2-(2-thiazonoyl)benzoic acid | 137382-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-thiazonoyl)benzoic acid
• 英文别名: 2-(1,3-thiazole-2-carbonyl)benzoic acid
• CAS: 137382-37-7
• 化学式: C₁₁H₇NO₃S
• 分子量: 233.247
• InChiKey: XPUKCSUVCFDNRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-thiazonoyl)benzoic acid 在 sodium hydride 、 sodium carbonate 、 一水合肼 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 C₂₇H₂₉N₅O₂S
  参考文献：
  名称：

  4-Heteroaryl Phthalazin-1(2H)-one Derivatives as Potent Melanin Concentrating Hormone Receptor 1 (MCH-R1) Antagonists

  摘要：

  DOI：

  10.5012/bkcs.2012.33.7.2389
• 作为产物：
  描述：

  噻唑 、 苯酐 在 sodium hydride 作用下， 生成 2-(2-thiazonoyl)benzoic acid
  参考文献：
  名称：

  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 2. 4-(3-Pyridyl)-1(2H)-phthalazinones

  摘要：

  A series of novel 4-(3-pyridyl)-1(2H)-phthalazinone derivatives which possess dual activities of thromboxane A(2) (TXA(2)) synthetase inhibition and bronchodilation was synthesized, and their pharmacological activities were evaluated. While the length and the built of 2-alkyl substituents had no influence on either activity, the 2-substituents with polar groups reduced bronchodilatory activity. Furthermore, we introduced heteroaromatic nuclei into the 4-position of the phthalazinone and found that 1-imidazolyl (13a) and 5-thiazolyl (16b and 16c) derivatives were as active as the parent 3-pyridyl compound 5b. These findings suggest that heteroaromatic nuclei at the Li-position of phthalazinones play a critical role in TXA(2) synthetase inhibition, Additionally, the hydrophobicity of the compounds was found to exert a marked influence on bronchodilatory activity. These observations led to the selection of 2-ethyl-4-(3-pyridyl)-1 (2H)-phthalazinone (5b) (KK-505) and 2-methyl-4-(5-thiazolyl)-1(2H)-phthalazinone (16b) (KK-562) for further studies. Although their precise mechanism of action remains unclear, this series of novel phthalazinone derivatives represents a new class of antiasthma agents with dual activities.

  DOI：

  10.1021/jm00077a009

文献信息

• Synthesis and biological activities of 1-pyridylisoquinoline and 1-pyridyldihydroisoquinoline derivatives as PDE4 inhibitors
  作者：Tatsuzo Ukita、Masakatsu Sugahara、Yoshihiro Terakawa、Tooru Kuroda、Kazuteru Wada、Aya Nakata、Hideo Kikkawa、Katsuo Ikezawa、Kazuaki Naito

  DOI：10.1016/s0960-894x(03)00438-4

  日期：2003.7

  A novel series of 1-pyridylisoquinoline and 1-pyridyldihydroisoquinoline derivatives has been prepared. These compounds showed potent PDE4 inhibitory activities and a broad margin between the K-i value of the rolipram binding affinity and the IC50 value of PDE4 inhibition. They also exhibited potent inhibitory activities toward LPS-induced TNF-alpha production in mice. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 2. 4-(3-Pyridyl)-1(2H)-phthalazinones
  作者：Masahisa Yamaguchi、Kenshi Kamei、Takaki Koga、Michitaka Akima、Akinori Maruyama、Toshio Kuroki、Nobuhiro Ohi

  DOI：10.1021/jm00077a009

  日期：1993.12

  A series of novel 4-(3-pyridyl)-1(2H)-phthalazinone derivatives which possess dual activities of thromboxane A(2) (TXA(2)) synthetase inhibition and bronchodilation was synthesized, and their pharmacological activities were evaluated. While the length and the built of 2-alkyl substituents had no influence on either activity, the 2-substituents with polar groups reduced bronchodilatory activity. Furthermore, we introduced heteroaromatic nuclei into the 4-position of the phthalazinone and found that 1-imidazolyl (13a) and 5-thiazolyl (16b and 16c) derivatives were as active as the parent 3-pyridyl compound 5b. These findings suggest that heteroaromatic nuclei at the Li-position of phthalazinones play a critical role in TXA(2) synthetase inhibition, Additionally, the hydrophobicity of the compounds was found to exert a marked influence on bronchodilatory activity. These observations led to the selection of 2-ethyl-4-(3-pyridyl)-1 (2H)-phthalazinone (5b) (KK-505) and 2-methyl-4-(5-thiazolyl)-1(2H)-phthalazinone (16b) (KK-562) for further studies. Although their precise mechanism of action remains unclear, this series of novel phthalazinone derivatives represents a new class of antiasthma agents with dual activities.
• 4-Heteroaryl Phthalazin-1(2H)-one Derivatives as Potent Melanin Concentrating Hormone Receptor 1 (MCH-R1) Antagonists
  作者：Chae-Jo Lim、Ka-Eun Lee、Byung-Ho Lee、Kwang-Seok Oh、Kyu-Yang Yi

  DOI：10.5012/bkcs.2012.33.7.2389

  日期：2012.7.20