1-(3-C-Ethynyl-β-D-xylo-pentofuranosyl)thymine | 133634-74-9

• 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-(3-C-Ethynyl-β-D-xylo-pentofuranosyl)thymine
• 英文别名: 1-[(2R,3R,4R,5R)-4-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 133634-74-9
• 化学式: C₁₂H₁₄N₂O₆
• 分子量: 282.253
• InChiKey: GVFXQDTVLQIXNR-CCCLYZFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-C-Ethynyl-β-D-xylo-pentofuranosyl)thymine 在 吡啶 、 硫酸 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 1-(2-O-Acetyl-3,5-cyclohexylidene-3-C-ethynyl-β-D-xylo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of 3′--ethynylnucleosides of thymine

  摘要：

  Reaction of 1-[2,5-di-O-(t-butyldimethylsilyl)-beta-D-erythro-pentofuranos-3-ulosyl]thymine with HC = CMgBr gives a (25:1) mixture of 3'-C-ethynyl nucleosides of thymine having beta-D-xylo and beta-D-ribo configuration. Reaction of 1-(2'-deoxy-5'-O-trityl-beta-D-glycero-pentofuran -3-ulosyl)thymine with HC = CMgBr gives the corresponding 3'-C-ethynyl-beta-D-threo-thymidine. The absolute configurations of the newly formed chiral centers at C-3' have been demonstrated by chemical means.

  DOI：

  10.1016/s0040-4020(01)96914-5
• 作为产物：
  描述：

  1-<2,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine 在 四丁基氟化铵 、 乙炔 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-(3-C-Ethynyl-β-D-xylo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of 3′--ethynylnucleosides of thymine

  摘要：

  Reaction of 1-[2,5-di-O-(t-butyldimethylsilyl)-beta-D-erythro-pentofuranos-3-ulosyl]thymine with HC = CMgBr gives a (25:1) mixture of 3'-C-ethynyl nucleosides of thymine having beta-D-xylo and beta-D-ribo configuration. Reaction of 1-(2'-deoxy-5'-O-trityl-beta-D-glycero-pentofuran -3-ulosyl)thymine with HC = CMgBr gives the corresponding 3'-C-ethynyl-beta-D-threo-thymidine. The absolute configurations of the newly formed chiral centers at C-3' have been demonstrated by chemical means.

  DOI：

  10.1016/s0040-4020(01)96914-5

文献信息

• 3'-SUBSTITUTED NUCLEOSIDE DERIVATIVES
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0747389A1

  公开（公告）日：1996-12-11

  The invention relates to a 3'-substituted nucleoside derivative represented by the following general formula (1): wherein B means a nucleic acid base which may have a substituent, Z represents a lower alkynyl or lower alkenyl group which may be substituted by a group represented by the formula: in which Ra, Rb and Rc are individually a lower alkyl group or a phenyl group, or an oxiranyl group which may have at least one lower alkyl group, R1 and R2 individually represent H or an ester-forming residue capable of easily leaving in a living body, and R3 is H, a mono- or polyphosphoric acid residue, or an ester-forming residue capable of easily leaving in a living body, with the proviso that the sugar moiety is ribose, or a pharmaceutically acceptable salt thereof. The 3'-substituted nucleoside derivative according to the invention has an excellent antitumor activity and is hence useful for treatment for and prevention of cancers.

  本发明涉及由以下通式（1）代表的 3'-取代的核苷衍生物： 其中 B 表示可具有取代基的核酸碱基，Z 表示可被式中代表的基团取代的低级炔基或低级烯基： 其中，Ra、Rb 和 Rc 分别为低级烷基或苯基，或可具有至少一个低级烷基的环氧乙烷基，R1 和 R2 分别代表 H 或可容易地留在生物体内的酯形成残基，R3 为 H、单磷酸或多磷酸残基或可容易地留在生物体内的酯形成残基，但糖基为核糖或其药学上可接受的盐。根据本发明，3'-取代的核苷衍生物具有优异的抗肿瘤活性，因此可用于治疗和预防癌症。
• US5763418A
  申请人：——

  公开号：US5763418A

  公开（公告）日：1998-06-09
• USRE38090E1
  申请人：——

  公开号：USRE38090E1

  公开（公告）日：2003-04-22
• Synthesis of 3′--ethynylnucleosides of thymine
  作者：Sophie Huss、Federico G. De las Heras、María José Camarasa

  DOI：10.1016/s0040-4020(01)96914-5

  日期：1991.1

  Reaction of 1-[2,5-di-O-(t-butyldimethylsilyl)-beta-D-erythro-pentofuranos-3-ulosyl]thymine with HC = CMgBr gives a (25:1) mixture of 3'-C-ethynyl nucleosides of thymine having beta-D-xylo and beta-D-ribo configuration. Reaction of 1-(2'-deoxy-5'-O-trityl-beta-D-glycero-pentofuran -3-ulosyl)thymine with HC = CMgBr gives the corresponding 3'-C-ethynyl-beta-D-threo-thymidine. The absolute configurations of the newly formed chiral centers at C-3' have been demonstrated by chemical means.