3-(4-methoxybenzylcarbamoyl)propanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxybenzylcarbamoyl)propanoic acid
• 英文别名: N-(p-methoxybenzyl)succinamic acid；3-(4-methoxybenzylcarbamoyl)-propanoic acid；4-[(4-Methoxybenzyl)amino]-4-oxobutanoic acid；4-[(4-methoxyphenyl)methylamino]-4-oxobutanoic acid
• 化学式: C₁₂H₁₅NO₄
• mdl: MFCD04153462
• 分子量: 237.255
• InChiKey: UCWWQJUWQZSRDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  紫朱牛舌草(ALKANNATINCTORIA)根提取物 、 3-(4-methoxybenzylcarbamoyl)propanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 以42.1%的产率得到1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(4-methoxybenzylamino)-4-oxobutanoate
  参考文献：
  名称：

  Novel naphthalene-enoates: Design and anticancer activity through regulation cell autophagy

  摘要：

  Eleven dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl) naphthalene derivatives as anticancer agents through regulating cell autophagy were designed and synthesized. The anticancer activity results indicated that most compounds manifested obvious un-toxic effect on GES-1 and L-02 with IC50 from 0.58 to 1.41 mM. Among them, (S, Z)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(3,4-dihydroisoquinolin- 2(1 H)-yl)-4-oxobut-2-enoate (compound 4i) could induce cancer cells apoptosis. Further experiments showed that autophagy played an important role in the pro-apoptotic effect of this compound. Preliminary mechanism indicated that this compound could inhibit phosphoinositide 3-kinase/protein kinase B and the mammalian target of rapamycin (PI3K/AKT/mTOR) pathway by mediating apoptosis in an autophagy-dependent manner.

  DOI：

  10.1016/j.biopha.2019.108747
• 作为产物：
  描述：

  5-hydroxy-1-(4-methoxybenzyl)pyrrolidin-2-one 在 1-羟基环己基苯基甲酮 、 水 、 sodium t-butanolate 作用下， 以 二氯甲烷 为溶剂， 以80 %的产率得到3-(4-methoxybenzylcarbamoyl)propanoic acid
  参考文献：
  名称：

  用 1-羟基环己基苯基酮将伯醇和醛氧化成羧酸

  摘要：

  伯醇氧化成相应的羧酸是有机合成中基本且有用的反应之一。在本文中，我们报告了通过 1-羟基环己基苯基酮介导的氢化物转移反应将伯醇和醛氧化为酸的综合结果。在叔丁醇钠的强碱性条件下，室温氧化可耐受一系列官能团，包括脆弱的叔丁亚磺酰胺、胺、硫化物、烯烃和杂环，并提供良好至优异的产率。最重要的是，我们的氧化过程可以应用于在仲醇存在下将伯醇和醛化学选择性氧化为羧酸。

  DOI：

  10.1021/acs.joc.3c00096

文献信息

• Synthesis and bradykinin inhibitory activity of novel non-peptide compounds, and evaluation of in vivo analgesic activity
  作者：Yoo Lim Kam、Hee-Kyung Rhee、Hwa-Jung Kim、Seung Keun Back、Heung Sik Na、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2010.01.050

  日期：2010.3

  A series of novel non-peptide diamide compounds was synthesized and evaluated as antibradykinin agents by utilizing guinea-pig ileum smooth muscle. Among the final compounds, (Z)-4-(4-(bis(4-fluorophenyl) methyl)piperazin-1-yl)-4-oxo-N-(4-phenylbutan-2-yl)but-2-enamide showed most favorable bradykinin inhibitory activity and demonstrated analgesic efficacies in the rat models of inflammatory and neuropathic pain. (C) 2010 Published by Elsevier Ltd.
• [EN] NEW NON-PEPTIDE COMPOUNDS, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS NON-PEPTIDIQUES, LEUR PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE LES CONTENANT
  申请人：PARK CHOO HEA-YOUNG

  公开号：WO2007142431A1

  公开（公告）日：2007-12-13

  [EN] The present invention relates to a novel non-peptide compound, a method for preparing the same, and a pharmaceutical composition comprising the same. The non-peptide compound of the present invention has excellent inhibitory effect on bradykinin activity, and on chronic neuropathic pain and inflammatory pain, thereby being used for preventing or treating a disease caused by bradykinin, in particular, pain.
  [FR] La présente invention concerne un nouveau composé non-peptidique, un procédé de préparation de celui-ci et une composition pharmaceutique le contenant. Le composé non-peptidique proposé par la présente invention présente un excellent effet inhibiteur sur l'activité bradykinine et sur la douleur neuropathique chronique et inflammatoire, étant ainsi utilisé pour la prévention ou le traitement d'une maladie ou une condition causée par la bradykinine, en particulier, la douleur.
• Novel naphthalene-enoates: Design and anticancer activity through regulation cell autophagy
  作者：Meng Di Yang、Xiao Bao Shen、Yang Sheng Hu、Yan Yan Chen、Xin Hua Liu

  DOI：10.1016/j.biopha.2019.108747

  日期：2019.5

  Eleven dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl) naphthalene derivatives as anticancer agents through regulating cell autophagy were designed and synthesized. The anticancer activity results indicated that most compounds manifested obvious un-toxic effect on GES-1 and L-02 with IC50 from 0.58 to 1.41 mM. Among them, (S, Z)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(3,4-dihydroisoquinolin- 2(1 H)-yl)-4-oxobut-2-enoate (compound 4i) could induce cancer cells apoptosis. Further experiments showed that autophagy played an important role in the pro-apoptotic effect of this compound. Preliminary mechanism indicated that this compound could inhibit phosphoinositide 3-kinase/protein kinase B and the mammalian target of rapamycin (PI3K/AKT/mTOR) pathway by mediating apoptosis in an autophagy-dependent manner.
• Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids with 1-Hydroxycyclohexyl Phenyl Ketone
  作者：Yi Lu、Wen-Yun Tan、Yuzhen Ding、Wen Chen、Hongbin Zhang

  DOI：10.1021/acs.joc.3c00096

  日期：2023.7.7

  The oxidation of primary alcohols to the corresponding carboxylic acids is one of the fundamental and useful reactions in organic synthesis. In this paper, we report our comprehensive results toward the oxidation of primary alcohols and aldehydes to acids via hydride transfer reactions mediated by 1-hydroxycyclohexyl phenyl ketone. Under the strong basic conditions of sodium tert-butoxide, the room

  伯醇氧化成相应的羧酸是有机合成中基本且有用的反应之一。在本文中，我们报告了通过 1-羟基环己基苯基酮介导的氢化物转移反应将伯醇和醛氧化为酸的综合结果。在叔丁醇钠的强碱性条件下，室温氧化可耐受一系列官能团，包括脆弱的叔丁亚磺酰胺、胺、硫化物、烯烃和杂环，并提供良好至优异的产率。最重要的是，我们的氧化过程可以应用于在仲醇存在下将伯醇和醛化学选择性氧化为羧酸。