N-(tert-butoxycarbonyl)dopamine | 37034-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(tert-butoxycarbonyl)dopamine
• 英文别名: tert-butyl 3,4-dihydroxyphenethylcarbamate；N-Boc-dopamine；N-tert-butoxycarbonyl-3,4-dihydroxiphenylethylamine；N-tert-butoxycarbonyl-3,4-dihydroxyphenylethylamine；[2-(3,4-dihydroxy-phenyl)ethyl]carbamic acid tert-butyl ester；tert-butyl [2-(3,4-dihydroxyphenyl)ethyl]carbamate；tert-butyl N-[2-(3,4-dihydroxyphenyl)ethyl]carbamate
• CAS: 37034-31-4
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: MBDFUYZNHQSWRD-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  442.8±35.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-(tert-butoxycarbonyl)dopamine 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3,4-bis(pivaloyloxy)dopamine
  参考文献：
  名称：

  Brain-Specific Delivery of Dopamine Mediated by N,N-Dimethyl Amino Group for the Treatment of Parkinson’s Disease

  摘要：

  Parkinson's disease (PD) has become one of the most deadly diseases due to a lack of effective treatment. Herein, N-3,4-bis(pivaloyloxy)dopamine-3-(dimethylamino)propanamide (PDDP), a brain-specific derivative of dopamine, was designed and synthesized, which consists of a brain targeted ligand, N,N-dimethyl amino group, and two dipivaloyloxy groups for lipophilic modification. PDDP was investigated both in vitro and in vivo by comparing with L-DOPA and another derivative (BPD) without N,N-dimethyl amino group. PDDP showed a more pronounced accumulation in mouse brain microvascular endothelial cells (bEnd.3) than BPD via an active transport process. The increased cellular uptake of PDDP was proven to be mediated by putative pyrilamine cationic transporters. Following intravenous administration, the concentration of PDDP in the brain was 269.28-fold and 6.41-fold higher than that of L-DOPA and BPD at 5 min, respectively. Additionally, PDDP effectively attenuated the striatum lesion caused by 6-hydroxydopamine (6-OHDA) in rats. More importantly, PDDP presented antioxidant and antiapoptotic effects on 6-OHDA-induced toxicity in human neuroblastoma cells (SH-SY5Y). Thus, N,N-dimethyl amino group-based PDDP represents an effective and safe treatment for PD.

  DOI：

  10.1021/mp500352p
• 作为产物：
  描述：

  N-叔丁氧羰基-3-O-甲基多巴胺 在 氧气 、 copper(II) perchlorate 、 维生素 C 作用下， 以 水 为溶剂， 生成 N-(tert-butoxycarbonyl)dopamine
  参考文献：
  名称：

  通过使用Cu2（+）-抗坏血酸-O2系统将邻甲氧基苯酚氧化转化为邻苯二酚来提高5-脂氧合酶抑制活性。

  摘要：

  Cu2（+）-抗坏血酸-O2系统将几种复杂的邻甲氧基苯酚高选择性氧化为邻苯二酚。这样，邻甲氧基苯酚的RBL-1 5-脂氧合酶抑制活性大大提高。[6] -Norgingerol（4）是衍生自[6] -gingerol（3）的新型化合物，由于其高抑制力（IC50 = 5.0 x 10（-8）M），因此有望作为新药的先导化合物。 。

  DOI：

  10.1248/cpb.38.842

文献信息

• [EN] NOVEL HIGH PENETRATION DRUGS AND THEIR COMPOSITIONS THEREOF FOR TREATMENT OF PARKINSON DISEASES<br/>[FR] NOUVEAUX MÉDICAMENTS À PÉNÉTRATION ÉLEVÉE ET LEURS COMPOSITIONS POUR LE TRAITEMENT DE MALADIES DE PARKINSON
  申请人：TECHFIELDS PHARMA CO LTD

  公开号：WO2014139161A1

  公开（公告）日：2014-09-18

  One aspect of the invention provides a composition of novel high penetration compositions (HPC) or a high penetration prodrug (HPP) for treatment of Parkinson's disease. The HPCs/HPPs are capable of being converted to parent active drugs or drug metabolites after crossing the biological barrier and thus can render treatments for the conditions that the parent drugs or metabolites can. Additionally, the HPPs are capable of reaching areas that parent drugs may not be able to access or to render a sufficient concentration at the target areas and therefore render novel treatments. The HPCs/HPPs can be administered to a subject through various administration routes, e.g., locally delivered to an action site of a condition with a high concentration or systematically administered to a biological subject and enter the general circulation with a faster rate.

  本发明的方面之一提供了用于治疗帕金森病的新型高渗透组合物（HPC）或高渗透前药（HPP）。HPCs/HPPs能够穿过生物屏障后转化为母药活性药物或药物代谢物，因此能够对母药或代谢物能够治疗的疾病进行治疗。此外，HPPs能够到达母药可能无法进入的区域或在目标区域达到足够的浓度，从而实现新的治疗方法。HPCs/HPPs可以通过各种给药途径给药给受试者，例如，局部施用于具有高浓度的疾病作用部位，或者系统性地给药给生物受试者，并以更快的速率进入全身循环。
• Lithium Ion Recognition with Nanofluidic Diodes through Host–Guest Complexation in Confined Geometries
  作者：Mubarak Ali、Ishtiaq Ahmed、Patricio Ramirez、Saima Nasir、Salvador Mafe、Christof M. Niemeyer、Wolfgang Ensinger

  DOI：10.1021/acs.analchem.8b00902

  日期：2018.6.5

  bind with lithium ions and when the modified pore is exposed to different alkali metal chloride solutions separately, significant changes in the ion current and rectification are only observed for lithium chloride. This fact suggests the generation of positively charged B12C4–Li+ complexes on the pore surface. Furthermore, the nanofluidic diode is able to recognize the lithium ion even in the presence

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• Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150210682A1

  公开（公告）日：2015-07-30

  The invention provides novel compounds having the general formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有一般公式的新化合物： 其中R1、R2、R3、R4、R5和R6如本文所述，包括这些化合物的组合物和使用这些化合物的方法。
• [EN] NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION<br/>[FR] NOUVELLES DIHYDROQUINOLIZINONES POUR LE TRAITEMENT ET LA PROPHYLAXIE D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015113990A1

  公开（公告）日：2015-08-06

  The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.

  这项发明提供了具有一般式（I）的新化合物，其中R1、R2、R3、R4、R5和R6如本文所述，包括这些化合物的组合物以及在治疗乙型肝炎病毒方面使用这些化合物的方法。
• Easy access to drug building-blocks through benzylic C–H functionalization of phenolic ethers by photoredox catalysis
  作者：Tobias Brandhofer、Martin Stinglhamer、Volker Derdau、María Méndez、Christoph Pöverlein、Olga García Mancheño

  DOI：10.1039/d1cc01756j

  日期：——

  A visible light-mediated photocatalyzed C–C-bond forming method for the benzylic C–H functionalization of phenolether containing synthetic building blocks based on a radical-cation/deprotonation strategy is reported. This method allows the mild, selective generation of benzyl radicals in phenolic complex molecules and drug-like compounds, providing new entries in synthetic and medicinal chemistry.

  报道了一种基于自由基阳离子/去质子化策略的可见光介导的光催化 C - C 键形成方法，用于含合成结构单元的苯酚醚的苄基 C-H 官能化。该方法允许在酚类复合物分子和类药物化合物中温和、选择性地生成苄基，为合成和药物化学提供了新的入口。