4-ethoxyphenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-beta-D-gluco-pyranosyl)indol-3-yl ketone | 903551-07-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 4-ethoxyphenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-beta-D-gluco-pyranosyl)indol-3-yl ketone
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(4-ethoxybenzoyl)-4-fluoroindol-1-yl]oxan-2-yl]methyl acetate
• CAS: 903551-07-5
• 化学式: C₃₁H₃₂FNO₁₁
• 分子量: 613.594
• InChiKey: ANEALKIXYCYKDJ-KLBVUYHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-ethoxyphenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-beta-D-gluco-pyranosyl)indol-3-yl ketone 在 甲醇 、 三乙基硅烷 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 chromium(III) chloride hexahydrate 、 sodium methylate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 3-(4-ethoxyphenylmethyl)-4-fluoro-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-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-fluoroindoline 在 aluminum (III) chloride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 4-ethoxyphenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-beta-D-gluco-pyranosyl)indol-3-yl ketone
  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

文献信息

• INDOLE DERIVATIVES
  申请人：NOMURA Sumihiro

  公开号：US20090258921A1

  公开（公告）日：2009-10-15

  Novel indole derivatives of formula (I) or a pharmaceutically acceptable salt thereof: wherein R 1 is halogen, or alkyl, R 2 is hydrogen, or halogen, Ar is phenyl, or thienyl, which may be substituted with halogen, alkyl, alkoxy, alkylthio, etc.

  式(I)的新型吲哚衍生物或其药学上可接受的盐：其中R1为卤素或烷基，R2为氢或卤素，Ar为苯基或噻吩基，可以被卤素、烷基、烷氧基、烷硫基等取代。
• Indole Derivatives
  申请人：Nomura Sumihiro

  公开号：US20080119422A1

  公开（公告）日：2008-05-22

  Novel indole derivatives of formula (I) or a pharmaceutically acceptable salt thereof: wherein R 1 is halogen, or alkyl, R 2 is hydrogen, or halogen, Ar is phenyl, or thienyl, which may be substituted with halogen, alkyl, alkoxy, alkylthio, etc.

  化合物的式子 (I) 或其药学上可接受的盐：其中 R1 是卤素或烷基，R2 是氢或卤素，Ar 是苯基或噻吩基，可以被卤素、烷基、烷氧基、烷硫基等取代。
• Indole derivatives
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US07935674B2

  公开（公告）日：2011-05-03

  Novel indole derivatives of formula (I) or a pharmaceutically acceptable salt thereof: wherein R1 is halogen, or alkyl, R2 is hydrogen, or halogen, Ar is phenyl, or thienyl, which may be substituted with halogen, alkyl, alkoxy, alkylthio, etc.

  式(I)的新型吲哚衍生物或其药学上可接受的盐：其中R1是卤素或烷基，R2是氢或卤素，Ar是苯基或噻吩基，可以用卤素、烷基、烷氧基、烷硫基等取代。
• US7935674B2
  申请人：——

  公开号：US7935674B2

  公开（公告）日：2011-05-03