5-sulfamoylfuran-3-carboxylic acid | 1423033-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-sulfamoylfuran-3-carboxylic acid
• CAS: 1423033-89-9
• 化学式: C₅H₅NO₅S
• mdl: MFCD22628364
• 分子量: 191.164
• InChiKey: NMPQYEHXSISBPT-UHFFFAOYSA-N

物化性质

• 熔点：
  176 - 178°C
• 沸点：
  480.0±55.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)
• 溶解度：
  碱性溶液（微溶），DMSO（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  、 5-sulfamoylfuran-3-carboxylic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] (2S)-1-(5-sulfamoylfuran-3-carbonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  A prodrug design for improved oral absorption and reduced hepatic interaction

  摘要：

  A series of estradiol-17-beta esters of N-(p-sulfomylbenzamide)-amino acids were prepared and evaluated for systemic and hepatic estrogenic activity after oral administration in ovariectomized rats. The alkyl substitution at nitrogen of amino acids such as proline or N-methyl-alanine produced compounds that exhibit potent oral activity. The proline analog (EC508) was further evaluated along with 17 beta-estradiol (E2) and ethinyl-estradiol (EE) and compared their effects on the uterus, angiotensin and HDL-cholesterol after oral administration to ovariectomized female rats. Orally administered EC508 produced systemic estrogenic activity 10 times greater than EE and a 100 times higher activity than E2 with no influence on levels of angiotensin and HDL-cholesterol, whereas EE and E2 reduced the HDL-cholesterol and increased the angiotensine plasma levels. EC508 might offer significant advantages in indications like fertility control and HRT based on its high oral bioavailability and lack of hepatic estrogenicity. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.08.027