4,5-Dihydronaphtho<1,2-d><1,2,3>thiadiazol | 73424-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-Dihydronaphtho<1,2-d><1,2,3>thiadiazol
• 英文别名: 4,5-dihydronaphtho[1,2-d][1,2,3]thiadiazole；4,5-dihydrobenzo[e][1,2,3]benzothiadiazole
• CAS: 73424-56-3
• 化学式: C₁₀H₈N₂S
• 分子量: 188.253
• InChiKey: LDRNYXFIZRDPJG-UHFFFAOYSA-N

物化性质

• 溶解度：
  <0.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-Dihydronaphtho<1,2-d><1,2,3>thiadiazol 在 氯磺酸 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以54%的产率得到4,5-Dihydro-3-thia-1,2-diaza-cyclopenta[a]naphthalene-8-sulfonic acid amide
  参考文献：
  名称：

  Synthesis and in vitro antifungal and cytotoxicity evaluation of substituted 4,5-dihydronaphtho[1,2-d][1,2,3]thia(or selena)diazoles

  摘要：

  Unsubstituted 4,5-dihydronaphtho[1,2-d][1,2,3]thia (or selena)diazoles (2a, 2b), prepared from the semicarbazone (1a), were nitrated using fuming nitric acid at 0 degrees C to yield various mono-nitrated dihydronaphthalenes (3a-3e). Related sulfamoyl derivatives (4a, 4b) were prepared using chlorosulfonic acid, followed by the addition of ammonia solution. Synthesis of 6,9-dimethoxy-4,5-dihydronaphtho[1,2-d][1,2,3]thiadiazole derivative (2c) was performed using 5,8-dimethoxy-alpha-tetralone semicarbazone (1b) and thionylchloride at low temperature. At 10 ppm concentration, all compounds showed low toxicity (higher than 80% survival) on brine shrimps, while at 100 ppm concentration compounds 2d, 3d, and 4b exhibited toxicity (less than 60% survival). Compounds 3a, 3e, and especially 4a showed significant antifungal activity against Cryptococcus neoformans. Compound 4a, while being the most active antifungal agent in this series, possessed low toxicity.

  DOI：

  10.1016/s0014-827x(02)00029-0
• 作为产物：
  描述：

  1-tetralone tosylhydrazone 在 氯化亚砜 作用下， 以64%的产率得到4,5-Dihydronaphtho<1,2-d><1,2,3>thiadiazol
  参考文献：
  名称：

  Meier, Herbert; Trickes, Georg; Laping, Elisabeth, Chemische Berichte, 1980, vol. 113, # 1, p. 183 - 192

  摘要：

  DOI：

文献信息

• MEIER H.; TRICKES G.; LAPING E.; MERKLE U., CHEM. BER., 1980, 113, NO 1, 183-192
  作者：MEIER H.、 TRICKES G.、 LAPING E.、 MERKLE U.

  DOI：——

  日期：——