N-<(tert-butyloxy)carbonyl>-5-hydroxy-6-methoxyisoindoline | 156422-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-<(tert-butyloxy)carbonyl>-5-hydroxy-6-methoxyisoindoline
• 英文别名: Tert-butyl 5-hydroxy-6-methoxy-1,3-dihydroisoindole-2-carboxylate
• CAS: 156422-97-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: GXQQOPBZBWMFJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(tert-butyloxy)carbonyl>-5-hydroxy-6-methoxyisoindoline 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49.0061 %的产率得到tert-butyl 4-chloro-5-hydroxy-6-methoxyisoindoline-2-carboxylate
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS USEFUL AS STING AGONISTS AND USES THEREOF
  [FR] NOUVEAUX COMPOSÉS UTILES EN TANT QU'AGONISTES DE STING ET LEURS UTILISATIONS

  摘要：

  提供了一般公式为S-1、S-2、S-3及其药学上可接受的盐的化合物，这些化合物可能有用作为I型干扰素产生的诱导剂，特别是作为STING活性剂。还提供了这些化合物的合成、组成和用途。

  公开号：

  WO2022199677A1
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 sodium perborate tetrahydrate 、 potassium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 N-<(tert-butyloxy)carbonyl>-5-hydroxy-6-methoxyisoindoline
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS USEFUL AS STING AGONISTS AND USES THEREOF
  [FR] NOUVEAUX COMPOSÉS UTILES EN TANT QU'AGONISTES STING ET LEURS UTILISATIONS

  摘要：

  提供了一般公式I、II、III、IV、V及其药学上可接受的盐的化合物，这些化合物可能作为诱导I型干扰素产生的诱导剂，特别是作为STING活性剂。还提供了这些化合物的合成、组成和用途。

  公开号：

  WO2022206725A1

文献信息

• [EN] NOVEL COMPOUNDS USEFUL AS STING AGONISTS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS UTILES EN TANT QU'AGONISTES STING ET LEURS UTILISATIONS
  申请人：JACOBIO PHARMACEUTICALS CO LTD

  公开号：WO2022206725A1

  公开（公告）日：2022-10-06

  Compounds of general Formula I, II, III, IV, V and their pharmaceutically acceptable salts, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are synthesis, compositions, and uses of such compounds.

  提供了一般公式I、II、III、IV、V及其药学上可接受的盐的化合物，这些化合物可能作为诱导I型干扰素产生的诱导剂，特别是作为STING活性剂。还提供了这些化合物的合成、组成和用途。
• [EN] VACCINE ADJUVANTS AND USES THEREOF<br/>[FR] ADJUVANTS DE VACCIN ET LEURS UTILISATIONS
  申请人：[en]JACOBIO PHARMACEUTICALS CO.LTD.

  公开号：WO2024032782A1

  公开（公告）日：2024-02-15

  Provided is a vaccine adjuvant containing a STING agonist and a use thereof. The vaccine adjuvant containing a STING agonist provided by the present invention can enhance an immune response, and is especially suitable for the prevention and treatment of diseases or disorders.
• [EN] COMPOUND-LINKER CONSTRUCTS COMPRISING NOVEL COMPOUNDS USEFUL AS STING AGONISTS AND USES THEREOF<br/>[FR] CONSTRUCTIONS LIEURS-COMPOSÉS COMPRENANT DE NOUVEAUX COMPOSÉS UTILES EN TANT QU'AGONISTES DE STING ET LEURS UTILISATIONS
  申请人：[en]JACOBIO PHARMACEUTICALS CO., LTD.

  公开号：WO2023109942A1

  公开（公告）日：2023-06-22

  Provided herein are compound-linker constructs and antibody-drug-conjugates of compounds of formula(Y-1), (Y-2), (Y-3), (A), (B), (C), I, II, III, IV or V that are useful as modulators of STING (Stimulator of Interferon Genes). Also provided are synthesis,compositions and uses of such compound-linker constructs and antibody-drug-conjugates.
• The Discovery of Capsazepine, the First Competitive Antagonist of the Sensory Neuron Excitants Capsaicin and Resiniferatoxin
  作者：Christopher S. J. Walpole、Stuart Bevan、Guenter Bovermann、Johann J. Boelsterli、Robin Breckenridge、John W. Davies、Glyn A. Hughes、Iain James、Lukas Oberer、Janet Winter、Roger Wrigglesworth

  DOI：10.1021/jm00039a006

  日期：1994.6.1

  Capsaicin and resiniferatoxin are natural products which act specifically on a subset of primary afferent sensory neurons to open a novel cation-selective ion channel in the plasma membrane. These sensory neurons are involved in nociception, and so, these agents are targets for the design of a novel class of analgesics. Although synthetic agonists at the capsaicin receptor have been described previously, competitive antagonists at this receptor would be interesting and novel pharmacological agents. Structure-activity relationships for capsaicin agonists have previously been rationalized, by ourselves and others, by dividing the capsaicin molecule into three regions-the A (aromatic ring)-, B (amide bond)-, and C (hydrophobic side chain)-regions. In this study, the effects on biological activity of conformational constraint of the A-region with respect to the B-region are discussed. Conformational constraint was achieved by the introduction of saturated ring systems of different sizes. The resulting compounds provided agonists of comparable potency to unconstrained analogues as well as a moderately potent antagonist, capsazepine. This compound is the first competitive antagonist of capsaicin and resiniferatoxin to be described and is active in various systems, in vitro and in vivo. It has recently attracted considerable interest as a tool for dissecting the mechanisms by which capsaicin analogues evoke their effects. NMR spectroscopy and X-ray crystallography experiments, as well as molecular modeling techniques, were used to study the conformational behavior of a representative constrained agonist and antagonist. The conformation of the saturated ring contraint in the two cases was found to differ markedly, dramatically affecting the relative disposition of the A-ring and B-region pharmacophores. In agonist structures, the A- and B-regions were virtually coplanar in contrast to those in the antagonist, in which they were approximately orthogonal. A rationale for agonist and antagonist activity at the capsaicin receptor is proposed, based on the consideration of these conformational differences.
• [EN] NOVEL COMPOUNDS USEFUL AS STING AGONISTS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS UTILES EN TANT QU'AGONISTES DE STING ET LEURS UTILISATIONS
  申请人：JACOBIO PHARMACEUTICALS CO LTD

  公开号：WO2022199677A1

  公开（公告）日：2022-09-29

  Compounds of general Formula S-1, S-2, S-3 and their pharmaceutically acceptable salts, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are synthesis, compositions, and uses of such compounds.

  提供了一般公式为S-1、S-2、S-3及其药学上可接受的盐的化合物，这些化合物可能有用作为I型干扰素产生的诱导剂，特别是作为STING活性剂。还提供了这些化合物的合成、组成和用途。