Fmoc-D-4-三氟甲基苯丙氨酸 | 238742-88-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - FMOC-氨基酸
• 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
• 中文名称: Fmoc-D-4-三氟甲基苯丙氨酸
• 中文别名: FMOC-D-4-三氟甲基苯丙氨酸；FMOC-4-(三氟甲基)-D-苯丙氨酸；N-(9-芴甲氧羰酰基)-D-4-三氟甲基苯丙氨酸
• 英文名称: Fmoc-DPhe(pCF3)-OH
• 英文别名: Fmoc-D-Phe(4-CF3)-OH；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(trifluoromethyl)phenyl]propanoic acid
• CAS: 238742-88-6
• 化学式: C₂₅H₂₀F₃NO₄
• 分子量: 455.433
• InChiKey: YMEGJWTUWMVZPD-JOCHJYFZSA-N

物化性质

• 熔点：
  136-142°C
• 沸点：
  619.0±55.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319

制备方法与用途

用途

FMOC-D-4-三氟甲基苯丙氨酸是一种氨基酸类衍生物，可作为有机中间体使用，同时也应用于标准品和对照品等领域。

反应信息

• 作为反应物：
  描述：

  Fmoc-D-4-三氟甲基苯丙氨酸 、 乙酸酐 、 N-Fmoc-N'-三苯甲基-L-组氨酸 、 Fmoc-L-色氨酸(Boc)-OH 、 alkaline earth salt of/the/ methylsulfuric acid 在 Rink amide resin 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.3h， 生成 Ac-His-DPhe(pCF3)-Arg-Trp-NH2
  参考文献：
  名称：

  Melanocortin Tetrapeptide Ac-His-DPhe-Arg-Trp-NH₂ Modified at the Para Position of the Benzyl Side Chain (DPhe): Importance for Mouse Melanocortin-3 Receptor Agonist versus Antagonist Activity

  摘要：

  The melanocortin-3 and -4 receptors (MC3R, MC4R) have been implicated in energy homeostasis and obesity. Whereas the physiological role of the MC4R is extensively studied, little is known about the MC3R. One caveat is the limited availability of ligands that are selective for the MC3R. Previous studies identified Ac-His-DPhe(p-I)-Arg-Trp-NH2, which possessed partial agonist/antagonist pharmacology at the mMC3R while retaining full nanomolar agonist pharrnacology at the mMC4R. These data allowed for the hypothesis that the DPhe position in melanocortin tetrapeptides can be used to examine ligand side-chain determinants important for differentiation of mMC3R agonist versus antagonist activity. A series of 15 DPhe(7) modified Ac-His-DPhe(7)-Arg-Trp-NH2 tetrapeptides has been synthesized and pharmacologically characterized. Most notable results include the identification of modifications that resulted in potent antagonists/partial agonists at the mMC3R and full, potent agonists at the mMC4R. These SAR studies provide experimental evidence that the molecular mechanism of antagonism at the mMC3R differentiates this subtype from the mMC4R.

  DOI：

  10.1021/jm800291b

文献信息

• Compounds Modifying Apoptosis
  申请人：Thastrup Ole

  公开号：US20080194537A1

  公开（公告）日：2008-08-14

  The present invention relates to compounds capable of inhibiting binding of the Smac protein to Inhibitors of apoptosis (IAPs). Such compounds are preferably capable of inhibiting IAP and thus may promote apoptosis or sensitize cells for apoptosis. The compounds may be used in the treatment of proliferative diseases, such as cancer.

  本发明涉及一种能够抑制Smac蛋白与凋亡抑制剂（IAPs）结合的化合物。这些化合物最好能够抑制IAP，从而可能促进细胞凋亡或增加细胞对凋亡的敏感性。这些化合物可用于治疗增生性疾病，如癌症。
• MACROCYCLIC COMPOUNDS FOR INHIBITION OF TUMOR NECROSIS FACTOR ALPHA
  申请人：Lee Jinbo

  公开号：US20100152099A1

  公开（公告）日：2010-06-17

  The invention provides macrocyclic compounds and methods for their synthesis and use. In particular, the invention provides macrocyclic compounds that modulate the activity of tumor necrosis factor alpha and/or are useful in the treatment of medical conditions, such as, rheumatoid arthritis, psoriasis, and asthma.

  该发明提供了大环化合物及其合成和使用方法。具体而言，该发明提供了调节肿瘤坏死因子α活性和/或用于治疗医学状况（如类风湿性关节炎、银屑病和哮喘）的大环化合物。
• Polymyxins with Potent Antibacterial Activity against Colistin-Resistant Pathogens: Fine-Tuning Hydrophobicity with Unnatural Amino Acids
  作者：Johan Storm Jørgensen、Elnaz Harifi Mood、Anne Sofie Holst Knap、Simone Eidnes Nielsen、Peter E. Nielsen、Dorota Żabicka、Carina Matias、Ilona Domraceva、Fredrik Björkling、Henrik Franzyk

  DOI：10.1021/acs.jmedchem.3c01908

  日期：2024.1.25

  discernible correlation with their antimicrobial activity. This trend was particularly pronounced for colistin-resistant pathogens. The most active compounds demonstrated competitive activity against a panel of Gram-negative pathogens, while exhibiting low in vitro cytotoxicity. Importantly, most of these hits also retained (or even had increased) potency against colistin-susceptible strains. These findings

  鉴于人类病原体中抗菌素耐药性的普遍性增加，迫切需要针对多重耐药 （MDR） 细菌的抗生素。特别是，对用于治疗严重革兰阴性 MDR 感染的最后手段抗生素粘菌素迅速出现的耐药性至关重要。在这里，探索了一系列含有非天然氨基酸的多粘菌素，一些类似物对大肠杆菌、肺炎克雷伯菌、鲍曼不动杆菌和铜绿假单胞菌表现出优异的抗菌活性。该系列化合物的疏水性（通过在反相分析 HPLC 中的保留性测量）与其抗菌活性表现出明显的相关性。这种趋势对于粘菌素耐药病原体尤为明显。最活跃的化合物对一组革兰氏阴性病原体表现出竞争活性，同时表现出低体外细胞毒性。重要的是，这些命中中的大多数还保留（甚至增加了）对粘菌素敏感菌株的效力。这些发现推断，微调疏水性可能使设计出具有良好活性特征的多粘菌素类似物。
• US8318717B2
  申请人：——

  公开号：US8318717B2

  公开（公告）日：2012-11-27
• US8338565B2
  申请人：——

  公开号：US8338565B2

  公开（公告）日：2012-12-25