5-decynyl-2'-deoxyuridine | 78824-46-1

• 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: 5-decynyl-2'-deoxyuridine
• 英文别名: 5-dec-1-ynyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 78824-46-1
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: CXQLEVUWAFTOOE-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  5-decynyl-2'-deoxyuridine 在 TEA 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 5-Dec-1-ynyl-4-[1,2,4]triazol-1-yl-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Bicyclic anti-VZV nucleosides: Thieno analogues retain full antiviral activity

  摘要：

  Thieno analogues of the potent and selective furo-pyrimidine anti-VZV nucleoside family are herein reported. The compounds retain full antiviral potency in comparison to the furo parent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00471-1
• 作为产物：
  描述：

  di-O-trimethylsilyl-5-iodo-2'-deoxyuridine 在 TEA 、 水 作用下， 生成 5-decynyl-2'-deoxyuridine
  参考文献：
  名称：

  Alcynyl-5脱氧2'尿苷与有机锌的偶合产物，碘代-s 0-3'，5'-双（三甲基甲硅烷基）脱氧尿苷，催化有机物和镍的配合物

  摘要：

  通过炔基锌试剂与0-3'，5'-双（三甲基甲硅烷基）脱氧尿苷的钯和镍催化反应，可以低至中等的产率获得5-炔基2'-脱氧尿苷

  DOI：

  10.1016/0040-4039(81)89015-6

文献信息

• [EN] ANTI-VIRAL PYRIMIDINE NUCLEOSIDE ANALOGUES<br/>[FR] ANALOGUES DE NUCLEOSIDES DE PYRIMIDINE ANTIVIRAUX
  申请人：UNIV CARDIFF

  公开号：WO1998049177A1

  公开（公告）日：1998-11-05

  A compound having formula (I), wherein R is selected from the group comprising C5 to C20 alkyl, C5 to C20 cycloalkyl, halogens, aryl and alkylaryl; 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, S and CY2, 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, N- alkyl, (CH2)n where n is 1 to 10, and CY2 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; U'' is H and U' is selected from H and CH2T, or U' and U'' are joined so as to form a ring moiety including Q wherein U'-U'' together is respectively selected from the group comprising -CTH-CT'T''- and -CT=CT- and -CT'=CT'-, so as to provide ring moieties selected from the group comprising formula (II) and (III) wherein T is selected from the group comprising OH, H, halogens, O-alkyl, O-acyl, O-aryl, CN, NH2 and N3; T' is selected from the group comprising H and halogens and where more than one T' is present they may be the same or different; T'' is selected from the group comprising H and halogens, and W is selected from the group comprising H, a phosphate group and a pharmacologically acceptable salt, derivative or prodrug thereof shows potent anti-viral activity against, for example, varicella zoster virus and cytomegalovirus.

  化合物的化学式为（I），其中R选择自C5到C20烷基，C5到C20环烷基，卤素，芳基和烷基芳基的群体；R'选择自氢，烷基，环烷基，卤素，氨基，烷基氨基，双烷基氨基，硝基，氰基，烷氧基，芳氧基，硫醇，烷硫醇，芳硫醇，烷基；R''选择自氢，烷基，环烷基，卤素，烷氧基，芳氧基和芳基；Q选择自O，S和CY2的群体，其中Y可以相同或不同，选择自氢，烷基和卤素；X选择自O，NH，S，N-烷基，（CH2）n，其中n为1至10，和CY2，其中Y可以相同或不同，选择自氢，烷基和卤素；Z选择自O，S，NH和N烷基；U''为H，U'选择自H和CH2T，或U'和U''结合形成包括Q的环基，其中U'-U''分别选择自-CTH-CT'T''-和-CT=CT-和-CT'=CT'-，从而提供从化学式（II）和（III）中选择的环基，其中T选择自OH，H，卤素，O-烷基，O-酰基，O-芳基，CN，NH2和N3；T'选择自H和卤素，当存在多个T'时，它们可以相同或不同；T''选择自H和卤素，W选择自H，磷酸盐基团和药理学上可接受的盐，衍生物或前药，表现出强大的抗病毒活性，例如对带状疱疹病毒和巨细胞病毒。
• Enzyme catalyzed therapeutic compounds
  申请人：——

  公开号：US20040077588A1

  公开（公告）日：2004-04-22

  This invention provides novel substrate compounds that selectively inhibit the proliferation f path logical cells, for example, pathological cells that endogenously overexpress a target enzyme that confers resistance to biologic and chemotherapeutic agents. The enzyme acts on a substrate compound to 1) convert it to a cellular toxin and/or 2) release a toxic byproduct. In one embodiment, the activity of the target enzyme has been greatly enhanced in a target cell as a result of loss f tum r suppressor function and/or selection resulting from previous exposure to chemotherapy. In another embodiment, the pathological cell contains a target enzyme that is an expression product of an infectious agent in the cell. Further provided by this invention is a method for treating a subject by delivering to the subject a prodrug as described herein. The prodrugs f this invention may be used alone or in combination with ther chemotherapeutics or alternative anti-cancer therapies such as radiation.

  本发明提供了新型底物化合物，其选择性地抑制病理细胞的增殖，例如，内源性过度表达靶酶的病理细胞，该靶酶赋予生物和化学治疗药物抵抗力。该酶作用于底物化合物，以1）将其转化为细胞毒素和/或2）释放有毒副产物。在一种实施例中，由于肿瘤抑制因子功能的丧失和/或先前接受化疗的选择，靶细胞中的靶酶活性已被大大增强。在另一种实施例中，病理细胞包含一个靶酶，该靶酶是细胞内感染因子的表达产物。本发明还提供了一种通过向受试者输送如本文所述的前药来治疗受试者的方法。本发明的前药可以单独使用或与其他化疗药物或替代抗癌疗法（例如放疗）联合使用。
• Novel phosphoramidate compounds and methods of use
  申请人：——

  公开号：US20030109697A1

  公开（公告）日：2003-06-12

  This invention provides compounds, compositions and methods for treating cancer, infectious disease, an autoimmune disorder or an inflammatory condition. Therapeutic compounds useful in the methods of this invention are 5′-phosphoramidatyl, 1,5-substituted pyrimidine compounds, derivatives, analogs and pharmaceutically acceptable salts thereof

  该发明提供了用于治疗癌症、传染病、自身免疫性疾病或炎症状况的化合物、组合物和方法。该发明方法中有用的治疗化合物是5'-磷酰胺基、1,5-取代嘧啶化合物、衍生物、类似物和药学上可接受的盐。
• Synergistic ECTA compositions
  申请人：——

  公开号：US20020147175A1

  公开（公告）日：2002-10-10

  This invention provides compositions containing an effective amount of a novel substrate compound that selectively inhibit the proliferation of hyperproliferative cells, for example, pathological cells that endogenously overexpress a target enzyme that confers resistance to biologic and chemotherapeutic agents and an effective amount of a nucleoside transport antagonistic agents. Further provided by this invention is a method for treating a subject by delivering to the subject the composition as described herein. The compositions of this invention may be used alone or in combination with other chemotherapeutics or alternative anti-cancer therapies such as radiation.

  本发明提供了一种含有有效量的新型底物化合物的组合物，该化合物选择性地抑制过度增殖的细胞，例如，内源性过度表达靶酶的病理细胞，并提供了有效量的核苷酸转运拮抗剂。本发明还提供了一种通过向受试者输送所述组合物来治疗受试者的方法。本发明的组合物可以单独使用或与其他化疗药物或替代抗癌疗法（如放疗）结合使用。
• Methods to treat autoimmune and inflammatory conditions
  申请人：——

  公开号：US20020151519A1

  公开（公告）日：2002-10-17

  This invention provides methods for treating inflammatory or autoimmune diseases by contacting the affected cell or tissue with a therapeutic compound as described herein. Such pathologies include, but are not limited to rheumatoid arthritis, systemic lupus erythmatosus, psoriatic arthritis, reactive arthritis, Crohn's disease, ulcerative colitis and scleroderma. Therapeutic compounds useful in the methods of this invention are selected from the group consisting of a 1,5-substituted pyrimidine derivative or analog and substituted furano-pyrimidone analog.

  这项发明提供了一种通过使用本发明所述的治疗化合物与受影响的细胞或组织接触来治疗炎症性或自身免疫性疾病的方法。这些病理包括但不限于类风湿性关节炎、系统性红斑狼疮、银屑病性关节炎、反应性关节炎、克罗恩病、溃疡性结肠炎和硬化症。本发明方法中有用的治疗化合物选自1,5-取代嘧啶衍生物或类似物和取代呋喃嘧啶酮类似物组成的群体。