4-iodo-(1'-t-butoxycarbonyl-1'-methyl)ethylbenzene | 228410-37-5

• 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: 4-iodo-(1'-t-butoxycarbonyl-1'-methyl)ethylbenzene
• 英文别名: Tert-butyl 2-(4-iodophenyl)-2-methylpropanoate
• CAS: 228410-37-5
• 化学式: C₁₄H₁₉IO₂
• 分子量: 346.208
• InChiKey: NNWRKNBAWQUVGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodo-(1'-t-butoxycarbonyl-1'-methyl)ethylbenzene 在 10percent Pd/C 盐酸 、 palladium diacetate 、 四丁基氯化铵 、 氢气 、 碳酸氢钠 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、310.27 kPa 条件下， 反应 86.92h， 生成 2-{4-[(S)-2-[1-(4-Methoxy-benzyl)-4-methyl-2-oxo-1,2-dihydro-pyridin-3-ylcarbamoyl]-2-(2-methyl-2-naphthalen-2-yl-propionylamino)-ethyl]-phenyl}-2-methyl-propionic acid
  参考文献：
  名称：

  Nonpeptidic, Monocharged, Cell Permeable Ligands for the p56lck SH2 Domain

  摘要：

  p561ck is a member of the src family of tyrosine kinases and plays a critical role in the signal transduction events that lead to T cell activation. Ligands for the p561ck SH2 domain have the potential to disrupt the interaction of p561ck with its substrates and derail the signaling cascade that leads to the production of cytokines such as interleukin-2. Starting from the quintuply charged (at physiological pH) phosphorylated tetrapeptide, AcpYEEI, we recently disclosed (J. Med. Chem. 1999, 42, 722 and J. Med. Chem. 1999, 42, 1757) the design of the modified dipeptide 3, which carries just two charges at physiological pH. Here we present the elaboration of 3 to the nonpeptidic, monocharged compound, 9S. This molecule displays good binding affinity for the p561ck SH2 domain (K-d 1 muM) and good cell permeation, and this combination of properties allowed us to demonstrate clear-cut inhibitory effects on a very early event in T cell activation, namely calcium mobilization.

  DOI：

  10.1021/jm000446q
• 作为产物：
  描述：

  4-iodo-(1'-carboxy-1'-methyl)ethylbenzene 在 草酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-iodo-(1'-t-butoxycarbonyl-1'-methyl)ethylbenzene
  参考文献：
  名称：

  Nonpeptidic, Monocharged, Cell Permeable Ligands for the p56lck SH2 Domain

  摘要：

  p561ck is a member of the src family of tyrosine kinases and plays a critical role in the signal transduction events that lead to T cell activation. Ligands for the p561ck SH2 domain have the potential to disrupt the interaction of p561ck with its substrates and derail the signaling cascade that leads to the production of cytokines such as interleukin-2. Starting from the quintuply charged (at physiological pH) phosphorylated tetrapeptide, AcpYEEI, we recently disclosed (J. Med. Chem. 1999, 42, 722 and J. Med. Chem. 1999, 42, 1757) the design of the modified dipeptide 3, which carries just two charges at physiological pH. Here we present the elaboration of 3 to the nonpeptidic, monocharged compound, 9S. This molecule displays good binding affinity for the p561ck SH2 domain (K-d 1 muM) and good cell permeation, and this combination of properties allowed us to demonstrate clear-cut inhibitory effects on a very early event in T cell activation, namely calcium mobilization.

  DOI：

  10.1021/jm000446q

文献信息

• [EN] PYRIDONES AS SRC FAMILY SH2 DOMAIN INHIBITORS<br/>[FR] PYRIDONES UTILISEES COMME INHIBITEURS DU DOMAINE SH2 DE LA FAMILLE SRC
  申请人：BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.

  公开号：WO1999031066A1

  公开（公告）日：1999-06-24

  (EN) This invention relates to compounds of formula (I) wherein Ring a, A, B, C, D, E, R and Q are defined herein. These compounds possess the ability to disrupt the interaction between regulatory proteins possessing one or more SH2 domains and their native ligands.(FR) Cette invention concerne des composés de formule (I), le noyau a, A, B, C, D, E, R et Q étant définis dans le descriptif. Ces composés possèdent la capacité d'interrompre l'interaction entre des protéines régulatrices comportant un ou plusieurs domaines SH2 et leurs ligands négatifs.

  这项发明涉及到式(I)的化合物，其中环a、A、B、C、D、E、R和Q在描述中有定义。这些化合物具有打断具有一个或多个SH2结构域的调节蛋白与其本来的配体之间相互作用的能力。
• COMPOUNDS USEFUL AS PHOSPHOTYROSINE MIMICS
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：EP1171113B1

  公开（公告）日：2004-06-02
• PYRIDONES AS SRC FAMILY SH2 DOMAIN INHIBITORS
  申请人：BOEHRINGER INGELHEIM PHARMACEUTICALS INC.

  公开号：EP1045836A1

  公开（公告）日：2000-10-25
• US6268365B1
  申请人：——

  公开号：US6268365B1

  公开（公告）日：2001-07-31
• US6284768B1
  申请人：——

  公开号：US6284768B1

  公开（公告）日：2001-09-04