N-[5-(4-chlorophenylthio)thien-2-ylmethyl]hydroxylamine | 139120-71-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-[5-(4-chlorophenylthio)thien-2-ylmethyl]hydroxylamine
• 英文别名: N-[[5-(4-chlorophenyl)sulfanylthiophen-2-yl]methyl]hydroxylamine
• CAS: 139120-71-1
• 化学式: C₁₁H₁₀ClNOS₂
• 分子量: 271.791
• InChiKey: BVLTXDCZZGCQRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲基硅基异氰酸酯 、 N-[5-(4-chlorophenylthio)thien-2-ylmethyl]hydroxylamine 以 1,4-二氧六环 为溶剂， 生成 1-hydroxy-1-[5-(4-chlorophenylthio)thien-2-ylmethyl]urea
  参考文献：
  名称：

  Pharmaceutical compounds

  摘要：

  公式为##STR1##的药物化合物，其中R.sup.1是卤代C.sub.1-10烷基，C.sub.1-10烷基硫基，卤代C.sub.1-10烷基硫基或可选择取代的苯硫基，R.sup.2是氢或C.sub.1-4烷基，R.sup.3和R.sup.4分别是氢或C.sub.1-4烷基，X是氧或硫；以及其盐。

  公开号：

  US05158971A1
• 作为产物：
  描述：

  5-(4-Chloro-phenylsulfanyl)-thiophene-2-carbaldehyde oxime 在 盐酸 、 吡啶硼烷 作用下， 生成 N-[5-(4-chlorophenylthio)thien-2-ylmethyl]hydroxylamine
  参考文献：
  名称：

  Structure−Activity Relationships of N-Hydroxyurea 5-Lipoxygenase Inhibitors

  摘要：

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.

  DOI：

  10.1021/jm9700474

文献信息

• Thien-2-yl methylurea derivatives as leukotriene inhibitors
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0459748A2

  公开（公告）日：1991-12-04

  A pharmaceutical compound of the formula in which R¹ is halo-C₁₋₁₀ alkyl, C₁₋₁₀ alkylthio, halo-C₁₋₁₀ alkylthio or optionally substituted phenylthio, R² is hydrogen or C₁₋₄ alkyl, R³ and R⁴ are each hydrogen or C₁₋₄ alkyl, and X is oxygen or sulphur; and salts thereof.

  一种药物化合物，其化学式为 其中 R¹ 是卤代-₁₋₁₀ 烷基、C₁₋₁₀ 烷硫基、卤代-₁₋₁₀ 烷硫基或任选取代的苯硫基、R² 是氢或 C₁₋₄ 烷基，R³ 和 R⁴ 分别是氢或 C₁₋₄ 烷基，X 是氧或硫；及其盐类。
• US5158971A
  申请人：——

  公开号：US5158971A

  公开（公告）日：1992-10-27
• Structure−Activity Relationships of <i>N</i>-Hydroxyurea 5-Lipoxygenase Inhibitors
  作者：Andrew O. Stewart、Pramila A. Bhatia、Jonathan G. Martin、James B. Summers、Karen E. Rodriques、Michael B. Martin、James H. Holms、Jimmie L. Moore、Richard A. Craig、Teodozyj Kolasa、James D. Ratajczyk、Hormoz Mazdiyasni、Francis A. J. Kerdesky、Shari L. DeNinno、Robert G. Maki、Jennifer B. Bouska、Patrick R. Young、Carmine Lanni、Randy L. Bell、George W. Carter、Clint D. W. Brooks

  DOI：10.1021/jm9700474

  日期：1997.6.1

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.
• Pharmaceutical compounds
  申请人：Lilly Industries limited

  公开号：US05158971A1

  公开（公告）日：1992-10-27

  A pharmaceutical compound of the formula ##STR1## in which R.sup.1 is halo-C.sub.1-10 alkyl, C.sub.1-10 alkylthio, halo-C.sub.1-10 alkylthio or optionally substituted phenylthio, R.sup.2 is hydrogen or C.sub.1-4 alkyl, R.sup.3 and R.sup.4 are each hydrogen or C.sub.1-4 alkyl, and X is oxygen or sulphur; and salts thereof.

  公式为##STR1##的药物化合物，其中R.sup.1是卤代C.sub.1-10烷基，C.sub.1-10烷基硫基，卤代C.sub.1-10烷基硫基或可选择取代的苯硫基，R.sup.2是氢或C.sub.1-4烷基，R.sup.3和R.sup.4分别是氢或C.sub.1-4烷基，X是氧或硫；以及其盐。