methyl 3-bromo-2-((tert-butoxycarbonyl)amino)propanoate | 1219200-16-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-bromo-2-((tert-butoxycarbonyl)amino)propanoate
• 英文别名: methyl 3-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1219200-16-4
• 化学式: C₉H₁₆BrNO₄
• 分子量: 282.134
• InChiKey: ODLDPRMMKCMNMD-UHFFFAOYSA-N

物化性质

• 沸点：
  322.3±32.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  methyl 3-bromo-2-((tert-butoxycarbonyl)amino)propanoate 、 甲巯咪唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以87%的产率得到methyl 2-[(tert-butoxycarbonyl)amino]-3-(3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazol-1-yl)propanoate
  参考文献：
  名称：

  Inhibitory effects of novel synthetic methimazole derivatives on mushroom tyrosinase and melanogenesis

  摘要：

  In this study, we synthesized 4 methimazole (2-mercapto-1-methylimidazole, MMI) derivatives. The kinetics of inhibition on mushroom tyrosinase by methimazole and its derivatives were investigated. The results indicated that tert-butyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate (compound 3; 3), 2-mercaptoimidazole (MI; compound 1; 1) and MMI (compound 2; 2) significantly inhibited tyrosinase activity in a dose-dependent manner, exhibiting an IC50 value of 1.50 mM, 4.11 mM, and 1.43 mM. However, compound 4 (4), compound 5 (5), and compound 6 (6) exerted no inhibitory effect on mushroom tyrosinase activity. Kinetic analysis indicated that 3 was a noncompetitive tyrosinase inhibitor, whereas both 1 and 2 were exhibited as mixed-type tyrosinase inhibitors. Furthermore, 3 exerted a potent inhibitory effect on intracellular melanin formation in the B16/F10 murine melanoma cells and did not cause cytotoxicity, as 1 and 2 did. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-SA license (http://creativecommons.org/licenses/by-nc-sa/3.0/).

  DOI：

  10.1016/j.bmc.2014.03.009
• 作为产物：
  描述：

  2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 3-bromo-2-((tert-butoxycarbonyl)amino)propanoate
  参考文献：
  名称：

  [EN] LIQUID COMPOSITIONS COMPRISING A LEVODOPA AMINO ACID CONJUGATE AND USES THEREOF
  [FR] COMPOSITIONS LIQUIDES COMPRENANT UN CONJUGUÉ D'ACIDES AMINÉS DE LÉVODOPA ET LEURS UTILISATIONS

  摘要：

  本文披露了包含左多巴氨基酸共轭物的液体药物配方，该共轭物可能进一步包含一个脱羧酶抑制剂，如卡比多巴，一种抗氧化剂，一种溶剂或任何其他药学上可接受的辅料。进一步披露了治疗神经退行性疾病和/或大脑中多巴胺水平降低的疾病的方法，例如帕金森病，包括给予披露的液体药物配方。还披露了LDAA共轭物化合物。

  公开号：

  WO2021044420A1

文献信息

• Palladium-Catalyzed Synthesis of (Hetero)Aryl Alkyl Sulfones from (Hetero)Aryl Boronic Acids, Unactivated Alkyl Halides, and Potassium Metabisulfite
  作者：Andre Shavnya、Kevin D. Hesp、Vincent Mascitti、Aaron C. Smith

  DOI：10.1002/anie.201505918

  日期：2015.11.9

  A palladium‐catalyzed one‐step synthesis of (hetero)aryl alkyl sulfones from (hetero)arylboronic acids, potassium metabisulfite, and unactivated or activated alkylhalides is described. This transformation is of broad scope, occurs under mild conditions, and employs readily available reactants. A stoichiometric experiment has led to the isolation of a catalytically active dimeric palladium sulfinate

  描述了由（杂）芳基硼酸，偏亚硫酸氢钾和未活化或活化的烷基卤化物以钯催化一步合成（杂）芳基烷基砜的方法。这种转化是广泛的，发生在温和的条件下，并使用容易获得的反应物。一个化学计量的实验导致了具有催化活性的二聚亚磺酸钯钯配合物的分离，该复合物通过X射线衍射分析进行了表征。
• [EN] LEVODOPA-PRODRUGS AND CARBIDOPA-PRODRUGS FOR USE IN THE TREATMENT OF PARKINSON'S DISEASE<br/>[FR] PROMÉDICAMENTS LEVODOPA ET PROMÉDICAMENTS CARBIDOPA POUR LE TRAITEMENT DE LA MALADIE DE PARKINSON
  申请人：MITSUBISHI TANABE PHARMA CORP

  公开号：WO2022191338A1

  公开（公告）日：2022-09-15

  An object of the present invention is to provide a combination medicament useful for treatment of Parkinson's disease. The present invention provides a prophylactic or therapeutic agent for Parkinson's disease, the agent containing a combination medicament containing a levodopa prodrug and a carbidopa prodrug.

  本发明的目的是提供一种组合药物，用于治疗帕金森病。本发明提供了一种预防或治疗帕金森病的药物，该药物含有一种组合药物，其中包含一种左旋多巴前药和一种卡比多巴前药。
• Nickel‐catalyzed umpolung C S radical reductive cross coupling of S‐(trifluoromethyl)arylsulfonothioates with alkyl halides
  作者：Yu-Zhong Yang、Gui-Fen Lv、Ming Hu、Yang Li、Jin-Heng Li

  DOI：10.1016/j.cclet.2023.108590

  日期：2023.11

  A new cooperative nickel reductive catalysis and N,N-dimethylformamide-mediated strategy for umpolung CS radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides to produce alkyl aryl thioethers is described. This reaction features excellent selectivity, wide functionality tolerance, broad substrate scope, and facile late-stage modification of biologically relevant

  描述了一种新的协同镍还原催化和N,N-二甲基甲酰胺介导的策略，用于S- (三氟甲基)芳基硫代磺酸酯与烷基卤的 C S 自由基还原交叉偶联生产烷基芳基硫醚。该反应具有优异的选择性、广泛的功能耐受性、广泛的底物范围以及易于对生物相关分子进行后期修饰。机理研究认识到，通过用 Sn 热诱导 DMF还原，最初生成酰胺自由基阴离子，然后进行反极化还原和亲核磺酰基部分的单电子转移，形成巯基自由基并与 Ni 0 /Ni I /Ni III接合/Ni I催化循环。