Boc-Ile-SH | 738590-97-1

• 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: Boc-Ile-SH
• 英文别名: (2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanethioic S-acid
• CAS: 738590-97-1
• 化学式: C₁₁H₂₁NO₃S
• 分子量: 247.359
• InChiKey: DLEUEBPWPDFTTC-YUMQZZPRSA-N

物化性质

• 沸点：
  343.8±25.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  56.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-Ile-SH 在 N,N'-二环己基-4-吗啉脒 、 磷酸 、 sodium hydride 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 3-({{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}[3-(L-isoleucylthio)propoxy]phosphoryl}oxy)propyl 2-(4-isobutylphenyl)propanoate
  参考文献：
  名称：

  Synthesis, anti-HBV activity and renal cell toxicity evaluation of mixed phosphonate prodrugs of adefovir

  摘要：

  A series of phosphonate ester prodrugs of adefovir incorporating L-amino (thio)acid and non-steroidal anti-inflammatory drug (NSAID) moieties were synthesized and their anti-HBV activity and renal cell toxicity were evaluated in HepG2 2.2.15 and HK-2 cells respectively. Bioactivity evaluation results revealed that this kind of adefovir prodrug have lower renal cell toxicity than adefovir dipivoxil. Compounds 8a and 8b, incorporating the NSAID ketoprofen and the L-amino acid (Val or Ile) structural fragments, exhibited more potent anti-HBV activity than adefovir dipivoxil with IC50 = 0.51 and 0.73 mu M, SI = 1697.64 and 881.92 respectively. In vitro stability studies showed that the synthesized prodrugs have higher chemical and plasma stability than the positive control adefovir dipivoxil. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.013
• 作为产物：
  描述：

  BOC-L-异亮氨酸 在 盐酸 N-甲基吗啉 、 硫化氢 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 生成 Boc-Ile-SH
  参考文献：
  名称：

  9- [2-（膦酰基甲氧基）乙基]腺嘌呤（PMEA）的新型双（L-氨基酸）酯前药的设计与合成，具有改善的抗HBV活性。

  摘要：

  合成了一系列新型的9- [2-（膦酰基甲氧基）乙基]腺嘌呤（PMEA）双（L-氨基酸）酯前药，并在HepG 2 2.2.15细胞中评估了它们的抗HBV活性。与用作阳性对照的阿德福韦酯相比，化合物11、12、21、22、26和27表现出更强的抗HBV活性和更高的选择性指数（SI）。被发现是最有效的化合物11，其效力是阿德福韦酯的5倍，EC50值为0.095 microM，CC50值为6636 microM。化合物11的SI值（> 69,000）分别比阿德福韦酯和拉米夫定高60倍和24倍。体外稳定性研究表明，化合物11比阿德福韦酯更稳定，t1 / 2为270分钟。

  DOI：

  10.1016/j.bmcl.2006.10.021

文献信息

• Design and synthesis of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity
  作者：Xiaozhong Fu、Saihong Jiang、Chuan Li、Jian Xin、Yushe Yang、Ruyun Ji

  DOI：10.1016/j.bmcl.2006.10.021

  日期：2007.1

  A series of novel bis(L-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl] adenine (PMEA) was synthesized and their anti-HBV activity was evaluated in HepG 2 2.2.15 cells. Compounds 11, 12, 21, 22, 26, and 27 demonstrated more potent anti-HBV activity and higher selective index (SI) than adefovir dipivoxil, which was used as a positive control. Compound 11, which was found to be the most potent

  合成了一系列新型的9- [2-（膦酰基甲氧基）乙基]腺嘌呤（PMEA）双（L-氨基酸）酯前药，并在HepG 2 2.2.15细胞中评估了它们的抗HBV活性。与用作阳性对照的阿德福韦酯相比，化合物11、12、21、22、26和27表现出更强的抗HBV活性和更高的选择性指数（SI）。被发现是最有效的化合物11，其效力是阿德福韦酯的5倍，EC50值为0.095 microM，CC50值为6636 microM。化合物11的SI值（> 69,000）分别比阿德福韦酯和拉米夫定高60倍和24倍。体外稳定性研究表明，化合物11比阿德福韦酯更稳定，t1 / 2为270分钟。
• A Novel Acid-Catalyzed Isomerization of Aib-Containing Thiodipeptides
  作者：Jürg Lehmann、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/(sici)1522-2675(19990609)82:6<888::aid-hlca888>3.0.co;2-5

  日期：1999.6.9
• Revisiting Oxytocin through the Medium of Isonitriles
  作者：Ting Wang、Samuel J. Danishefsky

  DOI：10.1021/ja3063452

  日期：2012.8.15

  The reaction of thioamino acids and N-terminal peptides, mediated by hindered isonitriles and hydroxybenzotriazole, gives rise to peptide bonds. In one pathway, oxytocin was synthesized by eight such reiterative amidations. In another stereospecific track, oxytocin was constructed by native chemical ligation, wherein the two building blocks were assembled by thioacid amine amidation. The NMR spectra of oxytocin and dihydrooxytocin suggest a high level of preorganization in the latter, perhaps favoring oxidative folding.
• Synthesis, anti-HBV activity and renal cell toxicity evaluation of mixed phosphonate prodrugs of adefovir
  作者：Xiao-Zhong Fu、Yu Ou、Jian-Ying Pei、Ying Liu、Jing Li、Wen Zhou、Yan-Yu Lan、Ai-Min Wang、Yong-Lin Wang

  DOI：10.1016/j.ejmech.2012.01.013

  日期：2012.3

  A series of phosphonate ester prodrugs of adefovir incorporating L-amino (thio)acid and non-steroidal anti-inflammatory drug (NSAID) moieties were synthesized and their anti-HBV activity and renal cell toxicity were evaluated in HepG2 2.2.15 and HK-2 cells respectively. Bioactivity evaluation results revealed that this kind of adefovir prodrug have lower renal cell toxicity than adefovir dipivoxil. Compounds 8a and 8b, incorporating the NSAID ketoprofen and the L-amino acid (Val or Ile) structural fragments, exhibited more potent anti-HBV activity than adefovir dipivoxil with IC50 = 0.51 and 0.73 mu M, SI = 1697.64 and 881.92 respectively. In vitro stability studies showed that the synthesized prodrugs have higher chemical and plasma stability than the positive control adefovir dipivoxil. (C) 2012 Elsevier Masson SAS. All rights reserved.