4-ethylpiperic acid | 911410-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-ethylpiperic acid
• 英文别名: (2E,4E)-4-(benzo[d][1,3]dioxol-5-ylmethylene)hex-2-enoic acid；(E,4E)-4-(1,3-benzodioxol-5-ylmethylidene)hex-2-enoic acid
• CAS: 911410-81-6
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: HAPJYNQWLWVDEY-AGLLBGTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethylpiperic acid 、 L-脯氨酸甲酯盐酸盐 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl (2S)-1-[(E,4E)-4-(1,3-benzodioxol-5-ylmethylidene)hex-2-enoyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Inhibition of Invasion in Pancreatic Cancer Cells by Conjugate of EPA with β^3,3-Pip-OH via PI3K/Akt/NF-kB Pathway

  摘要：

  The present work describes the anti-invasive effect of conjugate BC06, a novel conjugate of EPA, (2E,4E)-4-(benzo[d][1,3]dioxol-5-ylmethylene) hex-2-enoic acid with beta,beta-disubstituted-beta-amino acid, beta(3,3)-Pip-OH (2-(4-aminopiperidin-4-yl)acetic acid), in human pancreatic carcinoma. The conjugate BC06 inhibited invasion and migration of PANC-1 cells in wound healing, matrigel invasion, and gelatin degradation assays. Apart from suppressing PI3K/Akt/NF-kB signaling, which is involved in the up-regulation of matrix metalloproteinases, our study also demonstrated that dose-dependent treatment of BC06 results in the upregulation of TIMP-I and E-cadherin expression. Further, BC06 was found to be inhibiting the metastatic ability of PANC-1 cells by reducing MMP-2 and MMP-9 expression. These findings suggest that EPA conjugate with beta(3,3)-Pip-OH, BC06, may be used as an anti-invasive agent against human pancreatic carcinoma.

  DOI：

  10.1021/acsmedchemlett.5b00257
• 作为产物：
  描述：

  1-(3,4-亚甲二氧基苯基)-1-丙醇 在 sodium hydride 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 苯 为溶剂， 生成 4-ethylpiperic acid
  参考文献：
  名称：

  作为金黄色葡萄球菌的NorA外排泵抑制剂，哌酸（PA）和4-乙基哌酸（EPA）的氨基酸酰胺。

  摘要：

  合成了总共18种带有α-，β-和γ-氨基酸的哌酸（PA）和4-乙基哌酸（EPA）酰胺（C1-C18），表征并评估了其对耐环丙沙星葡萄球菌的外排泵抑制活性金黄色的。使用溴化乙锭作为NorA外排泵底物，针对过表达NorA的过表达金黄色葡萄球菌SA-1199B和野生型金黄色葡萄球菌SA-1199筛选酰胺。发现EPI C6最有效，环丙沙星的MIC降低了16倍，其次是C18，MIC降低了4倍。溴化乙锭的流出抑制和蓄积分析证明了这些化合物是NorA抑制剂。

  DOI：

  10.1016/j.bmcl.2016.07.062

文献信息

• Aromatic amides as potentiators of bioefficacy of anti-infective drugs
  申请人：Koul Surrinder

  公开号：US20070004645A1

  公开（公告）日：2007-01-04

  The present invention relates to an aromatic substituted pentadienoic acid amides and there use in combination of specific amounts of aromatic amides i.e. 4-alkyl-5-(substituted phenyl)-2(E),4(E)-pentadienoic acid amides, its geometrical isomers or their dihydro or tetrahydro derivatives and an anti-infective drug useful in potentiating the bioefficacy of antiinfective drug. The combination of the present invention is useful in the treatment of certain infections and disease at lower concentration of anti-infectives necessary to inhibit the growth of microbial strains and may also find applications in reducing the resistance in microorganisms.

  本发明涉及芳香取代的戊二烯酸酰胺及其在芳香酰胺的特定量的组合中的使用，即4-烷基-5-(取代苯基)-2(E),4(E)-戊二烯酸酰胺，其几何异构体或其二氢或四氢衍生物，以及一种抗感染药物，有助于增强抗感染药物的生物功效。本发明的组合物在治疗某些感染和疾病方面非常有用，可以在抑制微生物菌株生长所需的抗感染剂浓度较低的情况下发挥作用，并且还可以在减少微生物的抗药性方面发挥作用。
• Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus
  作者：Naiem Ahmad Wani、Samsher Singh、Saleem Farooq、Sudha Shankar、Surrinder Koul、Inshad Ali Khan、Rajkishor Rai

  DOI：10.1016/j.bmcl.2016.07.062

  日期：2016.9

  A total of eighteen piperic acid (PA) and 4-ethylpiperic acid (EPA) amides (C1-C18) with α-, β- and γ-amino acids were synthesized, characterized and evaluated for their efflux pump inhibitory activity against ciprofloxacin resistant Staphylococcus aureus. The amides were screened against NorA overexpressing S. aureus SA-1199B and wild type S. aureus SA-1199 using ethidium bromide as NorA efflux pump

  合成了总共18种带有α-，β-和γ-氨基酸的哌酸（PA）和4-乙基哌酸（EPA）酰胺（C1-C18），表征并评估了其对耐环丙沙星葡萄球菌的外排泵抑制活性金黄色的。使用溴化乙锭作为NorA外排泵底物，针对过表达NorA的过表达金黄色葡萄球菌SA-1199B和野生型金黄色葡萄球菌SA-1199筛选酰胺。发现EPI C6最有效，环丙沙星的MIC降低了16倍，其次是C18，MIC降低了4倍。溴化乙锭的流出抑制和蓄积分析证明了这些化合物是NorA抑制剂。
• AROMATIC AMIDES AS POTENTIATORS OF BIOEFFICACY OF ANTI-INFECTIVE DRUGS
  申请人：Council Of Scientific and Industrial Research

  公开号：US20140073595A1

  公开（公告）日：2014-03-13

  The present invention relates to an aromatic substituted pentadienoic acid amides and there use in combination of specific amounts of aromatic amides i.e. 4-alkyl-5-(substituted phenyl)-2(E),4(E)-pentadienoic acid amides, its geometrical isomers or their dihydro or tetrahydro derivatives and an anti-infective drug useful in potentiating the bioefficacy of antiinfective drug. The combination of the present invention is useful in the treatment of certain infections and disease at lower concentration of anti-infectives necessary to inhibit the growth of microbial strains and may also find applications in reducing the resistance in microorganisms.

  本发明涉及芳香基取代的戊二烯酸酰胺及其在特定量的芳香酰胺，即4-烷基-5-（取代苯基）-2（E），4（E）-戊二烯酸酰胺，其几何异构体或其二氢或四氢衍生物和抗感染药物的组合物中的使用，有助于增强抗感染药物的生物功效。本发明的组合物对于治疗某些感染和疾病有用，可在抑制微生物菌株生长所需的抗感染剂浓度较低的情况下发挥作用，并且还可在减少微生物的耐药性方面应用。
• US8580752B2
  申请人：——

  公开号：US8580752B2

  公开（公告）日：2013-11-12
• US9073860B2
  申请人：——

  公开号：US9073860B2

  公开（公告）日：2015-07-07