(S)-3-(3,5-dibromo-4-methoxyphenyl)-2-(dimethylamino)propanoic acid | 1378296-78-6

• 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: (S)-3-(3,5-dibromo-4-methoxyphenyl)-2-(dimethylamino)propanoic acid
• 英文别名: (s)-3-(3,5-Dibromo-4-methoxyphenyl)-2-(dimethylamino)-propanoic acid；(2S)-3-(3,5-dibromo-4-methoxyphenyl)-2-(dimethylamino)propanoic acid
• CAS: 1378296-78-6
• 化学式: C₁₂H₁₅Br₂NO₃
• 分子量: 381.064
• InChiKey: VNNAMEGANCGNNT-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(3,5-dibromo-4-methoxyphenyl)-2-(dimethylamino)propanoic acid 、 purpurealidin E 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到aplyzanzine A
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B

  摘要：

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

  DOI：

  10.1021/np300102z
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以85%的产率得到(S)-3-(3,5-dibromo-4-methoxyphenyl)-2-(dimethylamino)propanoic acid
  参考文献：
  名称：

  氯和溴化L-酪氨酸衍生物的抗寄生虫和细胞毒活性

  摘要：

  合成了21个L-酪氨酸衍生物，这些衍生物在芳香环的卤化方式上有修饰，并且在胺基和酚羟基上的甲基化程度不同。通过光谱分析确认所有中间体和目标化合物的结构是明确的。另外，所有化合物均针对20-702μgmL之间的恶性疟原虫和巴拿马利什曼原虫进行了评估。进行细胞毒性评估以确定每种化合物的选择性指数。六种化合物对巴拿马乳杆菌的EC50较低（有效浓度为50）。这些化合物之一是最有活性的，EC50为24.13μgmL（76.07μM）。所有衍生物均未显示出对恶性疟原虫的显着活性，并且在500μgmL下没有化合物具有体外抗真菌活性。

  DOI：

  10.21577/0103-5053.20180136

文献信息

• Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives
  作者：Manuel Pastrana Restrepo、Elkin Galeano Jaramillo、Alejandro Martínez Martínez、Sara Robledo Restrepo

  DOI：10.1007/s00044-018-2249-y

  日期：2018.12

  Twenty-two halogenated l-tyrosine derivatives were synthesized to examine new substances for the treatment of Chagas disease. The synthesis of these derivatives with different degree of substitution in the amino group with methyl iodide, giving primary, tertiary, and quaternary amino acids. All compounds were tested in vitro against intracellular amastigotes of Trypanosoma cruzi, and the cytotoxicity

  合成了二十二个卤化的1-酪氨酸衍生物，以研究用于治疗南美锥虫病的新物质。这些衍生物在甲基中具有甲基碘的不同取代度，可以合成伯，叔和季氨基酸。所有化合物均在体外针对克氏锥虫的胞内变形虫进行了测试，并通过单核细胞系U-937评估了细胞毒性。化合物25以75.52 µM的EC 50对抗克氏杆菌最具活性，而苯并硝唑的EC 50为58.79 µM的化合物最为有效。化合物3，4，7，和15种是具有最佳选择性指数（SI）的值分别为7.5、8.3、12.1和8.6的衍生物。最后，化合物7是对抗T. cruzi的更安全，更有前途的衍生物。
• Anti-Parasite and Cytotoxic Activities of Chloro and Bromo L-Tyrosine Derivatives
  作者：Manuel Restrepo、Elkin Jaramillo、Alejandro Martínez、Ana Arango、Sara Restrepo

  DOI：10.21577/0103-5053.20180136

  日期：——

  A series of twenty-one L-tyrosine derivatives with modifications in the halogenation pattern of the aromatic ring and different degree of methylations on the amine and phenolic hydroxyl groups were synthesized. The structures of all the intermediates and target compounds were confirmed unambiguous by spectroscopy analysis. Additionally, all compounds were evaluated against Plasmodium falciparum and

  合成了21个L-酪氨酸衍生物，这些衍生物在芳香环的卤化方式上有修饰，并且在胺基和酚羟基上的甲基化程度不同。通过光谱分析确认所有中间体和目标化合物的结构是明确的。另外，所有化合物均针对20-702μgmL之间的恶性疟原虫和巴拿马利什曼原虫进行了评估。进行细胞毒性评估以确定每种化合物的选择性指数。六种化合物对巴拿马乳杆菌的EC50较低（有效浓度为50）。这些化合物之一是最有活性的，EC50为24.13μgmL（76.07μM）。所有衍生物均未显示出对恶性疟原虫的显着活性，并且在500μgmL下没有化合物具有体外抗真菌活性。
• Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B
  作者：Suresh K. Kottakota、Dimitrios Evangelopoulos、Amani Alnimr、Sanjib Bhakta、Timothy D. McHugh、Mark Gray、Paul W. Groundwater、Emma C. L. Marrs、John D. Perry、Christopher D. Spilling、J. Jonathan Harburn

  DOI：10.1021/np300102z

  日期：2012.6.22

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.