3-chloro-2-(trimethoxymethyl)pyrrole | 226409-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-2-(trimethoxymethyl)pyrrole
• 英文别名: 3-chloro-2-(trimethoxymethyl)-1H-pyrrole
• CAS: 226409-98-9
• 化学式: C₈H₁₂ClNO₃
• 分子量: 205.641
• InChiKey: DNZNOUMIRGNNCF-UHFFFAOYSA-N

物化性质

• 沸点：
  261.1±35.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 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：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-2-(trimethoxymethyl)pyrrole 在 盐酸 、 lithium aluminium tetrahydride 、 2-iodoxybenzoic acid 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 3-氯-1H-吡咯-2-甲醛
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polyenylpyrrole Derivatives as Anticancer Agents Acting through Caspases-Dependent Apoptosis

  摘要：

  A class of polyenylpyrroles and their analogues were designed from a hit compound identified in a fungus. The compounds synthesized were evaluated for their cell cytotoxicity against human non-small-cell lung carcinoma cell lines A549. Two compounds were found to exhibit high cytotoxicity against A549 cells with IC50 of 0.6 and 0.01 mu M, respectively. The underlying mechanisms for the anticancer activity were demonstrated as caspases activation dependent apoptosis induction through loss of mitochondrial membrane potential, release of cytochrome c, increase in B-cell lymphoma-2-associated X protein (Bax) level, and decrease in B-cell lymphoma-2 (Bcl-2) level. The two compounds were nontoxic to normal human lung Beas-2b cells (IC50 > 80 mu M), indicating that they are highly selective in their cytotoxicity activities. Furthermore, one compound showed in vivo anticancer activity in human-lung-cancer-cell-bearing mice. These results open promising insights on how these conjugated polyenes mediate cytotoxicity and may provide a molecular rationale for future therapeutic interventions in carcinogenesis.

  DOI：

  10.1021/jm100619x
• 作为产物：
  描述：

  2-甲基吡咯啉 在 N-氯代丁二酰亚胺 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 73.5h， 生成 3-chloro-2-(trimethoxymethyl)pyrrole
  参考文献：
  名称：

  COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO KIT

  摘要：

  本文描述了用于治疗与突变KIT相关的疾病的化合物和组合物。

  公开号：

  US20150111887A1

文献信息

• COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO KIT
  申请人：Hodous Brian L.

  公开号：US20150111887A1

  公开（公告）日：2015-04-23

  Compounds and compositions useful for treating disorders related to mutant KIT are described herein.

  本文描述了用于治疗与突变KIT相关的疾病的化合物和组合物。
• Synthesis of 2-acyl-3-chloropyrroles: Application to the synthesis of the trail pheromone of the ant Atta texana
  作者：Kourosch Abbaspour Tehrani、Didier Borremans、Norbert De Kimpe

  DOI：10.1016/s0040-4020(99)00106-4

  日期：1999.3

  alkoxides in the corresponding alcohol and final acid hydrolysis of the resulting orthoester or acetal functions into the 3-chloropyrrole. The developed strategy is applied to the synthesis of the trail pheromone of the ant Atta texana.

  3-氯吡咯-2-羧酸烷基酯和2-烷酰基-3-氯吡咯烷基可以方便地由2-烷基-1-吡咯啉与N-氯代琥珀酰亚胺四卤代和五卤代，随后在相应的醇中用醇钠进行碱诱导的芳构化制得。最终的原酸酯或缩醛官能团的最终酸水解成3-氯吡咯。所开发的策略被应用于蚂蚁Atta texana的尾信息素的合成。
• [EN] COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO KIT<br/>[FR] COMPOSITIONS UTILES POUR LE TRAITEMENT DE TROUBLES ASSOCIÉS À L'ENZYME KIT
  申请人：BLUEPRINT MEDICINES CORP

  公开号：WO2015057873A1

  公开（公告）日：2015-04-23

  Compounds and compositions useful for treating disorders related to mutant KIT are described herein.

  本文描述了用于治疗与突变KIT相关的疾病的化合物和组合物。
• Compositions useful for treating disorders related to kit
  申请人：Blueprint Medicines Corporation

  公开号：US10807985B2

  公开（公告）日：2020-10-20

  Compounds and compositions useful for treating disorders related to mutant KIT are described herein.

  本文描述了用于治疗与突变 KIT 相关疾病的化合物和组合物。
• PROCESS FOR PREPARING COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO KIT
  申请人：Blueprint Medicines Corporation

  公开号：EP3409674B1

  公开（公告）日：2022-04-06

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