ethyl 5-chloro-2-fluoro-4-nitrophenylacetate | 852994-66-2

• 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: ethyl 5-chloro-2-fluoro-4-nitrophenylacetate
• 英文别名: Ethyl 2-(5-chloro-2-fluoro-4-nitrophenyl)acetate；ethyl 2-(5-chloro-2-fluoro-4-nitrophenyl)acetate
• CAS: 852994-66-2
• 化学式: C₁₀H₉ClFNO₄
• 分子量: 261.637
• InChiKey: HSZYMTBWFLBAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-chloro-2-fluoro-4-nitrophenylacetate 在 sodium acetate 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以91%的产率得到ethyl 2-(4-amino-5-chloro-2-fluorophenyl)acetate
  参考文献：
  名称：

  Identification of 4-[1-[3-chloro-4-[N’-(5-fluoro-2-methylphenyl)ureido]phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid as a potent, orally active VLA-4 antagonist

  摘要：

  Optimization of benzoic acid derivatives by introducing substituents into the diphenyl urea moiety led to the identification of compound 201 as a potent VLA-4 antagonist. Compound 201 inhibited eosinophil infiltration into bronchial alveolar lavage fluid in a murine asthma model by oral dosing and its efficacy was comparable to anti-mouse alpha 4 antibody (R1-2). Furthermore, this compound significantly blocked bronchial hyper-responsiveness in the model. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.020
• 作为产物：
  描述：

  乙醇 、 di(tert-butyl) (5-chloro-2-fluoro-4-nitrophenyl)malonate 在 盐酸 、 溶剂黄146 、 硫酸 作用下， 以 水 为溶剂， 反应 5.0h， 以74%的产率得到ethyl 5-chloro-2-fluoro-4-nitrophenylacetate
  参考文献：
  名称：

  Identification of 4-[1-[3-chloro-4-[N’-(5-fluoro-2-methylphenyl)ureido]phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid as a potent, orally active VLA-4 antagonist

  摘要：

  Optimization of benzoic acid derivatives by introducing substituents into the diphenyl urea moiety led to the identification of compound 201 as a potent VLA-4 antagonist. Compound 201 inhibited eosinophil infiltration into bronchial alveolar lavage fluid in a murine asthma model by oral dosing and its efficacy was comparable to anti-mouse alpha 4 antibody (R1-2). Furthermore, this compound significantly blocked bronchial hyper-responsiveness in the model. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.020

文献信息

• Identification of the 5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine derivatives as highly selective PDE4B inhibitors
  作者：Taiji Goto、Akiko Shiina、Takeshi Murata、Masato Tomii、Takanori Yamazaki、Ken-ichi Yoshida、Toshiharu Yoshino、Osamu Suzuki、Yoshitaka Sogawa、Kiyoshi Mizukami、Nana Takagi、Tomomi Yoshitomi、Maki Etori、Hiroshi Tsuchida、Tsuyoshi Mikkaichi、Naoki Nakao、Mizuki Takahashi、Hisashi Takahashi、Shigeki Sasaki

  DOI：10.1016/j.bmcl.2013.12.076

  日期：2014.2

  A PDE4B subtype selective inhibitor is expected to have a wider therapeutic window than non-selective PDE4 inhibitors. In this Letter, two series of 7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivatives and 5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivatives were evaluated for their PDE4B subtype selectivity using human PDE4B2 and PDE4D2 full length enzymes. To improve their PDE4B selectivity over PDE4D, we optimized the substituents on the pyrimidine ring and the side chain phenyl ring, resulting in several derivatives with more than 100-fold selectivity for PDE4B. Consequently, we identified 2-( 3-chloro-4-methoxy-phenyl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivative 54 as a highly selective PDE4B inhibitor, which had potent hPDE4B inhibitory activity with an IC50 value of 3.0 nM and 433-fold PDE4B selectivity over PDE4D. (C) 2014 Elsevier Ltd. All rights reserved.
• Identification of 4-[1-[3-chloro-4-[N’-(5-fluoro-2-methylphenyl)ureido]phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid as a potent, orally active VLA-4 antagonist
  作者：Fumihito Muro、Shin Iimura、Yoshiyuki Yoneda、Jun Chiba、Toshiyuki Watanabe、Masaki Setoguchi、Yutaka Iigou、Gensuke Takayama、Mika Yokoyama、Tohru Takashi、Atsushi Nakayama、Nobuo Machinaga

  DOI：10.1016/j.bmc.2008.10.020

  日期：2008.12

  Optimization of benzoic acid derivatives by introducing substituents into the diphenyl urea moiety led to the identification of compound 201 as a potent VLA-4 antagonist. Compound 201 inhibited eosinophil infiltration into bronchial alveolar lavage fluid in a murine asthma model by oral dosing and its efficacy was comparable to anti-mouse alpha 4 antibody (R1-2). Furthermore, this compound significantly blocked bronchial hyper-responsiveness in the model. (c) 2008 Elsevier Ltd. All rights reserved.