58861-90-8Relevant academic research and scientific papers
Method for site-selective alkylation of Diazine-N-oxide using phosphonium ylides
-
Paragraph 0146; 0147; 0233; 0237; 0239, (2021/04/06)
- N - Oxide (Diazine -)N-The position selective Oxides-C alkylation of H) relates to a method alkylation. To the present invention, a plurality of diazine compounds can be alkylated by selectively introducing an alkyl group to a diazine compound known as a core unit structure in a medicine, and synthesis of a plurality of diazine compounds (varenicline) paenibacillin A, which is a natural product, can be synthesized.
Site-Selective C-H Alkylation of Diazine N-Oxides Enabled by Phosphonium Ylides
Ghosh, Prithwish,Kwon, Na Yeon,Han, Sangil,Kim, Saegun,Han, Sang Hoon,Mishra, Neeraj Kumar,Jung, Young Hoon,Chung, Sang J.,Kim, In Su
supporting information, p. 6488 - 6493 (2019/08/20)
The synthesis of alkylated diazine derivatives is important for their practical utilization as pharmaceuticals and for other purposes. Herein, we describe the metal-free site-selective C-H alkylation of diazine N-oxides using phosphonium ylides that affords a variety of alkylated diazine derivatives with broad functional group tolerance. The utility of this method is showcased by the late-stage functionalization of a commercially available drug such as varenicline. Notably, the sequential C-H alkylation of pyrazine N-oxides for the total synthesis of a pyrazine-containing natural product, paenibacillin A, highlights the importance of this method.
Cushing's syndrome: Development of highly potent and selective CYP11B1 inhibitors of the (pyridylmethyl)pyridine type
Emmerich, Juliette,Hu, Qingzhong,Hanke, Nina,Hartmann, Rolf W.
supporting information, p. 6022 - 6032 (2013/09/02)
Potent and selective CYP11B1 inhibitors could be promising therapeutics for the treatment of Cushing's syndrome. Optimization of Ref 1 (5-((1H-imidazol-1- yl)methyl)-2-phenylpyridine) led to compound 44 (5-((5-methylpyridin-3-yl) methyl)-2-phenylpyridine) with a 50-fold improved IC50 value of 2 nM toward human CYP11B1 and an enhanced inhibition of the rat enzyme (IC 50 = 2440 nM) compared to Ref 1 (IC50 > 10000 nM). Furthermore, selectivities over CYP11B2, CYP17, and CYP19 were observed, as well as satisfying metabolic stability not only in human and rat plasma but also in liver S9 fraction. Investigation of cytotoxicity and inhibition of hepatic CYP2A6 and CYP3A4 showed that 44 fulfills first safety criteria and can be considered for further in vivo evaluation in rats.
SELECTIVE CYP11B1 INHIBITORS FOR THE TREATMENT OF CORTISOL DEPENDENT DISEASES
-
Page/Page column 75-76, (2012/05/05)
The present invention relates to compounds which selectively inhibit CYP11B1. Preferably, the compounds of the present invention do not substantially inhibit CYP11B2. Moreover, the compounds of the present invention do not substantially inhibit CYP17 and/or CYP19, either. Amongst other applications of the compounds of the present invention, they can be used for the treatment of Cushing's syndrome or metabolic disease.
Ladderlike oligomers; Intramolecular hydrogen bonding, push - pull character, and electron affinity
Pieterse, Koen,Vekemans, Jef A.J.M.,Kooijman, Huub,Spek, Anthony L.,Meijer
, p. 4597 - 4603 (2007/10/03)
Symmetrical 2,5-bis(2-aminophenyl)pyrazines have been synthesized by application of the Stille coupling strategy. These cotrimers feature three important properties, namely strong intramolecular hydrogen bonding, push-pull character, and high electron aff
DECHLORINATION OF SOME CHLOROPYRAZINES AND THEIR N-OXIDES
Akita, Yasuo,Ohta, Akihiro
, p. 1325 - 1328 (2007/10/02)
By heating with sodium formate and tetrakis(triphenylphosphine)palladium, chloropyrazines were converted to the parent pyrazines in satisfactory yields.The chlorine atoms of chloropyrazine N-oxides could also be removed, leaving the N-O group.
Reactions of organolithium-diazine adducts and dihydrodiazines with electrophilic reagents
Stoel, R. E. van der,Plas, H. C. van der,Jongejan, H.,Hoeve, L.
, p. 234 - 238 (2007/10/02)
Some organolithium-diazine adducts and some dihydropyrimidines were treated with electrophilic reagents.Both 4,6-diphenyl-1(3)-lithio-1,4(3,4)-dihydropyrimidine and 4,6-diphenyl-1,4(3,4)-dihydropyrimidine were attacked by the electrophilic reagent methyl
