N-[(3-乙酰基-1,2-恶唑-5-基)甲基]乙酰胺 | 390817-71-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-[(3-乙酰基-1,2-恶唑-5-基)甲基]乙酰胺
• 英文名称: 5-acetamidomethyl-3-acetylisoxazole
• 英文别名: N-((3-Acetylisoxazol-5-yl)methyl)acetamide；N-[(3-acetyl-1,2-oxazol-5-yl)methyl]acetamide
• CAS: 390817-71-7
• 化学式: C₈H₁₀N₂O₃
• 分子量: 182.179
• InChiKey: GNXCLPKPGFLYJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(3-乙酰基-1,2-恶唑-5-基)甲基]乙酰胺 在 phenyltrimethylammonium tribromide 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 1.33h， 生成 N-[3-(2-{N'-[2-(2-methoxy-phenyl)-ethyl]-guanidino}-thiazol-4-yl)-isoxazol-5-ylmethyl]-acetamide
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 5. 2-(Substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues

  摘要：

  To extend the SAR study of guanidinothiazoles as a structurally novel class of anti-H. pylori agents, a series of 2-(substituted guanidino)-4-arylthiazoles and some 4-aryloxazole analogues were synthesized and evaluated for antimicrobial activity against H. pylori, Some of them were also subjected to H2 antagonist and gastric antisecretory assays. Several arylthiazoles were identified as potent anti-H. pylori agents, and of these, thienylthiazole derivative 44 exhibited the strongest activity (MIC = 0.0065 mug/mL) among the compounds obtained in our guanidinothiazole studies. Although 44 was void of H2 antagonist activity, pyridylthiazole derivative 39 had both potent anti-H. pylori and H2 antagonist activities. Thiazolylthiazole derivative 46 also showed potent anti-H. pylori activity, but the H2 antagonist activity was weak. On the other hand, no attractive activities were found in pyrimidyl, oxazolyl, isoxazolyl, imidazolyl, and oxadiazolylthiazole derivatives. The anti-H. pylori activity of the aryloxazole analogues was weaker than those of the corresponding arylthiazole derivatives, though they had potent H2 antagonist activity.

  DOI：

  10.1021/jm010217j
• 作为产物：
  描述：

  N-羟基-2-氧代-丙亚氨酰氯 、 N-(2-丙炔基)乙酰胺 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以7.5 g的产率得到N-[(3-乙酰基-1,2-恶唑-5-基)甲基]乙酰胺
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 5. 2-(Substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues

  摘要：

  To extend the SAR study of guanidinothiazoles as a structurally novel class of anti-H. pylori agents, a series of 2-(substituted guanidino)-4-arylthiazoles and some 4-aryloxazole analogues were synthesized and evaluated for antimicrobial activity against H. pylori, Some of them were also subjected to H2 antagonist and gastric antisecretory assays. Several arylthiazoles were identified as potent anti-H. pylori agents, and of these, thienylthiazole derivative 44 exhibited the strongest activity (MIC = 0.0065 mug/mL) among the compounds obtained in our guanidinothiazole studies. Although 44 was void of H2 antagonist activity, pyridylthiazole derivative 39 had both potent anti-H. pylori and H2 antagonist activities. Thiazolylthiazole derivative 46 also showed potent anti-H. pylori activity, but the H2 antagonist activity was weak. On the other hand, no attractive activities were found in pyrimidyl, oxazolyl, isoxazolyl, imidazolyl, and oxadiazolylthiazole derivatives. The anti-H. pylori activity of the aryloxazole analogues was weaker than those of the corresponding arylthiazole derivatives, though they had potent H2 antagonist activity.

  DOI：

  10.1021/jm010217j

文献信息

• Anti-<i>Helicobacter </i><i>p</i><i>ylori</i> Agents. 5. 2-(Substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues
  作者：Yousuke Katsura、Shigetaka Nishino、Yoshikazu Inoue、Kazuo Sakane、Yoshimi Matsumoto、Chizu Morinaga、Hirohumi Ishikawa、Hisashi Takasugi

  DOI：10.1021/jm010217j

  日期：2002.1.1

  To extend the SAR study of guanidinothiazoles as a structurally novel class of anti-H. pylori agents, a series of 2-(substituted guanidino)-4-arylthiazoles and some 4-aryloxazole analogues were synthesized and evaluated for antimicrobial activity against H. pylori, Some of them were also subjected to H2 antagonist and gastric antisecretory assays. Several arylthiazoles were identified as potent anti-H. pylori agents, and of these, thienylthiazole derivative 44 exhibited the strongest activity (MIC = 0.0065 mug/mL) among the compounds obtained in our guanidinothiazole studies. Although 44 was void of H2 antagonist activity, pyridylthiazole derivative 39 had both potent anti-H. pylori and H2 antagonist activities. Thiazolylthiazole derivative 46 also showed potent anti-H. pylori activity, but the H2 antagonist activity was weak. On the other hand, no attractive activities were found in pyrimidyl, oxazolyl, isoxazolyl, imidazolyl, and oxadiazolylthiazole derivatives. The anti-H. pylori activity of the aryloxazole analogues was weaker than those of the corresponding arylthiazole derivatives, though they had potent H2 antagonist activity.