Methyl-α-cyano-β-methyl-β-phenylacrylat | 14505-27-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Methyl-α-cyano-β-methyl-β-phenylacrylat
• 英文别名: trans-α-Cyano-β-methyl-zimtsaeure-methylester；cis-α-Cyano-β-methyl-zimtsaeure-methylester；2-Cyan-3-phenyl-buten-(2)-saeure-methylester；2-Cyan-3-phenyl-but-2-en-saeure-methylester；Methyl 2-cyano-3-phenylbut-2-enoate
• CAS: 14505-27-2
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: MMZBOJAMZZUGPN-UHFFFAOYSA-N

物化性质

• 沸点：
  150-165 °C(Press: 9 Torr)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  Methyl-α-cyano-β-methyl-β-phenylacrylat 在 溶剂黄146 、 锌 作用下， 生成 methyl 2-cyano-3-phenylbutyrate
  参考文献：
  名称：

  Morel,G.; Foucaud,A., Bulletin de la Societe Chimique de France, 1970, p. 2354 - 2366

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮 、 氰乙酸甲酯 在 ammonium acetate 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 生成 Methyl-α-cyano-β-methyl-β-phenylacrylat
  参考文献：
  名称：

  Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

  摘要：

  Inactivation of the NF-kappa B signaling pathway by inhibition of IKK beta is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKb inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-alpha, which are well-known inflammatory responses generated by activated NF-kappa B. However, no inhibitory activity against IKK beta was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 mu M. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.058

文献信息

• Addition nucleophile des anions d'esters α-cyanoacetiques sur les cations succinimidosulfonium
  作者：G. Morel、M.A. LeMoing-Orliac、S. Khamsitthideth、A. Foucaud

  DOI：10.1016/0040-4020(82)80097-5

  日期：1982.1

  by the formation of instable σ-sulfurane intermediates. Homolytic cleavage of these intermediates gave radical pairs, then the coupling products. Heterocyclic clevage gave new sulfonium salts which rearranged via sulfonium ylides.

  取代的氰基乙酸根阴离子4与S，S-二芳基琥珀酰亚氨基os盐的反应通常导致N-烷基硫代甲基亚乙基亚胺和α-烷基硫代甲基酯的形成。还获得了与阴离子4d偶联的产物，仅在苯基氰基乙酸甲酯阴离子4b的情况下观察到。结果是由不稳定的σ-硫烷中间体的形成所解释的。这些中间体的均相裂解产生自由基对，然后产生偶联产物。杂环开裂产生了新的via盐，这些salts盐通过yl叶立德重排。
• Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents
  作者：Jee Sun Yang、Chun-Ho Park、Chulho Lee、Hwan Kim、Changmok Oh、Yejoo Choi、Jong Soon Kang、Jieun Yun、Jin-Hyun Jeong、Myung-Hwa Kim、Gyoonhee Han

  DOI：10.1016/j.ejmech.2014.08.001

  日期：2014.10

  The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C-6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Peseke, Klaus; Michalik, Manfred; Goerges, Knut, Zeitschrift fur Chemie, 1984, vol. 24, # 9, p. 327 - 328
  作者：Peseke, Klaus、Michalik, Manfred、Goerges, Knut

  DOI：——

  日期：——