4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzoic acid isopropyl ester | 1187187-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzoic acid isopropyl ester
• 英文别名: isopropyl 4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)benzoate；propan-2-yl 4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzoate
• CAS: 1187187-16-1
• 化学式: C₁₇H₁₇BO₅
• 分子量: 312.13
• InChiKey: LUWWYWOIORWVRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzoic acid isopropyl ester 在 CD-1 female mouse plasma 作用下， 生成 克立硼罗杂质Z9
  参考文献：
  名称：

  Design and synthesis of boron-containing PDE4 inhibitors using soft-drug strategy for potential dermatologic anti-inflammatory application

  摘要：

  PDE4 inhibitors are a validated approach as anti-inflammatory agents but are limited by systemic side effects including emesis. We report a soft-drug strategy incorporating a carboxylic ester group into boron-containing PDE4 inhibitors leading to the discovery of a series of benzoxaborole compounds with good potency (for example IC(50) = 47 nM of compound 2) and low emetic activity. These compounds are intended for dermatological use further limiting possible systemic side effects. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.010
• 作为产物：
  描述：

  克立硼罗杂质Z9 、 异丙醇 在 硫酸 作用下， 反应 48.0h， 以60%的产率得到4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzoic acid isopropyl ester
  参考文献：
  名称：

  Design and synthesis of boron-containing PDE4 inhibitors using soft-drug strategy for potential dermatologic anti-inflammatory application

  摘要：

  PDE4 inhibitors are a validated approach as anti-inflammatory agents but are limited by systemic side effects including emesis. We report a soft-drug strategy incorporating a carboxylic ester group into boron-containing PDE4 inhibitors leading to the discovery of a series of benzoxaborole compounds with good potency (for example IC(50) = 47 nM of compound 2) and low emetic activity. These compounds are intended for dermatological use further limiting possible systemic side effects. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.010

文献信息

• Design and synthesis of boron-containing PDE4 inhibitors using soft-drug strategy for potential dermatologic anti-inflammatory application
  作者：Yong-Kang Zhang、Jacob J. Plattner、Tsutomu Akama、Stephen J. Baker、Vincent S. Hernandez、Virginia Sanders、Yvonne Freund、Richard Kimura、Wei Bu、Karin M. Hold、Xiao-Song Lu

  DOI：10.1016/j.bmcl.2010.02.010

  日期：2010.4

  PDE4 inhibitors are a validated approach as anti-inflammatory agents but are limited by systemic side effects including emesis. We report a soft-drug strategy incorporating a carboxylic ester group into boron-containing PDE4 inhibitors leading to the discovery of a series of benzoxaborole compounds with good potency (for example IC(50) = 47 nM of compound 2) and low emetic activity. These compounds are intended for dermatological use further limiting possible systemic side effects. (C) 2010 Elsevier Ltd. All rights reserved.