7-bromo-1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indole | 1202714-17-7

• 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: 7-bromo-1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indole
• 英文别名: 7-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-5-fluoro-3-methylindole
• CAS: 1202714-17-7
• 化学式: C₁₈H₁₅BrFNO₂
• 分子量: 376.225
• InChiKey: IBATXJCIZLJSPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-bromo-1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indole 、 氯甲酸乙酯 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以76%的产率得到Ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-5-fluoro-3-methylindole-7-carboxylate
  参考文献：
  名称：

  A general approach to indole-7-yl derivatives of isoxazole, oxadiazole, thiadiazole and pyrazole

  摘要：

  Isosteric replacement of the alpha,beta-unsaturated amide at the C-7 position of indoles with a diverse set of five-membered amino-heterocycles including isoxazole, oxadiazole, thiadiazole and pyrazole followed by subsequent derivatization of the heterocyclic amino group to yield amides, sulfonamides and phosphoramides is described. Distinctive features of these procedures include the versatility and robust nature of the synthetic steps along with the high yields of the targeted molecules. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.073
• 作为产物：
  描述：

  7-溴-5-氟-3-甲基-1H-吲哚 、 6-(溴甲基)-2,3-二氢苯并[b][1,4]二噁英 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以80%的产率得到7-bromo-1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indole
  参考文献：
  名称：

  Structure−Activity Relationship Studies Leading to the Identification of (2E)-3-[l-[(2,4-Dichlorophenyl)methyl]-5-fluoro-3-methyl-lH-indol-7-yl]-N-[(4,5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a Potent and Selective Prostanoid EP3 Receptor Antagonist, as a Novel Antiplatelet Agent That Does Not Prolong Bleeding

  摘要：

  The EP(3) receptor on the platelet mediates prostaglandin E(2) potentiation of thrombogenic coagonists including collagen and adenosine diphosphate (ADP). A pharmacophore driven approach led to the identification of diverse peri-substituted heterocycles as potent and selective EP(3) receptor antagonists. A simultaneous chemical optimization and druglike assessment of prioritized molecules converged oil a lead compound 50 (DG-041) that displayed favorable in vitro and functional activities as an inhibitor of human platelet aggregation. This agent is currently in human clinical trials for the treatment of atherothrombosis.

  DOI：

  10.1021/jm9005912

文献信息

• Structure−Activity Relationship Studies Leading to the Identification of (2<i>E</i>)-3-[l-[(2,4-Dichlorophenyl)methyl]-5-fluoro-3-methyl-l<i>H</i>-indol-7-yl]-<i>N</i>-[(4,5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a Potent and Selective Prostanoid EP3 Receptor Antagonist, as a Novel Antiplatelet Agent That Does Not Prolong Bleeding
  作者：Jasbir Singh、Wayne Zeller、Nian Zhou、Georgeta Hategan、Rama K. Mishra、Alex Polozov、Peng Yu、Emmanuel Onua、Jun Zhang、José L. Ramírez、Gudmundur Sigthorsson、Margret Thorsteinnsdottir、Alex. S. Kiselyov、David E. Zembower、Thorkell Andrésson、Mark E. Gurney

  DOI：10.1021/jm9005912

  日期：2010.1.14

  The EP(3) receptor on the platelet mediates prostaglandin E(2) potentiation of thrombogenic coagonists including collagen and adenosine diphosphate (ADP). A pharmacophore driven approach led to the identification of diverse peri-substituted heterocycles as potent and selective EP(3) receptor antagonists. A simultaneous chemical optimization and druglike assessment of prioritized molecules converged oil a lead compound 50 (DG-041) that displayed favorable in vitro and functional activities as an inhibitor of human platelet aggregation. This agent is currently in human clinical trials for the treatment of atherothrombosis.
• A general approach to indole-7-yl derivatives of isoxazole, oxadiazole, thiadiazole and pyrazole
  作者：Alexandre M. Polozov、Georgeta Hategan、Hua Cao、Alex S. Kiselyov、Wayne Zeller、Jasbir Singh

  DOI：10.1016/j.tetlet.2009.11.073

  日期：2010.1

  Isosteric replacement of the alpha,beta-unsaturated amide at the C-7 position of indoles with a diverse set of five-membered amino-heterocycles including isoxazole, oxadiazole, thiadiazole and pyrazole followed by subsequent derivatization of the heterocyclic amino group to yield amides, sulfonamides and phosphoramides is described. Distinctive features of these procedures include the versatility and robust nature of the synthetic steps along with the high yields of the targeted molecules. (C) 2009 Elsevier Ltd. All rights reserved.