(S)-2-amino-3-(3-bromo-4-methoxyphenyl)propanoic acid | 98778-82-6

• 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)-2-amino-3-(3-bromo-4-methoxyphenyl)propanoic acid
• 英文别名: (s)-2-Amino-3-(3-bromo-4-methoxyphenyl)-propanoic acid；(2S)-2-amino-3-(3-bromo-4-methoxyphenyl)propanoic acid
• CAS: 98778-82-6
• 化学式: C₁₀H₁₂BrNO₃
• 分子量: 274.114
• InChiKey: GOIIMFXNXRYVHU-QMMMGPOBSA-N

物化性质

• 沸点：
  401.3±45.0 °C(Predicted)
• 密度：
  1.543±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-3-(3-bromo-4-methoxyphenyl)propanoic acid 在 1-羟基苯并三唑 、 三氟乙酸酐 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.75h， 生成 (±)-2-(benzyloxyimino)-3-(3-bromo-4-methoxyphenyl)-N-(2-(3,5-dibromo-4-(3-(dimethylamino)propoxy)phenyl)-2-hydroxyethyl)-propanamide trifluoroacetate
  参考文献：
  名称：

  Bromotyrosine Alkaloids from the Australian Marine Sponge Pseudoceratina verrucosa

  摘要：

  Two new bromotyrosine alkaloids, pseudoceralidinone A (1) and aplysamine 7 (2), along with three known compounds were isolated from the Australian sponge Pseudoceratina verrucosa. Their structures were characterized by NMR and MS data and the synthetic route. Their cytotoxicity was evaluated against cancer cell lines (HeLa and PC3) and a noncancer cell line (NFF).

  DOI：

  10.1021/np300648d
• 作为产物：
  描述：

  4-甲氧基-L-苯丙氨酸 在 溴 、 溶剂黄146 作用下， 反应 3.0h， 以80%的产率得到(S)-2-amino-3-(3-bromo-4-methoxyphenyl)propanoic acid
  参考文献：
  名称：

  Bromotyrosine Alkaloids from the Australian Marine Sponge Pseudoceratina verrucosa

  摘要：

  Two new bromotyrosine alkaloids, pseudoceralidinone A (1) and aplysamine 7 (2), along with three known compounds were isolated from the Australian sponge Pseudoceratina verrucosa. Their structures were characterized by NMR and MS data and the synthetic route. Their cytotoxicity was evaluated against cancer cell lines (HeLa and PC3) and a noncancer cell line (NFF).

  DOI：

  10.1021/np300648d

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。
• Preparation of prodrugs for selective drug delivery
  申请人：Mills L. Randell

  公开号：US20050080260A1

  公开（公告）日：2005-04-14

  Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。
• 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。
• Antimicrobial Peptides Incorporating Halogenated Marine-Derived Amino Acid Substituents
  作者：Alexander J. Craig、Yuri Ermolovich、Alan Cameron、Agnes Rodler、Helen Wang、Jeffrey A. Hawkes、Madlen Hubert、Fredrik Björkling、Natalia Molchanova、Margaret A. Brimble、Lindon W. K. Moodie、Johan Svenson

  DOI：10.1021/acsmedchemlett.3c00093

  日期：2023.6.8

  here, we explore the activity of 19 linear cationic tripeptides against five different pathogenic bacteria and fungi, including clinical isolates. The compounds incorporated modified hydrophobic amino acids inspired by motifs often found in bioactive marine secondary metabolites in combination with different cationic residues to probe the possibility of generating active compounds with improved safety

  阳离子抗菌肽的小型合成模拟物代表了一类有前途的化合物，在治疗持续性微生物感染的临床开发中处于领先地位。这些化合物的活性和选择性依赖于疏水性和阳离子成分之间的平衡，在这里，我们探索了 19 种线性阳离子三肽针对 5 种不同病原细菌和真菌（包括临床分离株）的活性。这些化合物结合了修饰的疏水性氨基酸，其灵感来自于生物活性海洋次生代谢物中常见的基序，并与不同的阳离子残基相结合，以探索产生具有改进的安全性的活性化合物的可能性。几种化合物表现出高活性（低 μM 浓度），与阳性对照 AMC-109、阿莫西林和两性霉素 B 相当。观察到针对真菌菌株的较高活性，并且针对真菌菌株观察到较低的体外脱靶毒性。红细胞和 HeLa 细胞，从而说明了调节短抗菌肽活性和选择性的有效方法。
• Organic chemistry of L-tyrosine. 1. General synthesis of chiral piperazines from amino acids
  作者：Michael E. Jung、John C. Rohloff

  DOI：10.1021/jo00224a051

  日期：1985.11