2'-O-phthalimidopropyl-5-methyl-2-thiouridine | 182496-02-2

• 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: 2'-O-phthalimidopropyl-5-methyl-2-thiouridine
• 英文别名: 2-[3-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(5-methyl-4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxypropyl]isoindole-1,3-dione
• CAS: 182496-02-2
• 化学式: C₂₁H₂₃N₃O₇S
• 分子量: 461.496
• InChiKey: XPHLYYLNHNFSHQ-AXHMDWHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  161
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-O-phthalimidopropyl-5-methyl-2-thiouridine 、 肼 在 二氯甲烷 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 2'-O-Aminopropyl-5-methyl-2-thiouridine
  参考文献：
  名称：

  Oligoribonucleotides and ribonucleases for cleaving RNA

  摘要：

  本发明提供了包括寡核苷酸和寡核苷甙在内的寡聚化合物，其中包含2'-戊糖基核苷酸的亚序列，可激活dsRNase。这些寡核苷酸和寡核苷甙可以包括取代基团，以增加与互补核酸链的结合亲和力，以及取代基团，以增加核酸酶抵抗力。这些寡聚化合物可用于诊断和其他研究目的，用于调节生物体中蛋白质的表达，以及用于诊断、检测和治疗其他易感于寡核苷酸治疗的疾病。本发明还包括哺乳动物核酸酶，即降解RNA的酶，以及这种核酸酶的底物。这样的核酸酶在本文中被称为dsRNase，其中“ds”表示RNase对某些双链RNA底物的特异性。本发明所描述的dsRNase的人工底物可用于制备亲和力基质，以纯化哺乳动物核酸酶以及非降解RNA结合蛋白。

  公开号：

  US20020165189A1

文献信息

• Process for the synthesis of 2' -O-substituted pyrimidines and oligomeric compounds therefrom
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US20030050454A1

  公开（公告）日：2003-03-13

  oligonucleotide analogs are disclosed having pyrimidine monomeric sub-units therein that are modified at the 2′ and 5′ positions. Monomeric sub-units having these modifications may be further modified at the 2′ position. Improved processes for the synthesis of 2′-O-substituted pyrimidine nucleosides are also provided. The processes feature alkylation of a 2,2′-anhydropyrimidine nucleoside or a 2S,2′-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  本文披露了含有嘧啶单体亚基的寡核苷酸类似物，其在2'和5'位置进行了修饰。具有这些修饰的单体亚基可以进一步在2'位置进行修饰。还提供了改进的2'-O-取代嘧啶核苷合成过程。该过程采用弱亲核试剂在Lewis酸存在下与2,2'-脱水嘧啶核苷或2S,2'-脱水嘧啶核苷烷基化的方法。
• Processes for the synthesis of 2'-O-substituted pyrimidines and oligomeric compounds therefrom
  申请人：Cook Dan Phillip

  公开号：US20050059815A1

  公开（公告）日：2005-03-17

  Oligonucleotide analogs are disclosed having pyrimidine monomeric sub-units therein that are modified at eh 2′ and 5′ positions. Monomeric sub-units having these modifications may be further modified at the 2′ position. Improved processes for the synthesis of 2′-O-substituted pyrimidine nucleosides are also provided. The processes feature alkylation of a 2,2′-anhydropyrimidine nucleoside or a 2S,2′-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  本文揭示了含有嘧啶单体亚基的寡核苷酸类似物，其在2'和5'位置被修饰。具有这些修饰的单体亚基可以在2'位置进一步修饰。还提供了改进的2'-O-取代嘧啶核苷的合成过程。该过程特点是在Lewis酸存在下，使用弱亲核试剂烷基化2,2'-苯并嘧啶核苷或2S,2'-苯并嘧啶核苷。
• Process for the synthesis of 2'-O-substituted pyrimidines
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US05760202A1

  公开（公告）日：1998-06-02

  Improved processes for the synthesis of 2'-O-substituted pyrimidine nucleosides are provided. The processes feature alkylation of a 2,2'-anhydropyrimidine nucleoside or a 2S,2'-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  提供了用于合成2'-O-取代嘧啶核苷的改进工艺。该工艺特点是在路易斯酸的存在下，使用弱亲核试剂烷基化2,2'-无水嘧啶核苷或2S,2'-无水嘧啶核苷。
• Process for the synthesis of 2′-O-substituted pyrimidines and oligomeric compounds therefrom
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06222025B1

  公开（公告）日：2001-04-24

  Oligonucleotide analogs are disclosed having pyrimidine monomeric sub-units therein that are modified at the 2′ and 5 positions. Monomeric sub-units having these modifications may be further modified at the 2 position. Improved processes for the synthesis of 2′-O-substituted pyrimidine nucleosides are also provided. The processes feature alkylation of a 2,2′-anhydropyrimidine nucleoside or a 2S,2′-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  披露了含有嘧啶单体亚单位的寡核苷酸类似物，其在2'和5'位置进行了修饰。具有这些修饰的单体亚单位可以在2'位置进一步修饰。还提供了改进的2'-O-取代嘧啶核苷合成方法。该方法特征是在路易斯酸存在下，使用弱亲核试剂烷基化2,2'-脱水嘧啶核苷或2S,2'-脱水嘧啶核苷。
• Process For The Synthesis Of 2'-O-Substituted Pyrimidines And Oligomeric Compounds Therefrom
  申请人：Cook Dan Phillip

  公开号：US20070232798A1

  公开（公告）日：2007-10-04

  Oligonucleotide analogs are disclosed having pyrimidine monomeric sub-units therein that are modified at the 2′ and 5′ positions. Monomeric sub-units having these modifications may be further modified at the 2′ position. Improved processes for the synthesis of 2′-O-substituted pyrimidine nucleosides are also provided. The processes feature alkylation of a 2,2′-anhydropyrimidine nucleoside or a 2S,2′-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.

  本发明揭示了含有嘧啶单体亚单位的寡核苷酸类似物，其在2'和5'位置进行了修饰。具有这些修饰的单体亚单位可以在2'位置进一步修饰。还提供了改进的合成2'-O-取代嘧啶核苷的过程。该过程的特点是在弱亲核试剂存在下，与Lewis酸一起烷基化2,2'-无水嘧啶核苷或2S,2'-无水嘧啶核苷。