methyl 4-((1,3-dioxoisoindolin-2-yl)methyl)benzoate | 34211-05-7

• 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: methyl 4-((1,3-dioxoisoindolin-2-yl)methyl)benzoate
• 英文别名: 4-Phthalimidomethyl-benzoesaeure-methylester；Methyl-α-phthalimido-p-toluat；4-phthalimidomethyl-benzoic acid methyl ester；methyl 4-[(1,3-dioxoisoindol-2-yl)methyl]benzoate
• CAS: 34211-05-7
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: RVVRWHZJBHWUCT-UHFFFAOYSA-N

物化性质

• 沸点：
  465.9±38.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-((1,3-dioxoisoindolin-2-yl)methyl)benzoate 在 PPA 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-benzooxazol-2-yl-benzylamine
  参考文献：
  名称：

  抗菌剂。2.取代的苯并噻唑基苄胺和相关化合物。

  摘要：

  DOI：

  10.1021/jm00294a025
• 作为产物：
  描述：

  对甲基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 4-((1,3-dioxoisoindolin-2-yl)methyl)benzoate
  参考文献：
  名称：

  The development of a novel transforming growth factor-β (TGF-β) inhibitor that disrupts ligand-receptor interactions

  摘要：

  Transforming growth factor-beta (TGF-beta) plays an important role in regulating epithelial to mesenchymal transition (EMT) and the TGF-beta signaling pathway is a potential target for therapeutic intervention in the development of many diseases, such as fibrosis and cancer. Most currently available inhibitors of TGF-beta signaling function as TGF-beta receptor I (T beta R-I) kinase inhibitors, however, such kinase inhibitors often lack specificity. In the present study, we targeted the extracellular protein binding domain of the TGF-beta receptor II (T beta R-II) to interfere with the protein-protein interactions (PPIs) between TGF-beta and its receptors. One compound, CJJ300, inhibited TGF-beta signaling by disrupting the formation of the TGF-beta-T beta R-I-T beta R-II signaling complex. Treatment of A549 cells with CJJ300 resulted in the inhibition of downstream signaling events such as the phosphorylation of key factors along the TGF-beta pathway and the induction of EMT markers. Concomitant with these effects, CJJ300 significantly inhibited cell migration. The present study describes for the first time a designed molecule that can regulate TGF-beta-induced signaling and EMT by interfering with the PPIs required for the formation of the TGF-beta signaling complex. Therefore, CJJ300 can be an important lead compound with which to study TGF-beta signaling and to design more potent TGF-beta signaling antagonists. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112042

文献信息

• HDAC7 Inhibition by Phenacetyl and Phenylbenzoyl Hydroxamates
  作者：Jeffrey Y. W. Mak、Kai-Chen Wu、Praveer K. Gupta、Sheila Barbero、Maddison G. McLaughlin、Andrew J. Lucke、Jiahui Tng、Junxian Lim、Zhixuan Loh、Matthew J. Sweet、Robert C. Reid、Ligong Liu、David P. Fairlie

  DOI：10.1021/acs.jmedchem.0c01967

  日期：2021.2.25

  exploit a cavity in HDAC7, filled by Tyr303 in HDAC1, to derive new inhibitors. Phenacetyl hydroxamates and 2-phenylbenzoyl hydroxamates bind to Zn2+ and are 50–2700-fold more selective inhibitors of HDAC7 than HDAC1. Phenylbenzoyl hydroxamates are 30–70-fold more potent HDAC7 inhibitors than phenacetyl hydroxamates, which is attributed to the benzoyl aromatic group interacting with Phe679 and Phe738.

  含锌的组蛋白脱乙酰基酶HDAC7正在成为免疫代谢和癌症的重要调节剂。在这里，我们利用HDAC7中的一个空腔（由HDAC1中的Tyr303填充）来衍生新的抑制剂。苯乙酰基异羟肟酸酯和2-苯基苯甲酰基异羟肟酸酯与Zn 2+结合与HDAC1相比，它们是HDAC7选择性抑制剂的50-2700倍。苯甲酰基异羟肟酸酯比苯乙酰基异羟肟酸酯的有效HDAC7抑制剂高30-70倍，这归因于苯甲酰基芳基与Phe679和Phe738相互作用。邻苯二甲酰亚胺封端基团（包括糖精类似物）会降低旋转自由度，并提供氢键受体羰基/磺酰胺氧，从而增加抑制剂的效力，肝脏微粒体的稳定性，溶解度和细胞活性。尽管是迄今为止最有效的HDAC7抑制剂，但它们在IIa类酶中没有选择性。这些策略可能有助于产生用于询问与HDAC7催化位点有关的生物学工具。
• 10.1021/acs.joc.4c00871
  作者：Wu, Kang、Wang, Tian-Zhang、Zhang, Chao-Peng、Guan, Yu-Qiu、Liang, Yu-Feng

  DOI：10.1021/acs.joc.4c00871

  日期：——

  reaction of N-methoxyphthalimides with alkyl halides is described, where N-methoxyphthalimides serve as nitrogen electrophiles. This tactic provides a new approach to construct C–N bonds under mild neutral conditions. Alkyl chlorides, bromides, iodides, and sulfonates are all fit to this transformation. Moreover, the reaction could tolerate a broad substrate scope, especially base-sensitive functional

  N-烷氧基邻苯二甲酰亚胺是邻苯二甲酰亚胺衍生物的一种，在合成中具有重要意义，主要用作自由基前体。而邻苯二甲酰亚胺装置长期以来一直被视为废物流的一部分。 C-N键的构建一直是一个热点，特别是在还原交叉耦合方面。本文描述了N-甲氧基邻苯二甲酰亚胺与卤代烷的镍催化还原交叉偶联反应，其中N-甲氧基邻苯二甲酰亚胺充当氮亲电子试剂。这种策略提供了一种在温和中性条件下构建 C-N 键的新方法。烷基氯、烷基溴、烷基碘和磺酸盐都适合这种转化。此外，该反应可以耐受广泛的底物范围，特别是碱敏感的官能团（硼或硅基团），以及竞争性亲核基团（酚和酰胺），这些与传统的Gabriel合成在碱性条件下不相容，表现出互补性这项工作的作用为加布里埃尔合成。
• Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides
  作者：Rammohan Devulapally、Nicolas Fleury-Brégeot、Gary A. Molander、Dave G. Seapy

  DOI：10.1016/j.tetlet.2011.12.062

  日期：2012.2

  Potassium imidomethyltrifluoroborate salts were efficiently synthesized. Potassium phthalimidomethyltrifluoroborate was successfully used in Suzuki-Miyaura-like cross-coupling reactions with a variety of aryl chlorides. (C) 2011 Elsevier Ltd. All rights reserved.
• BASIC AMINE COMPOUND AND USE THEREOF
  申请人：Kureha Corporation

  公开号：EP1724263B1

  公开（公告）日：2014-03-05
• US7157078B2
  申请人：——

  公开号：US7157078B2

  公开（公告）日：2007-01-02