2-(L-valyl)aminoethanol | 86150-10-9

• 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: 2-(L-valyl)aminoethanol
• 英文别名: (2S)-2-amino-N-(2-hydroxyethyl)-3-methylbutanamide
• CAS: 86150-10-9
• 化学式: C₇H₁₆N₂O₂
• 分子量: 160.216
• InChiKey: YGXOCCKTFXPKPQ-LURJTMIESA-N

物化性质

• 沸点：
  349.9±27.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(L-valyl)aminoethanol 在 四丁基氟化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 tert-butyl N-[(2S,3S,5R)-5-benzyl-3-hydroxy-5-{[(1S)-1-[(2-hydroxyethyl)carbamoyl]-2-methylpropyl]carbamoyl}-1-phenylpentan-2-yl]carbamate
  参考文献：
  名称：

  Design and synthesis of HIV protease inhibitors. Variations of the carboxyterminus of the HIV protease inhibitor L-682,679

  摘要：

  A series of tetrapeptide analogues of 1 (L-682,679), in which the carboxy terminus has been shortened and modified, was prepared and their inhibitory activity measured against the HIV protease in a peptide cleavage assay. Selected examples were tested as inhibitors of virus spread in cell culture. Compound 12 was a 10-fold more potent enzyme inhibitor than 1 in vitro and 30-fold more potent in inhibiting the viral spread in cells.

  DOI：

  10.1021/jm00113a025
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙二醇二甲醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.33h， 生成 2-(L-valyl)aminoethanol
  参考文献：
  名称：

  Design and synthesis of HIV protease inhibitors. Variations of the carboxyterminus of the HIV protease inhibitor L-682,679

  摘要：

  A series of tetrapeptide analogues of 1 (L-682,679), in which the carboxy terminus has been shortened and modified, was prepared and their inhibitory activity measured against the HIV protease in a peptide cleavage assay. Selected examples were tested as inhibitors of virus spread in cell culture. Compound 12 was a 10-fold more potent enzyme inhibitor than 1 in vitro and 30-fold more potent in inhibiting the viral spread in cells.

  DOI：

  10.1021/jm00113a025

文献信息

• HIV protease inhibitors useful for the treatment of aids
  申请人：MERCK & CO. INC.

  公开号：EP0337714A2

  公开（公告）日：1989-10-18

  Compounds of the form wherein A is an amine protecting group commonly employed in peptide synthesis, G a dipeptide isostere, B an amino acid or analog thereof, and J a small terminal group are described. These compounds are useful in the inhibition of HIV protease, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.

  描述了以下形式的化合物 其中 A 是肽合成中常用的胺保护基团，G 是二肽异构体，B 是氨基酸或其类似物，J 是小末端基团。这些化合物作为化合物、药学上可接受的盐、药物组合成分，无论是否与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用，都可用于抑制 HIV 蛋白酶、预防或治疗 HIV 感染以及治疗 AIDS。还描述了治疗艾滋病的方法和预防或治疗艾滋病毒感染的方法。
• Dipeptide alcohol-based inhibitors of eukaryotic DNA polymerase α
  作者：Isoko Kuriyama、Naoki Asano、Ikuo Kato、Kyoko Ikeda、Masaharu Takemura、Hiromi Yoshida、Kengo Sakaguchi、Yoshiyuki Mizushina

  DOI：10.1016/j.bmc.2004.12.052

  日期：2005.3

  We reported previously that a novel dipeptide alcohol, L-homoserylaminoethanol (Hse-Gly-ol), is a selective inhibitor of eukaryotic DNA polymerase epsilon (pol epsilon) [Bioorg. Med. Chem. 2004, 12, 957-962]. The discovery suggests that the dipeptide structure could be a chemical frame for a DNA polymerase inhibitor. Therefore, we chemically synthesized 27 different species of dipeptide alcohols, and tested this inhibitory capability. Compound 6 (L-aspartylaminoethanol, Asp-Gly-ol) was found to be the strongest pol alpha inhibitor. Compound 6 did not influence the activities of other replicative DNA polymerases such as delta and epsilon, and had no effect on the activities of prokaryotic DNA polymerases, nor DNA metabolic enzymes such as human immunodeficiency virus type I reverse transcriptase, T7 RNA polymerase and bovine deoxyribonuclease I. The inhibitory effect of compound 6 on pol alpha was dose-dependent, and 50% inhibition was observed at a concentration of 33.5 mu M. Compound 6-induced inhibition of pol alpha activity was noncompetitive with both the DNA template-primer and the dNTP substrate. This is the first report on a water-soluble pol alpha-specific inhibitor, sought for precise biochemical studies of pol alpha. The relationships between the structures of dipeptide alcohols and the inhibition of eukaryotic DNA polymerases are discussed. (c) 2005 Elsevier Ltd. All rights reserved.
• Gemcitabine Prodrugs, Pharmaceutical Compositions and Uses Thereof
  申请人：Gallop A. Mark

  公开号：US20080021208A1

  公开（公告）日：2008-01-24

  The present invention provides gemcitabine prodrugs, methods of making gemcitabine prodrugs, pharmaceutical compositions of gemcitabine prodrugs and methods of using gemcitabine prodrugs and pharmaceutical compositions of using gemcitabine prodrugs to treat or prevent diseases or disorders such as cancer or viral infections.
• GEMCITABINE PRODRUGS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
  申请人：Gallop Mark A.

  公开号：US20100016254A1

  公开（公告）日：2010-01-21

  The present invention provides gemcitabine prodrugs, methods of making gemcitabine prodrugs, pharmaceutical compositions of gemcitabine prodrugs and methods of using gemcitabine prodrugs and pharmaceutical compositions of using gemcitabine prodrugs to treat or prevent diseases or disorders such as cancer or viral infections.
• US7608602B2
  申请人：——

  公开号：US7608602B2

  公开（公告）日：2009-10-27