tert-butyl 3-(3-(trifluoromethyl)phenoxy)azetidine-1-carboxylate | 954232-85-0

• 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: tert-butyl 3-(3-(trifluoromethyl)phenoxy)azetidine-1-carboxylate
• 英文别名: tert-butyl 3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxylate
• CAS: 954232-85-0
• 化学式: C₁₅H₁₈F₃NO₃
• 分子量: 317.308
• InChiKey: YCAODWMJVJAXEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  353.3±42.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(3-(trifluoromethyl)phenoxy)azetidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 3-[3-(三氟甲基)苯氧基]氮杂环丁烷盐酸盐
  参考文献：
  名称：

  Biological activity and preclinical efficacy of azetidinyl pyridazines as potent systemically-distributed stearoyl-CoA desaturase inhibitors

  摘要：

  Potent and orally bioavailable SCD inhibitors built on an azetidinyl pyridazine scaffold were identified. In a one-month gDIO mouse model of obesity, we demonstrated that there was no therapeutic index even at low doses; efficacy in preventing weight gain tracked closely with skin and eye adverse events. This was attributed to the local SCD inhibition in these tissues as a consequence of the broad tissue distribution observed in mice for this class of compounds. The search for new structural scaffolds which may display a different tissue distribution was initiated. In preparation for an HTS campaign, a radiolabeled azetidinyl pyridazine displaying low non-specific binding in the scintillation proximity assay was prepared. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.107
• 作为产物：
  描述：

  间三氟甲基苯酚 、 1-Boc-3-碘氮杂环丁烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以3.1 g的产率得到tert-butyl 3-(3-(trifluoromethyl)phenoxy)azetidine-1-carboxylate
  参考文献：
  名称：

  BICYCLIC COMPOUND

  摘要：

  公开号：

  EP3225618B1

文献信息

• Bicyclic compound
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US10301292B2

  公开（公告）日：2019-05-28

  Provided is a bicyclic compound having an acetyl-CoA carboxylase inhibitory action. A compound represented by the formula: wherein each symbol is as described in the DESCRIPTION, or a salt thereof has an acetyl-CoA carboxylase inhibitory action, is useful for the prophylaxis or treatment of cancer, inflammatory diseases and the like, and has superior efficacy.

  提供了一种具有乙酰-CoA 羧化酶抑制作用的双环化合物。一种由式表示的化合物： 其中各符号如说明书所述，或其盐具有乙酰-CoA 羧化酶抑制作用，可用于预防或治疗癌症、炎症等疾病，且疗效显著。
• BICYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP3225618B1

  公开（公告）日：2020-05-06
• Biological activity and preclinical efficacy of azetidinyl pyridazines as potent systemically-distributed stearoyl-CoA desaturase inhibitors
  作者：Elise Isabel、David A. Powell、W. Cameron Black、Chi-Chung Chan、Sheldon Crane、Robert Gordon、Jocelyne Guay、Sebastien Guiral、Zheng Huang、Joël Robichaud、Kathryn Skorey、Paul Tawa、Lijing Xu、Lei Zhang、Renata Oballa

  DOI：10.1016/j.bmcl.2010.10.107

  日期：2011.1

  Potent and orally bioavailable SCD inhibitors built on an azetidinyl pyridazine scaffold were identified. In a one-month gDIO mouse model of obesity, we demonstrated that there was no therapeutic index even at low doses; efficacy in preventing weight gain tracked closely with skin and eye adverse events. This was attributed to the local SCD inhibition in these tissues as a consequence of the broad tissue distribution observed in mice for this class of compounds. The search for new structural scaffolds which may display a different tissue distribution was initiated. In preparation for an HTS campaign, a radiolabeled azetidinyl pyridazine displaying low non-specific binding in the scintillation proximity assay was prepared. (c) 2010 Elsevier Ltd. All rights reserved.