52898-32-5Relevant articles and documents
Determination of covalently bound hypusine and deoxyhypusine to protein using submilligram of protein samples by HPLC
Beppu, Takanobu,Shirahata, Akira,Samejima, Keijiro
, p. 1 - 5 (1996)
A sensitive and reliable method for the determination of hypusine and deoxyhypusine in elF-5A protein, an initiation factor of protein synthesis, was developed. An advantage of this method is the use of N(ε)-(5- aminopentyl)lysine, an analogue of deoxyhyp
Urea as the Most Reactive and Versatile Nitrogen Nucleophile for the Palladium(2+)-Catalized cyclization of Unsaturated Amines
Tamaru, Yoshinao,Hojo, Makoto,Higashimura, Hideyuki,Yoshida, Zen-ichi
, p. 3994 - 4002 (1988)
Urea (known as an ambident nucleophile) serves as a specific nitrogen nucleophile for the palladium(2+)-catalized aminocarbonylation of unsaturated amines.N-2-propenyl-, N-3-butenyl-, N-4-pentenyl, and N-5-hexenylureas undergo an aminocarbonylation (0.1-0.01 equiv of PdCl2, 3.0 equiv of CuCl2, 1 atm of CO in methanol at 0 deg C to room temperature) to provide 4--2-imidazolidinones, 4--3,4,5,6-tetrahydro-2(1H)-pyrimidinones, 1,3-diazabicyclononane-2,4-diones, and 1,3-diazabicyclodecane-2,4-diones, respectively, in high yields.The effects of solvents and the R1 and R2 substituents of N-2-propenylureas 1(2-propenyl)NCONHR2> and N-3-butenylureas 1(3-butenyl)NCONHR2> on the ease of cyclization and the relative reactivity of amino nucleophiles (urea>carbamate>tosylamide>benzamide) toward the cyclization are also discussed.
Electrochemical Synthesis of Allylic Amines from Terminal Alkenes and Secondary Amines
Targos, Karina,Wang, Diana J.,Wickens, Zachary K.
supporting information, p. 21503 - 21510 (2022/01/03)
Allylic amines are valuable synthetic targets en route to diverse biologically active amine products. Current allylic C-H amination strategies remain limited with respect to the viable N-substituents. Herein, we disclose a new electrochemical process to p
Tunable System for Electrochemical Reduction of Ketones and Phthalimides
Chen, Gong,Qiao, Tianjiao,Wang, Yaxin,Zhang, Jian,Zhao, Jianyou
supporting information, p. 3297 - 3302 (2021/10/14)
Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.
Pd-Catalyzed Remote Site-Selective and Stereoselective C(Alkenyl)-H Alkenylation of Unactivated Cycloalkenes
Mao, Chun-Li,Zhao, Sheng,Zang, Zhong-Lin,Xiao, Lin,Zhou, Cheng-He,He, Yun,Cai, Gui-Xin
, p. 774 - 787 (2020/01/09)
A palladium-catalyzed alkenylation involving remote δ-position C(alkenyl)-H activation of cycloalkenes reacting with electron-deficient alkenes is described. This method features excellent site selectivity and stereoselectivity to efficiently afford only E-selective highly substituted 1,3-diene derivatives with extra-ligand-free and good functional group tolerance including estrone and free N-H tryptamine under weakly alkaline conditions. Mechanistic studies suggest that picolinamide as a bidentate directing group enables the formation of unique alkenyl palladacycle intermediates.
Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene
Chen, Kun-Quan,Wang, Zhi-Xiang,Chen, Xiang-Yu
, p. 8059 - 8064 (2020/11/02)
While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.
Design, synthesis and structure-activity relationships of novel 15-membered macrolides: Quinolone/quinoline-containing sidechains tethered to the C-6 position of azithromycin acylides
Aldrich, Courtney,Brody, Scott,Cushman, Mark,Fan, Bing-Zhi,Hiasa, Hiroshi,Liang, Jian-Hua,Lv, Wei,Yang, Zhao-Yong
, (2020/03/23)
In the search for novel hybrid molecules by fusing two biologically active scaffolds into one heteromeric chemotype, we found that hybrids of azithromycin and ciprofloxacin/gatifloxacin 26j and 26l can inhibit the supercoiling activity of E. coli gyrase by poisoning it in a way similar to fluoroquinolones. This may modestly contribute to their potencies, which are equal to ciprofloxacin against constitutively resistant Staphylococcus aureus, whose growth is not inhibited by the presence of macrolides. In contrast, introduction of quinolines (the 3-quinoline 26b and the 6-quinoline 26o) with an optimized rigid spacer at the 6-OH of azithromycin acylides did not exert significant potency against constitutively resistant S. aureus, despite the fact that the quinoline-containing compounds, exemplified by 26o, were as active as telithromycin against susceptible, inducibly- and efflux-resistant pathogens. The novel dual modes of action involving protein synthesis inhibition and poisoning DNA replication may pave the way for restoration of antibacterial activities of the current macrolides against constitutively resistant clinical isolates.
As Rho kinase inhibitors of the six [...] -4 - yloxy benzamide compound (by machine translation)
-
Paragraph 0032; 0034; 0035; 0036, (2019/01/21)
The invention of the formula I shown six hydrogen nitrogen mixed outstanding - 4 - yloxy benzoyl amide compounds and/or their pharmaceutically acceptable salt and its preparation method, they can be used for treating and/or preventing with the Rho kinase
Intramolecular Mannich and Michael Annulation Reactions of Lactam Derivatives Bearing Enals to Afford Bicyclic N-Heterocycles
Krishna, Yarkali,Shilpa, Kola,Tanaka, Fujie
supporting information, p. 8444 - 8448 (2019/10/16)
Acid-catalyzed intramolecular vinylogous Mannich reactions and intramolecular Michael reactions affording pyrrolizinone-fused N-heterocycles from hydroxylactam derivatives bearing enals have been developed. Depending on the substituent on the hydroxylacta
Copper-Catalyzed 1,2-Bistrifluoromethylation of Terminal Alkenes
Oh, Hyunseok,Park, Areum,Jeong, Kyu-Sung,Han, Soo Bong,Lee, Hyuk
supporting information, p. 2136 - 2140 (2019/03/13)
Many efficient catalytic methods for the introduction of trifluoromethyl group (CF3) have been reported. Among them, the addition of CF3 and other components to alkenes is well known, and many components such as azides, cyanides, amines, and halides have been inserted into alkenes with CF3. However, to date the double catalytic insertion of CF3 into an alkene is unknown. Herein, we report the catalytic 1,2-bistrifluoromethylations of alkenes catalyzed by Copper (Cu). We used two CF3 sources, namely Umemoto's reagent and (trifluoromethyl)trimethylsilane (TMSCF3). Each reagent plays a unique role during this transformation; Umemoto's reagent generates CF3 radicals, while TMSCF3 is used to form CF3 anions. Copper (I) bromide (CuBr) exhibited the best catalytic activity for this reaction. We believe that CuBr oxidizes the alkyl radical, which is produced by the addition of the CF3 radical to the alkene, to the corresponding alkyl cation, which then reacts with the CF3 anion from TMSCF3 to produce the desired product. This reaction tolerates a diverse set of substrates bearing functional groups such as amides, esters, ethers, ketones, protected amines, tertiary amines, and phthalimides; hence this transformation is widely applicable to a wide variety of substrates. (Figure presented.).
