2-methoxy-6-chloro-9-(ω-hydroxy-pentylamino) acridine | 95100-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-methoxy-6-chloro-9-(ω-hydroxy-pentylamino) acridine
• 英文别名: 5-[(6-Chloro-2-methoxy-acridin-9-yl)amino]pentan-1-ol；5-[(6-chloro-2-methoxyacridin-9-yl)amino]pentan-1-ol
• CAS: 95100-75-7
• 化学式: C₁₉H₂₁ClN₂O₂
• 分子量: 344.841
• InChiKey: SBZHVJDTNXBZIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-6-chloro-9-(ω-hydroxy-pentylamino) acridine 在 氢气 作用下， 生成
  参考文献：
  名称：

  Asseline, U.; Barbier, C.; Thuong, N. T., Phosphorus and Sulfur and the Related Elements, 1986, vol. 26, p. 63 - 74

  摘要：

  DOI：
• 作为产物：
  描述：

  5-[(6-chloro-2-methoxyacridin-9-yl)amino]pentyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] hydrogen phosphate 生成 2-methoxy-6-chloro-9-(ω-hydroxy-pentylamino) acridine
  参考文献：
  名称：

  ASSELINE, U.;THUONG, NGUYEN T., TETRAHEDRON LETT., 30,(1989) N9, C. 2521-2524

  摘要：

  DOI：

文献信息

• A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3′-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and -peptide conjugates
  作者：Akira Sakakura、Yoshihiro Hayakawa、Hitoshi Harada、Masaaki Hirose、Ryoji Noyori

  DOI：10.1016/s0040-4039(99)00748-0

  日期：1999.6

  A new method for synthesis of 3′-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base-labile structures such as oligoDNA-OPO(OH)OCH2CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, 5′TGTCGACACCCAATT3′-OPO(OH)OCH2CH(NH2)COOH

  开发了一种新的通过烯丙基保护的亚磷酰胺法合成3'-端磷酸化DNA低聚物的新方法。此方法对于制备具有碱基不稳定结构的衍生物（例如oligoDNA-OPO（OH）OCH 2 CH（R）Z ）特别有用，其中Z是吸电子功能。例如，寡核苷酸-氨基酸偶联物，5' TGTCGACACCCAATT 3' -OPO（OH）OCH 2 CH（NH 2）COOH，和一个寡核苷酸-肽缀合物，5' TGTCGACACCCAATT 3' -OPO（OH）OCH 2 CH（已获得高纯度的NH 2 COOH。
• Synthetic models related to DNA intercalating molecules: Preparation of 9-aminoacridines linked to the nucleotide bases adenine, guanine and thymine
  作者：J. F. Constant、B. M. Carden、J. Lhomme

  DOI：10.1002/jhet.5570220422

  日期：1985.7

  A series of novel compounds were prepared in which the aromatic ring of the drug quinacrine (2-methoxy-6-chloro-9-alkylaminoacridine) is linked to the nucleotide bases adenine, guanine and thymine by penta-and hexamethylene bridges.

  制备了一系列新颖的化合物，其中药物奎纳克林的芳环（2-甲氧基-6-氯-9-烷基氨基ac啶）通过五-和六亚甲基桥与核苷酸碱基腺嘌呤，鸟嘌呤和胸腺嘧啶相连。
• Synthesis and characterization of o6-modified deoxyguanosine-containing oligodeoxyribonucleotides for triple-helix formation
  作者：Franqoise Raynaud、Ulysse Asseline、Victoria Roig、Nguyen Thanh Thuong

  DOI：10.1016/0040-4020(95)01043-2

  日期：1996.2

  Two new modified deoxyguanosine derivatives linked through their C-6 position to a psoralen and an acridine derivative have been synthesized and incorporated into oligonucleotide chains. Difficulties observed during the purification of oligonucleotides containing a stretch of G and one method used to solve this problem are discussed.

  已经合成了通过其C-6位连接到补骨脂素和an啶衍生物的两个新的修饰的脱氧鸟苷衍生物，并将其掺入寡核苷酸链中。讨论了在纯化包含一段G的寡核苷酸的过程中观察到的困难以及用于解决此问题的一种方法。
• Solid-phase synthesis of modified oligodeoxyribonucleotides with an acridine derivative or a thiophosphate group at their 3′end
  作者：U. Asseline、Nguyen T. Thuong

  DOI：10.1016/s0040-4039(01)80440-8

  日期：1989.1

  Use of a derivatized support involving the 2,2′-diethyldithio-group allows the automated synthesis of oligodeoxyribonucleotide bearing acridine derivative (via nucleoside-3′-acridinylphosphoramidite ) or 3′phosphorothioate group (including the sulfurization step for attachment of the first nucleoside to the support).

  使用涉及2,2'-二乙基二硫代基团的衍生化载体可以自动合成带有a啶衍生物（通过核苷3'-ac啶基亚磷酰胺基）或3'硫代磷酸酯基团的寡脱氧核糖核苷酸（包括用于将第一个核苷连接至的硫化步骤支撑）。
• Solid-phase preparation of 5′,3′-heterobifunctional oligodeoxyribonucleotides using modified solid supports
  作者：Ulysse Asseline、Edwige Bonfils、Robin Kurfürst、Marcel Chassignol、Victoria Roig、Nguyen Thanh Thuong

  DOI：10.1016/s0040-4020(01)90786-0

  日期：1992.1

  The solid-phase preparation of oligodeoxyribonucleotides attached to intercalator or reactive groups through their 5'- and (or) 3'-ends is reported. These syntheses implicate the introduction of suitable masked functional groups at the 5'-end of the oligonucleotide by the intermediate of their phosphoramidite derivatives or at the 3'-end of the oligonucleotide using modified solid supports. After full deblocking, the functional groups (phosphate, thiophosphate, primary amine or thiol) can be reacted with the suitable reactive group involved in the chosen ligand. These methods allow the preparation of heterobifunctional derivatized oligodeoxyribonucleotides.