异噻唑并[5,4-b]吡啶-3(2H)-酮,2-(4-溴苯基)- | 158093-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 异噻唑并[5,4-b]吡啶-3(2H)-酮,2-(4-溴苯基)-
• 英文名称: 2-(4-bromophenyl)isothiazolo<5,4-b>pyridin-3(2H)-one
• 英文别名: NSC 694615；2-(4-Bromophenyl)isothiazolo[5,4-b]pyridin-3(2H)-one；2-(4-bromophenyl)-[1,2]thiazolo[5,4-b]pyridin-3-one
• CAS: 158093-66-4
• 化学式: C₁₂H₇BrN₂OS
• 分子量: 307.17
• InChiKey: CKQMTCNNSSCNHW-UHFFFAOYSA-N

物化性质

• 沸点：
  478.0±51.0 °C(Predicted)
• 密度：
  1.714±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异噻唑并[5,4-b]吡啶-3(2H)-酮,2-(4-溴苯基)- 在 Oxone 、 oxone 作用下， 以 甲醇 、 水 为溶剂， 以92%的产率得到2-(4-Bromo-phenyl)-1-oxo-1,2-dihydro-1λ⁴-isothiazolo[5,4-b]pyridin-3-one
  参考文献：
  名称：

  Synthesis of 2-Substituted Isothiazolo[5,4-b]pyridin-3(2H)-one 1,1-Dioxides

  摘要：

  The Isothiazolo[5,4-b]pyridin-3(2H)-one 1,1-dioxides (3a - g) were prepared from the corresponding isothiazolo[5,4-b]pyridin-3(2H)-ones (1a - g) by means of an oxidation with oxone(R) (KHSO5) and sodium hypochlorite (NaOCl) in two steps. The influence of the substituents (R), in position 2 of this system, on the oxidation process was studied. While the oxidation of 1a - g with 3-chloroperoxybenzoic acid gave yields of 3a - g depending greatly on the nature of R, the combined KHSO5/NaOCl method gave good yields of 3a - g in all of the cases studied.

  DOI：

  10.3987/com-95-7196
• 作为产物：
  描述：

  2-巯基烟酸 在 氢氧化钾 、 三甲基乙酰氯 、 三乙胺 、 间氯过氧苯甲酸 、 三氯乙酸酐 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 26.25h， 生成 异噻唑并[5,4-b]吡啶-3(2H)-酮,2-(4-溴苯基)-
  参考文献：
  名称：

  Heteroaryl-Fused 2-Phenylisothiazolone Inhibitors of Cartilage Breakdown

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of N-phenyl heteroaryl-fused isothiazolones are described. These isothiazolones have been shown to exhibit potent, dose-dependent inhibition of IL-1 beta-induced breakdown of proteoglycan in a cartilage organ culture assay. This effect is likely due to inhibition of MMP activation and a consequent reduction in MMP activity following IL-1 beta stimulation. Thus these compounds potentially represent simple, non-peptidic disease-modifying agents for the treatment of arthritic diseases. To examine the effects of structure on in vitro activity, three general features of the molecules were varied, substituents on the pendant N-phenyl group, the position of ring fusion to the isothiazolone, and substituents on the fused ring peri to the isothiazolone sulfur.

  DOI：

  10.1021/jm00045a012