3-醛基-4-甲氧基苯硼酸频呢醇酯 | 866546-13-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-醛基-4-甲氧基苯硼酸频呢醇酯
• 英文名称: 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• 英文别名: 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde；2-Methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• CAS: 866546-13-6
• 化学式: C₁₄H₁₉BO₄
• 分子量: 262.113
• InChiKey: SZNYFXSMWMPULL-UHFFFAOYSA-N

物化性质

• 沸点：
  385.5±32.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-醛基-4-甲氧基苯硼酸频呢醇酯 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 三异丙基硅烷 、 四丁基溴化铵 、 水 、 sodium cyanoborohydride 、 三乙胺 、 cesium fluoride 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 120.0 ℃ 、1.72 MPa 条件下， 反应 5.5h， 生成 4-[3-(benzylaminomethyl)-4-methoxyphenyl]-3-bromo-5-hydroxy-5H-furan-2-one
  参考文献：
  名称：

  Toward the Discovery of New Agents Able to Inhibit the Expression of Microsomal Prostaglandin E Synthase-1 Enzyme as Promising Tools in Drug Development

  摘要：

  In our recent studies, we focused our attention on the synthesis of several γ‐hydroxybutenolides designed on the basis of petrosaspongiolide M 1 (PM) structure that has been recognized to potently inhibit the inflammatory process through the selective PLA2 enzyme inhibition. By means of a combination of computational methods and efficient synthetic strategies, we generated small collections of PM modified analogs to identify new potent PLA2 inhibitors, suitable for clinical development. In the course of the biological screening of our compounds, we discovered a potent and selective inhibitor of mPGES‐1 expression, the benzothiophene γ‐hydroxybutenolide 2, which so far represents the only product, together with resveratrol, able to reduce PGE2 production through the selective downregulation of mPGES‐1 enzyme. In consideration that microsomal prostaglandin E synthase 1 (mPGES‐1) is one of the most strategic target involved both in inflammation and in carcinogenesis processes, we decided to explore the biological effects of some structural changes of the γ‐hydroxybutenolide 2, hoping to improve its biological profile. This optimization process led to the identification of three strictly correlated compounds 14g, 16g, and 18 with higher inhibitory potency on PGE2 production on mouse macrophage cell line RAW264.7 through the selective modulation of mPGES‐1 enzyme expression.

  DOI：

  10.1111/j.1747-0285.2010.00984.x
• 作为产物：
  描述：

  频哪醇 、 3-甲酰基-4-甲氧基苯硼酸 以 乙酸乙酯 为溶剂， 反应 4.0h， 以92%的产率得到3-醛基-4-甲氧基苯硼酸频呢醇酯
  参考文献：
  名称：

  Toward the Discovery of New Agents Able to Inhibit the Expression of Microsomal Prostaglandin E Synthase-1 Enzyme as Promising Tools in Drug Development

  摘要：

  In our recent studies, we focused our attention on the synthesis of several γ‐hydroxybutenolides designed on the basis of petrosaspongiolide M 1 (PM) structure that has been recognized to potently inhibit the inflammatory process through the selective PLA2 enzyme inhibition. By means of a combination of computational methods and efficient synthetic strategies, we generated small collections of PM modified analogs to identify new potent PLA2 inhibitors, suitable for clinical development. In the course of the biological screening of our compounds, we discovered a potent and selective inhibitor of mPGES‐1 expression, the benzothiophene γ‐hydroxybutenolide 2, which so far represents the only product, together with resveratrol, able to reduce PGE2 production through the selective downregulation of mPGES‐1 enzyme. In consideration that microsomal prostaglandin E synthase 1 (mPGES‐1) is one of the most strategic target involved both in inflammation and in carcinogenesis processes, we decided to explore the biological effects of some structural changes of the γ‐hydroxybutenolide 2, hoping to improve its biological profile. This optimization process led to the identification of three strictly correlated compounds 14g, 16g, and 18 with higher inhibitory potency on PGE2 production on mouse macrophage cell line RAW264.7 through the selective modulation of mPGES‐1 enzyme expression.

  DOI：

  10.1111/j.1747-0285.2010.00984.x

文献信息

• CHEMICAL COMPOUNDS
  申请人：Deng Jianghe

  公开号：US20090143372A1

  公开（公告）日：2009-06-04

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  这项发明涉及新型吲哚羧酰胺衍生物。具体而言，该发明涉及符合以下式I的化合物： 其中R1、R2、R3、U和V如下定义，并且其药学上可接受的盐。该发明的化合物是IKK2的抑制剂，可用于治疗与不当IKK2（也称为IKKβ）活性相关的疾病，如类风湿性关节炎、哮喘和慢性阻塞性肺病（COPD）。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物抑制IKK2活性和治疗相关疾病的方法。
• Discovery of Potent 2-Aryl-6,7-dihydro-5<i>H</i>-pyrrolo[1,2-<i>a</i>]imidazoles as WDR5-WIN-Site Inhibitors Using Fragment-Based Methods and Structure-Based Design
  作者：Feng Wang、Kyu Ok Jeon、James M. Salovich、Jonathan D. Macdonald、Joseph Alvarado、Rocco D. Gogliotti、Jason Phan、Edward T. Olejniczak、Qi Sun、Shidong Wang、DeMarco Camper、Joannes P. Yuh、J. Grace Shaw、Jiqing Sai、Olivia W. Rossanese、William P. Tansey、Shaun R. Stauffer、Stephen W. Fesik

  DOI：10.1021/acs.jmedchem.8b00375

  日期：2018.7.12

  WDR5 is a chromatin-regulatory scaffold protein overexpressed in various cancers and a potential epigenetic drug target for the treatment of mixed-lineage leukemia. Here, we describe the discovery of potent and selective WDR5-WIN-site inhibitors using fragment-based methods and structure-based design. NMR-based screening of a large fragment library identified several chemically distinct hit series

  WDR5 是一种在多种癌症中过表达的染色质调节支架蛋白，也是治疗混合谱系白血病的潜在表观遗传药物靶点。在这里，我们描述了使用基于片段的方法和基于结构的设计发现了有效且选择性的 WDR5-WIN 位点抑制剂。基于 NMR 的大片段库筛选确定了几个化学上不同的命中序列，它们与 WDR5 内的 WIN 位点结合。使用基于结构的设计方法扩展了 6,7-二氢-5 H -吡咯并[1,2- a ]咪唑片段类的成员，以获得解离常数为 <10 nM 且针对 AML 具有微摩尔细胞活性的先导化合物-白血病细胞系。这些化合物代表了发现临床上有用的 WDR5 抑制剂用于治疗癌症的起点。
• [EN] AZAINDOLES USEFUL AS INHIBITORS OF JAK AND OTHER PROTEIN KINASES<br/>[FR] AZAINDOLES UTILES COMME INHIBITEURS DE JANUS KINASES ET D'AUTRES PROTEINES KINASES
  申请人：VERTEX PHARMA

  公开号：WO2005095400A1

  公开（公告）日：2005-10-13

  The present invention relates to compounds of formula (I), which are inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及式(I)的化合物，它们是蛋白激酶的抑制剂。该发明还提供了包括该发明的化合物的药物组合物，以及使用这些组合物治疗各种疾病的方法。
• Total synthesis of honokiol by selective samarium-mediated allylic benzoate reduction
  作者：Alicia M. Wright、Gregory W. O’Neil

  DOI：10.1016/j.tetlet.2016.06.066

  日期：2016.8

  The total synthesis of the biologically relevant compound honokiol has been completed featuring a samarium-mediated bis-benzoyl ester reduction to simultaneously install both allyl substituents found in the natural product. This reaction was performed after a Suzuki coupling was used to generate the biphenyl core, thereby avoiding problems associated with the acidity of these allyl groups and their

  已经完成了生物学上相关的化合物厚朴酚的全合成，其特征在于a介导的双-苯甲酰基酯还原，以同时安装天然产物中发现的两个烯丙基取代基。在使用Suzuki偶合生成联苯核之后进行该反应，从而避免了与这些烯丙基的酸度及其异构化倾向有关的问题。这样，厚朴酚的合成可以通过4个步骤完成，并且总产率为42％。
• Electrogenerated Chemiluminescent Chemodosimeter Based on a Cyclometalated Iridium(III) Complex for Sensitive Detection of Thiophenol
  作者：Kyoung-Rok Kim、Hoon Jun Kim、Jong-In Hong

  DOI：10.1021/acs.analchem.8b03445

  日期：2019.1.15

  body by inhalation and ingestion, which leads to serious internal injuries. Thus, there is an urgent need for real-time and accurate monitoring of thiophenol. Despite remarkable advantages of electrogenerated chemiluminescence (ECL) analysis, ECL thiophenol probes have never been reported. Herein, a new strategy for the rapid detection of thiophenol by use of an ECL turn-on chemodosimeter based on

  硫酚是最简单的芳香族硫醇，可用于工业和农业的各种应用。但是，应谨慎使用，因为硫酚会通过吸入和食入轻易吸收到人体中，从而导致严重的内部伤害。因此，迫切需要对苯硫酚进行实时和准确的监测。尽管电化学发光（ECL）分析具有显着优势，但从未报道过ECL硫酚探针。在本文中，描述了一种新的策略，该策略通过使用基于环金属化Ir（III）配合物的ECL开启化学计量仪快速检测苯硫酚。与常规荧光方法相比，该分析系统显示出出众的灵敏度[检测限（LOD）值3.8 nM]。此外，与其他分析物相比，我们的系统对苯硫酚具有显着的选择性和反应速率。此外，它已成功应用于定量真实水样中的苯酚，为基于ECL的现场监测提供了新的概念验证。