1-(3,4-二氯苯基)-1-甲苯磺酰甲基异丁酯 | 263389-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3,4-二氯苯基)-1-甲苯磺酰甲基异丁酯
• 英文名称: (3,4-dichlorophenyl)[(4-methylphenyl)sulfonyl]methanisocyanide
• 英文别名: 1,2-dichloro-4-[isocyano(toluene-4-sulfonyl)methyl]benzene；(3,4-dichlorophenyl)tosylmethyl isonitrile；1,2-Dichloro-4-(isocyano(tosyl)methyl)benzene；1,2-dichloro-4-[isocyano-(4-methylphenyl)sulfonylmethyl]benzene
• CAS: 263389-52-2
• 化学式: C₁₅H₁₁Cl₂NO₂S
• 分子量: 340.23
• InChiKey: KNIKDPRISVIPBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-缬氨酸甲酯盐酸盐 、 乙醛酸 、 1-(3,4-二氯苯基)-1-甲苯磺酰甲基异丁酯 在 碳酸氢钠 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以83%的产率得到methyl (2S)-2-[4-(3,4-dichlorophenyl)imidazolyl]-3-methylbutanoate
  参考文献：
  名称：

  An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents¹

  摘要：

  This article describes efficient and mild protocols for preparing polysubstituted imidazoles in a single pot fi om aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and amine followed by addition of the TosMIC reagent delivers 1,4,5-trisubstituted imidazoles with predictable regiochemistry. Employing chiral amines and aldehydes, particularly those derived from or-amino acids, affords imidazoles with asymmetric centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles are also readily prepared by a simple variant of the above procedure. Selecting glyoxylic acid as the aldehyde component of this procedure leads to intermediates such as 48, which readily undergo decarboxylation and elimination oft;he tosyl moiety to deliver 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes delivers 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles from these TosMIC reagents and aldehydes is described.

  DOI：

  10.1021/jo991782l

文献信息

• Substituted Heterocycles as Therapeutic agents for treating cancer
  申请人：Doemling Alexander

  公开号：US20110313167A1

  公开（公告）日：2011-12-22

  MDM2 and MDM4 proteins prevent apoptosis of cancer cells by negatively regulating the transcription factor p53. Compounds according to Formula I are selective antagonists of MDM2 and MDM4 proteins, disrupting the p53/MDM2 and p53/MDM4 complex. These compounds therefore are candidate therapeutics for treating cancer as well as other cell proliferative disease states.

  MDM2和MDM4蛋白通过负调控转录因子p53来阻止癌细胞凋亡。根据公式I的化合物是MDM2和MDM4蛋白的选择性拮抗剂，破坏p53/MDM2和p53/MDM4复合物。因此，这些化合物是治疗癌症以及其他细胞增殖性疾病状态的候选治疗药物。
• Robust Generation of Lead Compounds for Protein-Protein Interactions by Computational and MCR Chemistry: p53/Hdm2 Antagonists
  作者：Anna Czarna、Barbara Beck、Stuti Srivastava、Grzegorz M. Popowicz、Siglinde Wolf、Yijun Huang、Michal Bista、Tad A. Holak、Alexander Dömling

  DOI：10.1002/anie.201001343

  日期：——

  multiple scaffolds useful to antagonize the cancer‐relevant protein–protein interaction p53/Hdm2 is described. The new method is based on the tightly interwoven interplay of multicomponent reaction chemistry, structural biology, computational chemistry, and high‐content NMR‐based screening.

  描述了可用于拮抗癌症相关蛋白-蛋白相互作用 p53/Hdm2 的多个支架的并行发现。新方法基于多组分反应化学、结构生物学、计算化学和基于核磁共振的高内涵筛选紧密交织的相互作用。
• SUBSTITUTED HETEROCYCLES AS THERAPEUTIC AGENTS FOR TREATING CANCER
  申请人：DOEMLING Alexander

  公开号：US20130211079A1

  公开（公告）日：2013-08-15

  MDM2 and MDM4 proteins prevent apoptosis of cancer cells by negatively regulating the transcription factor p53. Compounds according to Formula I are selective antagonists of MDM2 and MDM4 proteins, disrupting the p53/MDM2 and p53/MDM4 complex. These compounds therefore are candidate therapeutics for treating cancer as well as other cell proliferative disease states.

  MDM2和MDM4蛋白通过负调节转录因子p53来防止癌细胞凋亡。公式I中的化合物是MDM2和MDM4蛋白的选择性拮抗剂，破坏p53 / MDM2和p53 / MDM4复合物。因此，这些化合物是治疗癌症以及其他细胞增殖性疾病状态的候选药物。