5-氯-6-甲氧基-2,3-二氢苯并恶唑-2-酮 | 1750-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 5-氯-6-甲氧基-2,3-二氢苯并恶唑-2-酮
• 英文名称: 5-chloro-6-methoxy-2,3-dihydro-1,3-benzoxazol-2-one
• 英文别名: 5-chloro-6-methoxy-2-benzoxazolinone；5-chloro-6-methoxy-3H-benzooxazol-2-one；5-Chlor-6-methoxy-benzoxazolinon-(2)；5-Chlor-6-methoxy-2-benzoxazolon；5-chloro-6-methoxy-3H-1,3-benzoxazol-2-one
• CAS: 1750-47-6
• 化学式: C₈H₆ClNO₃
• 分子量: 199.594
• InChiKey: QQQYQWNSMUHSCK-UHFFFAOYSA-N

物化性质

• 熔点：
  225-227 °C
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-溴丙酸 、 5-氯-6-甲氧基-2,3-二氢苯并恶唑-2-酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以29%的产率得到3-(5-chloro-6-methoxy-2-oxobenzo[d]oxazol-3(2H)-yl)propanoic acid
  参考文献：
  名称：

  一系列Kynurenine 3-Monooxygenase抑制剂的开发导致治疗急性胰腺炎的临床候选药物

  摘要：

  最近，我们报道了KMO在急性胰腺炎（AP）发病机理中的新作用。犬尿氨酸3-单加氧酶（KMO）的许多抑制剂以前已被描述为神经退行性疾病，尤其是亨廷顿舞蹈病的潜在治疗方法。然而，迄今为止报道的抑制剂相对于其细胞效力而言，其水溶性不足以与AP中所需的静脉内（iv）给药途径相容。我们已经鉴定并优化了一系列具有良好理化特性的新型高亲和力KMO抑制剂。最主要的例子是选择性强，在两个物种中清除率低，在急性胰腺炎的大鼠模型中预防肺和肾脏的损害，并正在向临床前发展。

  DOI：

  10.1021/acs.jmedchem.7b00055
• 作为产物：
  描述：

  6-甲氧基-2-苯唑啉酮 在 磺酰氯 作用下， 以 苯 为溶剂， 反应 0.17h， 生成 5-氯-6-甲氧基-2,3-二氢苯并恶唑-2-酮
  参考文献：
  名称：

  Allelopathic potential of 5-chloro-6-methoxy-2-benzoxazolinone

  摘要：

  A new benzoxazolinone, 5-chIoro-6-methoxy-2-benzoxazolinone (Cl-MBOA) caused growth inhibition of roots and shoots of oat (Avena sativa), timothy (Phleum pratense), crabgrass (Digitaria sanguinalis), ryegrass (Lolium multiflorum), cockscomb (Amaranthus Caudatus), cress (Lepidium sativum) and lettuce (Lactuca sativa); increasing the dose of Cl-MBOA increased inhibition. The concentrations for 49% inhibition of root growth were 0.12, 0.14, 0.17, 0.19, 0.46, 0.57 and 0.76 mM for timothy, crabgrass, ryegrass, oat; cockscomb, cress and lettuce, respectively, and the concentrations for 40% inhibition of shoot growth were 0.25, 0.28, 0.36, 0.40, 7.9, 12.5 and 19.6 mM for timothy, crabgrass, ryegrass, cockscomb, cress and lettuce, respectively. The contents of Cl-MBOA. in shoots and roots of 14-day-old maize (Zea mays) seedlings were 37.5 and 8.7 mu g g(-1) fr. wt. The presence of this compound in maize seedlings, coupled with its effect on growth, suggest that it may play an important role in maize allelopathy. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00029-6

文献信息

• Development of a Series of Kynurenine 3-Monooxygenase Inhibitors Leading to a Clinical Candidate for the Treatment of Acute Pancreatitis
  作者：Ann L. Walker、Nicolas Ancellin、Benjamin Beaufils、Marylise Bergeal、Margaret Binnie、Anne Bouillot、David Clapham、Alexis Denis、Carl P. Haslam、Duncan S. Holmes、Jonathan P. Hutchinson、John Liddle、Andrew McBride、Olivier Mirguet、Christopher G. Mowat、Paul Rowland、Nathalie Tiberghien、Lionel Trottet、Iain Uings、Scott P. Webster、Xiaozhong Zheng、Damian J. Mole

  DOI：10.1021/acs.jmedchem.7b00055

  日期：2017.4.27

  Recently, we reported a novel role for KMO in the pathogenesis of acute pancreatitis (AP). A number of inhibitors of kynurenine 3-monooxygenase (KMO) have previously been described as potential treatments for neurodegenerative conditions and particularly for Huntington’s disease. However, the inhibitors reported to date have insufficient aqueous solubility relative to their cellular potency to be compatible

  最近，我们报道了KMO在急性胰腺炎（AP）发病机理中的新作用。犬尿氨酸3-单加氧酶（KMO）的许多抑制剂以前已被描述为神经退行性疾病，尤其是亨廷顿舞蹈病的潜在治疗方法。然而，迄今为止报道的抑制剂相对于其细胞效力而言，其水溶性不足以与AP中所需的静脉内（iv）给药途径相容。我们已经鉴定并优化了一系列具有良好理化特性的新型高亲和力KMO抑制剂。最主要的例子是选择性强，在两个物种中清除率低，在急性胰腺炎的大鼠模型中预防肺和肾脏的损害，并正在向临床前发展。
• Allelopathic potential of 5-chloro-6-methoxy-2-benzoxazolinone
  作者：Hisashi Kato-Noguchi、Seiji Kosemura、Shosuke Yamamura

  DOI：10.1016/s0031-9422(98)00029-6

  日期：1998.6

  A new benzoxazolinone, 5-chIoro-6-methoxy-2-benzoxazolinone (Cl-MBOA) caused growth inhibition of roots and shoots of oat (Avena sativa), timothy (Phleum pratense), crabgrass (Digitaria sanguinalis), ryegrass (Lolium multiflorum), cockscomb (Amaranthus Caudatus), cress (Lepidium sativum) and lettuce (Lactuca sativa); increasing the dose of Cl-MBOA increased inhibition. The concentrations for 49% inhibition of root growth were 0.12, 0.14, 0.17, 0.19, 0.46, 0.57 and 0.76 mM for timothy, crabgrass, ryegrass, oat; cockscomb, cress and lettuce, respectively, and the concentrations for 40% inhibition of shoot growth were 0.25, 0.28, 0.36, 0.40, 7.9, 12.5 and 19.6 mM for timothy, crabgrass, ryegrass, cockscomb, cress and lettuce, respectively. The contents of Cl-MBOA. in shoots and roots of 14-day-old maize (Zea mays) seedlings were 37.5 and 8.7 mu g g(-1) fr. wt. The presence of this compound in maize seedlings, coupled with its effect on growth, suggest that it may play an important role in maize allelopathy. (C) 1998 Elsevier Science Ltd. All rights reserved.