1-hydroxy-6-((4-methoxyphenyl)-diphenylmethylamino)-hexane | 114729-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-hydroxy-6-((4-methoxyphenyl)-diphenylmethylamino)-hexane
• 英文别名: 6-(4-monomethoxytritylamino)hexan-1-ol；6(monomethoxytritylamino)hexan-1-ol；6-[Methoxy(trityl)amino]hexanol；1-Hexanol, 6-[[(4-methoxyphenyl)diphenylmethyl]amino]-；6-[[(4-methoxyphenyl)-diphenylmethyl]amino]hexan-1-ol
• CAS: 114729-83-8
• 化学式: C₂₆H₃₁NO₂
• 分子量: 389.538
• InChiKey: TVPCVCIUPSVSBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxy-6-((4-methoxyphenyl)-diphenylmethylamino)-hexane 在 sodium periodate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 生成 6-氨基-1-己醇
  参考文献：
  名称：

  Selective Cleavage of O-(Dimethoxytrityl) Protecting Group with Sodium Periodate

  摘要：

  在水有机溶剂中，过碘酸钠在温和的反应条件下选择性地去除了O-(二甲氧基三苯甲基)保护基团。利用核苷衍生物进行了裂解的选择性研究，这些核苷衍生物受到核苷和核苷酸化学中常用的各种基团的保护。

  DOI：

  10.1135/cccc20020502
• 作为产物：
  描述：

  6-氨基-1-己醇 、 4-甲氧基三苯基氯甲烷 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以88%的产率得到1-hydroxy-6-((4-methoxyphenyl)-diphenylmethylamino)-hexane
  参考文献：
  名称：

  Polymer support synthesis of oligodeoxyribonucleotide with an aminoethyl or aminohexyl group at the 5' end by the phosphite-triester approach.

  摘要：

  在N-保护的3'-苯甲氧基脱氧核糖核苷的5'-磷酸基团上引入了N-单甲氧基三苯基氧乙基或六基团。经过3'-O-去苯甲酰化和磷酰化后，它们被转化为3'-磷酰胺衍生物。这些衍生物在合成具有氨基乙基或氨基己基的18个脱氧核苷酸的最后偶联反应中使用，采用磷酸三酯法在长链烷基胺控制的孔玻璃珠上进行。经过硫酚和氨处理的部分去保护寡聚物，通过利用单甲氧基三苯基基团的疏水性，迅速在反相C-18硅胶柱上分离。经过醋酸处理，获得了5'端带有氨基乙基或氨基己基的18聚体，随后与荧光化合物进行偶联。与互补寡核苷酸杂交后，测量了紫外-温度特征。

  DOI：

  10.1248/cpb.36.1386

文献信息

• [EN] OLIGONUCLEOTIDES, COMPOSITIONS AND METHODS THEREOF<br/>[FR] OLIGONUCLÉOTIDES, COMPOSITIONS ET MÉTHODES ASSOCIÉES
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2017210647A1

  公开（公告）日：2017-12-07

  The present disclosure pertains to the recognition that immune responses mediated by CpG oligonucleotides can be affected by the stereochemistry of modified internucleotidic linkages such as phosphorothioates. In some embodiments, the present disclosure relates to chirally controlled CpG oligonucleotide compositions comprising CpG oligonucleotides comprising multiple modified internucleotidic linkages such as phosphorothioate linkages, wherein the oligonucleotides comprise one or more CpG region motifs having defined stereochemistry patterns of chiral internucleotidic linkages. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are capable of agonizing an immune response. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are antagonistic. Methods for making and using chirally controlled CpG oligonucleotide compositions are also described. In some embodiments, no immune modulation is desired, and the present disclosure provides methods of identifying chirally controlled oligonucleotide compositions which have decreased immune modulation.

  本公开涉及到一种认识，即由CpG寡核苷酸介导的免疫反应可能会受到修饰的核苷酸间连接的立体化学结构的影响，例如磷酸硫酯。在某些实施例中，本公开涉及到手性控制的CpG寡核苷酸组合物，包括包含多个修饰的核苷酸间连接，如磷酸硫酯连接的CpG寡核苷酸，其中这些寡核苷酸包含一个或多个具有定义的手性核苷酸间连接模式的CpG区域基序。在某些实施例中，包含一个或多个CpG区域基序的CpG寡核苷酸能够激活免疫反应。在某些实施例中，包含一个或多个CpG区域基序的CpG寡核苷酸是拮抗性的。还描述了制备和使用手性控制的CpG寡核苷酸组合物的方法。在某些实施例中，不需要免疫调节，本公开提供了一种识别具有降低免疫调节的手性控制寡核苷酸组合物的方法。
• Polymer support synthesis of oligodeoxyribonucleotide with an aminoethyl or aminohexyl group at the 5' end by the phosphite-triester approach.
  作者：TOSHIKI TANAKA、YASUKI YAMADA、MORIO IKEHARA

  DOI：10.1248/cpb.36.1386

  日期：——

  An N-monomethoxytrityloxyethyl or-hexyl group was introduced onto the 5'-phosphoryl group of N-protected-3'-benzoyldeoxynucleosides. After 3'-O-debenzoylation and phosphitylation, they were converted 3'-phosphoramidite derivatives. These were used at the last coupling reaction in the synthesis of octadecadeoxynucleotides with an aminoethyl or aminohexyl group at the 5' end by the phosphite-triester method on long-chain alkylamine controlled pore glass beads. Partially deblocked oligomers, after thiophenol and ammonia treatment, were separated rapidly on a reversed-phase C-18 silica gel column by utilizing the hydrophobic nature of the monomethoxy-trityl group. After AcOH treatment, the octadecamers with an aminoethyl or aminohyxyl group at the 5' end were obtained and then coupled with a fluorescent compound. The ultraviolet-temperature profiles were measured after hybridization with a complementary oligonucleotide.

  在N-保护的3'-苯甲氧基脱氧核糖核苷的5'-磷酸基团上引入了N-单甲氧基三苯基氧乙基或六基团。经过3'-O-去苯甲酰化和磷酰化后，它们被转化为3'-磷酰胺衍生物。这些衍生物在合成具有氨基乙基或氨基己基的18个脱氧核苷酸的最后偶联反应中使用，采用磷酸三酯法在长链烷基胺控制的孔玻璃珠上进行。经过硫酚和氨处理的部分去保护寡聚物，通过利用单甲氧基三苯基基团的疏水性，迅速在反相C-18硅胶柱上分离。经过醋酸处理，获得了5'端带有氨基乙基或氨基己基的18聚体，随后与荧光化合物进行偶联。与互补寡核苷酸杂交后，测量了紫外-温度特征。
• Polyamide-oligonucleotide derivatives, their preparation and use
  申请人：Hoechst Marion Roussel Deutschland GmbH

  公开号：US20030203359A1

  公开（公告）日：2003-10-30

  Polyamide-oligonucleotide derivatives of the formula F[(DNA-Li) q (PNA-Li) r (DNA-Li) s (PNA) t ] x F′ wherein q, r, s, t are, independently of one another, zero or 1, where the total of two or more adjacent q, r, s and t≧2; x is 1 to 20; DNA is a nucleic acid such as DNA or RNA or a known derivative thereof; Li is a covalent linkage between DNA and PNA, where the covalent linkage comprises a bond or an organic radical with at least one atom from the series consisting of C, N, O or S; PNA is a polyamide structure which contains at least one nucleotide base which is different from thymine; and F and F′ are end groups and/or are linked together by a covalent bond, and the physiologically tolerated salts thereof, a process for their preparation and their use as pharmaceutical, as gene probe and as primer, are described.

  本文描述了式F[(DNA-Li)q(PNA-Li)r(DNA-Li)s(PNA)t]xF′的聚酰胺-寡核苷酸衍生物，其中q，r，s，t独立地为0或1，相邻的q，r，s和t之和大于等于2；x为1至20；DNA是核酸，例如DNA或RNA或其已知衍生物；Li是DNA和PNA之间的共价连接，其中共价连接包括一个键或一个有机基团，该有机基团至少包含来自C、N、O或S系列的一个原子；PNA是聚酰胺结构，其中至少包含一种与胸腺嘧啶不同的核苷酸碱基；F和F′是末端基团和/或通过共价键连接在一起，并描述了其生理耐受盐的制备方法以及作为制药、基因探针和引物的用途。
• Oligonucleotide compositions and methods thereof
  申请人：WAVE LIFE SCIENCES LTD.

  公开号：US10450568B2

  公开（公告）日：2019-10-22

  Among other things, the present disclosure relates to designed oligonucleotides, compositions, and methods thereof. In some embodiments, provided oligonucleotide compositions provide altered splicing of a transcript. In some embodiments, provided oligonucleotide compositions have low toxicity. In some embodiments, provided oligonucleotide compositions provide improved protein binding profiles. In some embodiments, provided oligonucleotide compositions have improved delivery. In some embodiments, provided oligonucleotide compositions have improved uptake. In some embodiments, the present disclosure provides methods for treatment of diseases using provided oligonucleotide compositions.

  除其他外，本公开涉及设计的寡核苷酸、组合物及其方法。在一些实施方案中，所提供的寡核苷酸组合物能改变转录本的剪接。在一些实施方案中，所提供的寡核苷酸组合物具有低毒性。在一些实施方案中，所提供的寡核苷酸组合物提供了改进的蛋白质结合概况。在一些实施方案中，所提供的寡核苷酸组合物具有更好的传递性。在一些实施方案中，所提供的寡核苷酸组合物改善了吸收。在一些实施方案中，本公开提供了使用所提供的寡核苷酸组合物治疗疾病的方法。
• Oligonucleotides, compositions and methods thereof
  申请人：WAVE LIFE SCIENCES LTD.

  公开号：US11013757B2

  公开（公告）日：2021-05-25

  The present disclosure pertains to the recognition that immune responses mediated by CpG oligonucleotides can be affected by the stereochemistry of modified internucleotidic linkages such as phosphorothioates. In some embodiments, the present disclosure relates to chirally controlled CpG oligonucleotide compositions comprising CpG oligonucleotides comprising multiple modified internucleotidic linkages such as phosphorothioate linkages, wherein the oligonucleotides comprise one or more CpG region motifs having defined stereochemistry patterns of chiral internucleotidic linkages. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are capable of agonizing an immune response. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are antagonistic. Methods for making and using chirally controlled CpG oligonucleotide compositions are also described. In some embodiments, no immune modulation is desired, and the present disclosure provides methods of identifying chirally controlled oligonucleotide compositions which have decreased immune modulation.

  本公开涉及这样一种认识，即 CpG 寡核苷酸介导的免疫反应可受硫代磷酸酯等修饰的核苷酸间连接的立体化学的影响。在一些实施方案中，本公开涉及手性控制的 CpG 寡核苷酸组合物，该组合物包含CpG 寡核苷酸，该CpG 寡核苷酸包含多个修饰的核苷酸间连接，如硫代磷酸酯连接，其中寡核苷酸包含一个或多个 CpG 区域基序，该 CpG 区域基序具有手性核苷酸间连接的确定立体化学模式。在一些实施方案中，包含一个或多个 CpG 区域基团的 CpG 寡核苷酸能够激动免疫反应。在某些实施方案中，包含一个或多个 CpG 区域基团的 CpG 寡核苷酸具有拮抗作用。还描述了制作和使用啁啾控制 CpG 寡核苷酸组合物的方法。在某些实施方案中，不需要免疫调节，本公开提供了确定免疫调节性降低的手性控制寡核苷酸组合物的方法。