methyl 10-azidodecanoate | 186788-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 10-azidodecanoate
• 英文别名: Decanoic acid, 10-azido-, methyl ester
• CAS: 186788-41-0
• 化学式: C₁₁H₂₁N₃O₂
• 分子量: 227.307
• InChiKey: XDEJNLKBVFTPNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 10-azidodecanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 methyl 10-aminodecanoate
  参考文献：
  名称：

  New Rev-transport inhibitor with anti-HIV activity from Valerianae Radix

  摘要：

  Bioassay-guided separation by use of the fission yeast expressing NES of Rev, a HIV-1 viral regulatory protein, resulted in isolation of valtrate (1) as a new Rev-transport inhibitor from the nucleus to cytoplasm from Valerianae Radix. Valtrate (1) also inhibited the p-24 production of HIV-1 virus without showing any cytotoxicity against the host MT-4 cells. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00624-8
• 作为产物：
  描述：

  methyl 10-<(methylsulfonyl)oxy>decanoate 在 sodium azide 、 四丁基溴化铵 作用下， 生成 methyl 10-azidodecanoate
  参考文献：
  名称：

  New Rev-transport inhibitor with anti-HIV activity from Valerianae Radix

  摘要：

  Bioassay-guided separation by use of the fission yeast expressing NES of Rev, a HIV-1 viral regulatory protein, resulted in isolation of valtrate (1) as a new Rev-transport inhibitor from the nucleus to cytoplasm from Valerianae Radix. Valtrate (1) also inhibited the p-24 production of HIV-1 virus without showing any cytotoxicity against the host MT-4 cells. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00624-8

文献信息

• Non-Peptide Macrocyclic Histone Deacetylase Inhibitors
  作者：Adegboyega K. Oyelere、Po C. Chen、William Guerrant、Sandra C. Mwakwari、Rebecca Hood、Yunzhe Zhang、Yuhong Fan

  DOI：10.1021/jm801128g

  日期：2009.1.22

  Inhibition of histone deacetylase inhibitors (HDACi) hold great promise in cancer therapy because of their demonstrated ability to arrest proliferation of nearly all transformed cell types. Of the several structurally distinct small molecule HDACi reported, macrocyclic depsipeptides have the most complex recognition cap-group moieties and present an excellent opportunity for the modulation of the biological activities of HDACi. Unfortunately, the structure-activity relationship (SAR) studies for this class of compounds have been impaired largely because most macrocyclic HDACi known to date comprise complex peptide macrocycles. In addition to retaining the pharmacologically disadvantaged peptidyl backbone, they offer only limited opportunity for side chain modifications. Here, we report the discovery of a new class of macrocyclic HDAG based on the macrolide antibiotics skeletons. SAR studies revealed that these compounds displayed both linker-length and macrolide-type dependent HDAC inhibition activities with IC50 in the low nanomolar range. In addition, these non-peptide macrocyclic HDACi are more selective against HDACs 1 and 2 relative to HDAC 8, another class I HDAC isoform, and hence have subclass HDAC isoform selectivity.
• Mild Method for the Selective Esterification of Carboxylic Acids Based on the Garegg−Samuelsson Reaction
  作者：Sara P. Morcillo、Luis Álvarez de Cienfuegos、Antonio J. Mota、José Justicia、Rafael Robles

  DOI：10.1021/jo102395c

  日期：2011.4.1

  A mild method for the selective esterification of primary alcohols is described. The use of different phosphines, I-2, and imidazole allows the selective esterification: of a wide variety of acids with excellent results. The generation of a bulky phosphonitun-carboxylate salt as intermediate could justify the selectivity observed in this process. Additionally, amides also can be synthesized with use of this method.
• New Rev-transport inhibitor with anti-HIV activity from Valerianae Radix
  作者：Nobutoshi Murakami、Ying Ye、Motoyuki Kawanishi、Shunji Aoki、Nobuaki Kudo、Minoru Yoshida、Emi E. Nakayama、Tatsuo Shioda、Motomasa Kobayashi

  DOI：10.1016/s0960-894x(02)00624-8

  日期：2002.10

  Bioassay-guided separation by use of the fission yeast expressing NES of Rev, a HIV-1 viral regulatory protein, resulted in isolation of valtrate (1) as a new Rev-transport inhibitor from the nucleus to cytoplasm from Valerianae Radix. Valtrate (1) also inhibited the p-24 production of HIV-1 virus without showing any cytotoxicity against the host MT-4 cells. (C) 2002 Elsevier Science Ltd. All rights reserved.