1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol | 64332-73-6

• 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: 1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol
• 英文别名: 4(R)-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-2(R)-(hydroxymethyl)tetrahydrofuran-3(S)-ol；2-deoxyisouridine；1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl)-1H-pyrimidine-2,4-dione；1-[(3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]pyrimidine-2,4-dione
• CAS: 64332-73-6
• 化学式: C₉H₁₂N₂O₅
• 分子量: 228.205
• InChiKey: XQXOEBXJABEVDU-JKMUOGBPSA-N

物化性质

• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol 在 吡啶 、 二氯乙酸 、 TPS-TAZ 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (2R,3S,4R)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(2-chloro-phenoxy)-phosphoryloxymethyl]-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Discovery of a nuclease-resistant, non-natural dinucleotide that inhibits HIV-1 integrase

  摘要：

  Integration of HIV viral DNA into human chromosomal DNA catalyzed by HIV integrase is essential for the replication of HIV. Discovery of novel inhibitors of HIV integrase is of considerable significance in approaches to the development of therapeutic agents against AIDS. We have synthesized a new dinucleotide 1 with an internucleotide phosphate bond that is unusually resistant to exonucleases. This compound exhibits potent anti-HIV-1 integrase activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00231-1
• 作为产物：
  描述：

  [(3aR,4R,6aS)-2,2-dioxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiol-4-yl]methoxy-tert-butyl-diphenylsilane 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 22.5h， 生成 1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol
  参考文献：
  名称：

  异构核苷的新通用合成

  摘要：

  描述了一种有效的合成异核苷的新方法。合成中的关键步骤是嘌呤和嘧啶碱基与碳水化合物中间体的环状硫酸盐直接偶联。该反应以高区域专一性和立体专一性进行。

  DOI：

  10.1016/s0040-4039(01)01118-2

文献信息

• Purinyl and pyrimidinyl tetrahydrofurans
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0464769A2

  公开（公告）日：1992-01-08

  Antiviral activity is exhibited by compounds having the formula and its pharmaceutically acceptable salts.

  具有以下式子的化合物具有抗病毒活性 及其药学上可接受的盐类。
• Anti-infective compositions, methods and systems for treating pathogen-induced disordered tissues
  申请人：Johnson Ron B.

  公开号：US20060135464A1

  公开（公告）日：2006-06-22

  Compositions, methods and systems for treating disordered epithelial tissues, such as is caused by pathogens and/or by toxins produced thereby. The invention relates to the use of an anti-infective and/or antimicrobial active agent in a carrier, with vigorous agitation of the disordered epithelial tissue for topical treatment thereof under such conditions sufficient to achieve clinically discernable improvement of the disordered epithelial tissue. The preferred anti-infective and/or antimicrobial active agent comprises a nucleoside, such as acyclovir, valcyclovir, penciclovir, famciclovir, ganciclovir, cidofovir, adefovir, and tenofovir, and derivatives, analogs, or metabolites thereof, or a mixture thereof, or 1-docosanol, optionally in combination with an organohalide. The inventive compositions and methods may employ the use of an applicator adapted for use in promoting the penetration of the treatment composition and/or the vigorous agitation of the disordered tissue.

  用于治疗紊乱上皮组织的组合物、方法和系统，例如由病原体和/或由此产生的毒素引起的紊乱上皮组织。本发明涉及在载体中使用抗感染和/或抗菌活性剂，并对紊乱的上皮组织进行剧烈搅拌，在足以使紊乱的上皮组织得到临床上可识别的改善的条件下进行局部治疗。优选的抗感染和/或抗菌活性剂包括核苷类药物，如阿昔洛韦、valcyclovir、penciclovir、famciclovir、ganciclovir、cidofovir、adefovir 和 tenofovir 及其衍生物、类似物或代谢物，或其混合物，或 1-docosanol，可选择与有机卤化物结合使用。本发明的组合物和方法可以使用适用于促进治疗组合物渗透和/或剧烈搅拌紊乱组织的涂抹器。
• Synthesis of Isonucleosides Related to AZT and AZU
  作者：David F. Purdy、Lawrence B. Zintek、Vasu Nair

  DOI：10.1080/15257779408013230

  日期：1994.3

  Approaches to 1,4-anhydro-3-azido-2,3-dideoxy-2-[3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl]-D-arabinitol, and the related uracil derivative, have been developed. These conceptually new, optically active analogs of AZT, derived from 1,4-anhydro-D-ribitol, are among the first examples of regioisomeric analogs of AZT.
• Synthesis and Antiviral Studies of Unsaturated Analogues of Isomeric Dideoxynucleosides
  作者：Sanjib Bera、Travis Mickle、Vasu Nair

  DOI：10.1080/07328319908044614

  日期：1999.11

  Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal Xray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.
• Resistance towards exonucleases of dinucleotides with stereochemically altered internucleotide phosphate bonds
  作者：Vasu Nair、Suresh Pal

  DOI：10.1016/j.bmcl.2003.07.034

  日期：2004.1

  Kinetic constants for the hydrolytic susceptibility of the internucleotide phosphate bond in normal dinucleotides [e.g., 2'-deoxycytidylyl-(3' > 5')-2'-deoxyuridine (dCpdU) and 2'-deoxyadenylyl-(3'--> 5')-2-deoxycytidine (dApdC)] and isomeric dinucleotides [e.g., 2-deoxycytidylyl-(3' --> 5')-1'-deoxy-2-isouridine (dCpisodU) and 1'-deoxy-2'-isoadenylyl-(3' --> 5')-2-deoxycytidine (isodApdC)], toward 5'- and 3'-exonucleases, phosphodiesterase I (PDE I) and phosphodiesterase II (PDE II) were experimentally determined and remarkable differences emerged. The study is of importance in the discovery of nuclease-stable inhibitors of HIV integrase, but may also have ramifications in the area of anti-sense oligonucleotides of therapeutic interest. (C) 2003 Elsevier Ltd. All rights reserved.