N-[1-(quinolin-2-yl)methyl]hydroxylamine | 190601-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[1-(quinolin-2-yl)methyl]hydroxylamine
• 英文别名: n-[(Quinolin-2-yl)methyl]hydroxylamine；N-(quinolin-2-ylmethyl)hydroxylamine
• CAS: 190601-87-7
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: VPPCTGDXVJUQHB-UHFFFAOYSA-N

物化性质

• 沸点：
  362.0±44.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基硅基异氰酸酯 、 N-[1-(quinolin-2-yl)methyl]hydroxylamine 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.0h， 以69%的产率得到N-hydroxy-N-[1-(quinolin-2-yl)methyl]urea
  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
• 作为产物：
  描述：

  2-氯甲基喹啉盐酸盐 在 甲醇 、 羟胺 、 sodium ethanolate 作用下， 反应 2.0h， 生成 N-[1-(quinolin-2-yl)methyl]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

• 3, 6-BICYCLOLIDES
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：EP1830858A2

  公开（公告）日：2007-09-12
• [EN] 3, 6-BICYCLOLIDES<br/>[FR] 3,6-BICYCLOLIDES
  申请人：ENANTA PHARM INC

  公开号：WO2006063039A2

  公开（公告）日：2006-06-15

  [EN] The present invention discloses compounds of formula (I) or pharmaceutically acceptable salts, esters, or prodrugs thereof (I), which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.
  [FR] Composés de formule (I) ou sels, esters ou promédicaments desdits composés acceptables sur le plan pharmaceutique, qui présentent des propriétés antibactériennes. La présente invention concerne également des compositions pharmaceutiques contenant les composés susmentionnés et destinées à être administrées à un sujet nécessitant un traitement antibiotique. La présente invention concerne en outre des méthodes de traitement d'une infection bactérienne chez un sujet par administration d'une composition pharmaceutique contenant les composés selon la présente invention. Elle concerne enfin un procédé permettant de produire les composés selon la présente invention.
• 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.