3',5'-bis(3-carboxypentanoyl)-5-fluoro-2'-deoxyuridine | 99194-68-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-bis(3-carboxypentanoyl)-5-fluoro-2'-deoxyuridine
• 英文别名: 6-[[(2R,3S,5R)-3-(5-carboxypentanoyloxy)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-6-oxohexanoic acid
• CAS: 99194-68-0
• 化学式: C₂₁H₂₇FN₂O₁₁
• 分子量: 502.451
• InChiKey: JHXUDNWPKBNDDY-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  191.29
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  5-氟-2'-脱氧脲核苷 、 己二酰氯 生成 3',5'-bis(3-carboxypentanoyl)-5-fluoro-2'-deoxyuridine
  参考文献：
  名称：

  KAVAGUTI, TAKEHO;SAJTO, MASAXIKO;SUDZUKI, JOSIKI

  摘要：

  DOI：

文献信息

• Specificity of esterases and structures of prodrug esters. III. Activity of rat tissue homogenates, rat plasma and porcine liver esterase for the hydrolysis of 3',5'-bis-dicarboxylic acid hemiesters of 5-fluoro-2'-deoxyuridine.
  作者：TAKEO KAWAGUCHI、YOSHIKI SUZUKI、NAOKI NAMBU、TSUNEJI NAGAI

  DOI：10.1248/cpb.33.2956

  日期：——

  Five acidic 3', 5'-diesters of 5-fluoro-2'-deoxyuridine (FUdR) including 3-carboxypropionate, 4-carboxybutyrate, 5-carboxypentanoate, 6-carboxyhexanoate and 7-carboxyheptanoate were synthesized, and their susceptibility to porcine liver, rat liver homogenate, rat intestinal homogenate and rat plasma esterase preparations was studied. The susceptibility of the derivatives to porcine liver esterase preparation increased as the number of methylene groups in the ester promoiety increased in both acidic (pH 5.0) and neutral (pH 7.0) solutions. The derivatives showed about 100 times higher reactivity to the esterase at pH 5.0 than at pH 7.0. With the rat tissue homogenates and plasma preparations, the longer the ester chain the higher the susceptibility, except for 3', 5'-bis (3-carboxypropionyl) FUdR (I) with rat liver homogenate. Though the reactivity of I was the lowest with porcine liver esterase preparation and not measurable with rat intestinal homogenate and plasma, I showed the highest reactivity with the rat liver homogenate.

  合成了 5-氟-2'-脱氧尿苷（FUdR）的五种酸性 3'，5'-二酯，包括 3-羧基丙酸酯、4-羧基丁酸酯、5-羧基戊酸酯、6-羧基己酸酯和 7-羧基庚酸酯，并研究了它们对猪肝、大鼠肝匀浆、大鼠肠匀浆和大鼠血浆酯酶制剂的敏感性。在酸性（pH 值 5.0）和中性（pH 值 7.0）溶液中，随着酯原基中亚甲基数目的增加，衍生物对猪肝酯酶制剂的敏感性也随之增加。在 pH 值为 5.0 时，衍生物与酯酶的反应性比 pH 值为 7.0 时高约 100 倍。在大鼠组织匀浆和血浆制剂中，酯链越长，敏感性越高，但 3'，5'-双（3-羧基丙酰基）FUdR（I）在大鼠肝脏匀浆中除外。虽然 I 在猪肝酯酶制剂中的反应性最低，在大鼠肠匀浆和血浆中也无法测量，但 I 在大鼠肝匀浆中的反应性最高。
• KAWAGUCHI, TAKEO;SAITO, MASAHIKO;SUZUKI, YOSHIKI
  作者：KAWAGUCHI, TAKEO、SAITO, MASAHIKO、SUZUKI, YOSHIKI

  DOI：——

  日期：——