N-piperoylglycine | 90778-74-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-piperoylglycine
• 英文别名: N-(5-benzo[1,3]dioxol-5-yl-penta-2,4-dienoyl)-glycine；Piperoylglycin；2-[5-(1,3-Benzodioxol-5-yl)penta-2,4-dienoylamino]acetic acid
• CAS: 90778-74-8
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: YJGUOUOJYSSXTR-UHFFFAOYSA-N

物化性质

• 沸点：
  587.4±50.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胡椒碱 在 吡啶 、 氢氧化钾 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.25h， 生成 N-piperoylglycine
  参考文献：
  名称：

  Design, development and synthesis of mixed bioconjugates of piperic acid–glycine, curcumin–glycine/alanine and curcumin–glycine–piperic acid and their antibacterial and antifungal properties

  摘要：

  In the present communication different curcumin bioconjugates viz. 4,4'-di-O-glycinoyl-curcumin, 4,4'-di-O-D-alaninoyl-curcumin, 4,4'-di-O-(glycinoyl-di-N-piperoyl)-curcumin, 4,4'-di-O-piperoyl curcumin, curcumin-4,4'-di-O-P-D-glucopyranoside, 4,4'-di-O-acetyl-curcumin along with piperoyl glycine, have been synthesised and characterised by spectra UV, H-1 NMR and elemental analysis. All the covalent bonds used are biodegradable. This makes these derivatives as potent prodrugs, which can get hydrolysed at the target sites. These bioconjugates were tested in vitro against different bacteria and fungi. The 4,4'-di-O-(glycinoyl-di-N-piperoyl)-curcumin and 4,4'-di-O-acetyl-curcumin are more effective than Cefepime, an antibacterial drug available in market, at the same concentration. The 4,4'-di-O-(glycinoyl-di-N-piperoyl)-curcumin and 4,4'-di-O-piperoyl curcumin had antifungal activity in vitro almost comparable with fluconazole, the most popular antifungal drug. The enhanced activity of these bioconjugates vis-A-vis the parent molecule that is curcumin may be due to improved cellular uptake or reduced metabolism of these bioconjugates resulting in building up of enough concentration inside the infected cells. It opens a new era for exploring suitably designed curcurnin bioconjugates as potential antibacterial/antifungal drugs. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.057

文献信息

• Design, development and synthesis of mixed bioconjugates of piperic acid–glycine, curcumin–glycine/alanine and curcumin–glycine–piperic acid and their antibacterial and antifungal properties
  作者：Satyendra Mishra、Upma Narain、Roli Mishra、Krishna Misra

  DOI：10.1016/j.bmc.2004.12.057

  日期：2005.3.1

  In the present communication different curcumin bioconjugates viz. 4,4'-di-O-glycinoyl-curcumin, 4,4'-di-O-D-alaninoyl-curcumin, 4,4'-di-O-(glycinoyl-di-N-piperoyl)-curcumin, 4,4'-di-O-piperoyl curcumin, curcumin-4,4'-di-O-P-D-glucopyranoside, 4,4'-di-O-acetyl-curcumin along with piperoyl glycine, have been synthesised and characterised by spectra UV, H-1 NMR and elemental analysis. All the covalent bonds used are biodegradable. This makes these derivatives as potent prodrugs, which can get hydrolysed at the target sites. These bioconjugates were tested in vitro against different bacteria and fungi. The 4,4'-di-O-(glycinoyl-di-N-piperoyl)-curcumin and 4,4'-di-O-acetyl-curcumin are more effective than Cefepime, an antibacterial drug available in market, at the same concentration. The 4,4'-di-O-(glycinoyl-di-N-piperoyl)-curcumin and 4,4'-di-O-piperoyl curcumin had antifungal activity in vitro almost comparable with fluconazole, the most popular antifungal drug. The enhanced activity of these bioconjugates vis-A-vis the parent molecule that is curcumin may be due to improved cellular uptake or reduced metabolism of these bioconjugates resulting in building up of enough concentration inside the infected cells. It opens a new era for exploring suitably designed curcurnin bioconjugates as potential antibacterial/antifungal drugs. (C) 2005 Elsevier Ltd. All rights reserved.