7-iodo-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide | 54371-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 7-iodo-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 7-iodo-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one；3-Oxo-dihydro-1,2,4-benzothiadiazin-1,1-dioxid；7-iodo-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-one；7-iodo-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-one
• CAS: 54371-87-8
• 化学式: C₇H₅IN₂O₃S
• 分子量: 324.099
• InChiKey: ZLGJPKHGNRMMNB-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 密度：
  2.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-iodo-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide 在 吡啶 、 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 7-iodo-3-cyclobutylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Toward Tissue-Selective Pancreatic B-Cells K_ATP Channel Openers Belonging to 3-Alkylamino-7-halo-4H-1,2,4-benzothiadiazine 1,1-Dioxides

  摘要：

  3-(Alkylamino)-7-halo-4H-1,2,4-benzothiadiazine 1,1-dioxides were synthesized, and their activity on rat-insulin-secreting cells and rat aorta rings was compared to that of the K-ATP channel activators diazoxide and pinacidil. Structure-activity relationships indicated that an improved potency and selectivity for the pancreatic tissue was obtained by introducing a fluorine atom in the 7-position and a short linear (preferably ethyl) or cyclic (preferably cyclobutyl) hydrocarbon chain on the nitrogen atom in the 3-position. By contrast, strong myorelaxant activity was gained by the introduction of a halogen atom different from the fluorine atom in the 7-position and a bulky branched alkylamino chain in the 3-position. Thus, 3-(ethylamino)-7-fluoro-4H-1,2,4-benzothiadiazine 1,1-dioxide (11) expressed a marked inhibitory activity on pancreatic B-cells (IC50 = 1 muM) associated with a weak vasorelaxant effect (ED50 > 300 muM), whereas 7-chloro-3-(1,1-dimethylpropyl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxide (27), which was only slightly active on insulin-secreting cells (IC50 > 10 muM), was found to be very potent on vascular smooth muscle cells (ED50 = 0.29 muM). Radioisotopic and electrophysiological. investigations performed with 7-chlorinated, 7-iodinated, and 7-fluorinated 3-alkylamino-4H-1,2,4-benzothiadiazine 1,1-dioxides confirmed that the drugs activated K-ATP channels. The present data revealed that subtle structural modifications of 3-(alkylamino)-7-halo-4H-1,2,4-benzothiadiazine 1,1-dioxides can generate original compounds activating K-ATP channels and exhibiting different in vitro tissue selectivity profiles.

  DOI：

  10.1021/jm021117w
• 作为产物：
  描述：

  2-amino-5-iodobenzenesulfonamide 、 尿素 生成 7-iodo-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Di Bella; Rinaldi; Coppi, Farmaco, Edizione Scientifica, 1974, vol. 29, # 12, p. 915 - 922

  摘要：

  DOI：