3-(3-Bromo-2-methylphenyl)prop-2-en-1-ol | 1089205-87-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 3-(3-Bromo-2-methylphenyl)prop-2-en-1-ol
• 英文别名: (E)-3-(3-bromo-2-methylphenyl)prop-2-en-1-ol
• CAS: 1089205-87-7
• 化学式: C₁₀H₁₁BrO
• 分子量: 227.101
• InChiKey: DVEIISXHSBOGCH-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3-Bromo-2-methylphenyl)prop-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Chemical and Biological Studies of Nakiterpiosin and Nakiterpiosinone

  摘要：

  Nakiterpiosin and nakiterpiosinone are two related C-nor-D-homosteroids isolated from the sponge Terpios hoshinota that show promise as anticancer agents. We have previously described the asymmetric synthesis and revision of the relative configuration of nakiterpiosin. We now provide detailed information on the stereochemical analysis that supports our structure revision and the synthesis of the originally proposed and revised nakiterpiosin. In addition, we herein describe a refined approach for the synthesis of nakiterpiosin, the first synthesis of nakiterpiosinone, and preliminary mechanistic studies of nakiterpiosin's action in mammalian cells. Cells treated with nakiterpiosin exhibit compromised formation of the primary cilium, an organelle that functions as an assembly point for components of the Hedgehog signal transduction pathway. We provide evidence that the biological effects exhibited by nakiterpiosin are mechanistically distinct from those of well-established antimitotic agents such as taxol. Nakiterpiosin may be useful as an anticancer agent in those tumors resistant to existing antimitotic agents and those dependent on Hedgehog pathway responses for growth.

  DOI：

  10.1021/ja908626k
• 作为产物：
  描述：

  ethyl (E)-3-(3-bromo-2-methylphenyl)acrylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3-Bromo-2-methylphenyl)prop-2-en-1-ol
  参考文献：
  名称：

  Chemical and Biological Studies of Nakiterpiosin and Nakiterpiosinone

  摘要：

  Nakiterpiosin and nakiterpiosinone are two related C-nor-D-homosteroids isolated from the sponge Terpios hoshinota that show promise as anticancer agents. We have previously described the asymmetric synthesis and revision of the relative configuration of nakiterpiosin. We now provide detailed information on the stereochemical analysis that supports our structure revision and the synthesis of the originally proposed and revised nakiterpiosin. In addition, we herein describe a refined approach for the synthesis of nakiterpiosin, the first synthesis of nakiterpiosinone, and preliminary mechanistic studies of nakiterpiosin's action in mammalian cells. Cells treated with nakiterpiosin exhibit compromised formation of the primary cilium, an organelle that functions as an assembly point for components of the Hedgehog signal transduction pathway. We provide evidence that the biological effects exhibited by nakiterpiosin are mechanistically distinct from those of well-established antimitotic agents such as taxol. Nakiterpiosin may be useful as an anticancer agent in those tumors resistant to existing antimitotic agents and those dependent on Hedgehog pathway responses for growth.

  DOI：

  10.1021/ja908626k

文献信息

• [EN] BIPHENYL COMPOUND AS IMMUNOMODULATORY AGENT AND USE THEREOF<br/>[FR] COMPOSÉ DE BIPHÉNYLE EN TANT QU'AGENT IMMUNOMODULATEUR ET SON UTILISATION<br/>[ZH] 作为免疫调节剂的联苯化合物及其用途
  申请人：SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD

  公开号：WO2020043154A1

  公开（公告）日：2020-03-05

  公开了涉及式I所示的联苯类化合物、其制备方法及其制药用途。式I中各基团的定义如说明书所述。所述化合物能够阻断PD-1/PD-L1信号通路之间的相互作用，可用于治疗或预防与该信号通路相关的疾病，例如癌症、自身免疫性疾病或慢性感染性疾病。 (I)