N³-benzoyl-2'-deoxy-5-fluorouridine | 74233-80-0

• 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: N³-benzoyl-2'-deoxy-5-fluorouridine
• 英文别名: 3-Benzoyl-2'-deoxy-5-fluorouridine；3-benzoyl-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 74233-80-0
• 化学式: C₁₆H₁₅FN₂O₆
• 分子量: 350.303
• InChiKey: CPBKROZHSSOGKJ-YNEHKIRRSA-N

物化性质

• 沸点：
  543.1±60.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N³-benzoyl-2'-deoxy-5-fluorouridine 生成 N³-benzoyl-2'-deoxy-5'-O-ethyl-5-fluorouridine
  参考文献：
  名称：

  FUDZII, SEHTSUO;YAMASITA, DZYUNITI;TAKEHDA, SEHTSUO;TEHRADA, TADASI;YASUM+

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 、 5-氟-2'-脱氧脲核苷 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以49%的产率得到N³-benzoyl-2'-deoxy-5-fluorouridine
  参考文献：
  名称：

  抗肿瘤药的研究。8.2′-脱氧-5-（三氟甲基）尿苷和2′-脱氧-5-氟尿苷的O-烷基衍生物的抗肿瘤活性。

  摘要：

  合成了2'-脱氧-5-（三氟甲基）尿苷（F3Thd）和2'-脱氧-5-氟尿苷（FUdR）的O-苄基和O-乙基衍生物。检查了化合物对小鼠肉瘤180的口服抗肿瘤活性。F3Thd的5'-O-乙基（3b），3'-O-乙基（3c），5'-O-苄基（3e）和3'-O-苄基（3f）衍生物的活性高4倍比F3Thd本身。在F3Thd的取代苄基衍生物中，3'-O-（对氯苄基）-F3Thd（3h）显示最高的活性，ED50不到F3Thd的十分之一。FUdR的5'-O-苄基（7c）和3'-O-苄基（7d）衍生物的活性与F3Thd的有效O-烷基衍生物的活性相等。

  DOI：

  10.1021/jm00121a025

文献信息

• 2'-deoxy-5-substituted uridine derivatives
  申请人：Taiho Pharmaceutical Company, Ltd.

  公开号：US05250673A1

  公开（公告）日：1993-10-05

  Novel 2'-deoxy-5-substituted uridine derivative represented by the general formula, ##STR1## wherein R.sub.1 is a hydrogen atom, a benzoyl group or a tetrahydrofuranyl group; R.sub.2 is a fluorine atom or a trifluoromethyl group; and any one of R.sub.3 and R.sub.4 is a hydrogen atom and the other one is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a benzyl group having as the substituents selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms and a nitro group, or an alkyl group having 1 to 3 carbon atoms having one or two phenyl groups as the substituents. The novel 2'-deoxy-5-substituteduridine derivative possesses excellent antitumor activity with less toxicity, thus it is useful as antitumor agent.

  通式为##STR1##的新型2'-去氧-5-取代尿苷衍生物，其中R.sub.1是氢原子、苯甲酰基或四氢呋喃基；R.sub.2是氟原子或三氟甲基基团；R.sub.3和R.sub.4中的任意一个是氢原子，另一个是具有1至10个碳原子的烷基基团、具有2至6个碳原子的烯基基团、苄基基团，其取代基选择自卤原子、具有1至4个碳原子的烷基团、具有1至4个碳原子的烷氧基团和硝基，或具有1至3个碳原子的烷基团，其中一个或两个取代基是苯基。该新型2'-去氧-5-取代尿苷衍生物具有优异的抗肿瘤活性和较低的毒性，因此可用作抗肿瘤剂。
• Novel 2'-deoxy-5-substituted uridine derivatives, processes for
  申请人：Taiho Pharmaceutical Company Limited

  公开号：US04886877A1

  公开（公告）日：1989-12-12

  Novel 2'-deoxy-5-substituted uridine derivative represented by the general formula, ##STR1## wherein R.sub.1 is a hydrogen atom, a benzoyl group or a tetrahydrofuranyl group; R.sub.2 is a fluorine atom or a trifluoromethyl group; and any one of R.sub.3 and R.sub.4 is a hydrogen atom and the other one is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a benzyl group having as the substituents selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms and a nitro group, or an alkyl group having 1 to 3 carbon atoms having one or two phenyl groups as the substituents. The novel 2'-deoxy-5-substituteduridine derivative possesses excellent antitumor activity with less toxicity, thus it is useful as antitumor agent.

  一种新型的2'-脱氧-5-取代尿苷衍生物，其一般式为##STR1##其中，R.sub.1为氢原子、苯甲酰基或四氢呋喃基；R.sub.2为氟原子或三氟甲基基团；R.sub.3和R.sub.4中的任意一个为氢原子，另一个为具有1至10个碳原子的烷基、具有2至6个碳原子的烯基、苄基，其中苄基的取代基选自卤原子、具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基和硝基，或具有1至3个碳原子且具有一或两个苯基取代基的烷基。该新型的2'-脱氧-5-取代尿苷衍生物具有出色的抗肿瘤活性，毒性较小，因此可用作抗肿瘤剂。
• Novel 2'-deoxy-5-substituted uridine derivatives, processes for preparing the same and antitumor agent containing the same
  申请人：TAIHO PHARMACEUTICAL COMPANY LIMITED

  公开号：EP0129984A1

  公开（公告）日：1985-01-02

  Novel 2'-deoxy-5-substituted uridine derivative represented by the general formula, wherein R, is a hydrogen atom, a benzoyl group or a tetrahydrofuranyl group; R2 is a fluorine atom or a trifluoromethyl group; and any one of R3 and R4 is a hydrogen atom and the other one is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a benzyl group having as the substituents selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms and a nitro group, or an alkyl group having 1 to 3 carbon atoms having one or two phenyl groups as the substituents. The novel 2'-deoxy-5-substituteduridine derivative possesses excellent antitumor activity with less toxicity, thus it is useful as antitumor agent.

  由通式代表的新型 2'-脱氧-5-取代尿苷衍生物、 其中 R 是氢原子、苯甲酰基或四氢呋喃基；R2 是氟原子或三氟甲基；R3和R4中的任何一个是氢原子，另一个是具有1至10个碳原子的烷基、具有2至6个碳原子的烯基、取代基选自以下组别的苄基：卤素原子、具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基和硝基，或具有1至3个碳原子的烷基，取代基为一个或两个苯基。 新型 2'-deoxy-5 取代尿苷衍生物具有极佳的抗肿瘤活性，毒性较低，因此可用作抗肿瘤药物。
• 2'-Deoxy-5-fluorouridine derivatives
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0331032A1

  公开（公告）日：1989-09-06

  2′-Deoxy-5-fluorouridine derivatives of the formula wherein, R¹ is hydrogen atom or an acyl group and R² and R³ are respectively hydrogen atom, an acyl group or a group of the formula wherein X¹ and X² are respectively oxygen atom or sulfur atom; R⁴ is a phenyl group, a benzyl group or a naphthyl group each of which may be substituted by an alkyl group, an alkoxyl group, an alkoxycarbonyl group, an alkyl­thio group, an acyl group, a halogen atom, trifluoromethyl group, nitro group, cyano group, carboxyl group and/or methy­lenedioxy group and R⁵ is an alkyl group, an alkenyl group or one of the groups represented by R⁴ which is the same as or different from R⁴, at least one of R² and R³ being a group of the formula which exhibit excellent antitumour activities and have lower toxicity, methods of the production thereof and antitumour compositions containing said 2′-deoxy-­5-fluorouridine derivatives.

  式中的 2′-脱氧-5-氟尿苷衍生物 其中，R¹为氢原子或酰基，R²和R³分别为氢原子、酰基或式中的基团 其中，X¹ 和 X² 分别为氧原子或硫原子；R⁴ 是苯基、苄基或萘基，每个苯基、苄基或萘基可被烷基、烷氧基、烷氧羰基、烷硫基、酰基、卤素原子、三氟甲基、硝基、氰基、羧基、卤素原子、三氟甲基、硝基、氰基、羧基取代、R⁵是烷基、烯基或与 R⁴ 相同或不同的 R⁴ 所代表的基团之一，R² 和 R³ 中至少有一个是式中的基团。 这些衍生物具有优异的抗肿瘤活性和较低的毒性，其生产方法以及含有所述 2′-脱氧-5-氟尿嘧啶衍生物的抗肿瘤组合物。
• KODAMA, TSUTOMU;SEHNOURA, MASAAKI;AOYAMA, XADZIMEH;YAMAGUTI, TOMONOBU;KIT+
  作者：KODAMA, TSUTOMU、SEHNOURA, MASAAKI、AOYAMA, XADZIMEH、YAMAGUTI, TOMONOBU、KIT+

  DOI：——

  日期：——