5 -甲氧基-3,4二氢- 1(2H)-异喹啉 | 129075-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 5 -甲氧基-3,4二氢- 1(2H)-异喹啉
• 中文别名: 5-甲氧基-3,4二氢-1(2H)-异喹啉；5-甲氧基-3,4二氢-1(2H)-异喹啉酮
• 英文名称: 3,4-dihydro-5-methoxy-1(2H)-isoquinolinone
• 英文别名: 5-methoxy-3,4-dihydro-2H-isoquinolin-1-one；5-methoxy-3,4-dihydroisoquinolin-1(2H)-one；5-methoxy-3,4-dihydroisoquinolin-1-one
• CAS: 129075-49-6
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: OESOLVOZJGIVMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  5 -甲氧基-3,4二氢- 1(2H)-异喹啉 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.75h， 生成 2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl)-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Development of 3,4-dihydroisoquinolin-1(2H)-one derivatives for the Positron Emission Tomography (PET) imaging of σ2 receptors

  摘要：

  sigma(2) Receptors are promising biomarkers for cancer diagnosis given the relationship between the proliferative status of tumors and their density. With the aim of contributing to the research of sigma(2) receptor Positron Emission Tomography (PET) probes, we developed 243-16,7-dimethoxy-3,4dihydroisoquinolin-2(1H)-yllpropy11-3,4-dihydroisoquinolin-1(2H)-one (3), with optimal sigma(2) pharmacological properties and appropriate lipophilicity. Hence, 3 served as the lead compound for the development of a series of dihydroisoquinolinones amenable to radiolabeling. Radiosynthesis for compound 26, which displayed the most appropriate sigma(2) profile, was developed and sigma(2) specific binding for the corresponding [18F1-26 was confirmed by in vitro autoradiography on rat brain slices. Despite the excellent in vitro properties, [189-26 could not successfully image sigma(2) receptors in the rat brain in vivo, maybe because of its interaction with P-gp. Nevertheless, [189-26 may still be worthy of further investigation for the imaging of sigma(2) receptors in peripheral tumors devoid of P-gp overexpression. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.018
• 作为产物：
  描述：

  5-羟基-3,4-二氢-2H-异喹啉-1-酮 在 硫酸二甲酯 作用下， 以 甲醇 、 sodium hydroxide 、 水 为溶剂， 以5.3 g (89%)的产率得到5 -甲氧基-3,4二氢- 1(2H)-异喹啉
  参考文献：
  名称：

  Substituted dihydroisoquinolinones and related compounds as potentiators

  摘要：

  这项发明涉及选择的、新颖的、以及已知的异喹啉酮类化合物及其药学上可接受的盐；新颖的药物组合物；以及一种增强对肿瘤细胞的致命效应的方法，该方法包括对具有DNA损伤活性的治疗方法进行增强，例如电离辐射或化疗药物。

  公开号：

  US05177075A1

文献信息

• [EN] 17a-HYDROXYLASE/C17,20-LYASE INHIBITORS<br/>[FR] INHIBITEURS DE LA 17?-HYDROXYLASE/C17,20-LYASE
  申请人：NOVARTIS AG

  公开号：WO2012035078A1

  公开（公告）日：2012-03-22

  The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

  本发明提供了式（I）的化合物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、A和n如本文所定义。还提供了式（I）化合物的氘代衍生物。
• 17a-HYDROXYLASE/C17,20-LYASE INHIBITORS
  申请人：Bock Mark Gary

  公开号：US20140045872A1

  公开（公告）日：2014-02-13

  The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

  本发明提供了式（I）的化合物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、A和n如本文所定义。还提供了式（I）化合物的氘代衍生物。
• COMPOUNDS USEFUL AS IMMUNOMODULATORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20170107202A1

  公开（公告）日：2017-04-20

  The present disclosure generally relates to compounds useful as immunomodulators. Provided herein are compounds, compositions comprising such compounds, and methods of their use. The disclosure further pertains to pharmaceutical compositions comprising at least one compound according to the disclosure that are useful for the treatment of various diseases, including cancer and infectious diseases.

  本发明公开一般涉及可用作免疫调节剂的化合物。本发明提供了化合物、包含此类化合物的组合物及其使用方法。本发明还涉及包含至少一种根据本发明的化合物的药物组合物，这些药物组合物可用于治疗各种疾病，包括癌症和传染病。
• Structure-Based Design and Discovery of New M₂ Receptor Agonists
  作者：Inbar Fish、Anne Stößel、Katrin Eitel、Celine Valant、Sabine Albold、Harald Huebner、Dorothee Möller、Mary J. Clark、Roger K. Sunahara、Arthur Christopoulos、Brian K. Shoichet、Peter Gmeiner

  DOI：10.1021/acs.jmedchem.7b01113

  日期：2017.11.22

  structure-guided pharmacophore design followed by docking, we found two agonists (compounds 3 and 17), out of 19 docked and synthesized compounds, that fit the receptor well and were predicted to form a hydrogen-bond conserved among known agonists. Structural optimization led to compound 28, which was 4-fold more potent than its parent 3. Fortified by the discovery of this new scaffold, we sought a broader range

  毒蕈碱受体激动剂的特征在于，它们的叔胺或季胺及其与酯或相关中心的距离显然受到严格限制。基于毒蕈碱M 2受体与吡咯酮复合的活性状态晶体结构，我们探索了缺乏先前已知配体高度保守的功能的潜在激动剂。使用结构引导的药效团设计，然后对接，我们在19种对接和合成的化合物中发现了两种激动剂（化合物3和17），它们与受体非常吻合，并被预测会在已知的激动剂中形成保守的氢键。结构优化导致化合物28的效价比其母体3高4倍。由于发现了这种新型支架，我们对接了220万个片段，寻求了更广泛的化学型，这揭示了另外三种与28种毒蕈碱或已知毒蕈碱无关的微摩尔激动剂。甚至像毒蕈碱一样严格定义和深入研究的口袋也揭示了基于结构的设计和发现新化学型的机会。
• A study on the conversion of indanones into carbostyrils
  作者：Yasuhiro Torisawa、Takao Nishi、Jun-ichi Minamikawa

  DOI：10.1016/s0968-0896(03)00116-0

  日期：2003.5

  surveyed the utility of Beckmann rearrangement for the conversion of indanones into carbostyrils. Initial attempts at the conversion of 6-methoxy indanone oxime under classical conditions resulted in the formation of the two unusual products: 2-sulfonyloxyindanone and the dimeric product. This unusual rearrangement was also observed by the treatment of some metal triflates species. Further investigation

  我们已经调查了贝克曼重排用于将茚满酮转化为咔唑的效用。在经典条件下进行6-甲氧基茚满酮肟转化的初步尝试导致形成两种不同的产物：2-磺酰氧基茚满酮和二聚产物。通过处理一些金属三氟甲磺酸盐物种也观察到了这种异常的重排。进一步的研究导致了从甲磺酸肟（不是甲苯磺酸肟）开始的可靠条件的发展，其中在常规或非常规溶剂系统中使用了一些强路易斯酸催化剂（ZrCl（4））。通过简单的后处理和直接分离产品（65％的分离产率）突出了新协议的优势。