(NE)-N-[(3,4-dichlorophenyl)methylidene]-4-methylbenzenesulfonamide | 951762-63-3

• 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)-N-[(3,4-dichlorophenyl)methylidene]-4-methylbenzenesulfonamide
• CAS: 951762-63-3
• 化学式: C₁₄H₁₁Cl₂NO₂S
• 分子量: 328.219
• InChiKey: GBTPTGCJHYXOBQ-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (NE)-N-[(3,4-dichlorophenyl)methylidene]-4-methylbenzenesulfonamide 、 2-(3-chlorobenzyl)-2,3-butadienoic acid 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 124.0h， 生成 2(3-chlorophenyl)-6-(3,4-dichlorophenyl)-1-(toluene-4-sulfonyl)-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：

  对甲苯磺酰胺 、 3,4-二氯苯甲醛 在 三氟化硼乙醚 作用下， 生成 (NE)-N-[(3,4-dichlorophenyl)methylidene]-4-methylbenzenesulfonamide
  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

文献信息

• Asymmetric Friedel−Crafts Addition of Indoles to <i>N</i>-Sulfonyl Aldimines:  A Simple Approach to Optically Active 3-Indolyl-methanamine Derivatives
  作者：Yi-Xia Jia、Jian-Hua Xie、Hai-Feng Duan、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1021/ol0602001

  日期：2006.4.1

  [reaction: see text] The enantioselective copper(II)-catalyzed Friedel-Crafts addition of indoles to N-sulfonyl aldimines was developed using chiral bisoxazoline as ligands, and high enantioselectivities (up to 96% ee) were achieved.

  [反应：见正文]使用手性双恶唑啉作为配体，开发了对映体选择性铜（II）催化的吲哚的弗里德-克来福特将吲哚添加到N-磺酰基醛亚胺中，并实现了高对映选择性（ee高达96％）。
• A highly diastereoselective synthesis of 3-carbethoxy-2,5-disubstituted-3-pyrrolines by phosphine catalysis
  作者：Xue-Feng Zhu、Christopher E. Henry、Ohyun Kwon

  DOI：10.1016/j.tet.2005.03.104

  日期：2005.6

  Tributylphosphine was used as catalyst to facilitate a [3+2] cycloaddition between gamma-substituted allenoates and N-sulfonylimines. The resulting adducts, 3-carbethoxy-2,5-disubstituted-3-pyrrolines were formed in excellent yields with high diastereoselectivity. The reaction went to completion in several hours at room temperature, and the starting materials were easily prepared with one step from commercially available compounds via known procedures. (c) 2005 Elsevier Ltd. All rights reserved.
• 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