ethyl 17-cyanoheptadecanoate | 1393801-96-1

• 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: ethyl 17-cyanoheptadecanoate
• 英文别名: ethyl 17-cyanoheptadecanote
• CAS: 1393801-96-1
• 化学式: C₂₀H₃₇NO₂
• 分子量: 323.519
• InChiKey: PBCFIXBEFDDVNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  23
• 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：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 17-cyanoheptadecanoate 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 ethyl 18-[(ethylcarbamoyl)amino]octadecanoate
  参考文献：
  名称：

  Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells

  摘要：

  ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

  DOI：

  10.1021/jm501083y
• 作为产物：
  描述：

  11-溴十一酸 在 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride 、 乙酰氯 、 lithium bromide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 22.0h， 生成 ethyl 17-cyanoheptadecanoate
  参考文献：
  名称：

  Antiproliferative and Antimigratory Actions of Synthetic Long Chain n-3 Monounsaturated Fatty Acids in Breast Cancer Cells That Overexpress Cyclooxygenase-2

  摘要：

  Cyclooxygenase-2 (COX-2) is overexpressed in many human cancers and converts the n-6 polyunsaturated fatty acid (PUFA) arachidonic acid to prostaglandin E-2 (PGE(2)), which drives tumorigenesis; in contrast, n-3 PUFA inhibit tumorigenesis. We tested the hypothesis that these antitumor actions of n-3 PUFA may involve the n-3 olefinic bond. n-3 Monounsaturated fatty acids (MUFAs) of chain length C16-C22 were synthesized and evaluated in MDA-MB-468 breast cancer cells that stably overexpressed COX-2 (MDA-COX-2 cells). Longer chain (C19-C22) n-3 MUFAs inhibited proliferation, activated apoptosis, decreased PGE2 formation, and decreased cell invasion; C16-C18 analogues were less active. Molecular modeling showed that interactions of Arg120, Tyr355, and several hydrophobic amino acid residues in the COX-2 active site with C19-C22 MUFA analogues were favored. Thus, longer-chain n-3 MUFAs may be prototypes of novel anticancer agents that decrease the formation of PGE2 in tumor cells that contain high levels of COX-2.

  DOI：

  10.1021/jm300673z

文献信息

• Iron-Catalyzed Alkyl-Alkyl Suzuki-Miyaura Coupling
  作者：Takuji Hatakeyama、Toru Hashimoto、Kalum K. A. D. S. Kathriarachchi、Takeshi Zenmyo、Hirofumi Seike、Masaharu Nakamura

  DOI：10.1002/anie.201202797

  日期：2012.8.27

  Chemoselective Suzuki–Miyaura coupling of primary and secondary alkyl halides is realized by using an iron/Xantphos catalyst. Primary and secondary alkyl bromides undergo the reaction to give the coupling products in good yields. Application to the synthesis of long‐chain fatty acid derivatives is also described (see scheme).

  化学选择性铃木-宫浦伯和仲烷基卤化物偶联是通过使用铁/加入Xantphos催化剂实现。伯和仲烷基溴进行反应，得到偶联产物以良好的收率。还描述了在长链脂肪酸衍生物合成中的应用（参见方案）。
• Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells
  作者：Herryawan Ryadi Eziwar Dyari、Tristan Rawling、Kirsi Bourget、Michael Murray

  DOI：10.1021/jm501083y

  日期：2014.9.11

  ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.
• Antiproliferative and Antimigratory Actions of Synthetic Long Chain n-3 Monounsaturated Fatty Acids in Breast Cancer Cells That Overexpress Cyclooxygenase-2
  作者：Pei H. Cui、Tristan Rawling、Kirsi Bourget、Terry Kim、Colin C. Duke、Munikumar R. Doddareddy、David E. Hibbs、Fanfan Zhou、Bruce N. Tattam、Nenad Petrovic、Michael Murray

  DOI：10.1021/jm300673z

  日期：2012.8.23

  Cyclooxygenase-2 (COX-2) is overexpressed in many human cancers and converts the n-6 polyunsaturated fatty acid (PUFA) arachidonic acid to prostaglandin E-2 (PGE(2)), which drives tumorigenesis; in contrast, n-3 PUFA inhibit tumorigenesis. We tested the hypothesis that these antitumor actions of n-3 PUFA may involve the n-3 olefinic bond. n-3 Monounsaturated fatty acids (MUFAs) of chain length C16-C22 were synthesized and evaluated in MDA-MB-468 breast cancer cells that stably overexpressed COX-2 (MDA-COX-2 cells). Longer chain (C19-C22) n-3 MUFAs inhibited proliferation, activated apoptosis, decreased PGE2 formation, and decreased cell invasion; C16-C18 analogues were less active. Molecular modeling showed that interactions of Arg120, Tyr355, and several hydrophobic amino acid residues in the COX-2 active site with C19-C22 MUFA analogues were favored. Thus, longer-chain n-3 MUFAs may be prototypes of novel anticancer agents that decrease the formation of PGE2 in tumor cells that contain high levels of COX-2.