3-(2-(pyrrolidin-1-yl)ethoxy)-5-(trifluoromethyl)aniline | 900254-40-2

• 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: 3-(2-(pyrrolidin-1-yl)ethoxy)-5-(trifluoromethyl)aniline
• 英文别名: 3-(2-Pyrrolidin-1-ylethoxy)-5-(trifluoromethyl)aniline
• CAS: 900254-40-2
• 化学式: C₁₃H₁₇F₃N₂O
• 分子量: 274.286
• InChiKey: HTADMYBCCMQADI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-(pyrrolidin-1-yl)ethoxy)-5-(trifluoromethyl)aniline 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 4-{2-[3-(2-pyrrolidin-1-yl-ethoxy)-5-trifluoromethyl-phenylamino]-1H-benzimidazol-5-yloxy}-pyridine-2-carboxylic acid methylamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Orally Active Benzimidazoles and Benzoxazoles as Vascular Endothelial Growth Factor-2 Receptor Tyrosine Kinase Inhibitors

  摘要：

  Inhibition of the VEGF signaling pathway has become a valuable approach in the treatment of cancers. Guided by X-ray crystallography and molecular modeling, a series of 2-aminobenzimidazoles and 2-aminobenzoxazoles were identified as potent inhibitors of VEGFR-2 (KDR) in both enzymatic and HUVEC cellular proliferation assays. In this report we describe the synthesis and structure-activity relationship of a series of 2-aminobenzimidazoles and benzoxazoles, culminating in the identification of benzoxazole 22 as a potent and selective VEGFR-2 inhibitor displaying a good pharmacokinetic profile. Compound 22 demonstrated efficacy in both the murine matrigel model for vascular permeability (79% inhibition observed at 100 mg/kg) and the rat corneal angiogenesis model (ED(50) = 16.3 mg/kg).

  DOI：

  10.1021/jm070034i
• 作为产物：
  描述：

  3-硝基-5-(三氟甲基)苯酚 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、101.33 kPa 条件下， 反应 168.0h， 生成 3-(2-(pyrrolidin-1-yl)ethoxy)-5-(trifluoromethyl)aniline
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Orally Active Benzimidazoles and Benzoxazoles as Vascular Endothelial Growth Factor-2 Receptor Tyrosine Kinase Inhibitors

  摘要：

  Inhibition of the VEGF signaling pathway has become a valuable approach in the treatment of cancers. Guided by X-ray crystallography and molecular modeling, a series of 2-aminobenzimidazoles and 2-aminobenzoxazoles were identified as potent inhibitors of VEGFR-2 (KDR) in both enzymatic and HUVEC cellular proliferation assays. In this report we describe the synthesis and structure-activity relationship of a series of 2-aminobenzimidazoles and benzoxazoles, culminating in the identification of benzoxazole 22 as a potent and selective VEGFR-2 inhibitor displaying a good pharmacokinetic profile. Compound 22 demonstrated efficacy in both the murine matrigel model for vascular permeability (79% inhibition observed at 100 mg/kg) and the rat corneal angiogenesis model (ED(50) = 16.3 mg/kg).

  DOI：

  10.1021/jm070034i

文献信息

• Cinnamide and hydrocinnamide derivatives with kinase inhibitory activity
  申请人：Adams S. Ruth

  公开号：US20060160803A1

  公开（公告）日：2006-07-20

  The present invention provides novel cinnamide compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various diseases.

  本发明提供了一种新型的肉桂酰胺化合物，可用作蛋白激酶的抑制剂。该发明还提供了包括该发明化合物的药物组合物，以及在治疗各种疾病中使用这些组合物的方法。
• [EN] FUSED AZOLES SUCH AS 2,5-DISUBSTITUTED BENZIMIDAZOLES, BENZOXAZOLES AND BENZOTHIAZOLES AS KINASE INHIBITORS<br/>[FR] AZOLES FUSIONNES TELS QUE BENZIMIDAZOLES, BENZOXAZOLES ET BENZOTHIAZLES 2,5-DISUBSTITUES COMME INHIBITEURS DE KINASE
  申请人：AMGEN INC

  公开号：WO2004085425A1

  公开（公告）日：2004-10-07

  The invention relates to compounds of the formulae (I) to (III) wherein the substituents are as defined in the specification. These compounds have kinase inhibitory activity, such as VEGFR/KDR inhibitory activity. Accordingly, the compounds of the formulae (I) to (III) would be useful in the prevention and treatment of angiogenesis related disorders, ophthalmological conditions, proliferative diseases, inflammatory diseases, and other pathological conditions as described in the specification.

  这项发明涉及式(I)至(III)的化合物，其中取代基如规范中所定义。这些化合物具有激酶抑制活性，如VEGFR/KDR抑制活性。因此，式(I)至(III)的化合物在预防和治疗与血管生成相关的疾病、眼科疾病、增生性疾病、炎症性疾病以及规范中描述的其他病理状况中将会有用。
• Bicyclic compounds with kinase inhibitory activity
  申请人：Calderwood F. Emily

  公开号：US20070149533A1

  公开（公告）日：2007-06-28

  The present invention provides novel bicyclic compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various diseases.

  本发明提供了一种新颖的双环化合物，可用作蛋白激酶抑制剂。本发明还提供了包括本发明化合物的制药组合物以及使用该组合物治疗各种疾病的方法。
• [EN] TETRAHYDROTHIENO PYRIDINE DERIVATIVES AS DDRS INHIBITORS<br/>[FR] DÉRIVÉS DE TÉTRAHYDROTHIÉNO PYRIDINE EN TANT QU'INHIBITEURS DE DDR
  申请人：CHIESI FARM SPA

  公开号：WO2022200580A1

  公开（公告）日：2022-09-29

  The present invention relates to compounds of general formula (I) inhibiting Discoidin Domain Receptors (DDR inhibitors), methods of preparing such compounds, pharmaceutical compositions containing them and therapeutic use thereof.The compounds of the invention may be useful for instance in the treatment of many disorders associated with DDR mechanisms.

  本发明涉及一般式(I)的化合物，可抑制圆盘素结构域受体（DDR抑制剂），制备这种化合物的方法，包含它们的药物组合物以及其治疗用途。本发明的化合物可能有用于治疗与DDR机制相关的许多疾病。
• 一种杂环衍生物及其在医药上的应用
  申请人：四川海思科制药有限公司

  公开号：CN115340552A

  公开（公告）日：2022-11-15

  本发明涉及一种通式(I)或(II)所述的化合物或者其立体异构体、氘代物、溶剂化物、前药、代谢产物、药学上可接受的盐或共晶，及其中间体和制备方法，以及在制备治疗与RET活性或表达量相关疾病的药物中的应用。