[2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid | 1089216-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: [2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid
• 英文别名: 2-(2-(3-butylureido)-7-(cyclohexylmethyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)acetic acid；2-[2-(butylcarbamoylamino)-7-(cyclohexylmethyl)-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-6-yl]acetic acid
• CAS: 1089216-06-7
• 化学式: C₂₀H₂₉N₅O₄
• 分子量: 403.481
• InChiKey: ZXSAXUIKNYHUTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 生成 4-(2-(2-(2-(3-butylureido)-7-(cyclohexylmethyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)acetoxy)ethoxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis of a Redox-Responsive Quadruple Hydrogen-Bonding Unit for Applications in Supramolecular Chemistry

  摘要：

  A redox-responsive quadruple hydrogen-bonding module (eDAN) has been developed. The strong binding between the reduced form and its partner (DeUG) can be significantly decreased upon oxidation but restored upon subsequent reduction. This on-off switch was successfully applied to provide reversible control of macroscopic supramolecular polymer networks.

  DOI：

  10.1021/ja2069278
• 作为产物：
  描述：

  [2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid ethyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以98%的产率得到[2-(3-butylureido)-7-cyclohexanemethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-acetic acid
  参考文献：
  名称：

  Hydrogen-Bonded DeUG·DAN Heterocomplex: Structure and Stability and a Scalable Synthesis of DeUG with Reactive Functionality

  摘要：

  A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. K-assoc for the 1.2 heterocomplex was estimated to be 2 x 10(8) M-1 in chloroform.

  DOI：

  10.1021/ol802344w

文献信息

• Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions
  作者：Yagang Zhang、Steven C Zimmerman

  DOI：10.3762/bjoc.8.55

  日期：——

  The facile coupling of azobenzene dyes to the quadruply hydrogen-bonding modules 2,7-diamido-1,8-naphthyridine (DAN) and 7-deazaguanine urea (DeUG) is described. The coupling of azobenzene dye 2 to mono-amido DAN units 4, 7, and 9 was effected by classic 4-(dimethylamino)pyridine (DMAP)-catalyzed peptide synthesis with N-(3-dimethylaminopropyl)-N’-ethyl carbodiimide hydrochloride (EDC) as activating agent, affording the respective amide products 5, 8, and 10 in 60–71% yield. The amide linkage was formed through either the aliphatic or aromatic ester group of 2, allowing both the flexibility and absorption maximum to be tuned. Azobenzene dye 1 was coupled to the DeUG unit 11 by Steglich esterification to afford the product amide 12 in 35% yield. Alternatively, azobenzene dye 16 underwent a room-temperature copper-catalyzed azide–alkyne Huisgen cycloaddition with DeUG alkyne 17 to give triazole 18 in 71% yield. Azobenzene coupled DAN modules 5, 8, and 10 are bright orange–red in color, and azobenzene coupled DeUG modules 12 and 18 are orange–yellow in color. Azobenzene coupled DAN and DeUG modules were successfully used as colorimetric indicators for specific DAN–DeUG and DAN–UPy (2-ureido-4(1H)-pyrimidone) quadruply hydrogen-bonding interactions.

  本文描述了将偶氮苯染料与四重氢键模块2,7-二氨基-1,8-萘啶（DAN）和7-去氧鸟嘌呤脲（DeUG）轻松耦合的方法。通过经典的4-(二甲氨基)吡啶（DMAP）催化的肽合成，使用N-(3-二甲氨基丙基)-N'-乙基碳酰亚胺盐酸盐（EDC）作为活化剂，将偶氮苯染料2与单氨基DAN单元4、7和9偶联，得到相应的酰胺产物5、8和10，收率为60-71%。酰胺连接通过2的脂肪族或芳香族酯基形成，从而实现了灵活性和吸收最大值的调节。偶氮苯染料1通过Steglich酯化与DeUG单元11偶联，得到产物酰胺12，收率为35%。另外，偶氮苯染料16与DeUG炔基17在室温下进行铜催化的偶氮-炔Huisgen环加成反应，得到三唑18，收率为71%。偶氮苯偶联的DAN模块5、8和10呈亮橙红色，偶氮苯偶联的DeUG模块12和18呈橙黄色。偶氮苯偶联的DAN和DeUG模块成功地用作特定DAN-DeUG和DAN-UPy（2-脲基-4（1H）-嘧啶酮）四重氢键相互作用的比色指示剂。
• Hydrogen-Bonded DeUG·DAN Heterocomplex: Structure and Stability and a Scalable Synthesis of DeUG with Reactive Functionality
  作者：Darrell W. Kuykendall、Cyrus A. Anderson、Steven C. Zimmerman

  DOI：10.1021/ol802344w

  日期：2009.1.1

  A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. K-assoc for the 1.2 heterocomplex was estimated to be 2 x 10(8) M-1 in chloroform.
• Synthesis of a Redox-Responsive Quadruple Hydrogen-Bonding Unit for Applications in Supramolecular Chemistry
  作者：Ying Li、Taiho Park、J. Kwansima Quansah、Steven C. Zimmerman

  DOI：10.1021/ja2069278

  日期：2011.11.2

  A redox-responsive quadruple hydrogen-bonding module (eDAN) has been developed. The strong binding between the reduced form and its partner (DeUG) can be significantly decreased upon oxidation but restored upon subsequent reduction. This on-off switch was successfully applied to provide reversible control of macroscopic supramolecular polymer networks.