(4-bromo-2-thienyl)(4-methoxyphenyl)methanol | 944644-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-bromo-2-thienyl)(4-methoxyphenyl)methanol
• 英文别名: (4-Bromothiophen-2-yl)-(4-methoxyphenyl)methanol
• CAS: 944644-86-4
• 化学式: C₁₂H₁₁BrO₂S
• 分子量: 299.188
• InChiKey: RLTKGVKFFJXCID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-bromo-2-thienyl)(4-methoxyphenyl)methanol 在 ammonium hydroxide 、 N-氯代丁二酰亚胺 、 正丁基锂 、 二氧化硫 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 、 丙酮 为溶剂， 反应 1.08h， 生成 5-<1-hydroxy-1-(4-methoxyphenyl)methyl>-3-thiophenesulfonamide
  参考文献：
  名称：

  5-Substituted 3-thiophenesulfonamides as carbonic anhydrase inhibitors

  摘要：

  A series of 5-substituted 3-thiophenesulfonamides was prepared from 4-bromo-2-thiophene carboxaldehyde. Several of these compounds inhibited carbonic anhydrase II in vitro at concentrations of less than 10 nM. In the ex vivo assay, these compounds have inhibitory values in the 25-81% range. Additionally, none of these compounds exhibit sensitization potential as determined by in vitro measurement of cysteine reactivity.

  DOI：

  10.1016/0223-5234(96)89133-1
• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 、 p-methoxyphenyllithium 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 2.5h， 生成 (4-bromo-2-thienyl)(4-methoxyphenyl)methanol
  参考文献：
  名称：

  5-Substituted 3-thiophenesulfonamides as carbonic anhydrase inhibitors

  摘要：

  A series of 5-substituted 3-thiophenesulfonamides was prepared from 4-bromo-2-thiophene carboxaldehyde. Several of these compounds inhibited carbonic anhydrase II in vitro at concentrations of less than 10 nM. In the ex vivo assay, these compounds have inhibitory values in the 25-81% range. Additionally, none of these compounds exhibit sensitization potential as determined by in vitro measurement of cysteine reactivity.

  DOI：

  10.1016/0223-5234(96)89133-1

文献信息

• Discovery of Ipragliflozin (ASP1941): A novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus
  作者：Masakazu Imamura、Keita Nakanishi、Takayuki Suzuki、Kazuhiro Ikegai、Ryota Shiraki、Takashi Ogiyama、Takeshi Murakami、Eiji Kurosaki、Atsushi Noda、Yoshinori Kobayashi、Masayuki Yokota、Tomokazu Koide、Kazuhiro Kosakai、Yasufumi Ohkura、Makoto Takeuchi、Hiroshi Tomiyama、Mitsuaki Ohta

  DOI：10.1016/j.bmc.2012.03.051

  日期：2012.5

  several compounds, the benzothiophene derivative (14a) was found to have potent inhibitory activity against SGLT2 and good selectivity versus SGLT1. Through further optimization of 14a, a novel benzothiophene derivative (14h; ipragliflozin, ASP1941) was discovered as a highly potent and selective SGLT2 inhibitor that reduced blood glucose levels in a dose-dependent manner in diabetic models KK-Ay mice and

  合成了一系列具有各种杂芳族化合物的C-葡萄糖苷，并评估了其对SGLT的抑制活性。在筛选了几种化合物后，发现苯并噻吩衍生物（14a）对SGLT2具有有效的抑制活性，并且对SGLT1具有良好的选择性。通过进一步优化14a，发现了一种新型的苯并噻吩衍生物（14h ;伊格列净，ASP1941）是一种高效且选择性的SGLT2抑制剂，可在糖尿病模型KK-A y小鼠和STZ大鼠中以剂量依赖的方式降低血糖水平。