N³-benzoyl-2'-deoxy-5-(trifluoromethyl)uridine | 95969-47-4

• 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-(trifluoromethyl)uridine
• 英文别名: 3-Benzoyl-2'-deoxy-5-trifluoromethyluridine；3-benzoyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
• CAS: 95969-47-4
• 化学式: C₁₇H₁₅F₃N₂O₆
• 分子量: 400.311
• InChiKey: FMLOWUYBVWQKFK-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N³-benzoyl-2'-deoxy-5-(trifluoromethyl)uridine 在 ammonium hydroxide 、 silver(l) oxide 作用下， 以 乙醇 、 丙酮 、 丁酮 为溶剂， 反应 4.5h， 生成 3'-O-苄基-2'-脱氧-5-三氟甲基尿苷
  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
• 作为产物：
  描述：

  苯甲酰氯 、 三氟胸苷 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以56%的产率得到N³-benzoyl-2'-deoxy-5-(trifluoromethyl)uridine
  参考文献：
  名称：

  Studies on antitumor agents. VI. Syntheses and antitumor activities of acyl derivatives of 2'-deoxy-5-trifluoromethyluridine.

  摘要：

  合成了2'-脱氧-5-三氟甲基尿苷(F3Thd)的各种O-酰基和N-酰基衍生物,即5'-O-酰基、3', 5'-二-O-酰基、N3-酰基、3',5'-二-O-乙酰基-N3-酰基、3', 5'-二-O-氨甲酰基和3',5'-二-O-乙氧羰基化合物。还合成了2'-脱氧-5-三氟甲基胞苷的5'-O-酰基衍生物。通过给小鼠口服给药,考察了这些化合物对肉瘤180的抗癌活性。在具有脂肪族酸的5'-和3'5'-二酯化合物中,5'-O-己酰基化合物显示出最高的活性。用芳酰基或氨甲酰基保护糖部分的完全保护大大降低了活性,而3',5'-二-O-间氟苯甲酰基和3',5'-二-O-丁基氨甲酰基化合物的活性最小。N3-苯甲酰基化合物的效力略高于F3Thd,但它们中没有任何一种显示出比有效的O-酰基化合物更高的活性。在2'-脱氧-5-三氟甲基胞苷的5'-O-酰基化合物中,5'-O-苯甲酰基化合物显示出最高的活性。

  DOI：

  10.1248/cpb.35.2090

文献信息

• 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.

  由一般公式表示的新型2'-脱氧-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，其取代基被选择自卤素原子、具有1至4个碳原子的烷基基团、具有1至4个碳原子的烷氧基团和硝基基团的群组，或具有一个或两个苯基取代基的具有1至3个碳原子的烷基基团。这种新型2'-脱氧-5-取代尿苷衍生物具有出色的抗肿瘤活性且毒性较低，因此可用作抗肿瘤剂。
• 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 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-TRIFLUOROMETHYLURIDINE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
  申请人：TAIHO PHARMACEUTICAL COMPANY, LIMITED

  公开号：EP0252989A1

  公开（公告）日：1988-01-20

  2'-deoxy-5-trifluoromethyluridine derivatives represented by general formula (I), (wherein Tr represents a triphenylmethyl group and R represents a lower alkyl group or a benzyl group) and a process for their preparation. The derivatives are prepared by subjecting a 2'-deoxy-5 halogenuridine derivative represented by general formula (II), (wherein W represents an iodine atom or a bromine atom, Tr represents a triphenylmethyl group, and R represents a lower alkyl group or a benzyl group) to trifluoromethylation reaction with halogenotrifluoromethane in the presence of metallic copper.

  通式(I)代表的2'-脱氧-5-三氟甲基尿苷衍生物（其中Tr代表三苯甲基，R代表低级烷基或苄基）及其制备方法。这些衍生物的制备方法是将通式（II）代表的 2'-脱氧-5-卤尿苷衍生物（其中 W 代表碘原子或溴原子，Tr 代表三苯甲基，R 代表低级烷基或苄基）在金属铜存在下与卤代三氟甲烷进行三氟甲基化反应。
• J. Med. Chem. 1989, 32, 136-139
  作者：

  DOI：——

  日期：——