20172-97-8Relevant academic research and scientific papers
Inhibitors of fumarylacetoacetate hydrolase domain containing protein 1 (Fahd1)
Eder, Manuel Philip,Gstach, Hubert,Jansen-Dürr, Pidder,Klapec, Patrycia,Liedl, Klaus R.,Loeffler, Johannes R.,Monteleone, Stefania,Weiss, Alexander K. H.,Wurzer, Richard,von Grafenstein, Susanne
, (2021/08/26)
FAH domain containing protein 1 (FAHD1) acts as oxaloacetate decarboxylase in mitochondria, contributing to the regulation of the tricarboxylic acid cycle. Guided by a high-resolution X-ray structure of FAHD1 liganded by oxalate, the enzymatic mechanism of substrate processing is analyzed in detail. Taking the chemical features of the FAHD1 substrate oxaloacetate into account, the potential inhibitor structures are deduced. The synthesis of drug-like scaffolds afforded first-generation FAHD1-inhibitors with activities in the low micromolar IC50 range. The investigations disclosed structures competing with the substrate for binding to the metal cofactor, as well as scaffolds, which may have a novel binding mode to FAHD1.
Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones: A Divergent Approach to 1,8-Naphthalimides, Biphenyl-2,2′-dicarboxamides, and N-Heterocyclic Amides
Sakhare, Priyanka R.,Subramanian, Parthasarathi,Kaliappan, Krishna P.
, p. 2112 - 2125 (2019/02/14)
We report here a simple and efficient copper catalyzed oxidative C-C bond cleavage of stable aromatic cyclic-fused and acyclic 1,2-diketones to deliver amides and imides in high yields. This newly developed protocol provides an excellent tool to transform structurally different 1,2-diketones into different products under the same reaction conditions. The key synthetic features of this methodology are the formation of 1,8-naphthalimides and biphenyl-2,2′-dicarboxamide motifs in high yields. The fluorescent studies of 1,8-naphthalimide derivatives were also carried out in order to show the potential application of these scaffolds.
Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction
Fier, Patrick S.,Maloney, Kevin M.
supporting information, p. 3033 - 3036 (2017/06/07)
Parallel synthesis and mass-directed purification of a modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.
A synthesis method of grass amide derivatives (by machine translation)
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Paragraph 0017, (2017/08/28)
The present invention provides a D. amide derivatives of synthetic method. It adopts the D. amide and halogenated compound reaction, adding alkali, bidentate ligand, copper salt catalyst, solvent, the solvent reflux temperature of the reaction a certain period of time and then after treatment. The turf amide with a halo compound in a molar ratio of 1: 0.4 - 3.5; the turf amide with alkali molar ratio of 1: 1.0 - 3.0; the D. amide with the bidentate ligand molar ratio of 1:5 - 25 μM %; the turf amide with the molar ratio of the copper salt catalyst: 1:5 - 30 μM %. The process method is different from the reported oxalic acid diester or oxalyl with different amino substituted compound of method. The invention in the existing technology based on the use of a readily available and inexpensive D. as raw materials, accord with the green chemistry, to avoid colorless fuming liquid of the adding of the oxalyl, increase operability, is suitable for industrial production. (by machine translation)
Crystal structure and DNA-binding study of a monoclinic polymorph of N,N′-bis(2-pyridyl)oxamide
Zhang, Wan-Ju,Zhang, Kai,Wang, Fang
, p. 712 - 716 (2015/02/19)
A monoclinic polymorph of N,N′-bis(2-pyridyl)oxamide has been synthesized and characterized by single-crystal X-ray diffract ion method. It crystallizes in monoclinic, space group C2/c with crystallographic data: a = 10.596(3) A, b = 12.950(3) A, c = 8.612(2) A, β = 90.935(8)° and Z = 4. In the polymorph, two-dimensional network is formed by hydrogen bond and π-π stacking interact ion. The binding studies of the compound with calf thymus DNA (CT-DNA) have also been explored by elect ronic absorpt ion t it rat ion and fluorescence quenching experiments, and the results suggest that the compound binds to CT-DNA through groove binding.
Double anion capture reactions of anthranilic esters with oxaldiimidoyl dichlorides - Efficient synthesis of 2,2′-biquinazoline-4,4′(3H,3′H)-diones
Langer, Peter,Wuckelt, Joerg,Doering, Manfred,Goerls, Helmar
, p. 1503 - 1509 (2007/10/03)
The reaction of anthranilic acids with oxaldiimidoyl dichlorides offers a new and convenient synthesis of quinazolin-4-ones. Condensation of anthranilic esters with diimidoyl dichlorides affords 2,2′-biquinazoline-4,4′(3H,3′H)-diones, which constitute a n
Linear and macrocyclic ligands containing alternating pyridine and imidazolidin-2-one units
Meth-Cohn, Otto,Yan, Zegui
, p. 423 - 436 (2007/10/03)
Linear oligomers of alternating 2,6-disubstituted pyridine (P) and N,N′-disubstituted imidazolidine-2-one (I) units have been made rapidly and in high yield with up to nine repeating units, terminating in either pyridine or imidazolidin-2-one units, or one of each. Synthetic methods include: (1) the sodium hydride-mediated condensation of N-(tert-butyl)imidazolidin-2-one with 2,6-difluoropyridine (F-P-F) or with higher analogues such as F-PIP-F, to give IPI, IPIPI and IPIPIPI. (The tert-butyl protection is readily and quantitatively removed with acid.) (2) The caesium fluoride catalysed interaction of N,N′-[dimethyl(1,1,3-trimethylpropyl)]-protected IPI with But-IP-F sequentially leads firstly to IPIPIPI which by the same method reacts with F-P-F to give F-PIPIPIPIP-F. (3) F-P-F also reacts with 1,2-ethylenediamine (E) sequentially to give F-PEP-F, EPEPE and F-PEPEPEP-F while similar reactions starting from F-PIP-F give EPIPE and F-PEPIPEP-F in sequence. Alternative routes examined include: (1) the interaction of F-P-F with imidazole to give 2,6-bis(imidazol-1-yl)pyridine and salts therefrom followed by (unsuccessful) oxidation. (2) The reaction of 2,6-diaminopyridine with 2-chloroethyl isocyanate followed by cyclisation to give IPI. (3) The interaction of 2,6-diaminopyridine with oxalate esters (O) to give OPO or H2N-POP-NH2, the latter of which was reduced to H2N-PEP-NH2. Cyclisation of the linear assemblies was not successful. However macrocyclic systems were made by linking two IPI units with two ethoxyethyl or with two ethoxyethoxyethyl units. Also two F-PIP-F units were similarly reacted to give polyether-linked macrocycles. Mono- and bis-prop-2-ynylated IPI derivatives were made but could not be cyclised. Attempts to cyclise ethylenediamine and oxamide based systems were also unsuccessful. The linear and macrocyclic ligands showed calcium selectivity in a study of their metal complexing abilities.
