Methyl 2-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate | 476618-07-2

• 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: Methyl 2-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate
• 英文别名: methyl 2-(5-bromo-7-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-3-yl)acetate
• CAS: 476618-07-2
• 化学式: C₁₄H₁₃BrFNO₂
• 分子量: 326.165
• InChiKey: BNFJQBZRVZWVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  Methyl 2-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate 在 copper(l) iodide 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 19.25h， 生成 (6-Fluoro-8-sulfamoyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)-acetic acid methyl ester
  参考文献：
  名称：

  从烷基和芳基卤化物温和，方便地合成亚磺酸盐和磺酰胺

  摘要：

  已经开发了一种从相应的卤化物合成各种烷基和芳基亚磺酸盐和磺酰胺的通用，温和和方便的方法。该方法成功的关键是3-甲氧基-3-氧代丙烷-1-亚磺酸钠（SMOPS）的设计和简便合成，该试剂可将受保护的亚磺酸酯部分直接引入底物，从而避免使用氧化和其他苛刻的反应条件，例如有机锂或格氏试剂。该序列中容许许多官能团以及杂环。

  DOI：

  10.1016/s0040-4039(02)02073-7
• 作为产物：
  描述：

  Methyl 2-(8-bromo-6-fluoro-1-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 Methyl 2-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate
  参考文献：
  名称：

  Identification of prostaglandin D2 receptor antagonists based on a tetrahydropyridoindole scaffold

  摘要：

  A new series of indole-based antagonists of the PGD(2) receptor subtype 1 (DP1 receptor) was identified and the progress of the structure-activity relationship study to the identification of potent and selective antagonists is presented. Selective DP1 antagonists with high potency and selectivity were prepared. Of particular interest is the DP1 antagonist 26 with a K-i value of 1 nM for the DP1 receptor and an IC50 value of 4.6 nM in a DP1 functional assay for the inhibition of the PGD(2) induced cAMP production in platelet rich plasma (PRP). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.015

文献信息

• Dihydropyrrolo[1,2-a]indole and tetrahydropyrido[1,2-a]-indole derivatives as prostaglandin d2 receptor antagonists
  申请人：——

  公开号：US20040180934A1

  公开（公告）日：2004-09-16

  Dihydropyrroloindoles and tetrahydropyridoindoles are prostaglandin receptor antagonists useful for the treatment of prostaglandin-mediated diseases such as allergic rhinitis, nasal congestion and asthma.

  二氢吡咯吲啶和四氢吡咯吲啶是前列腺素受体拮抗剂，可用于治疗前列腺素介导的疾病，如过敏性鼻炎、鼻塞和哮喘。
• A mild, convenient synthesis of sulfinic acid salts and sulfonamides from alkyl and aryl halides
  作者：Jeremy M Baskin、Zhaoyin Wang

  DOI：10.1016/s0040-4039(02)02073-7

  日期：2002.11

  A general, mild, and convenient method has been developed for the synthesis of various alkyl and aryl sulfinic acid salts and sulfonamides from the corresponding halides. Key to the success of this methodology is the design and facile synthesis of sodium 3-methoxy-3-oxopropane-1-sulfinate (SMOPS), a reagent that serves to introduce the protected sulfinate moiety directly to the substrate, thus avoiding

  已经开发了一种从相应的卤化物合成各种烷基和芳基亚磺酸盐和磺酰胺的通用，温和和方便的方法。该方法成功的关键是3-甲氧基-3-氧代丙烷-1-亚磺酸钠（SMOPS）的设计和简便合成，该试剂可将受保护的亚磺酸酯部分直接引入底物，从而避免使用氧化和其他苛刻的反应条件，例如有机锂或格氏试剂。该序列中容许许多官能团以及杂环。
• Identification of prostaglandin D2 receptor antagonists based on a tetrahydropyridoindole scaffold
  作者：Christian Beaulieu、Daniel Guay、Zhaoyin Wang、Yves Leblanc、Patrick Roy、Claude Dufresne、Robert Zamboni、Carl Berthelette、Stephen Day、Nancy Tsou、Danielle Denis、Gillian Greig、Marie-Claude Mathieu、Gary O’Neill

  DOI：10.1016/j.bmcl.2008.03.015

  日期：2008.4

  A new series of indole-based antagonists of the PGD(2) receptor subtype 1 (DP1 receptor) was identified and the progress of the structure-activity relationship study to the identification of potent and selective antagonists is presented. Selective DP1 antagonists with high potency and selectivity were prepared. Of particular interest is the DP1 antagonist 26 with a K-i value of 1 nM for the DP1 receptor and an IC50 value of 4.6 nM in a DP1 functional assay for the inhibition of the PGD(2) induced cAMP production in platelet rich plasma (PRP). (C) 2008 Elsevier Ltd. All rights reserved.