ethyl 6-cyano-1-ethylindole-2-carboxylate | 200184-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 6-cyano-1-ethylindole-2-carboxylate
• CAS: 200184-02-7
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: RZAXAPLXTCHTSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-cyano-1-ethylindole-2-carboxylate 在 吡啶 、 sodium tetrahydroborate 、 羟胺 、 乙酸酐 、 碳酸氢钠 、 caesium carbonate 、 溶剂黄146 、 对甲苯磺酰氯 、 calcium iodide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[4-(6-Carbamimidoyl-1-ethyl-1H-indol-2-ylmethyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-yloxy]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  6-氰基吲哚-2-甲酸乙酯 、 碘乙烷 在 NaH 作用下， 以 N-甲基乙酰胺 为溶剂， 生成 ethyl 6-cyano-1-ethylindole-2-carboxylate
  参考文献：
  名称：

  Aromatic amidine derivatives useful as selective thrombin inhibitors

  摘要：

  本发明涉及一种新颖的凝血酶抑制剂，即使口服给药也有效。更具体地说，本发明涉及一种由公式（I）表示的芳香族酰胺衍生物及其盐，其对凝血酶具有强的选择性抑制活性，其中（a），R，R1，R2，R3，A，W，Y和n如说明书所述定义。

  公开号：

  US06201006B1

文献信息

• Aromatic amidine derivatives useful as selective thrombin inhibitors
  申请人：C & C Research Laboratories

  公开号：US06201006B1

  公开（公告）日：2001-03-13

  The present invention relates to a novel thrombin inhibitor which is effective even when orally administered. More specifically, the present invention relates to an aromatic amidine derivative represented by formula (I) and the salts thereof, which show potent selective inhibitory activity for thrombin in which (a), R, R1, R2, R3, A, W, Y and n are defined as described in the specification.

  本发明涉及一种新颖的凝血酶抑制剂，即使口服给药也有效。更具体地说，本发明涉及一种由公式（I）表示的芳香族酰胺衍生物及其盐，其对凝血酶具有强的选择性抑制活性，其中（a），R，R1，R2，R3，A，W，Y和n如说明书所述定义。
• AROMATIC AMIDINE DERIVATIVES USEFUL AS SELECTIVE THROMBIN INHIBITORS
  申请人：C & C Research Laboratories

  公开号：EP0918768B1

  公开（公告）日：2002-01-09
• US6201006B1
  申请人：——

  公开号：US6201006B1

  公开（公告）日：2001-03-13
• Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors
  作者：Wenrong Huang、Penglie Zhang、Jingmei F Zuckett、Lingyan Wang、John Woolfrey、Yonghong Song、Zhaozhong J Jia、Lane A Clizbe、Ting Su、Katherine Tran、Brian Huang、Paul Wong、Uma Sinha、Gary Park、Andrea Reed、John Malinowski、Stanley J Hollenbach、Robert M Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)00927-7

  日期：2003.2

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.