5-(4-methoxybenzamido)pentanoic acid

• 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: 5-(4-methoxybenzamido)pentanoic acid
• 英文别名: 5-[(4-Methoxybenzoyl)amino]pentanoic acid
• 化学式: C₁₃H₁₇NO₄
• mdl: MFCD19450450
• 分子量: 251.282
• InChiKey: DUUDYVDBJJFMJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methoxybenzamido)pentanoic acid 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-4-(5-(4-methoxybenzamido)pentanamido)octanoic acid
  参考文献：
  名称：

  Inhibitors of secreted phospholipase A 2 suppress the release of PGE 2 in renal mesangial cells

  摘要：

  The upregulation of PGE(2) by mesangial cells has been observed under chronic inflammation condition. In the present work, renal mesangial cells were stimulated to trigger a huge increase of PGE(2) synthesis and were treated in the absence or presence of known PLA(2) inhibitors. A variety of synthetic inhibitors, mainly developed in our labs, which are known to selectively inhibit each of GIVA cPLA(2), GVIA iPLA(2), and GIIA/GV sPLA(2), were used as tools in this study. Synthetic sPLA(2) inhibitors, such as GK115 (an amide derivative based on the non-natural amino acid (R)-gamma-norleucine) as well as GK126 and GK241 (2-oxoamides based on the natural (S)-alpha-amino acid leucine and valine, respectively) presented an interesting effect on the suppression of PGE(2) formation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.017
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 、 5-氨基颉草酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到5-(4-methoxybenzamido)pentanoic acid
  参考文献：
  名称：

  Inhibitors of secreted phospholipase A 2 suppress the release of PGE 2 in renal mesangial cells

  摘要：

  The upregulation of PGE(2) by mesangial cells has been observed under chronic inflammation condition. In the present work, renal mesangial cells were stimulated to trigger a huge increase of PGE(2) synthesis and were treated in the absence or presence of known PLA(2) inhibitors. A variety of synthetic inhibitors, mainly developed in our labs, which are known to selectively inhibit each of GIVA cPLA(2), GVIA iPLA(2), and GIIA/GV sPLA(2), were used as tools in this study. Synthetic sPLA(2) inhibitors, such as GK115 (an amide derivative based on the non-natural amino acid (R)-gamma-norleucine) as well as GK126 and GK241 (2-oxoamides based on the natural (S)-alpha-amino acid leucine and valine, respectively) presented an interesting effect on the suppression of PGE(2) formation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.017

文献信息

• Hydroxamic Acids Constitute a Novel Class of Autotaxin Inhibitors that Exhibit <i>in Vivo</i> Efficacy in a Pulmonary Fibrosis Model
  作者：Aikaterini Nikolaou、Ioanna Ninou、Maroula G. Kokotou、Eleanna Kaffe、Antreas Afantitis、Vassilis Aidinis、George Kokotos

  DOI：10.1021/acs.jmedchem.8b00232

  日期：2018.4.26

  Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) generating the lipid mediator lysophosphatidic acid (LPA). Both ATX and LPA are involved in various pathological inflammatory conditions, including fibrosis and cancer, and have attracted great interest as medicinal targets over the past decade. Thus, the development of novel potent ATX inhibitors is of great importance. We have developed a novel class of ATX inhibitors containing the zinc binding functionality of hydroxamic acid. Such novel hydroxamic acids that incorporate a non-natural delta-amino acid residue exhibit high in vitro inhibitory potency over ATX (IC50 values 50-60 nM). Inhibitor 32, based on delta-norleucine, was tested for its efficacy in a mouse model of pulmonary inflammation and fibrosis induced by bleomycin and exhibited promising efficacy. The novel hydroxamic ATX inhibitors provide excellent tools for the study of the role of the enzyme and could contribute to the development of novel therapeutic agents for the treatment of fibrosis and other chronic inflammatory diseases.
• Inhibitors of secreted phospholipase A 2 suppress the release of PGE 2 in renal mesangial cells
  作者：Sofia Vasilakaki、Efrosini Barbayianni、Victoria Magrioti、Oleksandr Pastukhov、Violetta Constantinou-Kokotou、Andrea Huwiler、George Kokotos

  DOI：10.1016/j.bmc.2016.05.017

  日期：2016.7

  The upregulation of PGE(2) by mesangial cells has been observed under chronic inflammation condition. In the present work, renal mesangial cells were stimulated to trigger a huge increase of PGE(2) synthesis and were treated in the absence or presence of known PLA(2) inhibitors. A variety of synthetic inhibitors, mainly developed in our labs, which are known to selectively inhibit each of GIVA cPLA(2), GVIA iPLA(2), and GIIA/GV sPLA(2), were used as tools in this study. Synthetic sPLA(2) inhibitors, such as GK115 (an amide derivative based on the non-natural amino acid (R)-gamma-norleucine) as well as GK126 and GK241 (2-oxoamides based on the natural (S)-alpha-amino acid leucine and valine, respectively) presented an interesting effect on the suppression of PGE(2) formation. (C) 2016 Elsevier Ltd. All rights reserved.