61414-14-0Relevant academic research and scientific papers
Anion and sugar recognition by 2,6-pyridinedicarboxamide bis-boronic acid derivatives
Martínez-Aguirre, Mayte A.,Otero, Diego Martínez,álvarez-Hernández, Magali L.,Torres-Blancas, Teresa,Dorazco-González, Alejandro,Yatsimirsky, Anatoly K.
, p. 171 - 180 (2017)
Two 2,6-pyridinedicarboxamide derivatives containing arylboronic acid fragments were prepared and fully characterized including X-ray crystal diffraction analysis of a pinacol ester. These compounds are potential bifunctional receptors for sugars and anions. Acid dissociation and stability constants for complexation of both receptors with glucose and fructose were determined by potentiometric titrations in aqueous DMSO. Also, binding of alizarin red S indicator was studied spectrophotometrically and a highly sensitive detection of fructose by an indicator displacement assay was proposed. Complexation with anions was studied by 1H NMR titrations in DMSO-d6. Binding of acetate anion occurs only via hydrogen bonding to OH groups of boronic acid fragments and does not affect signals of NH protons but chloride anion induces large shift of the signals of NH protons and small shifts of the signals of OH groups. This behavior makes possible anion discrimination based on preference in the type of binding site rather than simply on anion basicity as is typical for majority of neutral hydrogen bonding anion receptors.
Soft-donor dipicolinamide derivatives for selective actinide(iii)/lanthanide(iii) separation: The role of S-: Vs. O-donor sites
Lehman-Andino, Ingrid,Su, Jing,Papathanasiou, Konstantinos E.,Eaton, Teresa M.,Jian, Jiwen,Dan, David,Albrecht-Schmitt, Thomas E.,Dares, Christopher J.,Batista, Enrique R.,Yang, Ping,Gibson, John K.,Kavallieratos, Konstantinos
supporting information, p. 2441 - 2444 (2019/03/05)
Selectivity for An(iii) vs. Ln(iii) binding and extraction using dipicolinamide analogs containing the CO vs. CS groups was investigated in solution and the gas-phase, and by DFT calculations. The results show higher selectivity for complex formation and
Identification and SAR Evaluation of Hemozoin-Inhibiting Benzamides Active against Plasmodium falciparum
Wicht, Kathryn J.,Combrinck, Jill M.,Smith, Peter J.,Hunter, Roger,Egan, Timothy J.
, p. 6512 - 6530 (2016/07/23)
Quinoline antimalarials target hemozoin formation causing a cytotoxic accumulation of ferriprotoporphyrin IX (Fe(III)PPIX). Well-developed SAR models exist for β-hematin inhibition, parasite activity, and cellular mechanisms for this compound class, but no comparably detailed investigations exist for other hemozoin inhibiting chemotypes. Here, benzamide analogues based on previous HTS hits have been purchased or synthesized. Only derivatives containing an electron deficient aromatic ring and capable of adopting flat conformations, optimal for π-π interactions with Fe(III)PPIX, inhibited β-hematin formation. The two most potent analogues showed nanomolar parasite activity, with little CQ cross-resistance, low cytotoxicity, and high in vitro microsomal stability. Selected analogues inhibited hemozoin formation in Plasmodium falciparum causing high levels of free heme. In contrast to quinolines, introduction of amine side chains did not lead to benzamide accumulation in the parasite. These data reveal complex relationships between heme binding, free heme levels, cellular accumulation, and in vitro activity of potential novel antimalarials.
Nickel(II) complexes chelated by 2,6-pyridinedicarboxamide: Syntheses, characterization, and ethylene oligomerization
Zhang, Jie,Liu, Shaofeng,Li, Antai,Ye, Hongqi,Li, Zhibo
, p. 7027 - 7033 (2016/08/09)
N,N′-Bis(2,6-R-phenyl)-2,6-pyridinedicarboxamides (L: R = Cl, L1; R = F, L2; R = H, L3; R = Me, L4; R = Et, L5; R = iPr, L6) were designed as neutral ligands, and the corresponding nickel complexes LNiBr2 (Ni1-Ni6) were synthesized a
Synthesis of bis(N-arylcarboximidoylchloride)pyridine cobalt(ii) complexes and their catalytic behavior for 1,3-butadiene polymerization
Liu, Heng,Jia, Xiangyu,Wang, Feng,Dai, Quanquan,Wang, Baolin,Bi, Jifu,Zhang, Chunyu,Zhao, Liping,Bai, Chenxi,Hu, Yanming,Zhang, Xuequan
, p. 13723 - 13732 (2013/09/23)
A new family of bis(N-arylcarboximidoylchloride)pyridine cobalt(ii) complexes with the general formula [2,6-(ArNCCl)2C5H 3N]CoCl2 (Ar = 2,4,6-Me3C6H 2, 4a; 2,6-iPrsub
Chemical mustard containment using simple palladium pincer complexes: The influence of molecular walls
Wang, Qi-Qiang,Begum, Rowshan Ara,Day, Victor W.,Bowman-James, Kristin
supporting information, p. 17193 - 17199 (2013/12/04)
Six amide-based NNN palladium(II) pincer complexes Pd(L)(CH3CN) were synthesized, characterized, and examined for binding the sulfur mustard surrogate, 2-chloroethyl ethyl sulfide (CEES). The complexes all bind readily with CEES as shown by 1H NMR spectroscopy in CDCl3. The influence of para-substituents on the two amide phenyl appendages was explored as well as the effect of replacing the phenyl groups with larger aromatic rings, 1-naphthalene and 9-anthracene. While variations of the para-substituents had only a slight influence on the binding affinities, incorporation of larger aromatic rings resulted in a significant size-related increase in binding, possibly due to increasing steric and electronic interactions. In crystal structures of three CEES-bound complexes, the mustard binds through the sulfur atom and lies along the aromatic walls of the side appendages approximately perpendicular to the pincer plane, with increasingly better alignment progressing from phenyl to 1-naphthalene to 9-anthracene.
Anion complexation and transport by isophthalamide and dipicolinamide derivatives: DNA plasmid transformation in E. coli
Atkins, Jason L.,Patel, Mohit B.,Daschbach, Megan M.,Meisel, Joseph W.,Gokel, George W.
body text, p. 13546 - 13549 (2012/10/08)
Tris-arenes based on either isophthalic acid or 2,6-dipicolinic acid have been known for more than a decade to bind anions. Recent studies have also demonstrated their ability to transport various ions through membranes. In this report, we demonstrate two
Dianilides of dipicolinic acid function as synthetic chloride channels
Yamnitz, Carl R.,Negin, Saeedeh,Carasel, I. Alexandru,Winter, Rudolph K.,Gokel, George W.
supporting information; experimental part, p. 2838 - 2840 (2010/09/04)
We report that N2,N6-bis(4-nitrophenyl)pyridine-2,6- dicarboxamide, which is related to known isophthalic acid dianilides, transports Cl- ions through phospholipid bilayer membranes and shows clear evidence of channel acti
Hydrogen bonding in anion recognition: A family of versatile, nonpreorganized neutral and acyclic receptors
Kavallieratos, Konstantinos,Bertao, Christina M.,Crabtree, Robert H.
, p. 1675 - 1683 (2007/10/03)
The diamides and disulfonamides m-C6H4(CONHAr)2 (Ar = Ph, 1; p-n-BuC6H4, 2, 2,4,6-Me3C6H2, 3), m-C6H4(SO2NHPh)2, 4, and 2,6
