1-<5'-(benzylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil | 93842-00-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 1-<5'-(benzylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil
• CAS: 93842-00-3
• 化学式: C₁₈H₂₁N₃O₇
• 分子量: 391.381
• InChiKey: XSNMPICOFVUSRU-AALSBFMBSA-N

物化性质

• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  145.09
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-<5'-(benzylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil 在 Pd-BaSO₄ 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 2-[2-aminopropanoyl(methyl)amino]-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids

  摘要：

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.

  DOI：

  10.1021/jm00381a012
• 作为产物：
  描述：

  尿嘧啶多氧菌素 C 在 sodium hydroxide 、 sodium tetrahydroborate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 1-<5'-(benzylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids

  摘要：

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.

  DOI：

  10.1021/jm00381a012