2-(2,3-dihydro-1H-inden-2-yloxy)-1H-isoindole-1,3(2H)-dione | 945260-68-4

• 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: 2-(2,3-dihydro-1H-inden-2-yloxy)-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-(2,3-dihydro-1H-inden-2-yloxy)isoindole-1,3-dione
• CAS: 945260-68-4
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: RGXSCHUXNRQHKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,3-dihydro-1H-inden-2-yloxy)-1H-isoindole-1,3(2H)-dione 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 O-(2,3-dihydro-1H-inden-2-yl)-hydroxylamine
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a. potent sub-micromolar inhibitor of IDO1. Structure activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.028
• 作为产物：
  描述：

  2-茚酮 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 2-(2,3-dihydro-1H-inden-2-yloxy)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a. potent sub-micromolar inhibitor of IDO1. Structure activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.028

文献信息

• CONTROLLED RELEASE OF ACTIVE COMPOUNDS FROM DYNAMIC MIXTURES
  申请人：Herrmann Andreas

  公开号：US20100226875A1

  公开（公告）日：2010-09-09

  The present invention relates to a dynamic mixture in the form of a dynamic mixture obtained by reacting together, in the presence of water, at least one O-substituted hydroxylamine or S-substituted thiohydroxylamine derivative with at least one perfuming, flavoring, insect repellent or attractant, bactericide or fungicide aldehyde or ketone. This mixture is capable of releasing in a controlled and prolonged manner the aldehyde or ketone into the surrounding environment. Furthermore, the present invention concerns also the use of these dynamic mixtures as perfuming ingredients as well as the perfuming compositions or perfumed articles that include these mixtures.

  本发明涉及一种动态混合物，其为通过在水的存在下将至少一种O-取代羟胺或S-取代硫羟胺衍生物与至少一种香料、调味剂、驱虫剂或诱引剂、杀菌剂或杀真菌剂醛或酮反应而得到的动态混合物。该混合物能够以受控和延长的方式释放醛或酮进入周围环境。此外，本发明还涉及将这些动态混合物用作调香成分以及包括这些混合物的调香组合物或香气物品的用途。
• CONTROLLED RELEASE OF ACTIVE COMPOUNDS FROM DYNAMIC MIXTURES
  申请人：Firmenich S.A.

  公开号：EP2010293A2

  公开（公告）日：2009-01-07
• [EN] CONTROLLED RELEASE OF ACTIVE COMPOUNDS FROM DYNAMIC MIXTURES<br/>[FR] LIBERATION REGULEE DE COMPOSES ACTIFS PROVENANT DE MELANGES DYNAMIQUES
  申请人：FIRMENICH & CIE

  公开号：WO2007085991A2

  公开（公告）日：2007-08-02

  [EN] The present invention relates to a dynamic mixture in the form of a dynamic mixture obtained by reacting together, in the presence of water, at least one O-substituted hydroxylamine or S-substituted thiohydroxylamine derivative with at least one perfuming, flavoring, insect repellent or attractant, bactericide and/or fungicide aldehyde or ketone. The invention's mixture is capable of releasing in a controlled and prolonged manner said aldehyde or ketone in the surrounding environment. Furthermore, the present invention concerns also the use of said dynamic mixtures as perfuming ingredients as well as the perfuming compositions or perfumed articles comprising the invention's mixtures.
  [FR] La présente invention concerne un mélange dynamique sous la forme d'un mélange dynamique obtenu par la réaction, en présence d'eau, d'au moins un dérivé hydroxylamine O-substituée ou thiohydroxylamine S-substituée avec au moins un aldéhyde ou une cétone parfumant, aromatisant, insecticide ou insecticide-appât, bactéricide et/ou fongicide. Le mélange de l'invention est capable de libérer ledit aldéhyde ou ladite cétone d'une manière régulée et prolongée dans l'environnement proche. En outre, la présente invention concerne également l'utilisation desdits mélanges dynamiques en tant qu'ingrédients de parfum ainsi que des compositions de parfum ou des articles parfumés comprenant les mélanges de l'invention.