4-(p-nitroguaiacoxy)butanoic acid | 121329-77-9

• 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: 4-(p-nitroguaiacoxy)butanoic acid
• 英文别名: 4-(2-methoxy-4-nitrophenoxy)butanoic acid
• CAS: 121329-77-9
• 化学式: C₁₁H₁₃NO₆
• 分子量: 255.227
• InChiKey: XQJNOEBJVJPORG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(p-nitroguaiacoxy)butanoic acid 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 48.0h， 生成 2-[4-(2-methoxy-4-nitrophenoxy)butanoylamino]acetic acid
  参考文献：
  名称：

  红霉素光敏衍生物的合成及其生物活性。

  摘要：

  通过将芳基叠氮化物或对硝基苯基醚与9（S）-氨基红霉素连接，已经合成了五种红霉素的光敏衍生物。一种衍生物是通过与（5-叠氮基-2-甲酰基-苯氧基）乙酸反应形成的酰胺。三种衍生物也是酰胺，它们直接或通过插入氨基酸（甘氨酸或酪氨酸）与4-（对硝基愈创木酸）丁酸作为光反应性基团合成。最后的衍生物是氨基红霉素与10-（对硝基愈创木氧基）癸醛的醛缩合产物。通过用[3H]硼氢化物（芳基叠氮化物衍生物）还原或通过125 I碘化（4-（对硝基愈创木氧基）酪氨酰基衍生物），可以轻松地使这些衍生物中的两种具有放射性，以进行亲和标记研究。尽管受到不同程度的影响，这五种红霉素衍生物具有生物活性，并与细菌核糖体上的红霉素特异性位点结合。另外，这些基团的引入改变了肽键模型反应的红霉素抑制模式。

  DOI：

  10.1021/jm00129a027
• 作为产物：
  描述：

  methyl 4-(2-methoxy-4-nitrophenoxy)butanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以58%的产率得到4-(p-nitroguaiacoxy)butanoic acid
  参考文献：
  名称：

  Potent human glutaminyl cyclase inhibitors as potential anti-Alzheimer’s agents: Structure-activity relationship study of Arg-mimetic region

  摘要：

  Pyroglutamate-modified amyloid beta peptides (pGlu-A beta) are highly neurotoxic and promote the formation of amyloid plaques. The pGlu-A beta peptides are generated by glutaminyl cyclase (QC), and recent clinical studies indicate that QC represents an alternative therapeutic target to treat Alzheimer's disease (AD). We have previously developed a series of QC inhibitors with an extended pharmacophoric scaffold, termed the Arg-mimetic D-region. In the present study, we focused on the structure activity relationship (SAR) of analogues with modifications in the D-region and evaluated their biological activity. Most compounds in this series exhibited potent activity in vitro, and our SAR analysis and the molecular docking studies identified compound 202 as a potential candidate because it forms an additional hydrophobic interaction in the hQC active site. Overall, our study provides valuable insights into the Arg-mimetic pharmacophore that will guide the design of novel QC inhibitors as potential treatments for AD. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.01.015

文献信息

• AREVALO, M. ANGELES;TEJEDOR, FRANCISCO;POLO, FLORENTINO;BALLESTA, J. P. G+, J. MED. CHEM., 32,(1989) N, C. 2200-2204
  作者：AREVALO, M. ANGELES、TEJEDOR, FRANCISCO、POLO, FLORENTINO、BALLESTA, J. P. G+

  DOI：——

  日期：——
• AREVALO, M. ANGELES;TEJEDOR, FRANCISCO;POLO, FLORENTINO;BALLESTA, J. P. G+, J. MED. CHEM., 32,(1989) N, C. 2204-2210
  作者：AREVALO, M. ANGELES、TEJEDOR, FRANCISCO、POLO, FLORENTINO、BALLESTA, J. P. G+

  DOI：——

  日期：——
• Potent human glutaminyl cyclase inhibitors as potential anti-Alzheimer’s agents: Structure-activity relationship study of Arg-mimetic region
  作者：Van T.H. Ngo、Van-Hai Hoang、Phuong-Thao Tran、Jihyae Ann、Minghua Cui、Gyungseo Park、Sun Choi、Jiyoun Lee、Hee Kim、Hee-Jin Ha、Kwanghyun Choi、Young-Ho Kim、Jeewoo Lee

  DOI：10.1016/j.bmc.2018.01.015

  日期：2018.3

  Pyroglutamate-modified amyloid beta peptides (pGlu-A beta) are highly neurotoxic and promote the formation of amyloid plaques. The pGlu-A beta peptides are generated by glutaminyl cyclase (QC), and recent clinical studies indicate that QC represents an alternative therapeutic target to treat Alzheimer's disease (AD). We have previously developed a series of QC inhibitors with an extended pharmacophoric scaffold, termed the Arg-mimetic D-region. In the present study, we focused on the structure activity relationship (SAR) of analogues with modifications in the D-region and evaluated their biological activity. Most compounds in this series exhibited potent activity in vitro, and our SAR analysis and the molecular docking studies identified compound 202 as a potential candidate because it forms an additional hydrophobic interaction in the hQC active site. Overall, our study provides valuable insights into the Arg-mimetic pharmacophore that will guide the design of novel QC inhibitors as potential treatments for AD. (C) 2018 Elsevier Ltd. All rights reserved.
• Synthesis and biological activity of photoactive derivatives of erythromycin
  作者：M. Angeles Arevalo、Francisco Tejedor、Florentino Polo、J. P. G. Ballesta

  DOI：10.1021/jm00129a027

  日期：1989.9

  The last derivative is the product of the aldehyde condensation of aminoerythromycin with 10-(p-nitroguaiacoxy)decanal. Two of these derivatives can easily be made radioactive for affinity labeling studies either by reduction with [3H]borohydride (aryl azide derivative) or by 125I iodination (4-(p-nitroguaiacoxy)tyrosyl derivative). Although affected to different extents, the five erythromycin derivatives

  通过将芳基叠氮化物或对硝基苯基醚与9（S）-氨基红霉素连接，已经合成了五种红霉素的光敏衍生物。一种衍生物是通过与（5-叠氮基-2-甲酰基-苯氧基）乙酸反应形成的酰胺。三种衍生物也是酰胺，它们直接或通过插入氨基酸（甘氨酸或酪氨酸）与4-（对硝基愈创木酸）丁酸作为光反应性基团合成。最后的衍生物是氨基红霉素与10-（对硝基愈创木氧基）癸醛的醛缩合产物。通过用[3H]硼氢化物（芳基叠氮化物衍生物）还原或通过125 I碘化（4-（对硝基愈创木氧基）酪氨酰基衍生物），可以轻松地使这些衍生物中的两种具有放射性，以进行亲和标记研究。尽管受到不同程度的影响，这五种红霉素衍生物具有生物活性，并与细菌核糖体上的红霉素特异性位点结合。另外，这些基团的引入改变了肽键模型反应的红霉素抑制模式。