8α-Bromo-2',3',4',5'-tetraacetylriboflavin | 29084-53-5

• 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: 8α-Bromo-2',3',4',5'-tetraacetylriboflavin
• 英文别名: 8α-bromo-2',3',4',5'-tetra-O-acetylriboflavin；8α-bromotetraacetylriboflavin；O^2',O^3',O^4',O^5'-tetraacetyl-α⁸-bromo-riboflavin；[(2R,3S,4S)-2,3,4-triacetyloxy-5-[8-(bromomethyl)-7-methyl-2,4-dioxobenzo[g]pteridin-10-yl]pentyl] acetate
• CAS: 29084-53-5
• 化学式: C₂₅H₂₇BrN₄O₁₀
• 分子量: 623.414
• InChiKey: ONRTYVFCUMAZOR-VWPQPMDRSA-N

物化性质

• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8α-Bromo-2',3',4',5'-tetraacetylriboflavin 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  具有生物相关氧化还原活性部分的金属螯合物的设计：核黄素与双（2-吡啶基甲基）胺配体的偶联和铁配合物的制备

  摘要：

  两倍摩尔过量的双（2-吡啶基甲基）胺 DPA 与 8α-溴乙酸核黄素在干燥 DMF 中反应 24 小时，得到 8α-[双（2-吡啶基甲基）胺]-N-Ac4核黄素配体。该化合物可被描述为镊子，其中黄素部分充当潜在的电子介体。制备了三氯铁络合物，并与黄素部分的低电位还原波一起，观察到了可逆的 FeIII/FeII 对在更高电位的存在。脱乙酰配体 8α-[双（2-吡啶基甲基）胺]-N-核黄素很容易得到。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejic.200600789

文献信息

• 10H-BENZO[G]PTERIDINE-2,4-DIONE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF
  申请人：Maisch Tim

  公开号：US20140200220A1

  公开（公告）日：2014-07-17

  The present disclosure relates to 10H-benzo[g]pteridine-2,4-dione derivatives, to the production thereof, and to the use thereof.

  本公开涉及10H-苯并[g]喹啉-2,4-二酮衍生物，其生产以及使用。
• Allo- and isoalloxazines LI. Synthesis and antimicrobial activity of allo- and isoalloxazines
  作者：É. A. Rudzit、T. A. Zhilina、G. N. Neshchadim、N. S. Kirina、L. S. Tul'chinskaya、Zh. I. Litvak、N. A. Polyakova、V. M. Berezovskii

  DOI：10.1007/bf01188702

  日期：1978.1

  Staphylococcus aureus, with a minimum inhibitory concentration of 6.25-100 ~g/ml, is exhibited by a series of isoalloxazines substituted in the 7, 8, N 3, and N z~ positions [3]. Amino analogs of riboflavin (in particular, 8-dimethylaminonoriboflavin, XXXVII), strongly repress the synthesis of 6,7-dimethyl-8-D-ribityllumazine, the immediate precursor of riboflavin (in a concentration of 0.05 ~g/ml)

  已经发现核黄素的一些衍生物是已知的最强的维生素 B2 竞争性抑制剂，在依赖核黄素的干酪乳杆菌菌株中。因此，8 氨基降核黄素 (XXXIV) 和 8-D-核糖氨基核黄素 (XXXV) [i] 对干酪乳杆菌的抑制指数 (I50) 值分别为 32 和 9 [2]。一系列在 7、8、N 3 和 N z 位置取代的异恶嗪表现出对金黄色葡萄球菌的抗菌活性，最小抑制浓度为 6.25-100 μg/ml [3]。核黄素的氨基类似物（特别是 8-二甲氨基降核黄素，XXXVII），强烈抑制 6,7-二甲基-8-D-核黄素的合成，核黄素的直接前体（浓度为 0.05 μg/ml），并且在枯草芽孢杆菌菌株中显示出对核黄素合成酶活性的强烈竞争性抑制，其中核黄素操纵子具有不同的遗传构成 [4]。该化合物显示出抗菌活性 [5]。
• A possible chain reaction in photosensitized splitting of pyrimidine dimers by a protonated, oxidized flavin
  作者：Rosemarie F. Hartman、Seth D. Rose

  DOI：10.1021/jo00034a021

  日期：1992.4

  Pyrimidine dimer cycloreversion was photosensitized by protonated 2',3',4',5'-tetraacetylriboflavin (ac4rfH+), whereas the protonated flavin radical (ac4rfH2.+) failed to sensitize detectable dimer splitting. In acetonitrile containing 0.075% perchloric acid, the ac4rf absorption bands at 375 nm and 445 nm are replaced by a new band at 390 nm due to ac4rfH+. Irradiation of ac4rfH+ in the presence of cis,syn- or trans,syn-1,3-dimethyluracil dimer resulted in efficient cycloreversion to 1,3-dimethyluracil, probably induced by electron abstraction from the dimer by ac4rfH+ to produce the dimer radical cation. The quantum yeilds of splitting were large (PHI(spl) = 0.35 and 1.5 for cis,syn and trans,syn isomers, respectively, at [dimer] = 1.2 mM). Splitting quantum yields increased with dimer concentration in a quadratic fashion. These results are consistent with the occurrence of a chain reaction propagated by monomer.+ + dimer --> monomer + dimer.+ in the case of the dimethyluracil dimers. The fluorescence of the protonated flavin (lambda(em) = 507 nm) was found to be quenched by the dimers. In the presence of small amounts of added water, however, both the fluorescence quenching and splitting were abolished. Two cis,syn dimers in which the N(1)- and N(1')-atoms were tethered via a trimethylene bridge exhibited quantum yields of approximately 0.02 at the above dimer concentration. A compound in which ac4rf is covalently bound to a pyrimidine dimer was also found to undergo splitting in acidified acetonitrile (PHI = 0.03). These values are more than 1 order of magnitude greater than those reported for unprotonated flavins.