methyl 4-(4-nitrostyryl)benzoate | 136827-59-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 4-(4-nitrostyryl)benzoate
• 英文别名: methyl 4‐(4‐nitrostyryl)benzoate；Methyl 4-[2-(4-nitrophenyl)ethenyl]benzoate
• CAS: 136827-59-3
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: PTBDNZRVAGPHKG-UHFFFAOYSA-N

物化性质

• 沸点：
  422.0±24.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(4-nitrostyryl)benzoate 在 吗啉 、 palladium 10% on activated carbon 、 氢气 、 sulfur 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 methyl 4-[2-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate
  参考文献：
  名称：

  四氢苯并噻吩化合物

  摘要：

  本发明的目的在于提供具有肠道磷酸转运蛋白(NPT‑IIb)抑制作用、作为高磷血症的治疗剂和/或预防剂的有效成分的四氢苯并噻吩化合物或其立体异构体、几何异构体、互变异构体、氮氧化物、水合物、溶剂化物、代谢产物、酯、药学上可接受的盐或它的前药和药物组合物。

  公开号：

  CN105524053B
• 作为产物：
  描述：

  对硝基溴化苄 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 methyl 4-(4-nitrostyryl)benzoate
  参考文献：
  名称：

  四氢苯并噻吩化合物

  摘要：

  本发明的目的在于提供具有肠道磷酸转运蛋白(NPT‑IIb)抑制作用、作为高磷血症的治疗剂和/或预防剂的有效成分的四氢苯并噻吩化合物或其立体异构体、几何异构体、互变异构体、氮氧化物、水合物、溶剂化物、代谢产物、酯、药学上可接受的盐或它的前药和药物组合物。

  公开号：

  CN105524053B

文献信息

• Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response
  作者：Wei-Cheng Wu、Yi-Min Liu、Mei-Hsiang Lin、Yu-Hsuan Liao、Mei-Jung Lai、Hsun-Yueh Chuang、To-Yu Hung、Chun-Han Chen、Jing-Ping Liou

  DOI：10.1016/j.ejmech.2020.112158

  日期：2020.4

  Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI(50) of 22 +/- 2 and 12 +/- 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 mu M, and 1.47 mu M, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs. (c) 2020 Published by Elsevier Masson SAS.
• What doesn't fit is made to fit: Pim‐1 kinase adapts to the configuration of stilbene‐based inhibitors
  作者：Phil M. M. Hochban、Lukas Heyder、Andreas Heine、Wibke E. Diederich

  DOI：10.1002/ardp.202400094

  日期：——

  Recently, we have developed novel Pim‐1 kinase inhibitors starting from a dihydrobenzofuran core structure using a computational approach. Here, we report the design and synthesis of stilbene‐based Pim‐1 kinase inhibitors obtained by formal elimination of the dihydrofuran ring. These inhibitors of the first design cycle, which were obtained as inseparable cis/trans mixtures, showed affinities in the low single‐digit micromolar range. To be able to further optimize these compounds in a structure‐based fashion, we determined the X‐ray structures of the protein‐ligand‐complexes. Surprisingly, only the cis‐isomer binds upon crystallization of the cis/trans‐mixture of the ligands with Pim‐1 kinase and the substrate PIMTIDE, the binding mode being largely consistent with that predicted by docking. After crystallization of the exclusively trans‐configured derivatives, a markedly different binding mode for the inhibitor and a concomitant rearrangement of the glycine‐rich loop is observed, resulting in the ligand being deeply buried in the binding pocket.
• 四氢苯并噻吩化合物
  申请人：广东东阳光药业有限公司

  公开号：CN105524053B

  公开（公告）日：2020-06-05

  本发明的目的在于提供具有肠道磷酸转运蛋白(NPT‑IIb)抑制作用、作为高磷血症的治疗剂和/或预防剂的有效成分的四氢苯并噻吩化合物或其立体异构体、几何异构体、互变异构体、氮氧化物、水合物、溶剂化物、代谢产物、酯、药学上可接受的盐或它的前药和药物组合物。