N-(4-fluoro-3-nitrophenyl)-acrylamide | 1156229-23-0

• 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: N-(4-fluoro-3-nitrophenyl)-acrylamide
• 英文别名: N-(4-fluoro-3-nitro-phenyl)-acrylamide；N-(4-fluoro-3-nitrophenyl)prop-2-enamide
• CAS: 1156229-23-0
• 化学式: C₉H₇FN₂O₃
• 分子量: 210.165
• InChiKey: DTWKLSRHQLSXKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-fluoro-3-nitrophenyl)-acrylamide 在 铁粉 作用下， 以 乙醇 为溶剂， 生成 N-(3-amino-4-fluorophenyl)acrylamide
  参考文献：
  名称：

  Discovery of 4‐(4‐aminophenyl)‐6‐phenylisoxazolo[3,4‐ b ]pyridine‐3‐amine derivatives as novel FLT3 covalent inhibitors for the intervention of acute myeloid leukemia

  摘要：

  AbstractSmall molecule covalent drugs have proved to be desirable therapies especially on drug resistance related to point mutations. Secondary mutations of FLT3 have become the main mechanism of FLT3 inhibitors resistance which further causes the failure of treatment. Herein, a series of 4‐(4‐aminophenyl)‐6‐phenylisoxazolo[3,4‐b]pyridine‐3‐amine covalent derivatives were synthesized and optimized to overcome the common secondary resistance mutations of FLT3. Among these derivatives, compound F15 displayed potent inhibition activities against FLT3 (IC50 = 123 nM) and FLT3‐internal tandem duplication (ITD) by 80% and 26.06%, respectively, at the concentration of 1 μM. Besides, F15 exhibited potent activity against FLT3‐dependent human acute myeloid leukemia (AML) cell lines MOLM‐13 (IC50 = 253 nM) and MV4‐11 (IC50 = 91 nM), as well as BaF3 cells with variety of secondary mutations. Furthermore, cellular mechanism assays indicated that F15 inhibited phosphorylation of FLT3 and its downstream signaling factors. Notably, F15 could be considered for further development as potential drug candidate to treat AML.

  DOI：

  10.1002/ddr.22032
• 作为产物：
  描述：

  4-氟-3-硝基苯胺 、 丙烯酰氯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以74%的产率得到N-(4-fluoro-3-nitrophenyl)-acrylamide
  参考文献：
  名称：

  [EN] NOVEL FUSED PYRIMIDINE DERIVATIVES FOR INHIBITION OF TYROSINE KINASE ACTIVITY
  [FR] NOUVEAUX DÉRIVÉS FUSIONNÉS DE PYRIMIDINE POUR L'INHIBITION DE L'ACTIVITÉ TYROSINE KINASE

  摘要：

  公开号：

  WO2011162515A3

文献信息

• Fused pyrimidine derivatives for inhibition of tyrosine kinase activity
  申请人：Cha Mi Young

  公开号：US08957065B2

  公开（公告）日：2015-02-17

  The present invention relates to a novel fused pyrimidine derivative having an inhibitory activity for tyrosine kinases, and a pharmaceutical composition for preventing or treating cancers, tumors, inflammatory diseases, autoimmune diseases, or immunologically mediated diseases comprising same as an active ingredient.

  本发明涉及一种新型融合嘧啶衍生物，具有对酪氨酸激酶的抑制活性，以及一种药物组合物，包括该衍生物作为活性成分，用于预防或治疗癌症、肿瘤、炎症性疾病、自身免疫性疾病或免疫介导性疾病。
• NOVEL FUSED PYRIMIDINE DERIVATIVES FOR INHIBITION OF TYROSINE KINASE ACTIVITY
  申请人：Cha Mi Young

  公开号：US20130116213A1

  公开（公告）日：2013-05-09

  The present invention relates to a novel fused pyrimidine derivative having an inhibitory activity for tyrosine kinases, and a pharmaceutical composition for preventing or treating cancers, tumors, inflammatory diseases, autoimmune diseases, or immunologically mediated diseases comprising same as an active ingredient.

  本发明涉及一种新型融合嘧啶衍生物，具有对酪氨酸激酶的抑制活性，以及一种药物组合物，其作为活性成分用于预防或治疗癌症、肿瘤、炎症性疾病、自身免疫疾病或免疫介导性疾病。
• [EN] NOVEL FUSED PYRIMIDINE DERIVATIVES FOR INHIBITION OF TYROSINE KINASE ACTIVITY<br/>[FR] NOUVEAUX DÉRIVÉS FUSIONNÉS DE PYRIMIDINE POUR L'INHIBITION DE L'ACTIVITÉ TYROSINE KINASE
  申请人：HANMI HOLDINGS CO LTD

  公开号：WO2011162515A3

  公开（公告）日：2012-05-03
• NOVEL FUSED PYRIMIDINE DERIVATIVES FOR INHD3ITION OF TYROSINE KINASE ACTIVITY
  申请人：Hanmi Science Co., Ltd.

  公开号：EP2585470A2

  公开（公告）日：2013-05-01
• US8957065B2
  申请人：——

  公开号：US8957065B2

  公开（公告）日：2015-02-17