(+/-)-Methyl [9-(4-chlorobenzoyl)-6-fluoro-8-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate

• 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 [9-(4-chlorobenzoyl)-6-fluoro-8-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate
• 英文别名: methyl 2-[4-(4-chlorobenzoyl)-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-3-yl]acetate
• 化学式: C₂₂H₁₉ClFNO₅S
• 分子量: 463.914
• InChiKey: SYEVOQPMMFTGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-Methyl [9-(4-chlorobenzoyl)-6-fluoro-8-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (+/-)-[9-(4-chlorobenzoyl)-6-fluoro-8-(methylsulfonyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid
  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
• 作为产物：
  描述：

  (+/-)-methyl [8-bromo-9-(4-chlorobenzoyl)-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate 、 sodium methansulfinate 在 cupric iodide 乙酸乙酯 、 silica gel 、 Brine 、 Sodium sulfate-III 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 3.0h， 以to give (+/−)-methyl [9-(4-chlorobenzoyl)-6-fluoro-8-(methylsulfonyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate which的产率得到(+/-)-Methyl [9-(4-chlorobenzoyl)-6-fluoro-8-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate
  参考文献：
  名称：

  Dihydropyrrolo[1,2-a]indole and tetrahydropyrido[1,2-a]-indole derivatives as prostaglandin d2 receptor antagonists

  摘要：

  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。

  公开号：

  US20040180934A1

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。
• 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.