N-BOC-RS-茚满基甘氨酸 | 155172-73-9

• 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: N-BOC-RS-茚满基甘氨酸
• 英文名称: N^α-<(tert-butyloxy)carbonyl>-2-(2-indanyl)glycine
• 英文别名: Tert-butoxycarbonylamino-indan-2-YL-acetic acid；2-(2,3-dihydro-1H-inden-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 155172-73-9
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: VCHHRDDQOOBPTC-UHFFFAOYSA-N

物化性质

• 沸点：
  470.9±28.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 Amino-indan-2-yl-acetic acid; hydrochloride 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 N-BOC-RS-茚满基甘氨酸
  参考文献：
  名称：

  Design and Synthesis of Side-Chain Conformationally Restricted Phenylalanines and Their Use for Structure-Activity Studies on Tachykinin NK-1 Receptor

  摘要：

  Constrained analogues of phenylalanine have been conceptually designed for analyzing the binding pockets of Phe(7) (S-7) and Phe(8) (S-8), two aromatic residues important for the pharmacological properties of SP, i.e., L-tetrahydroisoquinoleic acid, L-diphenylalanine, L-9-fluorenylglycine (Flg), 2-indanylglycine, the diastereomers of L-1-indanylglycine (Ing) and L-1-benz[f]indanylglycine (Bfi), and the Z and E isomers of dehydrophenylalanine (Delta(z)Phe, Delta(E)Phe). Binding studies were performed with appropriate ligands and tissue preparations allowing the discrimination of the three tachykinin binding sites, NK-1, NK-2, and NK-3. The potencies of these agonists were evaluated in the guinea pig ileum bioassay. According to the binding data, we can conclude that the S-7 subsite is small, only the gauche (-) probe [(2S,3S)-Ing(7)]SP presents a high affinity for specific NK-1 binding sites. Surprisingly, the [Delta(E)Phe(7)]SP analogue, which projects the aromatic ring toward the trans orientation, is over 40-fold more potent than the Z isomer, [Delta(Z)Phe(7)]SP. A plausible explanation of these conflictual results Is that either the binding protein quenches the minor trans rotamer of [(2S,3S)-Ing(7)]SP in solution or this constrained amino acid side chain rotates when inserted in the protein. In position 8, the high binding affinities of [Flg(8)]SP and [(2S,3S)-Bfi(8)]SP suggest that the S-8 subsite is large enough to accept two aromatic rings in the gauche (-) and one aromatic ring in the trans direction. Peptides bearing two conformational probes in positions 7, 8, or 9 led to postulate that S-7, S-8, and S-9 subsites are independent from each other. The volumes available for side chains 7 and 8 can be estimated to be close to 110 and 240 Angstrom(3), respectively. The large volume of the S-8 subsite raises question on the localization of the SP-binding site in the NK-1 receptor. If SP were to bind in the transmembrane domains, the cleft defined by the seven transmembrane segments must rearrange during the binding process in order to bind a peptide in an ac-helical structure and at least one large binding subsite in position 8. Thus, indirect topographical analysis with constrained amino acids might contribute to the analysis of the receptor/ligand dynamics. Finally, this study demonstrates that a good knowledge of the peptidic backbone structure and a combination of constrained amino acids are prerequisites to confidently attribute the preferred orientation(s) of an amino acid side chain.

  DOI：

  10.1021/jm00037a009

文献信息

• Inhibitors of cysteine proteases and methods of use thereof
  申请人：Pardes Biosciences, Inc.

  公开号：US11124497B1

  公开（公告）日：2021-09-21

  The disclosure provides compounds with warheads and their use in treating medical diseases or disorders, such as viral infections. Pharmaceutical compositions and methods of making various compounds with warheads are provided. The compounds are contemplated to inhibit proteases, such as the 3C, CL- or 3CL-like protease. Exemplary compounds provided include Formula II-I, where R3, RB are provided herein:

  该披露提供了具有战斗头的化合物及其在治疗医学疾病或紊乱，如病毒感染方面的用途。提供了制药组合物和制备各种带有战斗头的化合物的方法。这些化合物被认为能够抑制蛋白酶，如3C、CL-或3CL样蛋白酶。提供的示例化合物包括Formula II-I，其中R3、RB如下所示：
• Tricyclic compounds protein kinase inhibitors for enhancing the efficacy of anti-neoplastic agents and radiation therapy
  申请人：Benedict Suzanne

  公开号：US20060004052A1

  公开（公告）日：2006-01-05

  Protein kinase, such as CHK-1, inhibiting tricyclic compounds of the following formula (wherein R 2 , R 3 and R 4 are as defined in the specification) pharmaceutical compositions containing effective amounts of said compounds or their salts are useful as a single agent or in combination with an anti-neoplastic agent or therapeutic radiation having an anti-neoplastic effect for treating diseases or conditions such as cancers.

  蛋白激酶（例如CHK-1）抑制下列式子中三环化合物（其中R2，R3和R4如规范中定义）的药物组合物（或其盐）在单独使用或与具有抗肿瘤作用的抗肿瘤剂或治疗性放射线组合使用时，可用于治疗癌症等疾病或病况。
• TRICYCLIC COMPOUNDS PROTEIN KINASE INHIBITORS FOR ENHANCING THE EFFICACY OF ANTI-NEOPLASTIC AGENTS AND RADIATION THERAPY
  申请人：Benedict Suzanne

  公开号：US20070135415A1

  公开（公告）日：2007-06-14

  Protein kinase, such as CHK-1, inhibiting tricyclic compounds of the following formula (wherein R 2 , R 3 and R 4 are as defined in the specification) pharmaceutical compositions containing effective amounts of said compounds or their salts are useful as a single agent or in combination with an anti-neoplastic agent or therapeutic radiation having an anti-neoplastic effect for treating diseases or conditions such as cancers. The current invention relates to the making and using of such compounds.

  蛋白激酶，例如CHK-1，抑制以下式子中三环化合物（其中R2，R3和R4如规范所定义）的制剂（或其盐）的有效量的制药组合物，可用作单一剂量或与抗肿瘤剂或具有抗肿瘤作用的治疗性放射线组合使用，用于治疗癌症等疾病或病情。本发明涉及制备和使用这种化合物。
• 1-6-Substituted (3R,6R)-3-(2,3-Dihydro-1H-Inden-2-Yl)-2,5-Piperazinedione Derivatives as Oxytocin Receptor Antagonists For the Treatment of Preterm Labour, Dysmenorrhea and Endometriosis
  申请人：Leach Colin Andrew

  公开号：US20080242666A1

  公开（公告）日：2008-10-02

  The present invention relates to Compound S of Formula (I).

  本发明涉及化合物S，其化学式为（I）。
• 1,6-SUBSTITUTED (3R,6R)-3-(2,3-DIHYDRO-1H-INDEN-2-YL)-2,5-PIPERAZINEDIONE DERIVATIVES AS OXYTOCIN RECEPTOR ANTAGONISTS FOR THE TREATMENT OF PRE-TERM LABOUR, DYSMENORRHEA AND ENDOMETRIOSIS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1831183A1

  公开（公告）日：2007-09-12