(2R,5R)-1-[2,5-Dihydro-5-(dimethoxy-phosphinyl)methoxy-2-furanyl]uracil | 1000863-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (2R,5R)-1-[2,5-Dihydro-5-(dimethoxy-phosphinyl)methoxy-2-furanyl]uracil
• 英文别名: 1-[(2R,5R)-5-(dimethoxyphosphorylmethoxy)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
• CAS: 1000863-87-5
• 化学式: C₁₁H₁₅N₂O₇P
• 分子量: 318.223
• InChiKey: VWHHTNNMDBOARC-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,5R)-1-[2,5-Dihydro-5-(dimethoxy-phosphinyl)methoxy-2-furanyl]uracil 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

  摘要：

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.038
• 作为产物：
  描述：

  dimethyl ((((2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate 在 双氧水 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到(2R,5R)-1-[2,5-Dihydro-5-(dimethoxy-phosphinyl)methoxy-2-furanyl]uracil
  参考文献：
  名称：

  Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

  摘要：

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.038

文献信息

• Nucleoside analogs
  申请人：Institute of Organic Chemistry and Biochemistry of the Academy of

  公开号：US05688778A1

  公开（公告）日：1997-11-18

  Provided are compounds of the following formulae: A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl; B is a purine or pyrimidine base. optionally R is taken together with X' to complete a cyclic phosphonate having the formula ##STR2## A 4'-phosphonomethoxytetrahydrofuranyl-1'-purine-pyrimidine of the formula ##STR3## wherein X and X' are the same or different and are hydrogen or alkyl, the dashed line is an optional bond, Y and Z are the same or different and are hydrogen, hydroxyl or alkyl or Y+Z are taken together to form an epoxide or cyclopropyl, and B is a purine or pyrimidine base.

  提供的化合物具有以下结构式：一种磷酸甲氧甲氧甲基嘌呤/嘧啶衍生物的结构式 ##STR1## 其中X和X'相同或不同，可以是氢或烷基。R和R'相同或不同，可以是氢、烷基、羟基烷基或酰基烷基；B是嘌呤或嘧啶碱基。可选地，R与X'结合形成具有结构式 ##STR2## 的环磷酸酯。一种4'-磷酸甲氧基四氢呋喃基-1'-嘌呤-嘧啶的结构式 ##STR3## 其中X和X'相同或不同，可以是氢或烷基，虚线是可选的键，Y和Z相同或不同，可以是氢、羟基或烷基，或者Y+Z结合形成环氧化物或环丙基，B是嘌呤或嘧啶碱基。
• Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates
  作者：Richard L. Mackman、Constantine G. Boojamra、Vidya Prasad、Lijun Zhang、Kuei-Ying Lin、Oleg Petrakovsky、Darius Babusis、James Chen、Janet Douglas、Deborah Grant、Hon C. Hui、Choung U. Kim、David Y. Markevitch、Jennifer Vela、Adrian Ray、Tomas Cihlar

  DOI：10.1016/j.bmcl.2007.10.038

  日期：2007.12

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.