69083-37-0Relevant academic research and scientific papers
5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2
Dickens, Michael P.,Roxburgh, Patricia,Hock, Andreas,Mezna, Mokdad,Kellam, Barrie,Vousden, Karen H.,Fischer, Peter M.
, p. 6868 - 6877 (2013/11/06)
Based on previous reports of certain 5-deazaflavin derivatives being capable of activating the tumour suppressor p53 in cancer cells through inhibition of the p53-specific ubiquitin E3 ligase HDM2, we have conducted an structure-activity relationship (SAR) analysis through systematic modification of the 5-deazaflavin template. This analysis shows that HDM2-inhibitory activity depends on a combination of factors. The most active compounds (e.g., 15) contain a trifluoromethyl or chloro substituent at the deazaflavin C9 position and this activity depends to a large extent on the presence of at least one additional halogen or methyl substituent of the phenyl group at N10. Our SAR results, in combination with the HDM2 RING domain receptor recognition model we present, form the basis for the design of drug-like and potent activators of p53 for potential cancer therapy.
A new synthetic approach to 5-deazaflavin and 5-deaza-10-thiaflavin
Chen,Tanaka,Yoneda
, p. 612 - 615 (2007/10/02)
A novel, one-step synthesis of 5-deazaflavin was developed, in which a [4 + 2]cycloaddition is presumably involved, to give the 5-deazaflavin derivative in moderate yield. This methodology was successfully applied to the stepwise preparation of its thio a
A New Synthetic Method for the Preparation of 5-Deazaflavins and 5-Deaza-10-oxaflavins
Chen, Xing,Nagata, Minako,Tanaka, Kiyoshi,Yoneda, Fumio
, p. 44 - 45 (2007/10/02)
The condensation of 6-chlorouracils with o-(substituted amino)benzyl alcohols and o-hydroxybenzyl alcohol gave directly 5-deazaflavin and 5-deaza-10-oxaflavin derivatives, respectively.
A New, General, and Convenient Synthesis of 5-Deazaflavins (5-Deazaisoalloxazines) and Bis-(5-deazaflavin-10-yl)alkanes
Nagamatsu, Tomohisa,Hashiguchi, Yuko,Yoneda, Fumio
, p. 561 - 565 (2007/10/02)
The condensation of 6-substituted aminouracils or bis(uracil-6-amino)alkanes with o-halogenobenzaldehydes in dimethylformamide led to the formation of the corresponding 5-deazaflavins or bid(5-deazaflavin-10-yl)alkanes in a single step.
A New, General, and Convenient Synthesis of 5-Deazaflavins (5-Deazaisoallooxazines)
Nagamatsu, Tomohisa,Hashigushi, Yuko,Higuchi, Masatsugu,Yoneda, Fumio
, p. 1085 - 1086 (2007/10/02)
The condensation of 6-substituted-aminouracils with o-halogenobenzaldehydes in dimethylformamide led to the formation of the corresponding 5-deazaflavins in a single step.
Synthesis of 10-Arylpyrimidoquinoline-2,4(3H,10H)diones (10-Aryl-5-deazaflavins) and Their Use in Oxidations of Alcohols and Amines
Yoneda, Fumio,Tsukuda, Kinshiro,Shinozuka, Kazuo,Hirayama, Fumitoshi,Uekama, Kaneto,Koshiro, Akira
, p. 3049 - 3056 (2007/10/02)
Treatment of aryl-bis(6-anilino-3-methyluracil-5-yl)methanes, which were prepared by the condensation of 6-anilino-3-methyluracils with arylaldehydes, with diethyl azodicarboxylate (DAD) in the presence of sulfolane led to the formation of the corresponding 10-arylpyrimidoquinoline-2,4(3H,10H)-diones (10-aryl-5-deazaflavins).Heating of the methanes alone in sulfolane without DAD gave the corresponding 5-aryl-5-deazaalloxazines.The oxidizing abilities of the 10-aryl-5-deazaflavins thus obtained were examined from both kinetic and synthetic viewpoints.The oxidations of benzyl alcohol and benzylamine by these 5-deazaflavins have been shown to recycle automatically, and more than 100percent yield of benzaldehyde (based on the 5-deazaflavins) was obtained.Keywords - pyrimidoquinoline; 5-deazaflavin; alcohol oxidation; amine oxidation; diethyl azodicarboxylate; aryl-bis(6-anilinouracil-5-yl)methane; 5-deazaalloxazine; turn-over catalyst; biomimetic axidation.
