N⁶-(4-methoxybenzoyl) adenine | 97025-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N⁶-(4-methoxybenzoyl) adenine
• 英文别名: N⁶-(4-methoxybenzoyl)adenine；6-(4-Methoxybenzoylamino)purine；N⁶-p-anisoyladenine；N⁶-anisoyl adenine；N6-(4-methoxybenzoyl)adenine；N⁶-(4-anisoyl)adenine；4-methoxy-N-(9H-purin-6-yl)benzamide；4-methoxy-N-(7H-purin-6-yl)benzamide
• CAS: 97025-97-3
• 化学式: C₁₃H₁₁N₅O₂
• 分子量: 269.263
• InChiKey: QSABPJKFCDBSJP-UHFFFAOYSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  92.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁶-(4-methoxybenzoyl) adenine 在 sodium hydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 9-[4-aminobenzyl]-N6-(4-methoxybenzoyl)adenine
  参考文献：
  名称：

  Gel formation properties of a uracil-appended cholesterol gelator and cooperative effects of the complementary nucleobases

  摘要：

  We designed and synthesized a uracil-appended cholesterol gelator (1) in order to control the gel stability and the gel morphology by addition of the complementary and non-complementary nucleobase derivatives. Compound 1 forms columnar stacks in cyclohexane due to the van der Waals interaction (cholesterol-cholesterol interaction) and the intergelator hydrogen bonding between uracil moieties. Addition of a 'monomeric' adenosine (3) into the gel only decreases the stability with increasing the concentration. The destabilization is ascribed to a lack of intergelator hydrogen bonding accompanied with forming the complementary base pairs between 1 and 3. In contrast, addition of adenine-appended cholesterol (7) induces a different behavior; with increasing 7 concentration the mixed gel is initially stabilized and then destabilized, giving rise to a maximum at the ratio of 1/7= 1:1 for the T-gel plot. One may consider, therefore, that when the additive has a common, column-forming cholesterol moiety, the cholesterol-cholesterol interaction can operate cooperatively with the complementary base pairing. In addition, the gel fiber structure is clearly changed by the addition of 7. Taking the fact that there is no report for such an additive effect inducing a structural change with maintaining the gel stability into consideration, our attempt combining cholesterol columnar stacks with the nucleobase additives provides a new methodology to control the stability and the morphology of organogels. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01059-1
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 、 腺嘌呤 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以42%的产率得到N⁶-(4-methoxybenzoyl) adenine
  参考文献：
  名称：

  N 6-苯甲酰腺嘌呤衍生物作为新型BRD4抑制剂的发现及其构效关系研究

  摘要：

  溴结构域和末端外结构域（BET）蛋白是表观遗传阅读器，可与组蛋白中的乙酰化赖氨酸结合。其中，BRD4是用于多种疾病（包括癌症和炎性疾病）的治疗剂的候选靶分子。作为我们对沙利度胺进行结构开发的持续研究的一部分，该研究基于“多模板”方法获得了广泛的生物改性剂，在这项工作中，我们着重于BRD4抑制活性，并发现N 6-苯甲酰腺嘌呤衍生物显示出这种活性。活动。结构与活性之间的关系研究导致了N 6-（2,4,5-三甲氧基苯甲酰基）腺嘌呤（29），其表现出强大的BRD4 bromodomain1抑制活性，IC 50值为0.427μM 。ñ6-苄基腺嘌呤似乎是开发BRD4抑制剂的新化学支架。

  DOI：

  10.1016/j.bmc.2015.01.022

文献信息

• Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers
  作者：Zoltán Timár、Lajos Kovács、Györgyi Kovács、Zoltán Schmél

  DOI：10.1039/a907832k

  日期：——

  acid 7 is described using partial hydrolysis of a dianisoylated derivative. Different methods were studied for guanine alkylation including (a) Mitsunobu reaction; (b) low-temperature, sodium hydride- and (c) N,N-diisopropylethylamine-mediated alkylation reactions to give preferentially N 9-substituted derivatives. Empirical rules are proposed for differentiating N 9/N 7-substituted guanines based on

  聚酰胺（肽）核酸（PNA）单体22–25的化学合成已使用Fmoc [ N-（2-氨基乙基）甘氨酸骨架]，异戊二烯基（腺嘌呤），4-叔丁基苯甲酰基（胞嘧啶）和异丁酰/二苯基氨基甲（鸟嘌呤）的保护基团的组合，从而允许在低聚物合成两个肽和寡核苷酸合成。描述了使用二异氰酸酯化衍生物的部分水解来制备（N 6-茴香酰腺苷-9-基）乙酸7的另一种方法。研究了鸟嘌呤烷基化的不同方法，包括：（a）Mitsunobu反应；（b）低温氢化钠-和（c）N，N-二异丙基乙胺介导的烷基化反应，优先得到N 9-取代的衍生物。提出了基于其13 C NMR化学位移差异来区分N 9 / N 7取代鸟嘌呤的经验规则。
• [EN] COMPOUNDS FOR IMPROVING MRNA SPLICING<br/>[FR] COMPOSÉS POUR AMÉLIORER L'ÉPISSAGE DE L'ARNM
  申请人：GEN HOSPITAL CORP

  公开号：WO2016115434A1

  公开（公告）日：2016-07-21

  Provided herein are compounds useful for improving mRNA splicing in a cell. Exemplary compounds provided herein are useful for improving mRNA splicing in genes comprising at least one exon ending in the nucleotide sequence CAA. Methods for preparing the compounds and methods of treating diseases of the central nervous system are also provided.

  本文提供了一些有助于改善细胞内mRNA剪接的化合物。本文提供的示例化合物有助于改善包含至少一个以核苷酸序列CAA结尾的外显子的基因的mRNA剪接。还提供了制备这些化合物的方法以及治疗中枢神经系统疾病的方法。
• The synthesis of polyamide nucleic acids using a novel monomethoxytrityl protecting-group strategy
  作者：David W. Will、Gerhard Breipohl、Dietrich Langner、Jochen Knolle、Eugen Uhlmann

  DOI：10.1016/0040-4020(95)00766-2

  日期：1995.10

  The preparation of novel monomethoxytrityl (Mmt) protected monomers for the synthesis of polyamide nucleic acids (PNAs) is described. The use of base-labile acyl-type nucleobase protecting groups and of a succinyl-linked solid-support offers a synthetic strategy similar to standard oligonucleotide synthesis conditions. This strategy has been successfully applied for the synthesis of PNAs of mixed base

  描述了用于合成聚酰胺核酸（PNA）的新型单甲氧基三苯甲基（Mmt）保护的单体的制备。碱不稳定的酰基型核碱基保护基和琥珀酰连接的固相支持物的使用提供了类似于标准寡核苷酸合成条件的合成策略。该策略已成功应用于合成混合碱基序列的PNA。
• Substituted N-ethylglycine derivatives for preparing PNA and PNA/DNA
  申请人：Hoechst Aktiengesellschaft

  公开号：US06075143A1

  公开（公告）日：2000-06-13

  There are described N-ethylglycine derivatives of the formula I ##STR1## in which PG is a urethane-type or trityl-type amino protective group which is labile to weak acids, X is NH, O or S, Y is CH.sub.2, NH or O, and B' are bases customary in nucleotide chemistry, the exocyclic amino or hydroxyl groups of which being protected by suitable, known protective groups, or are base substitute compounds, and their salts with tert-organic bases, as well as a process for their preparation. The N-ethylglycine derivatives of the formula I are used in the preparation of PNA and PNA/DNA hybrids.

  描述了公式I的N-乙基甘氨酸衍生物，其中PG是对弱酸敏感的脲型或三甲基基氨基保护基，X为NH、O或S，Y为CH.sub.2、NH或O，B'为核苷酸化学中常见的碱，其外环氨基或羟基团被适当的已知保护基保护，或者是基替代化合物，以及它们与叔有机碱的盐，以及它们的制备方法。公式I的N-乙基甘氨酸衍生物被用于PNA和PNA/DNA杂交物的制备。
• Erratum to: Synthesis of novel MMT/acyl-protected nucleo alanine monomers for the preparation of DNA/alanyl-PNA chimeras
  作者：G. N. Roviello、S. Gröschel、C. Pedone、U. Diederichsen

  DOI：10.1007/s00726-009-0455-0

  日期：2010.5

  phosphoramidites, whereas the nucleo amino acids make use of the acid labile monomethoxytrityl (MMT) group for temporary protection of the α-amino groups and acyl protecting groups for the exocyclic amino functions of the nucleobases. In this work, we realized for the first time the synthesis of all four MMT/acyl-protected nucleo alanines, achieved by deprotection/reprotection of the newly synthesized Boc/acyl intermediates

  丙氨酰肽核酸 (alanyl-PNA)/DNA 嵌合体是基于改进的分子信标概念被设想在有效 DNA 诊断中有益的寡聚体。丙氨酰-PNA/DNA嵌合体的合成可以基于在DNA合成条件下具有混合寡核苷酸/肽骨架的寡聚体的固相组装，其中核苷酸作为亚磷酰胺引入，而核氨基酸利用酸不稳定的单甲氧基三苯甲基 (MMT) 基团用于临时保护 α-氨基和酰基保护基团用于核碱基的环外氨基功能。在这项工作中，我们首次实现了所有四种 MMT/酰基保护的核丙氨酸的合成，这是通过对新合成的 Boc/酰基中间体进行去保护/再保护来实现的，