2-phenyl-1-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]ethanone | 152171-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-1-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]ethanone
• 英文别名: 3-(Phenylacetyl)-1-tosylpyrrole；1-[1-[(4-Methylphenyl)sulfonyl]-1H-pyrrol-3-yl]-2-phenylethanone；1-[1-(4-methylphenyl)sulfonylpyrrol-3-yl]-2-phenylethanone
• CAS: 152171-07-8
• 化学式: C₁₉H₁₇NO₃S
• 分子量: 339.415
• InChiKey: SLMGWGSSJLRMCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-1-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]ethanone 在 sodium hydroxide 、 sodium tetrahydroborate 、 二甲基亚砜 、 异丙醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.62h， 生成 3-(2-Phenylethenyl)pyrrole
  参考文献：
  名称：

  Synthesis of 3-vinylpyrrole

  摘要：

  DOI：

  10.1021/jo00079a040
• 作为产物：
  描述：

  1-(对甲苯磺酰基)吡咯 、 苯乙酰氯 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以100%的产率得到2-phenyl-1-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]ethanone
  参考文献：
  名称：

  Discovery of a Series of Phosphonic Acid-Containing Thiazoles and Orally Bioavailable Diamide Prodrugs That Lower Glucose in Diabetic Animals Through Inhibition of Fructose-1,6-Bisphosphatase

  摘要：

  Oral delivery of previously disclosed purine and benzimidazole fructose-1,6 bisphosphatase (FBPase) inhibitors via prodrugs failed, which was likely due to their high molecular wright (> 600) Therefore, a smaller scaffold was desired, and a series of phosphonic acid-containing thiazoles, which exhibited high potency against human liver FBPase (IC(50) of 10-30 nM) and high selectivity relative to other 5'-adenosinemonophosphate (AMP)-binding enzymes, were discovered using a structure-guided drug design approach The initial lead compound (30j) produced profound glucose lowering in rodent models of type 2 diabetes mellitus (T2DM) after parenteral administration Various phosphonate prodrugs were explored without success, until a novel phosphonic diamide prodrug approach was Implemented, which delivered compound 30j with good oral bioavailability (OBAV) (22-47%) Extensive lead optimization of both the thiazole FBPase inhibitors and their prodrugs culminated in the discovery of compound 35n (MB06322) as the first oral FBPase inhibitor advancing to human clinical trials as a potential treatment for T2DM

  DOI：

  10.1021/jm101035x