2-[(2-methyl-1-(2-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl)oxy]acetic acid methyl ester | 438623-89-3

• 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: 2-[(2-methyl-1-(2-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl)oxy]acetic acid methyl ester
• 英文别名: methyl 2-[[1-[(2-fluorophenyl)methyl]-2-methyl-7,8-dihydro-6H-cyclopenta[g]indol-4-yl]oxy]acetate
• CAS: 438623-89-3
• 化学式: C₂₂H₂₂FNO₃
• 分子量: 367.42
• InChiKey: SIBCLENNPKATCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2-methyl-1-(2-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl)oxy]acetic acid methyl ester 在 lithium hydroxide 、 氨 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 2-[[3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(2-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic Acid
  参考文献：
  名称：

  Carbocyclic[g]indole Inhibitors of Human Nonpancreatic s-PLA₂

  摘要：

  A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A(2). Each scaffold demonstrated potent enzyme activity in a chromogenic assay system, with select examples also demonstrating potent activity in a secondary DOC/PC assay. Compound 11, representative of the cyclopent[g]indole series, gave an IC50 of 10 nM for the inhibition of hnps-PLA(2) in the chromogenic assay.

  DOI：

  10.1021/jm0401309
• 作为产物：
  描述：

  1-(2-fluorobenzyl)-2-hydroxymethyl-4-methoxy-1,6,7,8-tetrahydrocyclopent[g]indole 在 sodium tetrahydroborate 、 三溴化硼 、 caesium carbonate 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 2-[(2-methyl-1-(2-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl)oxy]acetic acid methyl ester
  参考文献：
  名称：

  Carbocyclic[g]indole Inhibitors of Human Nonpancreatic s-PLA₂

  摘要：

  A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A(2). Each scaffold demonstrated potent enzyme activity in a chromogenic assay system, with select examples also demonstrating potent activity in a secondary DOC/PC assay. Compound 11, representative of the cyclopent[g]indole series, gave an IC50 of 10 nM for the inhibition of hnps-PLA(2) in the chromogenic assay.

  DOI：

  10.1021/jm0401309

文献信息

• Novel spla2 inhibitors
  申请人：——

  公开号：US20040077704A1

  公开（公告）日：2004-04-22

  A novel class of cycloalkyl fused indole compounds is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.

  揭示了一类新型的环烷基融合吲哚化合物，以及利用这些化合物抑制sPLA2介导的脂肪酸释放，用于治疗炎症性疾病，如感染性休克。
• CYCLOALKYFUSED [G]-INDOLE COMPOUNDS AS SPLA2-INHIBITORS IN THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1349834A2

  公开（公告）日：2003-10-08
• US6974831B2
  申请人：——

  公开号：US6974831B2

  公开（公告）日：2005-12-13
• [EN] NOVEL SPLA2 INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE SPLA2
  申请人：LILLY CO ELI

  公开号：WO2002050030A2

  公开（公告）日：2002-06-27

  A class of cycloalkylfused (g) indole compounds is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.
• Carbocyclic[<i>g</i>]indole Inhibitors of Human Nonpancreatic s-PLA₂
  作者：J. Scott Sawyer、Douglas W. Beight、Edward C. R. Smith、David W. Snyder、Marcia K. Chastain、Richard L. Tielking、Lawrence W. Hartley、Donald G. Carlson

  DOI：10.1021/jm0401309

  日期：2005.2.1

  A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A(2). Each scaffold demonstrated potent enzyme activity in a chromogenic assay system, with select examples also demonstrating potent activity in a secondary DOC/PC assay. Compound 11, representative of the cyclopent[g]indole series, gave an IC50 of 10 nM for the inhibition of hnps-PLA(2) in the chromogenic assay.