(5)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-yl)heptanoate | 1609191-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-yl)heptanoate
• 英文别名: (S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-yl)heptanoate；Tert-butyl (S)-7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-YL)heptanoate；tert-butyl (7S)-7-(1H-imidazol-2-yl)-7-(phenylmethoxycarbonylamino)heptanoate
• CAS: 1609191-04-9
• 化学式: C₂₂H₃₁N₃O₄
• 分子量: 401.506
• InChiKey: QLJCZVDPQQJJOH-SFHVURJKSA-N

物化性质

• 沸点：
  589.3±50.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-yl)heptanoate 在 N-碘代丁二酰亚胺 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 四丁基磷酸氢铵 、 三氟乙酸 、 sodium sulfite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 (S)-benzyl (1-(5-iodo-1H-imidazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate
  参考文献：
  名称：

  [EN] COMPOUNDS FOR USE IN THE TREATMENT OF PARASITIC DISEASES
  [FR] COMPOSÉS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE MALADIES PARASITAIRES

  摘要：

  本发明涉及用于治疗寄生虫病的化合物，这些疾病是由寄生虫引起或传播的传染病。本发明的化合物对疟疾病原体特别活跃。这些化合物是寄生虫组蛋白去乙酰化酶（PfHDAC）的选择性抑制剂，能够抑制寄生虫（如疟原虫）的生长，且所需浓度低于抑制哺乳动物细胞生长所需的浓度。

  公开号：

  WO2014067985A1
• 作为产物：
  描述：

  (S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-8-(methoxy(methyl)amino)-8-oxooctanoate 在 lithium aluminium tetrahydride 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.5h， 生成 (5)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(1H-imidazol-2-yl)heptanoate
  参考文献：
  名称：

  Discovery of a Selective Series of Inhibitors of Plasmodium falciparum HDACs

  摘要：

  The identification of a new series of P. falciparum growth inhibitors is described. Starting from a series of known human class I HDAC inhibitors a SAR exploration based on growth inhibitory activity in parasite and human cells-based assays led to the identification of compounds with submicromolar inhibition of P. falciparum growth (EC50 < 500 nM) and good selectivity over the activity of human HDAC in cells (up to >50-fold). Inhibition of parasital HDACs as the mechanism of action of this new class of selective growth inhibitors is supported by hyperacetylation studies.

  DOI：

  10.1021/acsmedchemlett.5b00468

文献信息

• COMPOUNDS FOR USE IN THE TREATMENT OF PARASITIC DISEASES
  申请人：IRBM - SCIENCE PARK S.P.A.

  公开号：US20150299163A1

  公开（公告）日：2015-10-22

  The present invention relates to compounds useful for treating parasitic diseases, which are infectious diseases caused or transmitted by a parasite. Compounds of the invention are particularly active against the causative pathogens in malaria. Such compounds are selective inhibitors of parasitic histone deacetylase (PfHDAC) and suppress the growth of parasites, such as Plasmodium falciparum , at a lower concentration than the concentration required for the inhibition of the growth of mammalian cells.

  本发明涉及用于治疗寄生虫病的化合物，这些疾病是由寄生虫引起或传播的传染病。本发明的化合物特别对疟疾病原体具有活性。这些化合物是寄生虫组蛋白去乙酰化酶(PfHDAC)的选择性抑制剂，可以在比抑制哺乳动物细胞生长所需浓度更低的浓度下抑制疟原虫等寄生虫的生长。
• US9365541B2
  申请人：——

  公开号：US9365541B2

  公开（公告）日：2016-06-14
• [EN] COMPOUNDS FOR USE IN THE TREATMENT OF PARASITIC DISEASES<br/>[FR] COMPOSÉS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE MALADIES PARASITAIRES
  申请人：IRBM SCIENCE PARK S P A

  公开号：WO2014067985A1

  公开（公告）日：2014-05-08

  The present invention relates to compounds useful for treating parasitic diseases, which are infectious diseases caused or transmitted by a parasite. Compounds of the invention are particularly active against the causative pathogens in malaria. Such compounds are selective inhibitors of parasitic histone deacetylase (PfHDAC) and suppress the growth of parasites, such as Plasmodium falciparum, at a lower concentration than the concentration required for the inhibition of the growth of mammalian cells.

  本发明涉及用于治疗寄生虫病的化合物，这些疾病是由寄生虫引起或传播的传染病。本发明的化合物对疟疾病原体特别活跃。这些化合物是寄生虫组蛋白去乙酰化酶（PfHDAC）的选择性抑制剂，能够抑制寄生虫（如疟原虫）的生长，且所需浓度低于抑制哺乳动物细胞生长所需的浓度。
• Discovery of a Selective Series of Inhibitors of <i>Plasmodium falciparum</i> HDACs
  作者：Jesus M. Ontoria、Giacomo Paonessa、Simona Ponzi、Federica Ferrigno、Emanuela Nizi、Ilaria Biancofiore、Savina Malancona、Rita Graziani、David Roberts、Paul Willis、Alberto Bresciani、Nadia Gennari、Ottavia Cecchetti、Edith Monteagudo、Maria V. Orsale、Maria Veneziano、Annalise Di Marco、Antonella Cellucci、Ralph Laufer、Sergio Altamura、Vincenzo Summa、Steven Harper

  DOI：10.1021/acsmedchemlett.5b00468

  日期：2016.5.12

  The identification of a new series of P. falciparum growth inhibitors is described. Starting from a series of known human class I HDAC inhibitors a SAR exploration based on growth inhibitory activity in parasite and human cells-based assays led to the identification of compounds with submicromolar inhibition of P. falciparum growth (EC50 < 500 nM) and good selectivity over the activity of human HDAC in cells (up to >50-fold). Inhibition of parasital HDACs as the mechanism of action of this new class of selective growth inhibitors is supported by hyperacetylation studies.