(NE)-4-methyl-N-[(1-methylpyrrol-2-yl)methylidene]benzenesulfonamide | 951762-74-6

• 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-[(1-methylpyrrol-2-yl)methylidene]benzenesulfonamide
• CAS: 951762-74-6
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: JQHNZWBVGBSPOY-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (NE)-4-methyl-N-[(1-methylpyrrol-2-yl)methylidene]benzenesulfonamide 、 2,3-butadienoic acid 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 1-(4-Methylphenyl)sulfonyl-2-(1-methylpyrrol-2-yl)-2,5-dihydropyrrole-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：

  N-甲基-2-吡咯甲醛 、 对甲苯磺酰胺 在 三氟化硼乙醚 作用下， 生成 (NE)-4-methyl-N-[(1-methylpyrrol-2-yl)methylidene]benzenesulfonamide
  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

• 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
• [EN] INHIBITORS OF PROTEIN PRENYLTRANSFERASES<br/>[FR] INHIBITEURS DE PRÉNYLTRANSFÉRASES PROTÉIQUES
  申请人：UNIV CALIFORNIA

  公开号：WO2007111948A2

  公开（公告）日：2007-10-04

  [EN] 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.
  [FR] Cette invention concerne des nouveaux composés. Ces composés peuvent être utiles pour inhiber l'activité de GGTase I. Les composés décrits dans cette invention peuvent également être utilisés en tant qu'agents thérapeutiques anti-neoplasiques, ils peuvent également être utilisés dans des traitements contre le cancer, dans des dosages biologiques et dans des trousses.
• 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.