2-[[3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(3-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester | 438623-61-1

• 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-[[3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(3-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester
• 英文别名: methyl 2-[[1-[(3-fluorophenyl)methyl]-2-methyl-3-oxamoyl-7,8-dihydro-6H-cyclopenta[g]indol-4-yl]oxy]acetate
• CAS: 438623-61-1
• 化学式: C₂₄H₂₃FN₂O₅
• 分子量: 438.455
• InChiKey: XJOYKEUYMKOUFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[[3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(3-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 以77%的产率得到[3-Aminooxalyl-1-(3-fluoro-benzyl)-2-methyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-4-yloxy]-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：

  2-[(2-methyl-1-(3-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl)oxy]acetic acid methyl ester 在 氨 作用下， 以 1,4-二氧六环 、 草酰氯 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 2-[[3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(3-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester
  参考文献：
  名称：

  Novel spla2 inhibitors

  摘要：

  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。

  公开号：

  US20040077704A1

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。
• sPLA2 inhibitors
  申请人：Beight Douglas Wade

  公开号：US06974831B2

  公开（公告）日：2005-12-13

  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.

  本发明揭示了一类新型环烷基融合吲哚化合物，以及使用这些化合物来抑制sPLA2介导的脂肪酸释放以治疗炎症性疾病，如感染性休克。
• US6974831B2
  申请人：——

  公开号：US6974831B2

  公开（公告）日：2005-12-13
• 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.