2,4-dihydroxy-L-phenylalanine | 89462-15-7

• 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: 2,4-dihydroxy-L-phenylalanine
• 英文别名: L-DOPA；2,4-dihydroxyphenyl-L-alanine；(+)-(S)-2,4-dihydroxyphenylalanine；D,L-2,4-Dihydroxyphenylalanine；levodopa；(2S)-2-azaniumyl-3-(2,4-dihydroxyphenyl)propanoate
• CAS: 89462-15-7
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: UTIMIHJZXIJZKZ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-dihydroxy-L-phenylalanine 在 NH₄OH-NH₄Cl buffer 、 磷酸吡哆醛 作用下， 反应 0.5h， 生成 4-(2-氨基乙基)苯-1,3-二醇
  参考文献：
  名称：

  Nakazawa, Hidetsugu; Kumagai, Hidehiko; Yamada, Hideaki, Agricultural and Biological Chemistry, 1981, vol. 45, # 11, p. 2543 - 2552

  摘要：

  DOI：
• 作为产物：
  描述：

  N-((S)-3-(2,4-dihydroxyphenyl)-1-oxo-1-(((S)-1-phenylethyl)-amino)-propan-2-yl) benzamide 在 氢溴酸 作用下， 以 水 为溶剂， 生成 2,4-dihydroxy-L-phenylalanine
  参考文献：
  名称：

  Interactions of phenylalanine derivatives with human tyrosinase: lessons from experimental and theoretical studies

  摘要：

  The pigmentation of the skin, modulated by different actors in melanogenesis, is mainly due to the melanins (protective pigments). In humans, these pigments’ precursors are synthetized by an enzyme known as tyrosinase (TyH). The regulation of the enzyme activity by specific modulators (inhibitors or activators) can offer a means to fight hypo‐ and hyper‐pigmentations responsible for medical, psychological and societal handicaps. Herein, we report the investigation of phenylalanine derivatives as TyH modulators. Interacting with the binuclear copper active site of the enzyme, phenylalanine derivatives combine effects induced by combination with known resorcinol inhibitors and natural substrate/intermediate (amino acid part). Computational studies including docking, molecular dynamics and free energy calculations combined with biological activity assays on isolated TyH and in human melanoma MNT‐1 cells, and X‐ray crystallography analyses with the TyH analogue Tyrp1, provide conclusive evidence of the interactions of phenylalanine derivatives with human tyrosinase. In particular, our findings indicate that an analogue of L‐DOPA, namely (S)‐3‐amino‐tyrosine, stands out as an amino phenol derivative with inhibitory properties against TyH.

  DOI：

  10.1002/cbic.202400235

文献信息

• Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use
  申请人：deLong A. Mitchell

  公开号：US20070254920A1

  公开（公告）日：2007-11-01

  This invention relates to novel homotopic prodrugs and medicaments and methods for their preparation, testing and use. In one embodiment, the homotopic prodrug has the general formula wherein is a biologically-active moiety comprising a carboxylic acid functional group, and R b is a homotopically-symmetrical alcohol bonded to the biologically-active moiety through the carboxylic acid functional group to form an ester linkage, as well as optical isomers, enantiomers, pharmaceutically acceptable salts, biohydrolyzable amides, esters, and imides thereof and combinations thereof.

  这项发明涉及新型同位素前药、药物以及其制备、测试和使用方法。在一个实施例中，同位素前药具有一般公式 其中 是包含羧酸官能团的生物活性基团，而 R b 是通过羧酸官能团与生物活性基团形成酯键的同位对称醇，以及其光学异构体、对映异构体、药用可接受盐、生物水解酰胺、酯、亚酰胺及其组合物。
• Bismuth-containing compounds, coordination polymers, methods for modulating pharmacokinetic properties of biologically active agents, and methods for treating patients
  申请人：Price John D.

  公开号：US10150792B2

  公开（公告）日：2018-12-11

  Bismuth-containing compounds include bismuth and a biologically active agent coordinated to the bismuth. The biologically active agent includes at least one heteroatom configured for coordination with the bismuth. Coordination polymers include a polymer matrix that contains a bismuth-containing compound. Methods for modulating a pharmacokinetic property of a biologically active agent include coordinating the biologically active agent to bismuth to form a bismuth-containing compound, and administering the bismuth-containing compound orally to a patient. Methods for treating Parkinson's disease, methods for treating hypothyroidism, methods for treating ulcerative colitis, and methods for treating cancer each include administering a bismuth-containing compound to a patient.

  含铋化合物包括铋和与铋配位的生物活性剂。生物活性剂包括至少一个用于与铋配位的杂原子。配位聚合物包括包含含铋化合物的聚合物基质。调节生物活性剂的药代动力学特性的方法包括将生物活性剂与铋配位形成含铋化合物，并将含铋化合物口服给患者。治疗帕金森病的方法，治疗甲状腺功能减退症的方法，治疗溃疡性结肠炎的方法，以及治疗癌症的方法各自包括向患者口服含铋化合物。
• Antagonists for treatment of CD/11CD18 adhesion receptor mediated disorders
  申请人：Burdick J. Daniel

  公开号：US20050203135A1

  公开（公告）日：2005-09-15

  Compounds of the general structure D-L-B-(AA), for example (A), that are useful for treating Mac-1 or LFA-1-mediated disorders such as inflammatory disorders, allergies, and autoimmune diseases are provided.

  提供了一些具有一般结构D-L-B-(AA)的化合物，例如(A)，这些化合物对治疗Mac-1或LFA-1介导的疾病如炎症性疾病、过敏和自身免疫疾病是有用的。
• Ophthamological drugs
  申请人：Toone J. Eric

  公开号：US20060135609A1

  公开（公告）日：2006-06-22

  The present invention relates generally to ophthamological drugs. More specifically, the inventon relates to a method of modifying (derivatizing) ophthamological drugs so as to increase their penetration through the cornea. The invention also relates to drugs modified (derivatized) in accordance with the instant method and to the use of same in treating conditions associated with elevated intraocular pressure, particularly, glaucoma.

  本发明一般涉及眼科药物。更具体地，本发明涉及一种修改（衍生化）眼科药物的方法，以增加它们通过角膜的渗透性。本发明还涉及根据本方法修改（衍生化）的药物，以及将其用于治疗与眼内压升高相关的疾病，特别是青光眼。
• OPHTHAMOLOGICAL DRUGS
  申请人：Toone Eric J.

  公开号：US20090318542A1

  公开（公告）日：2009-12-24

  The present invention relates generally to ophthamological drugs. More specifically, the invention relates to a method of modifying (derivatizing) ophthamological drugs so as to increase their penetration through the cornea. The invention also relates to drugs modified (derivatized) in accordance with the instant method and to the use of same in treating conditions associated with elevated intraocular pressure, particularly, glaucoma.

  本发明通常涉及眼科药物。更具体地说，本发明涉及一种改性（衍生化）眼科药物的方法，以增加它们穿过角膜的渗透性。本发明还涉及按照本方法改性（衍生化）的药物，以及将其用于治疗与眼内压升高有关的疾病，特别是青光眼。