10-(2'-methoxyethyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione | 176907-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 10-(2'-methoxyethyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione
• 英文别名: 10-(2-methoxyethyl)-7,8-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione；10-(2′-methoxyethyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione；10-(3'-oxabut-1'-yl)flavin；10-(2-Methoxyethyl)-7,8-dimethylbenzo[g]pteridine-2,4-dione
• CAS: 176907-07-6
• 化学式: C₁₅H₁₆N₄O₃
• 分子量: 300.317
• InChiKey: OQBAVJGVJZROAX-UHFFFAOYSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-(2'-methoxyethyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione 在 三溴化硼 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.67h， 生成 {(4aS,4bS,8aR,8bR)-5-[2-(3-Ethyl-7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-ethoxycarbonylmethyl]-2,4,6,8-tetraoxo-decahydro-1,3,5,7-tetraaza-biphenylen-1-yl}-acetic acid benzyl ester
  参考文献：
  名称：

  Investigation of Flavin-Containing DNA-Repair Model Compounds

  摘要：

  Irradiation of DNA with UV-B light causes the formation of mutagenic DNA lesions such as cis-syn and trans-syn cyclobutane pyrimidine dimers. DNA photolyases are flavin-dependent repair enzymes which directly revert the mutagenic cis-syn pyrimidine dimers into the corresponding monomers by a light-facilitated repair reaction. To gain deeper insight into the repair process, we recently prepared flavin-containing model compounds which are able to mimic the repair reaction (Carell, T.; Epple, R.; Gramlich, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 620-623). This publication now contains a detailed description of the synthesis of a series of related model compounds and a comprehensive investigation of their cleavage properties. The results obtained help to unravel the requirements necessary for an efficient, flavin-mediated cleavage of pyrimidine dimers and provide insight into the factors on which the enzymatic repair process depends. The investigation of the cleavage reaction with cis-syn, trans-syn, and hans-anti cyclobutane pyrimidine dimer model compounds reveal an enhanced vulnerability for the cis-syn isomer. The trans-syn dimer is 10 times more stable, These results are comparable to those observed in a recent study on the E. coli enzyme. The excellent solubility of some of the model compounds has allowed a medium-dependent investigation of the flavin-initiated cleavage reaction. increased cleavage efficiencies are observed in polar solvents such as water (phi = 0.06) and acetonitrile (phi = 0.05). The quantum yields decrease by a factor of 4 in solvents with very low polarity such as dioxane (phi = 0.01). These results are not in agreement with earlier solvent-dependent evaluations performed with non-flavin-containing model compounds (Hartzfeld, D. G.; Rose, S. D. J. Am. Chem. Soc. 1993, 115,850-854). The results, however, suggest that the unusually polar flavin-binding pocket, observed in the X-ray crystal structure of the E, coli. photolyase, might be required to increase the catalytic repair efficiency. Investigations of the cleavage reaction in the presence of acid and base in organic solvents emphasize the strict requirement for a deprotonated reduced riboflavin chromophore. The determined pH values for half-maximal (pH = 6.5) and maximal (7 less than or equal to pH less than or equal to 9) cleavage efficiencies are in agreement with the pK(a) value (pK(a) = 6.3) of the reduced riboflavin and reveal that physiological conditions are required to reach maximum catalytic cleavage efficiency.

  DOI：

  10.1021/ja964097u
• 作为产物：
  描述：

  4，5-二甲-2-硝基苯胺 在 palladium on activated charcoal 氢气 、 硼酸 、 potassium carbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 10-(2'-methoxyethyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Carell, Thomas; Epple, Robert; Gramlich, Volker, Angewandte Chemie, 1996, vol. 108, # 6, p. 676 - 679

  摘要：

  DOI：

文献信息

• Photooxidation of Benzyl Alcohols with Immobilized Flavins
  作者：Harald Schmaderer、Petra Hilgers、Robert Lechner、Burkhard König

  DOI：10.1002/adsc.200800576

  日期：2009.1

  Benzyl alcohols are oxidized cleanly and efficiently to the corresponding aldehydes under irradiation using flavin photocatalysts and aerial oxygen as the terminal oxidant in homogeneous aqueous solution. Turnover frequencies (TOF) of more than 800 h−1 and turnover numbers (TON) of up to 68 were obtained. Several flavin photocatalysts with fluorinated or hydrophobic aliphatic chains were immobilized

  使用黄素光催化剂和空气中的氧气作为末端氧化剂，在均匀的水溶液中，在照射下将苄醇清洁有效地氧化为相应的醛。超过800 h -1的周转频率（TOF）营业额（TON）达到68。将几种具有氟化或疏水性脂肪族链的黄素光催化剂固定在固体载体上，例如氟硅胶，反相硅胶或截留在聚乙烯粒料中。研究了非均相光催化剂对水中不同苄醇氧化的催化效率，并将其与类似的均相反应进行了比较。除去非均相光催化剂会立即停止反应转化，这表明固定化的黄素是催化活性物质。固定的催化剂是稳定的，如果与相应的均相系统相比，则保持其反应性，并且容易从反应混合物中除去并重复使用。TOF长达26 h -1异质黄素光催化剂可能具有280的TON和最多3个反应周期而不会失去活性。
• Copper-Mediated 3-N-Arylation of Flavins
  作者：Burkhard König、Bianca Attenberger、Harald Schmaderer

  DOI：10.1055/s-2008-1067045

  日期：2008.6

  applicable method for the direct 3-N-arylation of flavins using arylboronic acids and copper acetate was developed. The reaction conditions were optimized considering the lability of flavins in basic conditions and thermal heating. Donor- and acceptor-substituted arylboronic acids were used yielding 3-N-arylflavins in moderate to good yields by C(aryl)-N(imide) bond formation. UV and fluorescence measurements

  开发了一种使用芳基硼酸和乙酸铜对黄素进行直接 3-N-芳基化的普遍适用的方法。考虑黄素在碱性条件和加热条件下的不稳定性，对反应条件进行了优化。供体和受体取代的芳基硼酸通过 C(芳基)-N(酰亚胺) 键形成以中等至良好的收率产生 3-N-芳基黄素。紫外和荧光测量表明附加芳族取代基与黄素环系统的正交取向。芳烃取代基不与基态的黄素π-系统电子耦合，但3-N位的富电子芳烃取代基显着降低了黄素的发射强度。
• Discrimination of Redox-Responsible Biomolecules by a Single Molecular Sensor
  作者：Jinrok Oh、Jong-In Hong

  DOI：10.1021/ol303403x

  日期：2013.3.15

  A new application of a fluorescent sensor (PyDPA) for the discrimination of redox-responsible molecules is reported. Nicotinamide adenine dinucleotide/nicotinamide adenine dinucleotide phosphate (NAD+/NADP+) and flavin mononucleotide/flavin adenine dinucleotide (FMN/FAD) were differentiated by means of ratiometric fluorescence change from excimer–monomer equilibrium and time-dependent fluorescence

  据报道，荧光传感器（PyDPA）在氧化还原负责分子的判别中有新的应用。烟酰胺腺嘌呤二核苷酸/烟酰胺腺嘌呤二核苷酸磷酸盐（NAD + / NADP +）和黄素单核苷酸/黄素腺嘌呤二核苷酸（FMN / FAD）分别通过比例荧光变化与受激准分子-单体平衡和随时间变化的荧光变化进行区分。
• Thiourea-Enhanced Flavin Photooxidation of Benzyl Alcohol
  作者：Jiří Svoboda、Harald Schmaderer、Burkhard König

  DOI：10.1002/chem.200701319

  日期：2008.2.18

  irradiation, flavin oxidises 4-methoxybenzyl alcohol to the corresponding aldehyde using aerial O(2) as the terminal oxidant. We have observed that this reaction is significantly accelerated by the presence of thiourea. A series of thiourea-functionalised flavins has been prepared from flavin isothiocyanates and their photocatalytic efficiencies have been monitored by NMR. The alcohol photooxidation proceeds

  照射后，黄素使用航空O（2）作为末端氧化剂将4-甲氧基苄醇氧化为相应的醛。我们已经观察到，硫脲的存在大大促进了该反应。从异硫氰酸黄素制备了一系列硫脲官能化的黄素，并通过NMR监测了它们的光催化效率。酒精的光氧化反应迅速，清洁地进行，高达580个的高周转率，超过了先前报道的性能。从光谱学，电化学和动力学研究中得出了硫脲使光-氧化还原反应加速30倍以上的可能的机械原理。因此，硫脲充当了被激发的黄素对4-甲氧基苄醇进行初始光氧化的电子转移介体。该机制与黄素酶中的电子中继机制相似，为此提出了半胱氨酸亚磺酸中间体。硫脲介导的黄素光氧化还原过程的观察对于基于自然界最佳的氧化还原发色团设计更复杂的光催化剂具有重要价值。
• USE OF 10H-BENZO[G]PTERIDINE-2,4-DIONE DERIVATIVES
  申请人：Maisch Tim

  公开号：US20140128403A1

  公开（公告）日：2014-05-08

  Use of 10H-benzo[g]pteridine-2,4-dione derivatives as photosensitizers in the inactivation of microorganisms.

  10H-苯并[g]喹啉-2,4-二酮衍生物在灭活微生物中的光敏剂应用。