(E)-N-(4-(3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide | 127033-87-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-N-(4-(3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide
• 英文别名: (E)-N-(4-(3-(4-methoxyphenyl)-3-oxoprop-1-enyl)phenyl)acetamide；acetic acid-{4-[3-(4-methoxy-phenyl)-3-oxo-propenyl]-anilide}；4-Methoxy-ω-(4-acetamino-benzyliden)-acetophenon；4-Acetamino-4'-methoxy-chalkon；Essigsaeure-{4-[3-(4-methoxy-phenyl)-3-oxo-propenyl]-anilid}；N-[4-[(E)-3-(4-methoxyphenyl)-3-oxoprop-1-enyl]phenyl]acetamide
• CAS: 127033-87-8
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: FNZJTTXNRFTDIQ-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-碘苯基)乙酰胺 、 1-(4-甲氧基苯基)-3-二甲氨基-1-丙酮盐酸盐 在 palladium diacetate 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以41%的产率得到(E)-N-(4-(3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide
  参考文献：
  名称：

  A new Heck reaction modification using ketone Mannich bases as enone precursors: Parallel synthesis of anti-leishmanial chalcones

  摘要：

  A new Heck-type reaction for the synthesis of chalcones has been established using Mannich bases as enone precursors. The novel reaction proceeds rapidly in air atmosphere under ligandless conditions and can be adapted for library synthesis in a parallel reactor station. Screening of the synthesized chalcones revealed N-{4-[(1E)-3-oxo-3-(3-pyridinyl)-1-propenyl]phenyl} benzamide (3f) to be a potent anti-leishmanial agent. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.112

文献信息

• Chalcone‐Supported Cardiac Mesoderm Induction in Human Pluripotent Stem Cells for Heart Muscle Engineering
  作者：Farah S. Raad、Taukeer A. Khan、Tilman U. Esser、James E. Hudson、Bhakti Irene Seth、Buntaro Fujita、Ravi Gandamala、Lutz F. Tietze、Wolfram-Hubertus Zimmermann

  DOI：10.1002/cmdc.202100222

  日期：2021.11.5

  Have a little heart: A screen for mesoderm inducing chalcones in human pluripotent stem cell cultures identified 4’-hydroxychalcone (4’HC) as an effective replacement for bone-morphogenetic protein 4 (BMP4) in supporting the derivation of engineered heart muscle (EHM)-formation competent cardiomyocytes.

  有点心：在人类多能干细胞培养物中筛选中胚层诱导查尔酮，发现 4'-羟基查尔酮 (4'HC) 可以有效替代骨形态发生蛋白 4 (BMP4)，支持工程化心肌 (EHM) 的衍生)-形成能力心肌细胞。
• Chalcones: a new class of antimitotic agents
  作者：Michael L. Edwards、David M. Stemerick、Prasad S. Sunkara

  DOI：10.1021/jm00169a021

  日期：1990.7

  A series of chalcones was evaluated as antimitotic agents. One of these, (E)-1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-2-methyl-2-pr open- 1-one) (73), was found to be an effective antimitotic agent at a concentration of 4 nM in an in vitro HeLa cell test system. When evaluated in experimental tumor models in vivo, this compound exhibited antitumor activity against L1210 leukemia and B16 melanoma.
• EDWARDS, MICHAEL L.;STEMERICK, DAVID M.;SUNKARA, PRASAD S., J. MED. CHEM., 33,(1990) N, C. 1948-1954
  作者：EDWARDS, MICHAEL L.、STEMERICK, DAVID M.、SUNKARA, PRASAD S.

  DOI：——

  日期：——
• A new Heck reaction modification using ketone Mannich bases as enone precursors: Parallel synthesis of anti-leishmanial chalcones
  作者：Christina Reichwald、Orly Shimony、Nina Sacerdoti-Sierra、Charles L. Jaffe、Conrad Kunick

  DOI：10.1016/j.bmcl.2008.01.112

  日期：2008.3

  A new Heck-type reaction for the synthesis of chalcones has been established using Mannich bases as enone precursors. The novel reaction proceeds rapidly in air atmosphere under ligandless conditions and can be adapted for library synthesis in a parallel reactor station. Screening of the synthesized chalcones revealed N-4-[(1E)-3-oxo-3-(3-pyridinyl)-1-propenyl]phenyl} benzamide (3f) to be a potent anti-leishmanial agent. (C) 2008 Elsevier Ltd. All rights reserved.