Fmoc-4-氰基-D-苯丙氨酸 | 205526-34-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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-4-氰基-D-苯丙氨酸
• 中文别名: Fmoc-D-4-氰基苯丙氨酸；FMOC-D-4-氰基苯丙氨酸
• 英文名称: Fmoc-DPhe(pCN)-OH
• 英文别名: Fmoc-D-Phe(4-CN)-OH；Fmoc-4-cyano-D-phenylalanine；(2R)-3-(4-cyanophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 205526-34-7
• 化学式: C₂₅H₂₀N₂O₄
• mdl: MFCD00672560
• 分子量: 412.445
• InChiKey: JOPKKUTWCGYCDA-HSZRJFAPSA-N

物化性质

• 熔点：
  188.1 °C
• 沸点：
  531.88°C (rough estimate)
• 密度：
  1.2691 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  Fmoc-4-氰基-D-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(pCN)-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

• Melanocortin Receptor-Specific Peptides
  申请人：AstraZeneca AB

  公开号：US20150252077A1

  公开（公告）日：2015-09-10

  The invention relates to melanocortin receptor-specific cyclic peptides of Formula (I) or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , R 4a , R 4b , R 4c , R 5 , x and y are as defined in the specification. These compounds are particularly useful in the treatments of energy homeostasis and metabolism related (e.g. diabetes), food intake related and/or energy balance and body weight related diseases, disorders and/or conditions, including obesity, overweight and diseases, disorders and/or conditions associated with obesity and/or overweight, such as type 2 diabetes and metabolic syndrome.

  本发明涉及公式（I）的黑素皮质素受体特异性环肽或其药学上可接受的盐，其中R1、R2、R3、R4a、R4b、R4c、R5、x和y如规范中所定义。这些化合物在能量稳态和代谢相关（例如糖尿病）、食物摄入相关和/或能量平衡和体重相关的疾病、疾病和/或状况，包括肥胖、超重以及与肥胖和/或超重相关的疾病、疾病和/或状况的治疗中特别有用，例如2型糖尿病和代谢综合征。
• 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。
• Compounds That Inhibit Replication Of Human Immunodeficiency Virus
  申请人：Balzarini Maria Rene Jan

  公开号：US20080076824A1

  公开（公告）日：2008-03-27

  The present invention relates to the discovery of a novel class of compounds that inhibit the replication of human immunodeficiency virus (HIV) and approaches to identify these compounds. More specifically, it has been found that enzymatically prepared alpha-hydroxyglycinamide and synthetically prepared alpha-hydroxyglycinamide inhibit the replication of HIV in human serum. Embodiments include methods to identify modified glycinamide compounds that inhibit HUV, methods to isolate and synthesize modified glycinamide compounds, and therapeutic compositions comprising these compounds.

  本发明涉及一种新型化合物类别的发现，该类化合物能够抑制人类免疫缺陷病毒（HIV）的复制，并提供了鉴定这些化合物的方法。具体来说，发现经酶法制备的α-羟基甘氨酰胺和人工合成的α-羟基甘氨酰胺能够抑制HIV在人血清中的复制。实施例包括鉴定抑制HUV的改性甘氨酰胺化合物的方法，分离和合成改性甘氨酰胺化合物的方法，以及包含这些化合物的治疗组合物。
• 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。
• COMPOUNDS THAT INHIBIT REPLICATION OF HUMAN IMMUNODEFICIENCY VIRUS
  申请人：TRIPEP AB

  公开号：EP1799222A2

  公开（公告）日：2007-06-27