(-)-Zileuton | 143200-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (-)-Zileuton
• 英文别名: (-)-(S)-Zileuton；zileuton；ZINC00000850；(-)-(S)-1-(1-benzo[b]thien-2-ylethyl)-1-hydroxyurea；(S)-(-)-1-(1-benzo[b]thien-2-ylethyl)-1-hydroxyurea；(S)-N-Hydroxy-N-(1-benzo[b]thien-2-yl-ethyl)urea；Zileuton, (S)-；1-[(1S)-1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
• CAS: 143200-94-6
• 化学式: C₁₁H₁₂N₂O₂S
• 分子量: 236.294
• InChiKey: MWLSOWXNZPKENC-ZETCQYMHSA-N

物化性质

• 沸点：
  449.4±47.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  94.8
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

(-)-齐留通在人体内已知的代谢物包括齐留通亚砜和羟基齐留通。

(-)-zileuton has known human metabolites that include Zileuton sulfoxide and Hydroxyzileuton.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  齐留通 生成 (-)-Zileuton
  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

• LTA4H modulators and uses thereof
  申请人：Barchuk William T.

  公开号：US20080194630A1

  公开（公告）日：2008-08-14

  Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation.

  白三烯A4水解酶（LTA4H）抑制剂，含有它们的组合物，以及用于抑制LTA4H酶活性和治疗、预防或抑制炎症和/或与炎症相关疾病的方法。
• [EN] HETEROCYCLIC AMIDES USEFUL AS PROTEIN MODULATORS<br/>[FR] AMIDES HÉTÉROCYCLIQUES UTILES EN TANT QUE MODULATEURS DE PROTÉINE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017175147A1

  公开（公告）日：2017-10-12

  Disclosed are compounds having the formula (I-N), wherein q, r, s, A, B, C, RA1, RA2, RB1, RB2, RC1, RC2, R3, R4, R5, R6, R14, R15, R16, and R17, are as defined herein, or a tautomer thereof, or a salt, particularly a pharmaceutically acceptable salt, thereof.

  揭示了具有化学式（I-N）的化合物，其中q、r、s、A、B、C、RA1、RA2、RB1、RB2、RC1、RC2、R3、R4、R5、R6、R14、R15、R16和R17如本文所定义，或其互变异构体，或其盐，特别是其药用可接受盐。
• [EN] MODULATORS OF STIMULATOR OF INTERFERON GENES (STING) USEFUL IN TREATING HIV<br/>[FR] MODULATEURS DE STIMULATEUR DES GÈNES (STING) D'INTERFÉRON UTILES DANS LE TRAITEMENT DU VIH
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2019069269A1

  公开（公告）日：2019-04-11

  Disclosed are compounds having the formula: (I-N) wherein q, r, s, A, B, C, RA1, RA2, RB1, RB2, RC1, RC2, R3, R4, R5, R6, R14, R15, R16, and R17, are as defined herein, or a tautomer thereof, or a salt, particularly a pharmaceutically acceptable salt, thereof, along with combinations thereof, all of which are useful in HIV therapies.

  揭示了具有以下式的化合物：(I-N)其中q、r、s、A、B、C、RA1、RA2、RB1、RB2、RC1、RC2、R3、R4、R5、R6、R14、R15、R16和R17如本文所定义，或其互变异构体，或其盐，特别是其药用可接受盐，以及其组合物，所有这些在HIV疗法中是有用的。
• [EN] NITROGEN RING CONTAINING COMPOUNDS FOR TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] COMPOSÉS CONTENANT UN CYCLE AZOTÉ POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：WEINGARTEN M DAVID

  公开号：WO2012135669A1

  公开（公告）日：2012-10-04

  The invention provides compounds, pharmaceutical compositions and methods of treatment of inflammatory disorders including a compound of Formula I, or its pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative or prodrug wherein R1, R2, R3, R4, X, Y, W, Z and Q are as defined herein.

  这项发明提供了化合物、药物组合物和治疗炎症性疾病的方法，包括式I的化合物，或其药用可接受的盐、酯、药用可接受的衍生物或前药，其中R1、R2、R3、R4、X、Y、W、Z和Q如本文所定义。
• [EN] NRF2 REGULATORS<br/>[FR] RÉGULATEURS DE NRF2
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016203401A1

  公开（公告）日：2016-12-22

  The present invention relates to aryl analogs, pharmaceutical compositions containing them and their use as Nrf2 regulators.

  本发明涉及芳基类似物，含有它们的药物组合物以及它们作为Nrf2调节剂的用途。