3-碘-4-异丙基苯甲酸甲酯 | 100127-58-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 3-碘-4-异丙基苯甲酸甲酯
• 英文名称: methyl 3-iodo-4-isopropylbenzoate
• 英文别名: methyl 3-iodo-4-propan-2-ylbenzoate
• CAS: 100127-58-0
• 化学式: C₁₁H₁₃IO₂
• 分子量: 304.128
• InChiKey: VIUQYXQVBWXXBV-UHFFFAOYSA-N

物化性质

• 沸点：
  328.3±35.0 °C(Predicted)
• 密度：
  1.524±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-碘-4-异丙基苯甲酸甲酯 在 喹啉 、 sodium ethanolate 、 铜 作用下， 生成 1-丙-2-基-2-(2-丙-2-基苯基)苯
  参考文献：
  名称：

  Everitt et al., Journal of the Chemical Society, 1956, p. 2286,2289

  摘要：

  DOI：
• 作为产物：
  描述：

  4-异丙基苯甲酸 在 sodium periodate 、 硫酸 、 碘 、 potassium carbonate 作用下， 以 乙酸酐 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-碘-4-异丙基苯甲酸甲酯
  参考文献：
  名称：

  Novel Class of Colony-Stimulating Factor 1 Receptor Kinase Inhibitors Based on ano-Aminopyridyl Alkynyl Scaffold as Potential Treatment for Inflammatory Disorders

  摘要：

  Colony-stimulating factor 1 receptor (CSF-1R) is involved in inflammatory disorders as well as in many types of cancer. Based on high-throughput screening and docking results, we performed a detailed structure-activity-relationship study, leading to the discovery of a new series of compounds with nanomolar IC50 values against CSF-1R without the inhibition of fibroblast growth factor receptors. One of the most promising hits, compound 29, potently inhibited CSF-1R kinase with an IC50 value of 0.7 nM, while it showed no inhibition to the same family member FMS-like tyrosine kinase 3. Compound 29 displayed excellent anti-inflammatory effects against RAW264.7 macrophages indicated by significant inhibition against the activation of the CSF-1R pathway with low cytotoxicity. In addition, compound 29 exhibited strong in vivo anti-inflammatory efficacy alongside favorable drug characteristics. This novel compound 29 may serve as a new drug candidate with promising applications in inflammatory disorders.

  DOI：

  10.1021/acs.jmedchem.9b01912

文献信息

• Design and Optimization of 3′-(Imidazo[1,2-<i>a</i>]pyrazin-3-yl)-[1,1′-biphenyl]-3-carboxamides as Selective DDR1 Inhibitors
  作者：Cheng Mo、Zhang Zhang、Yupeng Li、Minhao Huang、Jian Zou、Jinfeng Luo、Zheng-Chao Tu、Yong Xu、Xiaomei Ren、Ke Ding、Xiaoyun Lu

  DOI：10.1021/acsmedchemlett.9b00495

  日期：2020.3.12

  DDR1 is considered as a promising target for cancer therapy, and selective inhibitors against DDR1 over other kinases may be considered as promising therapeutic agents. Herein, we have identified a series of 3'-(imidazo[1,2-alpha]pyrazin-3-yl)-[1,1'-biphenyl]-3-carboxamides as novel selective DDR1 inhibitors. Among these, compound 8v potently inhibited DDR1 with an IC50 of 23.8 nM, while it showed less inhibitory activity against DDR2 (IC50 = 1740 nM) and negligible activities against Bcr-Abl (IC50 > 10 mu M) and c-Kit (IC50 > 10 mu M). 8v also exhibited excellent selectivity in a KINOMEscan screening platform with 468 kinases. This compound dose-dependently suppressed NSCLC cell tumorigenicity, migration, and invasion. Collectively, these studies support its potential application for treatment of NSCLC.
• Design, Synthesis, and Biological Evaluation of 3-(Imidazo[1,2-<i>a</i>]pyrazin-3-ylethynyl)-4-isopropyl-<i>N</i>-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide as a Dual Inhibitor of Discoidin Domain Receptors 1 and 2
  作者：Zhen Wang、Yali Zhang、Daniel M. Pinkas、Alice E. Fox、Jinfeng Luo、Huocong Huang、Shengyang Cui、Qiuping Xiang、Tingting Xu、Qiuju Xun、Dongsheng Zhu、Zhengchao Tu、Xiaomei Ren、Rolf A. Brekken、Alex N. Bullock、Guang Liang、Ke Ding、Xiaoyun Lu

  DOI：10.1021/acs.jmedchem.8b01045

  日期：2018.9.13

  Discoidin-domain receptors 1 and 2 (DDR1 and DDR2) are new potential targets for anti-inflammatory-drug discovery. A series of heterocycloalkynylbenzimides were designed and optimized to coinhibit DDR1 and DDR2. One of the most promising compounds, Sn, tightly bound to DDR1 and DDR2 proteins with K-d values of 7.9 and 8.0 nM; potently inhibited the kinases with IC50 values of 9.4 and 20.4 nM, respectively; and was significantly less potent for a panel of 403 wild-type kinases at 1.0 mu M. DDR1- and DDR2-kinase inhibition by 5n was validated by Western-blotting analysis in primary human lung fibroblasts. The compound also dose-dependently inhibited lipopolysaccharide (LPS)-induced interleukin 6 (IL-6) release in vitro and exhibited promising in vivo anti-inflammatory effects in an LPS-induced-acute-lung-injury (ALI) mouse model. Compound 5n may serve as a lead compound for new anti-inflammatory drug discovery.
• Novel Class of Colony-Stimulating Factor 1 Receptor Kinase Inhibitors Based on an<i>o</i>-Aminopyridyl Alkynyl Scaffold as Potential Treatment for Inflammatory Disorders
  作者：Zhicheng Xie、Bing Wu、Yingqiang Liu、Wenming Ren、Linjiang Tong、Caigui Xiang、Aihuan Wei、Yuanzhuo Gao、Limin Zeng、Hua Xie、Wei Tang、Youhong Hu

  DOI：10.1021/acs.jmedchem.9b01912

  日期：2020.2.13

  Colony-stimulating factor 1 receptor (CSF-1R) is involved in inflammatory disorders as well as in many types of cancer. Based on high-throughput screening and docking results, we performed a detailed structure-activity-relationship study, leading to the discovery of a new series of compounds with nanomolar IC50 values against CSF-1R without the inhibition of fibroblast growth factor receptors. One of the most promising hits, compound 29, potently inhibited CSF-1R kinase with an IC50 value of 0.7 nM, while it showed no inhibition to the same family member FMS-like tyrosine kinase 3. Compound 29 displayed excellent anti-inflammatory effects against RAW264.7 macrophages indicated by significant inhibition against the activation of the CSF-1R pathway with low cytotoxicity. In addition, compound 29 exhibited strong in vivo anti-inflammatory efficacy alongside favorable drug characteristics. This novel compound 29 may serve as a new drug candidate with promising applications in inflammatory disorders.
• Everitt et al., Journal of the Chemical Society, 1956, p. 2286,2289
  作者：Everitt et al.

  DOI：——

  日期：——