N-(trishydroxymethylmethyl)urea | 67910-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-(trishydroxymethylmethyl)urea
• 英文别名: Urea, [2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-；[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]urea
• CAS: 67910-06-9
• 化学式: C₅H₁₂N₂O₄
• 分子量: 164.161
• InChiKey: IVSHBCMTAKLBIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[5-[4-(2-aminoethyl)benzyl]-2-(benzyloxy)-4-methylphenyl]-D-glucitol 、 N-(trishydroxymethylmethyl)urea 在 吡啶 、 对硝基苯基氯甲酸酯 作用下， 生成 (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl]-D-glucitol
  参考文献：
  名称：

  Discovery of a potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor (TP0438836) for the treatment of type 2 diabetes

  摘要：

  The design and synthesis of a novel class of low-absorbable SGLT1 inhibitors are described. To achieve low absorption in the new series, we performed an optimization study based on a strategy to increase TPSA. Fortunately, the optimization of an aglycon moiety and a side chain of the distal aglycon moiety led to the identification of compound 30b as a potent and low-absorbable SGLT1 inhibitor. Compound 30b showed a desirable PK profile in Sprague-Dawley (SD) rats and a favorable glucose-lowering effect in diabetic rats.

  DOI：

  10.1016/j.bmcl.2018.09.035
• 作为产物：
  描述：

  三羟甲基氨基甲烷 、 硝基脲 生成 N-(trishydroxymethylmethyl)urea
  参考文献：
  名称：

  NEC R., CHEM. PRUM. 1979, 29, NO 11, 589-592

  摘要：

  DOI：

文献信息

• NEC R., CHEM. PRUM. 1979, 29, NO 11, 589-592
  作者：NEC R.

  DOI：——

  日期：——
• Discovery of a potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor (TP0438836) for the treatment of type 2 diabetes
  作者：Shoichi Kuroda、Yohei Kobashi、Takahiro Oi、Hideaki Amada、Lisa Okumura-Kitajima、Fusayo Io、Koji Yamamto、Hiroyuki Kakinuma

  DOI：10.1016/j.bmcl.2018.09.035

  日期：2018.12

  The design and synthesis of a novel class of low-absorbable SGLT1 inhibitors are described. To achieve low absorption in the new series, we performed an optimization study based on a strategy to increase TPSA. Fortunately, the optimization of an aglycon moiety and a side chain of the distal aglycon moiety led to the identification of compound 30b as a potent and low-absorbable SGLT1 inhibitor. Compound 30b showed a desirable PK profile in Sprague-Dawley (SD) rats and a favorable glucose-lowering effect in diabetic rats.