dimethyl (2R,6S)-4-oxo-2,6-di(pyridin-2-yl)piperidine-3,5-dicarboxylate | 1008473-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl (2R,6S)-4-oxo-2,6-di(pyridin-2-yl)piperidine-3,5-dicarboxylate
• 英文别名: dimethyl (2S,6R)-4-oxo-2,6-dipyridin-2-ylpiperidine-3,5-dicarboxylate
• CAS: 1008473-57-1
• 化学式: C₁₉H₁₉N₃O₅
• 分子量: 369.377
• InChiKey: GIOJJBJMOWUBPI-STONLHKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,6S)-4-oxo-2,6-di(pyridin-2-yl)piperidine-3,5-dicarboxylate 在 sodium tetrahydroborate 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 86.0h， 生成
  参考文献：
  名称：

  羧基化 Bispidine 配体的结构变化：位置异构和刚性对其 Mn2+ 配合物的构象、稳定性、惰性和弛豫性的影响

  摘要：

  具有乙酸酯取代的双吡啶配体的 Mn(II) 配合物可以根据 N3 取代基采用不同的构象。椅椅构象的复合物表现出高弛豫性和强动力学惰性，这对于它们作为 MRI 造影剂的潜在用途非常重要。相比之下，船椅构象异构体经历快速解离并且不保留良好的弛豫性。

  DOI：

  10.1002/chem.202301880
• 作为产物：
  描述：

  吡啶-2-甲醛 、 1,3-丙酮二羧酸二甲酯 在 氨 作用下， 以 甲醇 为溶剂， 以33%的产率得到dimethyl (2R,6S)-4-oxo-2,6-di(pyridin-2-yl)piperidine-3,5-dicarboxylate
  参考文献：
  名称：

  Piperidone derivatives and medical uses thereof

  摘要：

  本发明涉及包含4-氧代哌啶羧酸酯及其衍生物的组合物，例如用苯基、硝基苯基或苄基取代的衍生物。它还教导了这些相关化合物的医药用途，用于治疗逆转录病毒性疾病，特别是HIV和HTLV，增殖性疾病，特别是慢性髓细胞白血病和锥虫病。

  公开号：

  EP2036556A1

文献信息

• Piperidone derivatives and medical uses thereof
  申请人：Heinrich-Pette-Institut

  公开号：EP2036556A1

  公开（公告）日：2009-03-18

  The present invention relates to compositions comprising 4-Oxo-piperidine-carboxylates and derivatives thereof, for example derivatives substituted with phenyl, nitrophenyl or benzyl groups. It also teaches the medical use of these and related compounds for treatment of retroviral diseases, in particular, HIV and HTLV, proliferative diseases, in particular CML and Trypanosomiasis.

  本发明涉及包含4-氧代哌啶羧酸酯及其衍生物的组合物，例如用苯基、硝基苯基或苄基取代的衍生物。它还教导了这些相关化合物的医药用途，用于治疗逆转录病毒性疾病，特别是HIV和HTLV，增殖性疾病，特别是慢性髓细胞白血病和锥虫病。
• In Search of Novel Agents for Therapy of Tropical Diseases and Human Immunodeficiency Virus
  作者：Tim Goebel、Daniela Ulmer、Holger Projahn、Jessica Kloeckner、Eberhard Heller、Melanie Glaser、Alicia Ponte-Sucre、Sabine Specht、Salem Ramadan Sarite、Achim Hoerauf、Annette Kaiser、Ilona Hauber、Joachim Hauber、Ulrike Holzgrabe

  DOI：10.1021/jm070763y

  日期：2008.1.1

  Malaria, sleeping sickness, Chagas' disease, Aleppo boil, and AIDS are among the tropical diseases causing millions of infections and cases of deaths per year because only inefficient chemotherapy is available. Since the targeting of the enzymes of the polyamine pathway may provide novel therapy options, we aimed to inhibit the deoxyhypusine hydroxylase, which is an important step in the biosynthesis of the eukaryotic initiation factor 5A. In order to identify new lead compounds, piperidines were produced and biologically evaluated. The 3,5-diethyl piperidone-3,5-dicarboxylates 11 and 13 substituted with 4-nitrophenyl rings in the 2 and 6 positions were found to be active against Trypanosoma brucei brucei and Plasmodium falciparum combined with low cytotoxicity against macrophages. The corresponding monocarboxylates are only highly active against the T. brucei brucei. The piperidine oximether 53 demonstrated the highest plasmodicidal activity. Moreover, compounds 11 and 53 were also able to inhibit replication of HIV-1.
• Structural Variations in Carboxylated Bispidine Ligands: Influence of Positional Isomerism and Rigidity on the Conformation, Stability, Inertness and Relaxivity of their Mn²⁺ Complexes
  作者：Daouda Ndiaye、Maryame Sy、Waygen Thor、Loïc J. Charbonnière、Aline M. Nonat、Éva Tóth

  DOI：10.1002/chem.202301880

  日期：2023.11.8

  Mn(II) complexes with acetate-substituted bispidine ligands can adopt different conformations depending on the N3 substituent. Complexes in chair-chair conformation display high relaxivity and strong kinetic inertness, both very important for their potential use as MRI contrast agents. In contrast, the boat-chair conformers undergo fast dissociation and do no retain good relaxivity.

  具有乙酸酯取代的双吡啶配体的 Mn(II) 配合物可以根据 N3 取代基采用不同的构象。椅椅构象的复合物表现出高弛豫性和强动力学惰性，这对于它们作为 MRI 造影剂的潜在用途非常重要。相比之下，船椅构象异构体经历快速解离并且不保留良好的弛豫性。