(3-Aminooxalyl-1-cyclohexylmethyl-2-methyl-1H-benzo[g]indol-4-yloxy)-acetic acid methyl ester | 443911-29-3

• 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: (3-Aminooxalyl-1-cyclohexylmethyl-2-methyl-1H-benzo[g]indol-4-yloxy)-acetic acid methyl ester
• 英文别名: 2-[[3-(2-amino-1,2-dioxoethyl)-1-cyclohexylmethyl-2-methyl-1H-benz[g]indol-4-yl]oxy]acetic acid methyl ester；methyl 2-[1-(cyclohexylmethyl)-2-methyl-3-oxamoylbenzo[g]indol-4-yl]oxyacetate
• CAS: 443911-29-3
• 化学式: C₂₅H₂₈N₂O₅
• 分子量: 436.508
• InChiKey: XBGAQWNONZFFFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-Aminooxalyl-1-cyclohexylmethyl-2-methyl-1H-benzo[g]indol-4-yloxy)-acetic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.0h， 以54%的产率得到(3-Aminooxalyl-1-cyclohexylmethyl-2-methyl-1H-benzo[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-[(1-cyclohexylmethyl-2-methyl-1H-benz[g]indol-4-yl)oxy]acetic acid methyl ester 在 氨 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 (3-Aminooxalyl-1-cyclohexylmethyl-2-methyl-1H-benzo[g]indol-4-yloxy)-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：US20040063967A1

  公开（公告）日：2004-04-01

  A novel class of benz[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.

  揭示了一类新型苯[g]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，用于治疗炎症性疾病，如败血症。
• Spla2 inhibitors
  申请人：Beight Douglas Wade

  公开号：US06916840B2

  公开（公告）日：2005-07-12

  A novel class of benz[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.

  本发明揭示了一类新型的苯[g]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。
• BENZ(G) INDOLES AND THEIR USE AS SPLA2 INHIBITORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1358156B1

  公开（公告）日：2007-02-21
• US6916840B2
  申请人：——

  公开号：US6916840B2

  公开（公告）日：2005-07-12
• 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.