N-(4-chlorobenzylidene)methanesulfonamide | 951762-70-2

• 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: N-(4-chlorobenzylidene)methanesulfonamide
• 英文别名: (NE)-N-[(4-chlorophenyl)methylidene]methanesulfonamide
• CAS: 951762-70-2
• 化学式: C₈H₈ClNO₂S
• 分子量: 217.676
• InChiKey: MXGFSAPDLCDHFA-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2,3-butadienoic acid 、 N-(4-chlorobenzylidene)methanesulfonamide 在 2-氯-1-甲基吡啶碘化物 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 41.0h， 生成 2-(4-chlorophenyl)-1-(methylsulfonyl)-2,5-dihydro-1H-pyrrole-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：

  甲基磺酰胺 、 4-氯苯甲醛 在 三氟化硼乙醚 作用下， 生成 N-(4-chlorobenzylidene)methanesulfonamide
  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

• Synthesis of α-amino nitriles through Strecker reaction of aldimines and ketoimines by using nanocrystalline magnesium oxide
  作者：M. Lakshmi Kantam、Koosam Mahendar、Bojja Sreedhar、B.M. Choudary

  DOI：10.1016/j.tet.2008.01.128

  日期：2008.4

  Strecker reactions of various aldimines as well as ketoimines with TMSCN proceeded smoothly under mild conditions to give the corresponding alpha-amino nitriles and alpha,alpha-disubstituted alpha-amino nitriles, respectively, in good to excellent yields in the presence of nanocrystalline magnesium oxide. The reaction proceeds through hypervalent silicate species by coordination to O2-/O- (Lewis basic site) of nanocrystalline magnesium oxide, proved by Si-29 NMR. (C) 2008 Elsevier Ltd. All rights reserved.
• Copper−Amidophosphine Catalyst in Asymmetric Addition of Organozinc to Imines
  作者：Hidetaka Fujihara、Kazushige Nagai、Kiyoshi Tomioka

  DOI：10.1021/ja005629g

  日期：2000.12.1
• INHIBITORS OF PROTEIN PRENYLTRANSFERASES
  申请人：Tamanoi Fuyuhiko

  公开号：US20100063114A1

  公开（公告）日：2010-03-11

  The present invention is directed to novel compounds. These compounds can be useful in inhibiting the activity of GGTase I. The compounds can also be used as anti-cancer therapeutics including as part of methods for treating cancer, in assays, and in kits.
• US8093274B2
  申请人：——

  公开号：US8093274B2

  公开（公告）日：2012-01-10
• US8815935B2
  申请人：——

  公开号：US8815935B2

  公开（公告）日：2014-08-26