4′-vinyl-d4T

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 4′-vinyl-d4T
• 英文别名: 4'-vinyl D4T；1-[(2R,5S)-5-(hydroxymethyl)-5-vinyl-2H-furan-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,5S)-5-ethenyl-5-(hydroxymethyl)-2H-furan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: DMMHWMLOGNSFSI-SKDRFNHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Acetic acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-vinyl-2,5-dihydro-furan-2-ylmethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 生成 4′-vinyl-d4T
  参考文献：
  名称：

  Synthesis of a highly active new anti-HIV agent 2′,3′-Didehydro-3′-deoxy-4′-ethynylthymidine

  摘要：

  Compounds having methyl, vinyl, and ethynyl groups at the 4'-position of stavudine (d4T: 2',3'-didehydro-3'-deoxythymidine) were synthesized. The compounds were assayed for their ability to inhibit the replication of HIV in cell culture. The 4'-ethynyl analogue (15) was found to be more potent and less toxic than the parent compound stavudine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.009

文献信息

• A NEW APPROACH TO THE SYNTHESIS OF 4′-CARBON-SUBSTITUTED NUCLEOSIDES: DEVELOPMENT OF A HIGHLY ACTIVE ANTI-HIV AGENT 2′, 3′-DIDEHYDRO-3′-DEOXY-4′-ETHYNYLTHYMIDINE
  作者：Kazuhiro Haraguchi、Shingo Takeda、Masanori Sumino、Hiromichi Tanaka、Ginger E. Dutschman、Yung-Chi Cheng、Takao Nitanda、Masanori Baba

  DOI：10.1081/ncn-200059774

  日期：2005.4.1

  Oxidation of 3'-O-TBDMS-4',5'-unsaturated thymidine 3 with dimethyldioxirane (DMDO) allowed the isolation of the epoxide 4. Upon reacting with organosilicon reagents in the Presence of SnCl4, 4 underwent stereoselective ring opening to give 4'-alpha-allyl (6), 4'-alpha-(2-bromoallyl) (7), 4'-alpha(cyclopenten-3-yl) (8), and 4'-alpha-cyano (9) derivatives of thymidine. Reactions of the 3'-epimer 12 with organoaluminum reagents gave 4-alpha-methyl (13), 4'-alpha-vinyl (14), and 4'-alpha-ethynyl (15) analogues. Compounds 13-15 were transformed into corresponding 2',3'-didehydro-3'-deoxy derivatives. Evaluation of their ability to inhibit the replication of HIV in cell culture showed that 4'-ethynyl-d4T (19) is more potent and less toxic than the parent compound d4T.
• [EN] LINE-1 INHIBITORS AS COGNITIVE ENHANCERS<br/>[FR] INHIBITEURS DE LINE-1 UTILISÉS EN TANT QU'ACTIVATEURS COGNITIFS
  申请人：[en]TRANSPOSON THERAPEUTICS, INC.

  公开号：WO2022256625A1

  公开（公告）日：2022-12-08

  The present disclosure provides methods of enhancing cognition, inhibiting cognitive decline, treating or preventing a cognitive deficit disorder, or treating or preventing Creutzfeldt-Jakob disease (CJD) in a subject in need thereof comprising administering a LINE-1 inhibitor, or a pharmaceutical composition thereof, to the subject.