752-13-6Relevant articles and documents
Comparison of the Optoelectronic Performance of Neutral and Cationic Forms of Riboflavin
Saltan, G?zde Murat,K?ymaz, Deniz Aykut,Zafer, Ceylan,Din?alp, Haluk
, p. 1975 - 1984 (2017)
The riboflavin dye 2,3,4,5-tetra-O-acetyl-1-[3-(6-bromohexyl)-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl]-1-deoxypentitol and its pyridinium salt were synthesized, and studied by absorption and fluorescence spectroscopy in solutions and
Formation of a Transient Radial Ion Pair in the Reactions of 1,5-Dihydroflavin with Hydride Acceptors
Ishikawa, Masashi,Yamamoto, Kazuhiko,Fukuzumi, Shunichi
, p. 1008 - 1009 (1992)
The formation of a transient radical ion pair has been detected directly in the reactions of 1,5-dihydroriboflavin-2',3',4',5'-tetraacetate (FIH2) with hydride acceptors (tetracyano-p-quinodimethane, tetracyanoethylene and p-benzoquinone derivatives) in deaerated acetonitrile, providing unequivocal evidence for an electron transfer pathway in the overall two-electron redox reactions of FIH2 with hydride acceptors.
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Tsibris et al.
, p. 504,507 (1965)
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Synthesis and evaluation of antimycobacterial activity of riboflavin derivatives
Chouhan, Dwarika Kumar,Harale, Bhaiyyasaheb,Khedkar, Vijay,Kidwai, Saqib,Ojha, Divya,Rode, Ambadas B.,Singh, Manisha,Singh, Ramandeep
supporting information, (2021/07/16)
The riboflavin biosynthetic pathway is a promising target for the development of novel antimycobacterial drugs given the lack of riboflavin transporter in M. tuberculosis. Herein, a series of riboflavin derivatives was designed, synthesized and screened for their antimycobacterial and antibacterial activity. The compounds 1a, 1b, 2a, 3a and 5a displayed noticeable antitubercular activity against M. tuberculosis with minimum inhibitory concentration (MIC99) in the range of 6.25 to 25 μM. The lead compound 5a had a selectivity index of 10.7 in the present study. The compounds 2a, 2b, 2c, 4c and 4d showed relatively low to moderate antibacterial activity (MIC = 100–200 μM) against gram-positive strains. Notably, the compounds do not show any inhibition against gram-negative strains even at 200 μM concentration. Further, molecular docking and binding experiments with representative flavin mononucleotide (FMN) riboswitch suggested that the riboflavin analogs exhibited antimycobacterial activity plausibly through FMN riboswitch-mediated repression of riboflavin biosynthesis. In addition to FMN riboswitch, flavoproteins involved in the flavin biosynthesis could also be target of riboflavin derivatives. In conclusion, the potency and low toxicity of riboflavin analogs particularly 5a (MIC99 = 6.25) make it a lead compound for the synthesis of new analogs for antimycobacterial therapy.
Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols
Zhang, Wen,Carpenter, Keith L.,Lin, Song
supporting information, p. 409 - 417 (2019/11/25)
Riboflavin-derived photocatalysts have been extensively studied in the context of alcohol oxidation. However, to date, the scope of this catalytic methodology has been limited to benzyl alcohols. In this work, mechanistic understanding of flavin-catalyzed oxidation reactions, in either the absence or presence of thiourea as a cocatalyst, was obtained. The mechanistic insights enabled development of an electrochemically driven photochemical oxidation of primary and secondary aliphatic alcohols using a pair of flavin and dialkylthiourea catalysts. Electrochemistry makes it possible to avoid using O2 and an oxidant and generating H2O2 as a byproduct, both of which oxidatively degrade thiourea under the reaction conditions. This modification unlocks a new mechanistic pathway in which the oxidation of unactivated alcohols is achieved by thiyl radical mediated hydrogen-atom abstraction.