1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-4-(hexyloxycarbonylamino)pyrimidin-2-one | 1609206-32-7

• 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: 1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-4-(hexyloxycarbonylamino)pyrimidin-2-one
• 英文别名: 2',2'-difluoro-2'-deoxycytidine-N4-hexyl formate；1-[(2R,4R,5R)-3,3-Difluoro-4-hydroxy-5-(hydroxy-methyl)oxolan-2-yl]-1,2-dihydro-4-(hexyloxycarbonylamino)pyrimidin-2-one；hexyl N-[1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• CAS: 1609206-32-7
• 化学式: C₁₆H₂₃F₂N₃O₆
• 分子量: 391.372
• InChiKey: ORAZTHSAWKQVRC-RAIGVLPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氯甲酸正己酯 、 吉西他滨 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.17h， 以27.8%的产率得到1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-4-(hexyloxycarbonylamino)pyrimidin-2-one
  参考文献：
  名称：

  基于核苷的自组装药物用于局部药物递送

  摘要：

  我们已经基于核苷类似物吉西他滨和拉米夫定合成了一系列凝胶剂，使用流变学和透射电子显微镜表征了该系列中的代表性凝胶。吉西他滨衍生物的生长抑制研究证实了这些化合物作为新疗法的可行性，表明基于核苷的胶凝剂在局部药物递送中的潜力。

  DOI：

  10.1002/cmdc.201800063

文献信息

• GEMCITABINE PRODRUGS AND USES THEREOF
  申请人：BoYen Therapeutics, Inc.

  公开号：US20140134160A1

  公开（公告）日：2014-05-15

  The present invention provides compounds according to formula I: and pharmaceutically acceptable salts thereof. For compounds of formula I, R 1 and R 2 are independently selected from the group consisting of H, —C(═O)—(CH 2 ) 2 -aryl, and —C(═O)—(CH 2 ) n —C(═O)—NH-aryl. The subscript n is from 2 to 6. R 3 is selected from the group consisting of H and —C(═O)—O—R 4 ; and R 4 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, arylalkyl, substituted arylalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl and substituted heteroalkyl. Compounds are provided wherein at least one of R 1 and R 2 is other than H. Pharmaceutical compositions, methods for inhibiting the growth of cancer cells, and methods for the treatment of cancer are also provided.

  本发明提供了公式I的化合物及其药学上可接受的盐。对于公式I的化合物，R1和R2独立地选择自H，—C（═O）—（CH2）2-芳基和—C（═O）—（CH2）n—C（═O）—NH-芳基的群组。下标n为2至6。R3选择自H和—C（═O）—O—R4的群组；而R4选择自烷基，取代烷基，烯基，取代烯基，炔基，取代炔基，芳基烷基，取代芳基烷基，环杂芳基烷基，取代环杂芳基烷基，杂基和取代杂基的群组。提供了至少一个R1和R2不是H的化合物。还提供了制药组合物，抑制癌细胞生长的方法和治疗癌症的方法。
• Gemcitabine prodrugs and uses thereof
  申请人：BoYen Therapeutics, Inc.

  公开号：US08956613B2

  公开（公告）日：2015-02-17

  The present invention provides compounds according to formula I: and pharmaceutically acceptable salts thereof. For compounds of formula I, R1 and R2 are independently selected from the group consisting of H, —C(═O)—(CH2)2-aryl, and —C(═O)—(CH2)n—C(═O)—NH-aryl. The subscript n is from 2 to 6. R3 is selected from the group consisting of H and —C(═O)—O—R4; and R4 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, arylalkyl, substituted arylalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl and substituted heteroalkyl. Compounds are provided wherein at least one of R1 and R2 is other than H. Pharmaceutical compositions, methods for inhibiting the growth of cancer cells, and methods for the treatment of cancer are also provided.

  本发明提供了公式I的化合物及其药学上可接受的盐。对于公式I的化合物，R1和R2分别选自H，—C(═O)—(CH2)2-芳基和—C(═O)—(CH2)n—C(═O)—NH-芳基。下标n为2至6。R3选自H和—C(═O)—O—R4；R4选自烷基，取代烷基，烯基，取代烯基，炔基，取代炔基，芳基烷基，取代芳基烷基，环杂芳基烷基，取代环杂芳基烷基，杂基和取代杂基。提供了至少其中之一的R1和R2不是H的化合物。还提供了药物组合物、抑制癌细胞生长的方法以及治疗癌症的方法。
• US8956613B2
  申请人：——

  公开号：US8956613B2

  公开（公告）日：2015-02-17
• US9540410B2
  申请人：——

  公开号：US9540410B2

  公开（公告）日：2017-01-10
• US9890189B2
  申请人：——

  公开号：US9890189B2

  公开（公告）日：2018-02-13