methyl (2S)-4-methylsulfanyl-2-(octadecanoylamino)butanoate | 121330-63-0

• 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: methyl (2S)-4-methylsulfanyl-2-(octadecanoylamino)butanoate
• CAS: 121330-63-0
• 化学式: C₂₄H₄₇NO₃S
• 分子量: 429.708
• InChiKey: JCXGASCYDPCDEJ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  29
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-4-methylsulfanyl-2-(octadecanoylamino)butanoate 在 sodium hydroxide 作用下， 生成 N-stearoyl-L-methionine
  参考文献：
  名称：

  Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine

  摘要：

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.028
• 作为产物：
  描述：

  (2S)-2-氨基-4-甲硫基丁酸甲酯 、 硬脂酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 生成 methyl (2S)-4-methylsulfanyl-2-(octadecanoylamino)butanoate
  参考文献：
  名称：

  Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine

  摘要：

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.028

文献信息

• Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine
  作者：Boyang Liu、Chunying Cui、Wei Duan、Ming Zhao、Shiqi Peng、Lili Wang、Hu Liu、Guohui Cui

  DOI：10.1016/j.ejmech.2009.02.028

  日期：2009.9

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.