4,5-Dichloro-2-(3-fluorophenyl)-(3H)-pyridazinone | 620619-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,5-Dichloro-2-(3-fluorophenyl)-(3H)-pyridazinone
• 英文别名: 4,5-dichloro-2-(3-fluorophenyl)(3H)-pyridazinon；4,5-dichloro-2-(3-fluorophenyl)pyridazin-3(2H)-one；4,5-dichloro-2-(3-fluorophenyl)pyridazin-3-one
• CAS: 620619-33-2
• 化学式: C₁₀H₅Cl₂FN₂O
• 分子量: 259.067
• InChiKey: ZFWLCVJZAXDZJF-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C
• 沸点：
  320.3±52.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-Dichloro-2-(3-fluorophenyl)-(3H)-pyridazinone 在 盐酸 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 生成 4-Cyclopentyloxy-2-(3-fluorophenyl)-5-piperazin-1-ylpyridazin-3-one
  参考文献：
  名称：

  The synthesis and structure–activity relationship of pyridazinones as glucan synthase inhibitors

  摘要：

  A structure-activity relationship study of the lead 5-[4-(benzylsulfonyl) piperazin-1-yl]-4-morpholino-2- phenyl-pyridazin-3(2H)-one 1 has resulted in the identification of 2-(3,5-difluorophenyl)-4-(3-fluorocyclopentyloxy)- 5-[4-(isopropylsulfonyl) piperazin-1-yl]-pyridazin-3(2H)-one 11c as a beta- 1,3-glucan synthase inhibitor. Compound 11c exhibited significant efficacy in an in vivo mouse model of Candida glabrata infection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.058
• 作为产物：
  描述：

  3,4-二氯-5-羟基-5H-呋喃-2-酮 、 (3-氟苯基)肼 在 盐酸 、 水 作用下， 反应 3.0h， 生成 4,5-Dichloro-2-(3-fluorophenyl)-(3H)-pyridazinone
  参考文献：
  名称：

  Discovery and structure–activity relationship analysis of Staphylococcus aureus sortase A inhibitors

  摘要：

  Methicillin resistant Staphylococcus aureus (MRSA) is a major health problem that has created a pressing need for new antibiotics. Compounds that inhibit the S. aureus SrtA sortase may function as potent anti-infective agents as this enzyme attaches virulence factors to the cell wall. Using high-throughput screening, we have identified several compounds that inhibit the enzymatic activity of the SrtA. A structure-activity relationship (SAR) analysis led to the identification of several pyridazinone and pyrazolethione analogs that inhibit SrtA with IC50 values in the sub-micromolar range. Many of these molecules also inhibit the sortase enzyme from Bacillus anthracis suggesting that they may be generalized sortase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.067

文献信息

• Substituted 2-phenyl-3(2h)-pyridazinones
  申请人：Schohe-Loop Rudolf

  公开号：US20060004015A1

  公开（公告）日：2006-01-05

  The invention relates to substituted 2-phenyl-3(2h)-pyridazinones, to a method for the production thereof, and to their use as medicaments used in the prophylaxis and/or treatment of diseases in humans and/or animals.

  本发明涉及替代的2-苯基-3（2H）-吡啶嗪酮，其制备方法，以及其作为用于预防和/或治疗人类和/或动物疾病的药物的用途。
• SUBSTITUIERTE 2-PHENYL-3(2H)-PYRIDAZINONE
  申请人：Bayer HealthCare AG

  公开号：EP1497269B1

  公开（公告）日：2008-04-23
• US7320977B2
  申请人：——

  公开号：US7320977B2

  公开（公告）日：2008-01-22
• The synthesis and structure–activity relationship of pyridazinones as glucan synthase inhibitors
  作者：Pauline C. Ting、Rongze Kuang、Heping Wu、Robert G. Aslanian、Jianhua Cao、David W. Kim、Joe F. Lee、John Schwerdt、Gang Zhou、Samuel Wainhaus、Todd A. Black、Anthony Cacciapuoti、Paul M. McNicholas、Yiming Xu、Scott S. Walker

  DOI：10.1016/j.bmcl.2011.01.058

  日期：2011.3

  A structure-activity relationship study of the lead 5-[4-(benzylsulfonyl) piperazin-1-yl]-4-morpholino-2- phenyl-pyridazin-3(2H)-one 1 has resulted in the identification of 2-(3,5-difluorophenyl)-4-(3-fluorocyclopentyloxy)- 5-[4-(isopropylsulfonyl) piperazin-1-yl]-pyridazin-3(2H)-one 11c as a beta- 1,3-glucan synthase inhibitor. Compound 11c exhibited significant efficacy in an in vivo mouse model of Candida glabrata infection. (C) 2011 Elsevier Ltd. All rights reserved.
• Discovery and structure–activity relationship analysis of Staphylococcus aureus sortase A inhibitors
  作者：Nuttee Suree、Sung Wook Yi、William Thieu、Melanie Marohn、Robert Damoiseaux、Albert Chan、Michael E. Jung、Robert T. Clubb

  DOI：10.1016/j.bmc.2009.08.067

  日期：2009.10

  Methicillin resistant Staphylococcus aureus (MRSA) is a major health problem that has created a pressing need for new antibiotics. Compounds that inhibit the S. aureus SrtA sortase may function as potent anti-infective agents as this enzyme attaches virulence factors to the cell wall. Using high-throughput screening, we have identified several compounds that inhibit the enzymatic activity of the SrtA. A structure-activity relationship (SAR) analysis led to the identification of several pyridazinone and pyrazolethione analogs that inhibit SrtA with IC50 values in the sub-micromolar range. Many of these molecules also inhibit the sortase enzyme from Bacillus anthracis suggesting that they may be generalized sortase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.