N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N4,N4-dimethyl-L-asparagine | 138585-02-1

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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
• 英文名称: N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N4,N4-dimethyl-L-asparagine
• 英文别名: Fmoc-N,N-dimethyl-L-Asparagine；(2S)-4-(dimethylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
• CAS: 138585-02-1
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: VXKRBLOYXZGVTI-SFHVURJKSA-N

物化性质

• 沸点：
  630.1±55.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Boc-L-叔亮氨酸 、 N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N4,N4-dimethyl-L-asparagine 、 生成 {(S)-1-[(S)-2-Dimethylcarbamoyl-1-(3,3,3-trifluoro-1-methyl-2-oxo-propylcarbamoyl)-ethylcarbamoyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Peptidomimetic Inhibitors of the Human Cytomegalovirus Protease

  摘要：

  The development of peptidomimetic inhibitors of the human cytomegalovirus (HCMV) :protease showing sub-micromolar potency in an enzymatic assay is described. Selective substitution of the amino acid residues of these inhibitors led to the identification of tripeptide inhibitors showing improvements in inhibitor potency cf 27-fold relative to inhibitor 39 based upon the natural tetrapeptide sequence. Small side chains at P-1 were well tolerated by this enzyme, a fact consistent with previous observations. The S-2 binding pocket of HCMV protease was very permissive, tolerating lipophilic and basic residues. The substitutions tried at P-3 indicated that a small increase in inhibitor potency could be realized by the substitution of a tert-leucine residue for valine. Substitutions of the N-terminal capping group did not significantly affect inhibitor potency. Pentafluoroethyl ketones, alpha,alpha-difluoro-beta-keto amides, phosphonates and a-keto amides were all effective substitutions for the activated carbonyl component and gave inhibitors which were selective for HCMV protease. A slight increase in potency was observed by lengthening the P-1' residue of the alpha-keto amide series of inhibitors. This position also tolerated a variety of groups making this a potential site for future modifications which could modulate the physicochemical properties of these molecules.

  DOI：

  10.1021/jm970104t
• 作为产物：
  描述：

  tert-butyl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N4,N4-dimethyl-L-asparaginate 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65%的产率得到N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N4,N4-dimethyl-L-asparagine
  参考文献：
  名称：

  [EN] IMMUNOMODULATORS
  [FR] IMMUNOMODULATEURS

  摘要：

  根据本公开，已发现一类宏环化合物，能够结合PD-L1并能够抑制PD-L1与PD-1和CD80的相互作用。这些宏环化合物在体外表现出免疫调节效果，因此成为治疗各种疾病包括癌症和传染病的治疗候选药物。

  公开号：

  WO2020237081A1

文献信息

• Inhibitor of ribonucleotide reductase of herpes viruses
  申请人：MERCK & CO. INC.

  公开号：EP0438873A1

  公开（公告）日：1991-07-31

  A series of substituted peptides have been found to possess antiviral potency - specifically against herpes viruses - by selectively inhibiting the viral ribonucleotide reductase enzyme.

  一系列替代肽已被发现具有抗病毒活性，特别针对疱疹病毒，通过选择性抑制病毒核糖核酸还原酶酶来实现。
• Structure–activity study at positions 3 and 4 of human neuropeptide S
  作者：Valeria Camarda、Claudio Trapella、Girolamo Calo’、Remo Guerrini、Anna Rizzi、Chiara Ruzza、Stella Fiorini、Erika Marzola、Rainer K. Reinscheid、Domenico Regoli、Severo Salvadori

  DOI：10.1016/j.bmc.2008.08.073

  日期：2008.10

  Neuropeptide S (NPS) has been identified as the endogenous ligand of a previously orphan receptor now named NPSR. Previous studies demonstrated that the N-terminal sequence Phe(2)-Arg(3)-Asn(4) of the peptide is crucial for biological activity. Here, we report on a focused structure-activity study of Arg(3) and Asn(4) that have been replaced with a series of coded and non-coded amino acids. Thirty-eight human NPS analogues were synthesized and pharmacologically tested for intracellular calcium mobilization using HEK293 cells stably expressing the mouse NPSR. The results of this study demonstrated the following NPS position 3 structure-activity features: (i) the guanidine moiety and its basic character are not crucial requirements, (ii) an aliphatic amino acid with a linear three carbon atom long side chain is sufficient to bind and fully activate NPSR, (iii) the receptor pocket allocating the position 3 side chain can accommodate slightly larger side chains at least to a certain degree [hArg, Arg(NO(2)) or Arg(Me)(2) but not Arg(Tos)]. Position 4 seems to be more sensitive to amino acids replacement compared to position 3; in fact, all the amino acid replacements investigated produced either an important decrease of biological activity or generated inactive derivatives suggesting a pivotal role of the Asn4 side chain for NPS bioactivity. (C) 2008 Elsevier Ltd. All rights reserved.
• IMMUNOMODULATORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3972694A1

  公开（公告）日：2022-03-30
• [EN] LIPIDATED PEPTIDE INHIBITORS OF INTERLEUKIN-23 RECEPTOR<br/>[FR] INHIBITEURS PEPTIDIQUES LIPIDÉS DU RÉCEPTEUR DE L'INTERLEUKINE-23
  申请人：[en]JANSSEN BIOTECH, INC.

  公开号：WO2023288019A2

  公开（公告）日：2023-01-19

  The present invention relates to novel lipidated peptide inhibitors of the interleukin-23 receptor (IL-23R) or pharmaceutically acceptable salts, solvates and/or other forms thereof, corresponding pharmaceutical compositions, methods and/or uses of the IL-23R inhibitors for treatment of autoimmune inflammation diseases and/or related disorders.