

  （A）由以下公式（I）表示的二酰化多巴胺衍生物：其中R.sup.1代表具有3至7个碳原子的烷基基团、具有3至6个碳原子的环烷基基团、取代或未取代的苯基团或取代或未取代的含氮杂环基团；R.sup.2代表氢原子或较低烷基基团；或其盐；以及（B）选自乳酸酯、脂肪酸单甘油酯和较高醇类化合物的一个或多个化合物；可选地与（C）不饱和脂肪酸单羟基醇酯一起。该制剂具有持久效果、高皮肤透过性和低皮肤刺激性。
• Effect of Enzymatic Sulfation on Biochemical and Pharmacological Properties of Catecholamines and Tyrosine-Containing Peptides.
  作者：Lisa KONISHI-IMAMURA、Dong-Hyun KIM、Kyuichi KOBASHI

  DOI：10.1248/cpb.39.2994

  日期：——

  Substrate specificity of a novel sulfotransferase produced by Eubacterium A-44 isolated from human feces has been studied. Phenolic drugs, catecholamines, were good acceptors of this bacterial enzyme. With regard to dopamine, sulfation mostly occurred at the 4-aromatic hydroxy group.We also investigated the effects of enzymatic sulfaction on pharmacologically active phenolic compounds. Sulfation of phenolic compounds generally led to inactivation (e.g. tyramine and Leu-enkephalin), with the exception of cholecystokinin (CCK) and some gastrointestinal peptides. Proteolytic hydrolysis in vitro did not occur at the C-terminal of the sulfated tyrosine residues of peptices such as Leu-enkephalin and kyotorphin. These results suggest that the sulfation by bacterial enzyme plays an important role in detoxification, activation and stability of phenolic compounds in the human body.

  研究人员对从人类粪便中分离出来的 A-44 脂肪酸杆菌所产生的一种新型磺基转移酶的底物特异性进行了研究。酚类药物、儿茶酚胺是这种细菌酶的良好受体。我们还研究了酶硫酸化对具有药理活性的酚类化合物的影响。除了胆囊收缩素（CCK）和一些胃肠肽外，酚类化合物的硫酸化通常会导致失活（如酪胺和亮脑啡肽）。在体外，硫酸化酪氨酸残基（如亮烯脑啡肽和京吗啡）的 C 端不会发生蛋白水解。这些结果表明，细菌酶的硫酸化作用在人体内酚类化合物的解毒、活化和稳定性方面发挥着重要作用。