methyl 5-(aminomethyl)-2-methoxybenzoate | 900641-76-1

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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-(aminomethyl)-2-methoxybenzoate
• CAS: 900641-76-1
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD04618243
• 分子量: 195.218
• InChiKey: JFKUPTRYVDEPDY-UHFFFAOYSA-N

物化性质

• 沸点：
  329.7±32.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(aminomethyl)-2-methoxybenzoate 在 吡啶 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-methoxy-5-(methylsulfonamidomethyl)benzoic acid
  参考文献：
  名称：

  1-PHENYL-2-PYRIDINYL ALKYL ALCOHOL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS

  摘要：

  本文描述的化合物（I）的公式是磷酸二酯酶4（PDE4）酶的抑制剂，可用于预防和/或治疗由气道阻塞特征的过敏病状态或呼吸道疾病。

  公开号：

  US20140155391A1
• 作为产物：
  描述：

  5-甲基水杨酸 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氨 、 potassium carbonate 作用下， 以 甲醇 、 四氯化碳 、 丙酮 为溶剂， 反应 2.0h， 生成 methyl 5-(aminomethyl)-2-methoxybenzoate
  参考文献：
  名称：

  4-Quinolone-3-carboxylic acids as cell-permeable inhibitors of protein tyrosine phosphatase 1B

  摘要：

  Protein tyrosine phosphatase 1B is a negative regulator in the insulin and leptin signaling pathways, and has emerged as an attractive target for the treatment of type 2 diabetes and obesity. However, the essential pharmacophore of charged phosphotyrosine or its mimetic confer low selectivity and poor cell permeability. Starting from our previously reported aryl diketoacid-based PTP1B inhibitors, a drug-like scaffold of 4-quinolone-3-carboxylic acid was introduced for the first time as a novel surrogate of phosphotyrosine. An optimal combination of hydrophobic groups installed at C-6, N-1 and C-3 positions of the quinolone motif afforded potent PTP1B inhibitors with low micromolar IC50 values. These 4-quinolone-3-carboxylate based PTP1B inhibitors displayed a 2-10 fold selectivity over a panel of PTP's. Furthermore, the bidentate inhibitors of 4-quinolone-3-carboxylic acids conjugated with aryl diketoacid or salicylic acid were cell permeable and enhanced insulin signaling in CHO/hIR cells. The kinetic studies and molecular modeling suggest that the 4-quinolone-3-carboxylates act as competitive inhibitors by binding to the PTP1B active site in the WPD loop closed conformation. Taken together, our study shows that the 4-quinolone-3-carboxylic acid derivatives exhibit improved pharmacological properties over previously described PTB1B inhibitors and warrant further preclinical studies.

  DOI：

  10.1016/j.bmc.2014.05.028

文献信息

• Discovery of a Novel Vascular Disrupting Agent Inhibiting Tubulin Polymerization and HDACs with Potent Antitumor Effects
  作者：Huajian Zhu、Yuchen Tan、Chen He、Yang Liu、Yiping Duan、Wenjian Zhu、Tiandong Zheng、Dahong Li、Jinyi Xu、Dong-Hua Yang、Zhe-Sheng Chen、Shengtao Xu

  DOI：10.1021/acs.jmedchem.2c00681

  日期：2022.8.25

  disrupting agents (VDAs) capable of inhibiting microtubule polymerization and histone deacetylases (HDACs) were designed and synthesized using the tubulin polymerization inhibitor TH-0 as the lead compound. Among them, compound TH-6 exhibited the most potent antiproliferative activity (IC50 = 18–30 nM) against a panel of cancer cell lines. As expected, TH-6 inhibited tubulin assembly and increased the acetylation

  大多数血管破坏剂（VDA）无法阻止肿瘤边缘血管的再生，导致肿瘤反弹和复发。在此，以微管聚合抑制剂TH-0为先导化合物，设计并合成了一系列能够抑制微管聚合的新型多功能血管破坏剂（VDA）和组蛋白去乙酰化酶（HDAC） 。其中，化合物TH-6对一组癌细胞系表现出最有效的抗增殖活性 (IC 50 = 18–30 nM)。正如所料，TH-6抑制微管蛋白组装并增加 HepG2 细胞中 HDAC 底物蛋白的乙酰化水平。进一步的体内抗肿瘤试验表明TH-6有效抑制肿瘤生长，无明显毒性。更重要的是，TH-6破坏了内部和外周肿瘤脉管系统，这有助于停药后的持续肿瘤抑制作用。总之，对于临床癌症治疗的新方法， TH-6值得进一步研究。
• SUBSTITUTED AMINO-BENZIMIDAZOLES, MEDICAMENTS COMPRIMISING SAID COMPOUND, THEIR USE AND THEIR METHOD OF MANUFACTURE
  申请人：Fuchs Klaus

  公开号：US20110288139A1

  公开（公告）日：2011-11-24

  The present invention relates to substituted amino-benzimidazoles of general formula (1) wherein the groups R 1 to R 14 and A, are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.
• US8426607B2
  申请人：——

  公开号：US8426607B2

  公开（公告）日：2013-04-23
• US9944612B2
  申请人：——

  公开号：US9944612B2

  公开（公告）日：2018-04-17
• [EN] 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] DÉRIVÉS D'ALCOOL 1-PHÉNYL-2-PYRIDINYL ALKYLIQUE EN TANT QU'INHIBITEURS DE PHOSPHODIESTÉRASE
  申请人：CHIESI FARMA SPA

  公开号：WO2014086865A1

  公开（公告）日：2014-06-12

  The present invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to 1-phenyl-2-pyridinyl alkyl alcohol derivatives, to processes for the preparation thereof, compositions comprising them, combinations and therapeutic uses thereof.