ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindole-2-carboxylate | 155143-15-0

• 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: ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindole-2-carboxylate
• 英文别名: ethyl 3-tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]-5-hydroxyindole-2-carboxylate
• CAS: 155143-15-0
• 化学式: C₂₂H₂₄ClNO₃S
• 分子量: 417.956
• InChiKey: WVWITEURVLYDGF-UHFFFAOYSA-N

物化性质

• 沸点：
  590.6±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindole-2-carboxylate 在 sodium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-Tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]-5-(quinolin-2-ylmethoxy)indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of indolylalkoxyiminoalkylcarboxylates as leukotriene biosynthesis inhibitors

  摘要：

  A series of substituted indolylalkoxyiminoalkylcarboxylates were found to be potent leuko triene biosynthesis inhibitors. The structure-activity relationships were investigated. Representative potent inhibitors identified were the quinolyl 3a (A-86885) and pyridyl 3b (A-86886) congeners with in vitro IC(50)s of 21 and 9 nM and in vivo leukotriene inhibition in the rat with oral ED(50)s of 0.9 and 1.7 mg/kg, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00265-9
• 作为产物：
  描述：

  ethyl 3-tert-butylthio-2-oxo-propionate 在 三氯化铝 、 sodium hydride 、 叔丁基硫醇 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 63.0h， 生成 ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindole-2-carboxylate
  参考文献：
  名称：

  Synthesis of indolylalkoxyiminoalkylcarboxylates as leukotriene biosynthesis inhibitors

  摘要：

  A series of substituted indolylalkoxyiminoalkylcarboxylates were found to be potent leuko triene biosynthesis inhibitors. The structure-activity relationships were investigated. Representative potent inhibitors identified were the quinolyl 3a (A-86885) and pyridyl 3b (A-86886) congeners with in vitro IC(50)s of 21 and 9 nM and in vivo leukotriene inhibition in the rat with oral ED(50)s of 0.9 and 1.7 mg/kg, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00265-9

文献信息

• Indole iminooxy derivatives which inhibit leukotriene biosynthesis
  申请人：Abbott Laboratories

  公开号：US05399699A1

  公开（公告）日：1995-03-21

  Compounds of the structure ##STR1## where A.sub.1 is alkylene or cycloalkylene; A.sub.2 is a valence bond, alkylene, or cycloalkylene; R.sub.1 is selected from hydrogen, alkylthio, optionally substituted phenylthio, optionally substituted phenylalkylthio, optionally substituted 2-, 3- and 4-pyridylthio, optionally substituted 2- and 3-thienylthio, and optionally substituted 2-thiazolylthio; R.sup.2 is selected from optionally substituted phenylalkyl and optionally substituted heteroarylakyl; R.sup.3 is selected from alkyl, alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylalkyl, optionally substituted phenylalkoxy, optionally substituted naphthyl,optionally substituted naphthyloxy, optionally substituted naphthylalkyl, optionally substituted naphthylalkoxy, optionally substituted heteroaryl, optionally substituted heteroaryloxy, optionally substituted heteroarylalkyl, and optionally substituted heteroarylalkoxy; R.sup.4 is selected from hydrogen and optionally substituted alkyl; and Z is selected from --COOB, --C(OB)R.sup.6 R.sup.6, --COOalkyl, --COOalkylaryl, --CONR.sup.5 R.sup.6, and --COR.sup.6 are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of leukotrienes. These compounds are useful in the treatment of amelioration of allergic and inflammatory disease states.

  结构为##STR1##的化合物，其中A.sub.1为烷基或环烷基；A.sub.2为价键，烷基或环烷基；R.sub.1从氢、烷基硫、可选择取代的苯硫、可选择取代的苯烷硫、可选择取代的2-、3-和4-吡啶硫、可选择取代的2-和3-噻吩硫、以及可选择取代的2-噻唑硫中选择；R.sup.2从可选择取代的苯烷基和可选择取代的杂环烷基中选择；R.sup.3从烷基、烷氧基、可选择取代的苯基、可选择取代的苯氧基、可选择取代的苯烷基、可选择取代的苯烷氧基、可选择取代的萘基、可选择取代的萘氧基、可选择取代的萘烷基、可选择取代的萘烷氧基、可选择取代的杂环基、可选择取代的杂环氧基、可选择取代的杂环烷基、以及可选择取代的杂环烷氧基中选择；R.sup.4从氢和可选择取代的烷基中选择；Z从--COOB、--C(OB)R.sup.6 R.sup.6、--COO烷基、--COO烷基芳基、--CONR.sup.5 R.sup.6和--COR.sup.6中选择，是脂氧酶酶的有效抑制剂，从而抑制白三烯的生物合成。这些化合物对于治疗和缓解过敏和炎症性疾病状态非常有用。
• US5399699A
  申请人：——

  公开号：US5399699A

  公开（公告）日：1995-03-21
• Synthesis of indolylalkoxyiminoalkylcarboxylates as leukotriene biosynthesis inhibitors
  作者：Teodozyj Kolasa、Pramila Bhatia、Clint D.W. Brooks、Keren I. Hulkower、Jennifer B. Bouska、Richard R. Harris、Randy L. Bell

  DOI：10.1016/s0968-0896(96)00265-9

  日期：1997.3

  A series of substituted indolylalkoxyiminoalkylcarboxylates were found to be potent leuko triene biosynthesis inhibitors. The structure-activity relationships were investigated. Representative potent inhibitors identified were the quinolyl 3a (A-86885) and pyridyl 3b (A-86886) congeners with in vitro IC(50)s of 21 and 9 nM and in vivo leukotriene inhibition in the rat with oral ED(50)s of 0.9 and 1.7 mg/kg, respectively. (C) 1997 Elsevier Science Ltd.