L-2',3'-dideoxy-5-iodo-uridine | 1417791-34-4

• 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: L-2',3'-dideoxy-5-iodo-uridine
• 英文别名: 1-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 1417791-34-4
• 化学式: C₉H₁₁IN₂O₄
• 分子量: 338.102
• InChiKey: OBGFSDPYSQAECJ-VDTYLAMSSA-N

物化性质

• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 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：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-2',3'-dideoxy-5-iodo-uridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 3-(2',3'-dideoxy-ribo-β-L-furanosyl)-6-(9-n-pentyloxynonyl)furo[2,3-d]pyrimidin-2(3H)-one
  参考文献：
  名称：

  CHEMICAL COMPOUNDS

  摘要：

  在碱基部分上含有6-取代基的3-(2′,3′-二脱氧-β-L-呋喃核糖基)[2,3-d]嘧啶-2(3H)-酮衍生物显示出抗病毒特性，特别是对天花病毒和麻疹病毒。这些化合物具有非自然的L-核糖立体化学结构。

  公开号：

  US20130012468A1
• 作为产物：
  描述：

  5′,3′-diacetyl-2′-bromo-2′-deoxyuridine 在 ammonium cerium (IV) nitrate 、 palladium 10% on activated carbon 、 氢气 、 碘 、 sodium methylate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 31.0h， 生成 L-2',3'-dideoxy-5-iodo-uridine
  参考文献：
  名称：

  Novel Antiviral Activity of l-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro

  摘要：

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.

  DOI：

  10.1021/jm301778x

文献信息

• [EN] CONDENSED PYRIMIDINE NUCLEOSIDE ANALOGS AS ANTI -VIRAL AGENTS<br/>[FR] ANALOGUES DE NUCLÉOSIDES DE PYRIMIDINE CONDENSÉS EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UNIV CARDIFF

  公开号：WO2013007992A1

  公开（公告）日：2013-01-17

  3-(2',3'-dideoxy-ribo-β-L-furanosyl)[2,3-d]pyrimidin-2(3H)-one derivatives comprising 6-substitutents on the base moiety are shown to have anti-viral properties, particularly with respect to vaccinia and measles. The compounds have unnatural L ribose stereochemistry.

  已知在嘌呤碱基部分具有6-取代基的3-(2',3'-二去氧-β-L-呋喃核苷基)[2,3-d]嘧啶-2(3H)-酮衍生物具有抗病毒性能，特别是针对天花病毒和麻疹病毒。这些化合物具有非天然的L核糖立体化学结构。
• Therapeutic nucleosides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0217580A2

  公开（公告）日：1987-04-08

  The present invention relates to certain novel 3'- azidonucleosides and pharmaceutically acceptable derivatives thereof; the use of certain 3'-azidonucleosides, their pharmaceutically acceptable derivatives and therapeutic combinations containing them, in therapy, particularly in the treatment and prophylaxis of gram negative bacterial infections and retroviral infections, especially AIDS; to processes for the preparation of 3'-azidonucleosides; and to formulations containing them.

  本发明涉及某些新型 3'-叠氮核苷及其药学上可接受的衍生物；某些 3'-叠氮核苷、其药学上可接受的衍生物和含有它们的治疗组合物在治疗中的用途，特别是在革兰氏阴性细菌感染和逆转录病毒感染（尤其是艾滋病）的治疗和预防中的用途；3'-叠氮核苷的制备工艺；以及含有它们的制剂。
• Method of gene mapping
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0309969A2

  公开（公告）日：1989-04-05

  The method described characterizes each DNA segment to be mapped by cleaving it to produce DNA fragments which are then end labeled with a reporter(s) specific to the end nucleotides of each fragment. The labeled fragments are again cleaved to produce short fragments which are separated according to size. The short fragments are analyzed as to reporter identity and size which is indicative of the character of each fragment. By derivatizing the cleaved ends of the primary cleaved fragments, the labeling may be delayed until the second cleavage. Prior to labeling the derivatized fragments, all underivatized fragments are removed, the derivatized fragments being immobilized.

  所述方法通过裂解 DNA 片段产生 DNA 片段，然后用特异于每个片段末端核苷酸的报告物对其进行末端标记，从而确定要绘制的每个 DNA 片段的特征。标记后的片段再次裂解，产生短片段，并根据大小将其分离。对短片段进行分析，以确定报告基因的特性和大小，这表明了每个片段的特性。通过对初级裂解片段的裂解末端进行衍生处理，可将标记延迟到第二次裂解。在对衍生片段进行标记之前，先移除所有未充分活化的片段，然后固定衍生片段。
• Anti-viral pyrimidine nucleoside analogues
  申请人：——

  公开号：US20030176370A1

  公开（公告）日：2003-09-18

  A compound, which can show potent anti-viral activity against, for example, cytomegalo virus, has the formula (I), wherein R is selected from the group comprising, optionally substituted, C 5 to C 20 alkyl and, optionally substituted, C 5 to C 20 cycloalkyl; R′ is selected from the group comprising hydrogen, alkyl, cycloalkyl, halogens, amino, alkylamino, dialkylamino, nitro, cyano, alkyoxy, aryloxy, thiol, alkylthiol, arythiol, alkyl; R″ is selected from the group comprising hydrogen, alkyl, cycloalkyl, halogens, alkyloxy, aryloxy and aryl; Q is selected from the group comprising O, NH, S, N-alkyl and CY 2 , where Y may be the same or different and is selected from H, alkyl and halogens; X is selected from the group comprising O, NH, S, Se, N-alkyl, (CH 2 ) n where n is 1 to 10, and CY 2 where Y may be the same or different and is selected from hydrogen, alkyl and halogens; Z is selected from the group comprising O, S, NH, and N-alkyl; T is selected from the group comprising H, halogens, alkyl (C 1 to C 10 ), O-alkyl (C 1 to C 10 ), N 3 and CN; T′ is selected from the group comprising H, halogens, O-alkyl (C 1 to C 10 ), N 3 and CN; or T and T′ together form a bridge which is selected from the group comprising —O—, —NH— and —(CH 2 ) p — wherein p is an integer from 1 to 6; T″ is selected from the group comprising H, OH, halogens, N 3 and CN; T′″ is selected from the group comprising H, OH, halogens, N 3 and CN; or T″ and T′″ together form a bridge which is selected from the group comprising —O—, —NH— and —(CH 2 ) p — wherein p is an integer from 1 to 6; or T and T′″ together form ═CH 2 ; and W is selected from the group comprising H, a phosphate group a phosphonate group; and a pharmacologically acceptable salt derivative or pro-drug thereof.

  一种可对例如巨细胞病毒表现出强效抗病毒活性的化合物具有式(I)，其中 R 选自由任选取代的 C 5 至 C 20 烷基和任选取代的 C 5 至 C 20 R′选自包括氢、烷基、环烷基、卤素、氨基、烷基氨基、二烷基氨基、硝基、氰基、烷氧基、芳氧基、硫醇、烷硫醇、芳硫醇、烷基在内的组；R″选自包括氢、烷基、环烷基、卤素、烷氧基、芳氧基和芳基在内的组；Q 选自包括 O、NH、S、N-烷基和 CY 2 其中 Y 可以相同或不同，选自 H、烷基和卤素； X 选自包括 O、NH、S、Se、N-烷基、(CH2) 2 ) n 其中 n 为 1 至 10，以及 CY 2 其中 Y 可以相同或不同，选自氢、烷基和卤素；Z 选自 O、S、NH 和 N-烷基；T 选自 H、卤素、烷基（C 1 至 C 10 ）、O-烷基（C 1 至 C 10 ), N 3 和 CN；T′选自包括 H、卤素、O-烷基（C 1 至 C 10 ), N 3 和 CN；或 T 和 T′共同形成一个桥，该桥选自包括 -O-、-NH- 和 -(CH)在内的组。 2 ) p - 其中 p 是 1 到 6 的整数；T″ 选自包括 H、OH、卤素、N 3 和 CN 所组成的组； T′″ 选自包括 H、OH、卤素、N 3 和 CN 所组成的组；或 T″ 和 T′″ 一起形成一个桥，该桥选自由 -O-、-NH- 和 -(CH 2) 组成的组。 2 ) p - 其中 p 是 1 到 6 的整数；或 T 和 T′″一起形成 ═CH 2 和 W 选自包括 H、磷酸基团、膦酸基团和药理学上可接受的盐衍生物或其原药的组。
• Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides
  作者：Naina A. Van Draanen、George W. Koszalka

  DOI：10.1080/15257779408009473

  日期：1994.9

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.