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β-ketoester (IV) where R2=(CH2)13CH3 and R1=ethyl | 322391-61-7

中文名称
——
中文别名
——
英文名称
β-ketoester (IV) where R2=(CH2)13CH3 and R1=ethyl
英文别名
Ethyl 2-ethyl-3-oxoheptadecanoate
β-ketoester (IV) where R2=(CH2)13CH3 and R1=ethyl化学式
CAS
322391-61-7
化学式
C21H40O3
mdl
——
分子量
340.547
InChiKey
ZEUODYXCAYZKIU-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    8
  • 重原子数:
    24
  • 可旋转键数:
    18
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.9
  • 拓扑面积:
    43.4
  • 氢给体数:
    0
  • 氢受体数:
    3

反应信息

  • 作为反应物:
    描述:
    β-ketoester (IV) where R2=(CH2)13CH3 and R1=ethylsodium ethanolate 作用下, 以 乙醇 为溶剂, 反应 13.0h, 生成 Compound (2)
    参考文献:
    名称:
    Design, Synthesis, and Characterization of the Antitumor Activity of Novel Ceramide Analogues
    摘要:
    A deficiency in apoptosis is one of the key events in the proliferation and resistance of malignant cells to antitumor agents; for these reasons, the search for apoptosis-inducing drugs represents a valuable approach for the development of novel anticancer therapies. In this study we report the first example of conformationally restrained analogues of ceramide (compounds 1-4), where the polar portion of the molecule has been replaced by a thiouracil (1, 3) or uracil (2, 4) ring. The evaluation of their biologic activity on CCRF-CEM human leukemia cells demonstrated that the most active was compound 1 followed by compound 2 (mean 50% inhibition of cell proliferation [IC50] 1.7 and 7.9 PM, respectively), while compounds 3 and 4 were inactive, as were uracil, thiouracil, and 5,6-dimethyluracil, the pyrimidine moieties of compounds 1-4. For comparison, the IC50 of the reference substance, the cell-permeable C-2-ceramide, was 31.6 muM. Compounds 1 and 2 and C-2-ceramide were able to trigger apoptosis, as shown by the occurrence of DNA and nuclear fragmentation, and to release cytochrome c from treated cells. The treatment of female CD-1 nu/nu athymic mice bearing a WiDr human colon xenograft with the most active compound 1 at 2, 10, 50, and 200 mg/kg ip daily for 10 days resulted in an antitumor effect that was equivalent at 50 mg/kg or superior (200 mg/kg) to that of cyclophosphamide, 20 mg/kg ip daily, delivered on the same schedule, with markedly lower systemic toxicity. In conclusion, the present study demonstrates that the new ceramide analogues 1 and 2 are characterized by in vitro and in vivo antitumor activity and low toxicity.
    DOI:
    10.1021/jm010947r
  • 作为产物:
    描述:
    pentadecanol chloride 在 lithium diisopropyl amide 氯化铵 作用下, 以 四氢呋喃 为溶剂, 反应 12.5h, 生成 β-ketoester (IV) where R2=(CH2)13CH3 and R1=ethyl
    参考文献:
    名称:
    Ceramide analogs, process for their preparation and their use as antitumor agents
    摘要:
    本发明涉及一般式(I)的神经酰胺类似化合物,其制备方法以及用于制备用于治疗肿瘤的药物配方的用途。
    公开号:
    US20050020533A1
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文献信息

  • Ceramide analogues in apoptosis: a new strategy for anticancer drug development
    作者:Marco Macchia、Simone Bertini、Stefano Fogli、Elisa Giovannetti、Filippo Minutolo、Simona Rapposelli、Romano Danesi
    DOI:10.1016/s0014-827x(03)00015-6
    日期:2003.3
    A survey on the role played by ceramide within the sphingolmyelin pathway is here reported, taking into account its importance as an intracellular effector molecule in apoptosis. Recently, several analogs of ceramide, able to pass the cell membrane and then to induce apoptosis, have been developed as a new potential approach in anticancer therapy.
  • Ceramide analogs, process for their preparation and their use as antitumor agents
    申请人:Macchia Bruno
    公开号:US20050020533A1
    公开(公告)日:2005-01-27
    The present invention is directed to ceramide analog compounds of general formula (I) the process for their preparation and use for the preparation of pharmaceutical formulations for the treatment of tumors.
    本发明涉及一般式(I)的神经酰胺类似化合物,其制备方法以及用于制备用于治疗肿瘤的药物配方的用途。
  • Design, Synthesis, and Characterization of the Antitumor Activity of Novel Ceramide Analogues
    作者:Marco Macchia、Silvia Barontini、Simone Bertini、Valeria Di Bussolo、Stefano Fogli、Elisa Giovannetti、Enzo Grossi、Filippo Minutolo、Romano Danesi
    DOI:10.1021/jm010947r
    日期:2001.11.1
    A deficiency in apoptosis is one of the key events in the proliferation and resistance of malignant cells to antitumor agents; for these reasons, the search for apoptosis-inducing drugs represents a valuable approach for the development of novel anticancer therapies. In this study we report the first example of conformationally restrained analogues of ceramide (compounds 1-4), where the polar portion of the molecule has been replaced by a thiouracil (1, 3) or uracil (2, 4) ring. The evaluation of their biologic activity on CCRF-CEM human leukemia cells demonstrated that the most active was compound 1 followed by compound 2 (mean 50% inhibition of cell proliferation [IC50] 1.7 and 7.9 PM, respectively), while compounds 3 and 4 were inactive, as were uracil, thiouracil, and 5,6-dimethyluracil, the pyrimidine moieties of compounds 1-4. For comparison, the IC50 of the reference substance, the cell-permeable C-2-ceramide, was 31.6 muM. Compounds 1 and 2 and C-2-ceramide were able to trigger apoptosis, as shown by the occurrence of DNA and nuclear fragmentation, and to release cytochrome c from treated cells. The treatment of female CD-1 nu/nu athymic mice bearing a WiDr human colon xenograft with the most active compound 1 at 2, 10, 50, and 200 mg/kg ip daily for 10 days resulted in an antitumor effect that was equivalent at 50 mg/kg or superior (200 mg/kg) to that of cyclophosphamide, 20 mg/kg ip daily, delivered on the same schedule, with markedly lower systemic toxicity. In conclusion, the present study demonstrates that the new ceramide analogues 1 and 2 are characterized by in vitro and in vivo antitumor activity and low toxicity.
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