(E)-3-(3-(4-hydroxyphenyl)acryloyl)-3-(2-morpholinoethyl)dihydrofuran-2(3H)-one | 1622868-93-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3-(4-hydroxyphenyl)acryloyl)-3-(2-morpholinoethyl)dihydrofuran-2(3H)-one
• 英文别名: 3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-3-(2-morpholin-4-ylethyl)oxolan-2-one
• CAS: 1622868-93-2
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: AZIBKTMTRZNFQC-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-酒石酸 、 (E)-3-(3-(4-hydroxyphenyl)acryloyl)-3-(2-morpholinoethyl)dihydrofuran-2(3H)-one 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Design and synthesis of γ-butyrolactone derivatives as potential spermicidal agents

  摘要：

  A series of γ-butyrolactone derivatives has been designed and synthesized from commercially available 2-acetyl butyrolactone (3-acetyldihydrofuran-2(3H)-one, 1) by aminoalkylating its active methylene followed by condensation with different aldehydes. Compounds having amino group were further converted to their respective tartrate salts and were evaluated for spermicidal activity against human sperm in vitro. Compounds showing appreciable spermicidal activity at ⩽0.5% [3c, 4d (0.5%); 2c, 3d (0.1%); 2d, 4c (0.05%)] were tested for safety studies against human cervical (HeLa) cell line. These compounds were found safer than, Nonoxynol-9. One of the two most active compounds was also found to be the safest (IC50=961 μg/ml; 4c), while the second compound exhibited lower safety against HeLa (IC50=269 μg/ml; 2d). The compound 4c significantly reduced the number of free thiols on human sperm. All the compounds were inactive against Trichomonas vaginalis.

  DOI：

  10.1016/j.bmcl.2014.06.045
• 作为产物：
  描述：

  N-(2-氯乙基)吗啉盐酸盐 在 哌啶 、 potassium carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 20.0h， 生成 (E)-3-(3-(4-hydroxyphenyl)acryloyl)-3-(2-morpholinoethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Design and synthesis of γ-butyrolactone derivatives as potential spermicidal agents

  摘要：

  A series of γ-butyrolactone derivatives has been designed and synthesized from commercially available 2-acetyl butyrolactone (3-acetyldihydrofuran-2(3H)-one, 1) by aminoalkylating its active methylene followed by condensation with different aldehydes. Compounds having amino group were further converted to their respective tartrate salts and were evaluated for spermicidal activity against human sperm in vitro. Compounds showing appreciable spermicidal activity at ⩽0.5% [3c, 4d (0.5%); 2c, 3d (0.1%); 2d, 4c (0.05%)] were tested for safety studies against human cervical (HeLa) cell line. These compounds were found safer than, Nonoxynol-9. One of the two most active compounds was also found to be the safest (IC50=961 μg/ml; 4c), while the second compound exhibited lower safety against HeLa (IC50=269 μg/ml; 2d). The compound 4c significantly reduced the number of free thiols on human sperm. All the compounds were inactive against Trichomonas vaginalis.

  DOI：

  10.1016/j.bmcl.2014.06.045

文献信息

• Design and synthesis of γ-butyrolactone derivatives as potential spermicidal agents
  作者：Rishi Ranjan Pandey、Akansha Srivastava、Shakti Deep Pachauri、Kiran Khandelwal、Arshi Naqvi、Richa Malasoni、Bhavana Kushwaha、Lokesh Kumar、Jagdamba Prasad Maikhuri、Garima Pandey、Sarvesh Paliwal、Gopal Gupta、Anil Kumar Dwivedi

  DOI：10.1016/j.bmcl.2014.06.045

  日期：2014.8

  A series of γ-butyrolactone derivatives has been designed and synthesized from commercially available 2-acetyl butyrolactone (3-acetyldihydrofuran-2(3H)-one, 1) by aminoalkylating its active methylene followed by condensation with different aldehydes. Compounds having amino group were further converted to their respective tartrate salts and were evaluated for spermicidal activity against human sperm in vitro. Compounds showing appreciable spermicidal activity at ⩽0.5% [3c, 4d (0.5%); 2c, 3d (0.1%); 2d, 4c (0.05%)] were tested for safety studies against human cervical (HeLa) cell line. These compounds were found safer than, Nonoxynol-9. One of the two most active compounds was also found to be the safest (IC50=961 μg/ml; 4c), while the second compound exhibited lower safety against HeLa (IC50=269 μg/ml; 2d). The compound 4c significantly reduced the number of free thiols on human sperm. All the compounds were inactive against Trichomonas vaginalis.