(NE)-4-methyl-N-[(3,4,5-trimethoxyphenyl)methylidene]benzenesulfonamide | 951762-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (NE)-4-methyl-N-[(3,4,5-trimethoxyphenyl)methylidene]benzenesulfonamide
• CAS: 951762-67-7
• 化学式: C₁₇H₁₉NO₅S
• 分子量: 349.408
• InChiKey: NQDBCOUASVNPRI-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (NE)-4-methyl-N-[(3,4,5-trimethoxyphenyl)methylidene]benzenesulfonamide 、 2-甲基-丁二烯酸 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 、 三丁基膦 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 1-(4-toluenesulfonyl)-6-(3,4,5-trimethoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid
  参考文献：
  名称：

  Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I

  摘要：

  Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics.

  DOI：

  10.1021/ja070274n
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲腈 在 C₈₄H₁₁₀N₁₀Zn₂ 作用下， 以 氘代苯 为溶剂， 反应 36.0h， 生成 (NE)-4-methyl-N-[(3,4,5-trimethoxyphenyl)methylidene]benzenesulfonamide
  参考文献：
  名称：

  锌催化通过氢化硅烷化将腈化学选择性还原为 N-甲硅烷基亚胺：反应机制的见解

  摘要：

  N ,N' -螯合共轭双胍 (CBG) 支持的氢化锌 ( Zn-1 ) 预催化了各种腈类的极具挑战性的化学选择性单氢化硅烷化反应，生成独特的 N-甲硅烷基亚胺和/或N,N' -报道了甲硅烷基二亚胺。此外，将预催化剂Zn-1的有效性与另一种预催化剂类似物，即二乙基NacNac氢化锌( Zn-2 )进行比较，以了解配体效应。我们观察到预催化剂Zn-1在将腈还原为 N-甲硅烷基亚胺方面表现出比预催化剂Zn-2更高的效率和更好的选择性。机理研究表明，腈的 C=N 键插入 Zn-H 中，形成亚乙烯基锌复合物（Zn-1'和Zn-2'）。通过NMR、质谱和单晶X射线衍射分析证实了活性催化剂Zn-1'和Zn-2' 。根据化学计量实验、活性催化剂分离和原位研究，已经探索了最合理的催化循环。此外，还证明了该协议的合成效用。

  DOI：

  10.1021/acs.inorgchem.3c00309

文献信息

• Catalytic Asymmetric Synthesis of Piperidine Derivatives through the [4 + 2] Annulation of Imines with Allenes
  作者：Ryan P. Wurz、Gregory C. Fu

  DOI：10.1021/ja053277d

  日期：2005.9.1

  there has been only very limited progress in achieving asymmetric catalysis with chiral phosphines. In this report, the first highly enantioselective variant of the Kwon annulation of imines with allenes is described. Thus, C2-symmetric chiral phosphepine 1 serves as an effective catalyst for this powerful process, furnishing an array of functionalized piperidine derivatives with very good stereoselectivity

  尽管叔膦已成为非常通用的亲核催化剂，但在使用手性膦实现不对称催化方面取得的进展非常有限。在这份报告中，描述了亚胺与丙二烯的 Kwon 环化的第一个高度对映选择性变体。因此，C2 对称手性膦 1 作为这一强大过程的有效催化剂，提供了一系列具有非常好的立体选择性的官能化哌啶衍生物。
• INHIBITORS OF PROTEIN PRENYLTRANSFERASES
  申请人：Kwon Ohyun

  公开号：US20110178138A1

  公开（公告）日：2011-07-21

  The present invention is directed to novel compounds. These compounds can be useful in inhibiting the activity of protein prenyltransferases including GGTase I and/or RabGGTase. The compounds can also be used as anti-cancer therapeutics including as part of methods for treating cancer, in assays, and in kits.
• US8815935B2
  申请人：——

  公开号：US8815935B2

  公开（公告）日：2014-08-26
• Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I
  作者：Sabrina Castellano、Hannah D. G. Fiji、Sape S. Kinderman、Masaru Watanabe、Pablo de Leon、Fuyuhiko Tamanoi、Ohyun Kwon

  DOI：10.1021/ja070274n

  日期：2007.5.1

  Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics.
• Zinc-Catalyzed Chemoselective Reduction of Nitriles to N-Silylimines through Hydrosilylation: Insights into the Reaction Mechanism
  作者：Rajata Kumar Sahoo、Sharanappa Nembenna

  DOI：10.1021/acs.inorgchem.3c00309

  日期：2023.8.7

  the C≡N bond of nitrile into Zn–H to form the zinc vinylidenamido complexes (Zn-1′ and Zn-2′). The active catalysts Zn-1′ and Zn-2′ are confirmed by NMR, mass spectrometry, and single-crystal X-ray diffraction analyses. A most plausible catalytic cycle has been explored depending on stoichiometric experiments, active catalysts isolation, and in situ studies. Moreover, the synthetic utility of this

  N ,N' -螯合共轭双胍 (CBG) 支持的氢化锌 ( Zn-1 ) 预催化了各种腈类的极具挑战性的化学选择性单氢化硅烷化反应，生成独特的 N-甲硅烷基亚胺和/或N,N' -报道了甲硅烷基二亚胺。此外，将预催化剂Zn-1的有效性与另一种预催化剂类似物，即二乙基NacNac氢化锌( Zn-2 )进行比较，以了解配体效应。我们观察到预催化剂Zn-1在将腈还原为 N-甲硅烷基亚胺方面表现出比预催化剂Zn-2更高的效率和更好的选择性。机理研究表明，腈的 C=N 键插入 Zn-H 中，形成亚乙烯基锌复合物（Zn-1'和Zn-2'）。通过NMR、质谱和单晶X射线衍射分析证实了活性催化剂Zn-1'和Zn-2' 。根据化学计量实验、活性催化剂分离和原位研究，已经探索了最合理的催化循环。此外，还证明了该协议的合成效用。