methyl 5-hydroxy-2-(2-methoxy-2-oxoethyl)benzoate | 21640-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-hydroxy-2-(2-methoxy-2-oxoethyl)benzoate
• CAS: 21640-24-4
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: WGHJLTXWFPWKFN-UHFFFAOYSA-N

物化性质

• 沸点：
  367.0±32.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-2-(2-methoxy-2-oxoethyl)benzoate 在 硫酸 、 potassium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 32.0h， 生成 (±)-5-methoxy-2-(2-sec-butoxy-2-oxo-ethyl)benzoic acid
  参考文献：
  名称：

  4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents

  摘要：

  4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.

  DOI：

  10.3390/molecules29071519
• 作为产物：
  描述：

  邻羧基苯乙酸 在 甲醇 、 硫酸 、 palladium 10% on activated carbon 、 甲酸铵 、 sodium nitrite 作用下， 反应 18.5h， 生成 methyl 5-hydroxy-2-(2-methoxy-2-oxoethyl)benzoate
  参考文献：
  名称：

  4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents

  摘要：

  4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.

  DOI：

  10.3390/molecules29071519

文献信息

• [EN] OXO-TETRAHYDRO-ISOQUINOLINE CARBOXYLIC ACIDS AS STING INHIBITORS<br/>[FR] ACIDES OXO-TÉTRAHYDRO-ISOQUINOLINE CARBOXYLIQUES EN TANT QU'INHIBITEURS DE LA PROTÉINE STING
  申请人：MERCK SHARP & DOHME

  公开号：WO2019182886A1

  公开（公告）日：2019-09-26

  The instant invention provides compounds of formula I which are STING inhibitors, and as such are useful for the treatment of STING-mediated diseases such as inflammation, asthma, COPD and cancer.

  本发明提供了一种式I的化合物，这些化合物是STING抑制剂，因此可用于治疗STING介导的疾病，如炎症、哮喘、慢性阻塞性肺病（COPD）和癌症。
• Design, synthesis and biological evaluation of 3-substituted indenoisoquinoline derivatives as topoisomerase I inhibitors
  作者：Qian Zhao、Xi Xu、Zhouling Xie、Xiao Liu、Qidong You、Qinglong Guo、Yi Zhong、Zhiyu Li

  DOI：10.1016/j.bmcl.2015.12.014

  日期：2016.2

  new series of indenoisoquinoline derivatives was designed and synthesized. The in vitro anti-proliferative activity of these novel compounds was evaluated in HepG2, A549 and HCT-116 cell lines. Compounds 9a, 9b, 10a, 10c, 10e, 18a and 18b manifested potent inhibitory activity against the three tested cancer cell lines. Nineteen compounds were also tested for Top I inhibition at 50 μM. Almost all the

  设计并合成了一系列新的茚并异喹啉衍生物。在HepG2，A549和HCT-116细胞系中评估了这些新型化合物的体外抗增殖活性。化合物9a，9b，10a，10c，10e，18a和18b表现出对三种测试癌细胞系的有效抑制活性。还测试了19种化合物在50μM下对Top I的抑制作用。在该浓度下，几乎所有测试的化合物都显示出有效的Top I抑制活性。最有效的化合物9a和10a 与HCPT和TPT相比，它具有更高的细胞毒性，并且在我们的生物学分析中，对Top I的抑制活性可与CPT相媲美。
• Oxo-tetrahydro-isoquinoline carboxylic acids as STING inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US11311528B2

  公开（公告）日：2022-04-26

  The instant invention provides compounds of formula I which are STING inhibitors, and as such are useful for the treatment of STING-mediated diseases such as inflammation, asthma, COPD and cancer.

  本发明提供的式 I 化合物是 STING 抑制剂，因此可用于治疗 STING 介导的疾病，如炎症、哮喘、慢性阻塞性肺病和癌症。
• Regulating miRNA-21 Biogenesis By Bifunctional Small Molecules
  作者：Hao Yan、Umesh Bhattarai、Zhi-Fo Guo、Fu-Sen Liang

  DOI：10.1021/jacs.7b00610

  日期：2017.4.12

  We report a new strategy to regulate microRNAs (miRNAs) biogenesis by using bifunctional small molecules that consist of a pre-miRNA binding unit connected by a linker to a Dicer inhibiting unit. In this effort, fluorescence polarization-based screening was used to identify neomycin as a pre-miR-21 binding ligand. Although neomycin cannot inhibit miR-21 maturation, linking it to the RNase inhibitor 1 forms the bifunctional conjugate 7A, which inhibits the production of miR-21. We expect that this strategy will be applicable to design other molecules for miRNA regulation.
• Design, synthesis and activity of light deactivatable microRNA inhibitor
  作者：Hao Yan、Umesh Bhattarai、Yabin Song、Fu-Sen Liang

  DOI：10.1016/j.bioorg.2018.07.003

  日期：2018.10

  miRNAs are key cellular regulators and their dysregulation is associated with many human diseases. They are usually produced locally in a spatiotemporally controlled manner to target mRNAs and regulate gene expression. Thus, developing chemical tools for manipulating miRNA with spatiotemporal precise is critical for studying miRNA. Herein, we designed a strategy to control miRNA biogenesis with light controllable inhibitor targeting the pre-miRNA processing by Dicer. By conjugating two non-inhibiting units, a low affinity Dicer inhibitor and a pre-miRNA binder, through a photocleavable linker, the bifunctional molecule obtained could inhibit miRNA production. Taking advantage of the photocleavable property of the linker, the bifunctional inhibitor can be fragmented into separate non-inhibiting units and therefore be deactivated by light. We expect that this strategy could be applied to generate chemical biological tools that allow light-mediated spatiotemporal control of miRNA maturation and contribute to the study of miRNA function.