N-{2-[(4-羟基苯基)硫基]乙基}丙酰胺 | 155196-03-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: N-{2-[(4-羟基苯基)硫基]乙基}丙酰胺
• 英文名称: N-propionyl-4-S-cysteaminylphenol
• 英文别名: N-[2-(4-Hydroxyphenylsulfanyl)ethyl]propionamide；N-[2-(4-hydroxyphenyl)sulfanylethyl]propanamide
• CAS: 155196-03-5
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: QSZDEDWYJWMGDI-UHFFFAOYSA-N

物化性质

• 沸点：
  465.2±30.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  N-{2-[(4-羟基苯基)硫基]乙基}丙酰胺 、 丙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以90%的产率得到N-[2-{(4-propionyloxyphenyl)thio}ethyl]propionamide
  参考文献：
  名称：

  A Simple and Efficient Synthesis ofN‐[2‐{(4‐Propionyloxyphenyl)thio}ethyl]propionamide (DIPCAP), a Tyrosine‐Dependent Cytotoxic Agent as a Topical Antimelanoma Therapy

  摘要：

  The synthesis of N-[2-{(4-propionyloxyphenyl)thio}ethyl]propionamide (DIPCAP), a tyrosine-dependent cytotoxic agent that is currently being evaluated as a topical antimelanoma treatment is described. Problems encountered in scaling up the original patent procedure have been eliminated and DIPCAP was obtained in an overall yield of 65% from commercially available starting materials.

  DOI：

  10.1081/scc-200026188
• 作为产物：
  描述：

  2-乙基-2-唑啉 、 4-羟基苯硫酚 反应 4.0h， 以97%的产率得到N-{2-[(4-羟基苯基)硫基]乙基}丙酰胺
  参考文献：
  名称：

  Synthesis and Antitumour Effect of the Melanogenesis-based Antimelanoma Agent N-Propionyl-4-S-cysteaminylphenol

  摘要：

  Chemotherapy of malignant melanoma is still a great challenge, as no effective drugs are available. The development of melanogenesis-based drugs is a promising area of research because melanogenesis is a unique biochemical pathway operating only in melanoma cells (and their normal counterparts) so that the tumour can be targeted. We have been using cysteinylphenol, a sulphur containing analogue of tyrosine, and derivatives for that purpose. N-Acetyl-4-S-cysteaminylphenol was found to have the best antimelanoma effect in cell culture systems and in mice bearing B16 melanoma rumours. It also caused depigmentation of the skin, suggesting the possibility of use as a hypopigmenting agent. To improve the efficiency of the drug, we thought of replacing the acetyl group in N-acetyl-4-S-cysteaminylphenol with a propionyl group in the hope that increased hydrophobicity would increase the cellular uptake of the drug. N-Propionyl-4-S-cysteaminylphenol was synthesized by condensing 4-hydroxythiophenol with 2-ethyl-2-oxazoline. The drug showed both cytostatic and cytocidal effects in a human melanotic melanoma cell line. The drug was found to be a good depigmenting agent for the black hair follicles of C57 black mice when given s.c. for 14 days. A 10-day treatment with N-propionyl-4-S-cysteaininylphenol at 300 mg/kg body weight reduced the growth rate of B16 melanoma s.c. rumours in mice by 36%. The propionyl derivative was found to increase the life span of mice bearing melanoma more effectively than did the acetyl derivative. BIOCHEM PHARMACOL 55;12:2023-2029, 1998. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(98)00090-2

文献信息

• Synthesis and Antitumour Effect of the Melanogenesis-based Antimelanoma Agent N-Propionyl-4-S-cysteaminylphenol
  作者：Manju Tandon、Panakkezhum D Thomas、Mohammed Shokravi、Shradha Singh、Satinder Samra、Daniel Chang、Kowichi Jimbow

  DOI：10.1016/s0006-2952(98)00090-2

  日期：1998.6

  Chemotherapy of malignant melanoma is still a great challenge, as no effective drugs are available. The development of melanogenesis-based drugs is a promising area of research because melanogenesis is a unique biochemical pathway operating only in melanoma cells (and their normal counterparts) so that the tumour can be targeted. We have been using cysteinylphenol, a sulphur containing analogue of tyrosine, and derivatives for that purpose. N-Acetyl-4-S-cysteaminylphenol was found to have the best antimelanoma effect in cell culture systems and in mice bearing B16 melanoma rumours. It also caused depigmentation of the skin, suggesting the possibility of use as a hypopigmenting agent. To improve the efficiency of the drug, we thought of replacing the acetyl group in N-acetyl-4-S-cysteaminylphenol with a propionyl group in the hope that increased hydrophobicity would increase the cellular uptake of the drug. N-Propionyl-4-S-cysteaminylphenol was synthesized by condensing 4-hydroxythiophenol with 2-ethyl-2-oxazoline. The drug showed both cytostatic and cytocidal effects in a human melanotic melanoma cell line. The drug was found to be a good depigmenting agent for the black hair follicles of C57 black mice when given s.c. for 14 days. A 10-day treatment with N-propionyl-4-S-cysteaininylphenol at 300 mg/kg body weight reduced the growth rate of B16 melanoma s.c. rumours in mice by 36%. The propionyl derivative was found to increase the life span of mice bearing melanoma more effectively than did the acetyl derivative. BIOCHEM PHARMACOL 55;12:2023-2029, 1998. (C) 1998 Elsevier Science Inc.
• A Simple and Efficient Synthesis of<i>N</i>‐[2‐{(4‐Propionyloxyphenyl)thio}ethyl]propionamide (DIPCAP), a Tyrosine‐Dependent Cytotoxic Agent as a Topical Antimelanoma Therapy
  作者：Lisa D. Coutts、Harold Meckler、Karl F. Popp

  DOI：10.1081/scc-200026188

  日期：2004.1

  The synthesis of N-[2-(4-propionyloxyphenyl)thio}ethyl]propionamide (DIPCAP), a tyrosine-dependent cytotoxic agent that is currently being evaluated as a topical antimelanoma treatment is described. Problems encountered in scaling up the original patent procedure have been eliminated and DIPCAP was obtained in an overall yield of 65% from commercially available starting materials.