methyl 4-amino-3,5-diethylbenzoate | 1001055-65-7

• 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 4-amino-3,5-diethylbenzoate
• CAS: 1001055-65-7
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: TXSRHSXTEGGGMO-UHFFFAOYSA-N

物化性质

• 沸点：
  353.8±42.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-3,5-diethylbenzoate 在 氢溴酸 、 sodium nitrite 、 铜 作用下， 生成 methyl 4-bromo-3,5-diethylbenzoate
  参考文献：
  名称：

  Design and synthesis of potent amido- and benzyl-substituted cis-3-amino-4-(2-cyanopyrrolidide)pyrrolidinyl DPP-IV inhibitors

  摘要：

  The cis-3-amino-4-(2-cyanopyrrolidide)-pyrrolidine template has been shown to afford low nanomolar inhibitors of human DPP-IV that exhibit a robust PK/PD profile. An X-ray co-crystal structure of 5 confirmed the proposed mode of binding. The potent single digit DPP-IV inhibitor 53 exhibited a preferred PK/PD profile in preclinical animal models and was selected for additional profiling.

  DOI：

  10.1016/j.bmcl.2007.10.063
• 作为产物：
  描述：

  在 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 生成 methyl 4-amino-3,5-diethylbenzoate
  参考文献：
  名称：

  Design and synthesis of potent amido- and benzyl-substituted cis-3-amino-4-(2-cyanopyrrolidide)pyrrolidinyl DPP-IV inhibitors

  摘要：

  The cis-3-amino-4-(2-cyanopyrrolidide)-pyrrolidine template has been shown to afford low nanomolar inhibitors of human DPP-IV that exhibit a robust PK/PD profile. An X-ray co-crystal structure of 5 confirmed the proposed mode of binding. The potent single digit DPP-IV inhibitor 53 exhibited a preferred PK/PD profile in preclinical animal models and was selected for additional profiling.

  DOI：

  10.1016/j.bmcl.2007.10.063

文献信息

• In Vitro and In Vivo Inhibition of the <i>Mycobacterium tuberculosis</i> Phosphopantetheinyl Transferase PptT by Amidinoureas
  作者：Samantha Ottavi、Sarah M. Scarry、John Mosior、Yan Ling、Julia Roberts、Amrita Singh、David Zhang、Laurent Goullieux、Christine Roubert、Eric Bacqué、H. Rachel Lagiakos、Jeremie Vendome、Francesca Moraca、Kelin Li、Andrew J. Perkowski、Remya Ramesh、Matthew M. Bowler、William Tracy、Victoria A. Feher、James C. Sacchettini、Ben S. Gold、Carl F. Nathan、Jeffrey Aubé

  DOI：10.1021/acs.jmedchem.1c01565

  日期：2022.2.10

  in analogues containing a para-substituted aromatic ring. Preliminary data reveal that while some analogues, including 1, have demonstrated cardiotoxicity (e.g., changes in cardiomyocyte beat rate, amplitude, and peak width) and inhibit Cav1.2 and Nav1.5 ion channels (although not hERG channels), inhibition of the ion channels is largely diminished for some of the para-substituted analogues, such as

  新近验证的结核病治疗靶点是磷酸泛酰巯基乙胺基转移酶，它是一种必需酶，在结核分枝杆菌的细胞脂质和毒力因子的生物合成中起关键作用。探索了最近公开的抑制剂脒脲 (AU) 8918 ( 1 ) 的构效关系，重点是生化效力、活性化合物全细胞靶向活性的测定以及选择性活性同源物的分析。这些研究表明，AU 8918 中的 AU 部分在很大程度上得到了优化，并且在含有对位取代芳环的类似物中获得了效力增强。初步数据显示，虽然一些类似物，包括1, 已证明有心脏毒性（例如，心肌细胞搏动率、幅度和峰宽的变化）并抑制 Ca v 1.2 和 Na v 1.5 离子通道（尽管不是 hERG 通道），对某些对离子通道的抑制作用大大减弱-取代的类似物，例如5k（对苯甲酰胺）和5n（对苯磺酰胺）。
• US6825355B2
  申请人：——

  公开号：US6825355B2

  公开（公告）日：2004-11-30
• Design and synthesis of potent amido- and benzyl-substituted cis-3-amino-4-(2-cyanopyrrolidide)pyrrolidinyl DPP-IV inhibitors
  作者：J.W. Corbett、K. Dirico、W. Song、B.P. Boscoe、S.D. Doran、D. Boyer、X. Qiu、M. Ammirati、M.A. VanVolkenburg、R.K. McPherson、J.C. Parker、E.D. Cox

  DOI：10.1016/j.bmcl.2007.10.063

  日期：2007.12

  The cis-3-amino-4-(2-cyanopyrrolidide)-pyrrolidine template has been shown to afford low nanomolar inhibitors of human DPP-IV that exhibit a robust PK/PD profile. An X-ray co-crystal structure of 5 confirmed the proposed mode of binding. The potent single digit DPP-IV inhibitor 53 exhibited a preferred PK/PD profile in preclinical animal models and was selected for additional profiling.