| 1493759-35-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• CAS: 1493759-35-5
• 化学式: C₃₂H₃₅NO₉
• 分子量: 577.631
• InChiKey: PEKWTGDUXBIXBF-HXBJCGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  119.36
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到3-(4-cyclopropylphenylmethyl)-1-(β-D-glucopyranosyl)indole
  参考文献：
  名称：

  Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes

  摘要：

  Inhibition of the renal sodium glucose cotransporter (SGLT) increases urinary glucose excretion (UGE) and thus reduces blood glucose levels during hyperglycemia. To explore the potential of new antihyperglycemic agents, we synthesized and determined the human SGLT2 (hSGLT2) inhibitory potential of novel substituted 3-benzylindole-N-glucosides 6. Optimization of 6 resulted in the discovery of 3-(4-cyclopropylbenzyl)-4-fluoroindole-N-glucoside 6a-4 (TA-1887), a highly potent and selective hSGLT2 inhibitor, with pronounced antihyperglycemic effects in high-fat diet-fed KK (HF-KK) mice. Our results suggest the potential of indole-N-glucosides as novel antihyperglycemic agents through inhibition of renal SGLT2.

  DOI：

  10.1021/ml400339b
• 作为产物：
  描述：

  1-(β-D-glucopyranosyl)indoline 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 magnesium 、 1,2-二溴乙烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 氯仿 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes

  摘要：

  Inhibition of the renal sodium glucose cotransporter (SGLT) increases urinary glucose excretion (UGE) and thus reduces blood glucose levels during hyperglycemia. To explore the potential of new antihyperglycemic agents, we synthesized and determined the human SGLT2 (hSGLT2) inhibitory potential of novel substituted 3-benzylindole-N-glucosides 6. Optimization of 6 resulted in the discovery of 3-(4-cyclopropylbenzyl)-4-fluoroindole-N-glucoside 6a-4 (TA-1887), a highly potent and selective hSGLT2 inhibitor, with pronounced antihyperglycemic effects in high-fat diet-fed KK (HF-KK) mice. Our results suggest the potential of indole-N-glucosides as novel antihyperglycemic agents through inhibition of renal SGLT2.

  DOI：

  10.1021/ml400339b