3197-61-3Relevant academic research and scientific papers
On-resin N-formylation of peptides: a head-to-head comparison of reagents in solid-phase synthesis of ligands for formyl peptide receptors
Christensen, Simon Bendt,Hansen, Anna Mette,Franzyk, Henrik
, p. 410 - 415 (2017)
General conditions for efficient on-resin N-formylation of peptides were identified by screening of a number of reagents comprising aliphatic formates (ethyl formate, 2,2,2-trifluoroethyl formate, and cyanomethyl formate), aromatic esters (phenyl formate and p-nitrophenyl formate), and N-formylimidazole and in situ activation of formic acid with the coupling reagent 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide. Initially, reaction time and influence of solvent were examined for the formylation of a short model peptide. The most efficient reagents were examined further by using different linkers and solid supports in the synthesis of an array of longer formyl peptide ligands. For p-nitrophenyl formate and N-formylimidazole, almost complete conversion was reached within 2?h, albeit longer peptides attached to Tentagel resins via different linkers required an extended reaction time. Overall, the commercially available activated ester p-nitrophenyl formate proved to be most convenient and versatile as high formylation degrees were obtained after 1–3?h at room temperature, while either conventional or microwave-assisted heating allowed reduction of the formylation time to 20?min. Copyright
Synthesis of new five-membered N-heterocycle derivatives of mono- and bis-phosphonic acids
Prishchenko, Andrey A.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Petrosyan, Valery S.
, p. 90 - 92 (2017)
The new functionalized hydroxymethylphosphonic and methylenebis(phosphonic) acids are synthesized via reaction of tris(trimethylsilyl) phosphite and N-formyl derivatives of five-membered N-heterocycles in the presence of trimethylsilyl triflate.
Preparation method of iguratimod intermediate
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Paragraph 0011; 0019-0023; 0025, (2021/01/24)
The invention discloses a preparation method of an iguratimod intermediate. The preparation method comprises the following steps: by using formic acid as a starting raw material, subjecting formic acid to reacting with N,N-carbonyldiimidazole (CDI) via an
UiO-66 as an efficient catalyst for N-formylation of amines with CO2 and dimethylamine borane as a reducing agent
Phatake, Vishal V.,Mishra, Ashish A.,Bhanage, Bhalchandra M.
supporting information, (2019/12/11)
The most effective way to make the best use of CO2, is the reductive formylation of amines, as formamides have many applications in industry. A new protocol has been developed for reductive N-formylation of amines with CO2 as a C1 carbon source and DMAB (Dimethylamine borane) as a reducing agent in the presence of Zr-containing metal–organic framework (MOF) as an efficient, heterogeneous recyclable catalyst. We used UiO-66 and UiO-66-NH2 as catalysts for N-formylation of amines and observed that both the catalyst performs equally. Therefore, we continued our studies with UiO-66 as a catalyst. The UiO-66 MOF shows good catalytic activity and affording the desired formamides in good to excellent yield. This catalytic system is very efficient for several amines including primary and secondary aliphatic cyclic and aromatic amines. Moreover, the prepared catalyst was recycled up to four recycled without a considerable decrease in catalytic activity.
A NHC-silyliumylidene cation for catalytic N?formylation of amines using carbon dioxide
Leong, Bi-Xiang,Teo, Yeow-Chuan,Condamines, Cloe,Yang, Ming-Chung,Su, Ming-Der,So, Cheuk-Wai
, p. 14824 - 14833 (2020/12/21)
This study describes the use of a silicon(II) complex, namely, the NHC-silyliumylidene cation complex [(IMe)2SiH]I (1, IMe =:C{N(Me)C(Me)}2), to catalyze the chemoselective N-formylation of primary and secondary amines using CO2 and PhSiH3 under mild conditions to afford the corresponding formamides as a sole product (average reaction time: 4.5 h; primary amines, average yield: 95%, average TOF: 8 h?1; secondary amines, average yield: 98%, average TOF: 17 h?1). The activity of 1 and product yields outperform the currently available non-transition-metal catalysts used for this catalysis. Mechanistic studies show that the silicon(II) center in complex 1 catalyzes the C?N bond formation via a different pathway in comparison with non-transition-metal catalysts. It sequentially activates CO2, PhSiH3, and amines, which proceeds via a dihydrogen elimination mechanism, to form formamides, siloxanes, and dihydrogen gas.
Tris(trimethylsilyl) phosphite as key synthon for convenient synthesis of new organosilicon(phosphorus)-containing N-heterocycles
Prishchenko, Andrey A.,Alekseyev, Roman S.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Petrosyan, Valery S.
, p. 149 - 154 (2017/10/31)
The new functionalized hydroxymethylphosphonic and methylenediphosphonic acids are synthesized via unique reaction of tris(trimethylsilyl) phosphite and N-formyl N-heterocycles, N-substituted 4-piperidones, 3-quinuclidone, and 2-adamantanone at the presence of effective catalyst – trimethylsilyl triflate under mild conditions.
MEPicides: α,β-Unsaturated Fosmidomycin Analogues as DXR Inhibitors against Malaria
Wang, Xu,Edwards, Rachel L.,Ball, Haley,Johnson, Claire,Haymond, Amanda,Girma, Misgina,Manikkam, Michelle,Brothers, Robert C.,McKay, Kyle T.,Arnett, Stacy D.,Osbourn, Damon M.,Alvarez, Sophie,Boshoff, Helena I.,Meyers, Marvin J.,Couch, Robin D.,Odom John, Audrey R.,Dowd, Cynthia S.
supporting information, p. 8847 - 8858 (2018/10/05)
Severe malaria due to Plasmodium falciparum remains a significant global health threat. DXR, the second enzyme in the MEP pathway, plays an important role to synthesize building blocks for isoprenoids. This enzyme is a promising drug target for malaria due to its essentiality as well as its absence in humans. In this study, we designed and synthesized a series of α,β-unsaturated analogues of fosmidomycin, a natural product that inhibits DXR in P. falciparum. All compounds were evaluated as inhibitors of P. falciparum. The most promising compound, 18a, displays on-target, potent inhibition against the growth of P. falciparum (IC50 = 13 nM) without significant inhibition of HepG2 cells (IC50 > 50 μM). 18a was also tested in a luciferase-based Plasmodium berghei mouse model of malaria and showed exceptional in vivo efficacy. Together, the data support MEPicide 18a as a novel, potent, and promising drug candidate for the treatment of malaria.
Polymer Meets Frustrated Lewis Pair: Second-Generation CO2-Responsive Nanosystem for Sustainable CO2 Conversion
Chen, Liang,Liu, Renjie,Yan, Qiang
supporting information, p. 9336 - 9340 (2018/07/25)
Frustrated Lewis pairs (FLP), a couple comprising a sterically encumbered Lewis acid and Lewis base, can offer latent reactivity for activating inert gas molecules. However, their use as a platform for fabricating gas-responsive materials has not yet developed. Merging the FLP concept with polymers, we report a new generation CO2-responsive system, differing from the first-generation ones based on an acid–base equilibrium mechanism. Two complementary Lewis acidic and basic block copolymers, installing bulky borane- and phosphine-containing blocks, were built as the macromolecular FLP. They can bind CO2 to drive micellar formation, in which CO2 as a cross-linker bridges the block chains. This dative bonding endows the assembly with ultrafast response (2 can function as nanocatalysts for recyclable C1 catalysis, opening a new direction of sustainable CO2 conversion.
Sulfated polyborate-catalyzed N-formylation of amines: a rapid, green and efficient protocol
Khatri, Chetan K.,Chaturbhuj, Ganesh U.
, p. 2513 - 2519 (2017/11/06)
Abstract: A rapid, green and efficient method for N-formylation reaction of various amines with formic acid in the presence of sulfated polyborate catalyst under solvent-free conditions has been described. The catalyst has the advantage of mild Bronsted as well as Lewis acid character. The catalyst is recyclable with no significant loss in catalytic activity. The present protocol is advantageous due to its solvent-free condition, short reaction time, high yields, easy workup and ability to tolerate a variety of functional groups.
Synthesis of new functionalized mono- and diphosphonic acids with five-membered aza-heterocycles moieties
Prishchenko, Andrey A.,Alekseyev, Roman S.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Terenin, Vladimir I.,Petrosyan, Valery S.
, (2017/01/17)
The new functionalized hydroxymethylphosphonic and methylenediphosphonic acids are synthesized via unique reaction of tris(trimethylsilyl)phosphite and N-formyl derivatives of five-membered aza-heterocycles at the presence of effective catalyst—trimethylsilyl triflate.
