Month: October 2022

Lisboa, Lynn S.; Riisom, Mie; Vasdev, Roan A. S.; Jamieson, Stephen M. F.; Wright, L. James; Hartinger, Christian G.; Crowley, James D. published an article in 2021. The article was titled 《Cavity-containing [Fe2L3] 4+ helicates: an examination of host-guest chemistry and cytotoxicity》, and you may find the article in Frontiers in Chemistry (Lausanne, Switzerland).Electric Literature of C5H3Br2N The information in the text is summarized as follows:

Two new di(2,2′-bipyridine) ligands, 2,6-bis([2,2′-bipyridin]-5-ylethynyl)pyridine (L1) and bis(4-([2,2′-bipyridin]-5-ylethynyl)phenyl)methane (L2) were synthesized and used to generate two metallosupramol. [Fe2(L)3](BF4)4 cylinders. The ligands and cylinders were characterized using elemental anal., electrospray ionization mass spectrometry, UV-vis, 1H-, 13C and DOSY NMR (NMR) spectroscopies. The mol. structures of the [Fe2(L)3](BF4)4 cylinders were confirmed using X-ray crystallog. Both the [Fe2(L1)3](BF4)4 and [Fe2(L2)3](BF4)4 complexes crystallized as racemic (rac) mixtures of the δδ (P) and λλ (M) helicates. However, 1H NMR spectra showed that in solution the larger [Fe2(L2)3](BF4)4 was a mixture of the rac δδ/λλ and meso-δλ isomers. The host-guest chem. of the helicates, which both feature a central cavity, was examined with several small drug mols. However, none of the potential guests were found to bind within the helicates. In vitro cytotoxicity assays demonstrated that both helicates were active against four cancer cell lines. The smaller [Fe2(L1)3](BF4)4 system displayed low μM activity against the HCT116 (IC50 = 7.1 ± 0.5 μM) and NCI-H460 (IC50 = 4.9 ± 0.4 μM) cancer cells. While the antiproliferative effects against all the cell lines examined were less than the well-known anticancer drug cisplatin, their modes of action would be expected to be very different. The experimental part of the paper was very detailed, including the reaction process of 2,6-Dibromopyridine(cas: 626-05-1Electric Literature of C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Electric Literature of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Gil-Martinez, Jon; Macias, Iratxe; Unione, Luca; Bernardo-Seisdedos, Ganeko; Lopitz-Otsoa, Fernando; Fernandez-Ramos, David; Lain, Ana; Sanz-Parra, Arantza; Mato, Jose M.; Millet, Oscar published an article in 2021. The article was titled 《Therapeutic targeting of fumaryl acetoacetate hydrolase in hereditary tyrosinemia type I》, and you may find the article in International Journal of Molecular Sciences.Electric Literature of C7H5N The information in the text is summarized as follows:

Fumarylacetoacetate hydrolase (FAH) is the fifth enzyme in the tyrosine catabolism pathway. A deficiency in human FAH leads to hereditary tyrosinemia type I (HT1), an autosomal recessive disorder that results in the accumulation of toxic metabolites such as succinylacetone, maleylacetoacetate, and fumarylacetoacetate in the liver and kidney, among other tissues. The disease is severe and, when untreated, it can lead to death. A low tyrosine diet combined with the herbicidal nitisinone constitutes the only available therapy, but this treatment is not devoid of secondary effects and long-term complications. In this study, we targeted FAH for the first-time to discover new chem. modulators that act as pharmacol. chaperones, directly associating with this enzyme. After screening several thousand compounds and subsequent chem. redesign, we found a set of reversible inhibitors that associate with FAH close to the active site and stabilize the (active) dimeric species, as demonstrated by NMR spectroscopy. Importantly, the inhibitors are also able to partially restore the normal phenotype in a newly developed cellular model of HT1. The results came from multiple reactions, including the reaction of 4-Ethynylpyridine(cas: 2510-22-7Electric Literature of C7H5N)

4-Ethynylpyridine(cas: 2510-22-7) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Electric Literature of C7H5N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Honnanayakanavar, Jyoti M.; Nanubolu, Jagadeesh Babu; Suresh, Surisetti published an article in 2021. The article was titled 《Tandem copper catalyzed regioselective N-arylation-amidation: synthesis of angularly fused dihydroimidazoquinazolinones and the anticancer agent TIC10/ONC201》, and you may find the article in Organic & Biomolecular Chemistry.Name: 2-Bromonicotinaldehyde The information in the text is summarized as follows:

Herein, a copper-catalyzed tandem reaction of 2-aminoimidazolines I (R = n-Bu, Ph, furan-2-ylmethyl, pyridin-4-ylmethyl, etc.) and ortho-halo(hetero)aryl carboxylic acids R1C(O)OH (R1 = 2-bromophenyl, 2-bromo-4,5-difluorophenyl, 2-bromopyridin-3-yl, 4-chloropyridin-3-yl, etc.) that causes the regioselective formation of angularly fused tricyclic 1,2-dihydroimidazo[1,2-a]quinazolin-5(4H)-one derivs II (R2 = H, OMe, F; R3 = H, OMe, Cl, Br, F, NO2; R4 = H, F), III and IV was presented. The reaction involved in the construction of the core six-membered pyrimidone moiety proceeded via regioselective N-arylation-condensation. The presented protocol has been successfully applied to accomplish the total synthesis of TIC10/ONC201 V, which is an active angular isomer acting as a tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL): a sought after anticancer clin. agent. In addition to this study using 2-Bromonicotinaldehyde, there are many other studies that have used 2-Bromonicotinaldehyde(cas: 128071-75-0Name: 2-Bromonicotinaldehyde) was used in this study.

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Name: 2-Bromonicotinaldehyde

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromideIn 2017 ,《(Aminomethylene)phosphonate Analogues as ZnII Chelators: Synthesis and Characterization》 appeared in European Journal of Inorganic Chemistry. The author of the article were Hevroni, Bosmat Levi; Jantz, Thomas; Gottlieb, Hugo E.; Fischer, Bilha. The article conveys some information:

A series of (aminomethylene)phosphonate (AMP) analogs, 8-14, bearing one or two heterocyclic moieties (imidazolyl, pyridyl, and thiazolyl) on the aminomethylene group, were synthesized as potential ZnII chelators. The complexes of analogs 8-14 with ZnII ions were characterized by their stoichiometry, geometry, coordination sites, acid/base equilibrium, and stability constants Analogs 8-14 form stable water-soluble 2:1 L/ZnII complexes, as established by ZnII titration, monitored by UV/visible spectrophotometry and by 1H and 31P NMR spectroscopy. Acidity and stability constants were established for each derivative by potentiometric pH titrations ML2 type ZnII complexes of AMP, bearing either an imidazolyl or pyridyl moiety, 8, 10, and 12, exhibit high log β values (17.68, 16.92, and 16.65, resp.), while for the AMP-thiazolyl (14) complex with ZnII, log β is 12.53. Generally, ligands 9, 11, and 13, bearing two heterocyclic moieties, present higher log β values (22.25, 21.00, and 18.28, resp.) vs. analogs bearing one heterocyclic moiety. Addnl., based on 1H, 13C, and 31P NMR spectroscopic data, the authors propose a structure of the AMP-(Im)2-ZnII complex in solution, where the ZnII coordination sites involve the phosphonate moiety and both imidazolyl rings of the two binding mols., forming an octahedral geometry around the ZnII ion. In summary, the authors propose a new family of water-soluble high-affinity ZnII chelators, in particular AMP-(Im)2, which forms the most stable complex (log β 22).2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide) was used in this study.

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of C6H5Br2NOOn June 1, 2011, Allcock, Robert W.; Blakli, Haakon; Jiang, Zhong; Johnston, Karen A.; Morgan, Keith M.; Rosair, Georgina M.; Iwase, Kazuhiko; Kohno, Yasushi; Adams, David R. published an article in Bioorganic & Medicinal Chemistry Letters. The article was 《Phosphodiesterase inhibitors. Part 1: Synthesis and structure-activity relationships of pyrazolopyridine-pyridazinone PDE inhibitors developed from ibudilast》. The article mentions the following:

Ibudilast [1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one] is a nonselective phosphodiesterase inhibitor used clin. to treat asthma. Efforts to selectively develop the PDE3- and PDE4-inhibitory activity of ibudilast led to replacement of the iso-Pr ketone by a pyridazinone heterocycle. Structure-activity relationship exploration in the resulting 6-(pyrazolo[1,5-a]pyridin-3-yl)pyridazin-3(2H)-ones revealed that the pyridazinone lactam functionality is a critical determinant for PDE3-inhibitory activity, with the nitrogen preferably unsubstituted. PDE4 inhibition is strongly promoted by introduction of a hydrophobic substituent at the pyridazinone N(2) center and a methoxy group at C-7′ in the pyrazolopyridine. Migration of the pyridazinone ring connection from the pyrazolopyridine 3′-center to C-4′ strongly enhances PDE4 inhibition. These studies establish a basis for development of potent PDE4-selective and dual PDE3/4-selective inhibitors derived from ibudilast. In addition to this study using 2,3-Dibromo-6-methoxypyridine, there are many other studies that have used 2,3-Dibromo-6-methoxypyridine(cas: 909720-21-4Electric Literature of C6H5Br2NO) was used in this study.

2,3-Dibromo-6-methoxypyridine(cas: 909720-21-4) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Electric Literature of C6H5Br2NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Peter, K.; Wietasch, H.; Peng, B.; Thelakkat, M. published an article in Applied Physics A: Materials Science & Processing. The title of the article was 《Dual-functional materials for interface modifications in solid-state dye-sensitised TiO2 solar cells》.Electric Literature of C12H10Cl2N2 The author mentioned the following in the article:

The concept of solid-state dye-sensitized TiO2 solar cells with an organic semiconductor as hole-transport medium is studied in detail by examining the dye-hole conductor interface. The facile transfer of holes from Ru-dye core to the hole conductor requires suitable interface modifiers which have the function of dye and hole transport moiety, but with exactly positioned anchor groups and antenna functions. The synthesis and characterization of such novel low mol. weight multifunctional mols. carrying dye units and triphenylamine moieties are presented and their influence as interface modifiers is studied. This interface modification results in doubling the external quantum efficiency of current conversion via improved charge transfer at the dye-hole conductor interface. Also, the recombination processes at this interface are drastically suppressed, which leads to higher open-circuit voltage and consequently higher power-conversion efficiency. The concept is also extended to polymers to obtain dye-centered polymeric hole conductors which carry a single Ru-dye unit in the middle of the poly(vinyltriphenylamine) chain that acts as hole-conductor polymer. The polymerization was carried out by atom-transfer radical polymerization of 4-bromostyrene followed by polymer amination and finally metalation with Ru-bis(bipyridyl) precursors. The experimental part of the paper was very detailed, including the reaction process of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Electric Literature of C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Electric Literature of C12H10Cl2N2The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2013,El Abidine Chamas, Zein; Marchi, Enrico; Modelli, Alberto; Fort, Yves; Ceroni, Paola; Mamane, Victor published 《Highly Fluorescent, π-Extended Indenopyrido[2,1-a]isoindolone Derivatives Prepared by a Palladium-Catalysed Cascade Reaction》.European Journal of Organic Chemistry published the findings.Electric Literature of C5H3BrClN The information in the text is summarized as follows:

A new family of heterocyclic pentacyclic compounds were prepared by a cascade reaction involving 2,5-dihalopyridines and (2-formylphenyl)boronic acids. Most of the compounds exhibit high quantum yields of fluorescence in dichloromethane. In some cases, small changes in the substitution pattern caused fluorescence quenching. To rationalize this effect, a detailed photophys. study combined with electrochem. and computational studies was performed on four representative derivatives It appears that the fluorescence quenching is caused by a thermally activated nonradiative deactivation process that can be prevented in a rigid matrix such as ethanol at 77 °K or PMMA. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-chloropyridine(cas: 53939-30-3Electric Literature of C5H3BrClN)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Electric Literature of C5H3BrClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Boronic acid derivatized lanthanide-polyoxometalates with novel B-OH-Ln and B-O-Nb bridges》 were Li, Shujun; Zhao, Yue; Qi, Huihui; Zhou, Yanfang; Liu, Shuxia; Ma, Xiaoming; Zhang, Jie; Chen, Xuenian. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2019. Application In Synthesis of Pyridin-3-ylboronic acid The author mentioned the following in the article:

Three new boronic acid derivatized lanthanide-polyoxometalates (BA-Ln-POMs) were synthesized, in which boronic acids served as bi- or tri-dentate ligands and exhibited interesting coordination ability towards POMs and LnIII. The pH is crucial in controlling the coordination modes of boronic acid and the formation of B-O-Ln and B-O-Nb bridges. Compared with the boronic acid-free Ln-POM, a longer lifetime was observed for compound 2Eu due to the coordination of boronic acids to the EuIII center. The results came from multiple reactions, including the reaction of Pyridin-3-ylboronic acid(cas: 1692-25-7Application In Synthesis of Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Application In Synthesis of Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《A New Schizophrenia Model: Immune Activation is Associated with the Induction of Different Neurotoxic Products which Together Determine Memory Impairments and Schizophrenia Symptom Dimensions》 were Sirivichayakul, Sunee; Kanchanatawan, Buranee; Thika, Supaksorn; Carvalho, Andre F.; Maes, Michael. And the article was published in CNS & Neurological Disorders: Drug Targets in 2019. Computed Properties of C6H5NO2 The author mentioned the following in the article:

Objective: Recently, we reported that stable-phase schizophrenia is characterized by two interrelated symptom dimensions: PHEMN (psychotic, hostility, excitation, mannerism and neg. symptoms); and DAPS (depressive, anxiety and physio-somatic symptoms) and that Major Neuro-Cognitive psychosis (MNP) is the full-blown phenotype of schizophrenia (largely overlapping with deficit schizophrenia). Herein we examined the effects of immune activation in association with tryptophan catabolite (TRYCAT) patterning and memory disorders on PHEMN/DAPS dimensions and MNP. Methods: Serum levels of macrophage inflammatory protein-1 (MIP-1), soluble interleukin (IL)-1 receptor antagonist (sIL-1RA), IL-10, eotaxin, IgA/IgM responses to TRYCATs, and Consortium to Establish a Registry for Alzheimer’s disease (CERAD) tests were assessed in 40 controls and 80 schizophrenia patients. Results: Schizophrenia and MNP were predicted by significantly increased levels of IL-10, eotaxin and TRYCATs. A large part of variance in both PHEMN/DAPS symptom dimensions (42.8%) was explained by cytokine levels and TRYCATs combined. The MIP+sIL-1RA+IL-10 composite score and eotaxin explained each around on the basis of 19% of the variance in symptom dimensions, and approx. 18% of memory deficits. Moreover, MIP+sIL-1RA+IL-10 was significantly associated with elevations in picolinic acid, xanthurenic acid and 3-OH-kynurenine. Partial Least Squares path modeling shows that highly significant effects of MIP+sIL-1RA+IL-10 on symptomatol. are mediated by the effects of noxious TRYCATs on memory deficits. Conclusion: Current findings indicate that in schizophrenia, immune activation may underpin activation of indoleamine-2,3-dioxygenase and kynurenine monooxygenase, while impairments in episodic and semantic memory may be caused by the neurotoxic effects of TRYCATs and eotaxin. The combined effects of immune activation, eotaxin and memory defects determine to a large extent, PHEMN/DAPS symptoms and the MNP phenotype. These findings indicate that schizophrenia phenomenol. is largely mediated by multiple neuro-immune pathways and that immune activation, increased production of eotaxin and neurotoxic TRYCATs (picolinic acid, xanthurenic acid and 3-OH-kynurenine) are new drug targets in schizophrenia and MNP.Picolinic acid(cas: 98-98-6Computed Properties of C6H5NO2) was used in this study.

Picolinic acid(cas: 98-98-6) is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.Computed Properties of C6H5NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Rational Design of Multi-Stimuli-Responsive Scaffolds: Synthesis of Luminescent Oligo(ethynylpyridine)-Containing Alkynylplatinum(II) Polypyridine Foldamers Stabilized by Pt···Pt Interactions》 were Chan, Michael Ho-Yeung; Leung, Sammual Yu-Lut; Yam, Vivian Wing-Wah. And the article was published in Journal of the American Chemical Society in 2019. Name: 2,6-Dibromopyridine The author mentioned the following in the article:

A series of oligo(ethynylpyridine)-containing alkynylplatinum(II) terpyridine/bzimpy (bzimpy = 2,6-bis(N-alkylbenzimidazol-2′-yl)pyridine) metallofoldamers [L3Pt(CC-1,3-Ar)nCCPtL3] (L3 = tpy, bzimpy; Ar = m-phenylene, 2,6-pyridinediyl) has been designed and synthesized to investigate the potential applications of metallofoldamers imparted by the rich spectroscopic responses of Pt···Pt interactions. Apart from the control of the folding/unfolding processes by solvent compositions and temperatures, this class of metallofoldamers has also been found to exhibit reversible folding/unfolding behaviors mediated by the addition of acids/bases due to the incorporation of the acid-sensitive oligo(ethynylpyridine) derivatives More importantly, the intramol. Pt···Pt interaction has been found to play a crucial role in governing the folded state conformation. The conformation of this class of metallofoldamers has been investigated by 2D ROESY NMR, electronic absorption, and emission spectroscopy, which provide further insights into the rational mol. design and multidimensional control of metallofoldamers upon the application of various external stimuli, leading to the preparation of multi-stimuli-responsive materials for potential applications in material sciences. In addition to this study using 2,6-Dibromopyridine, there are many other studies that have used 2,6-Dibromopyridine(cas: 626-05-1Name: 2,6-Dibromopyridine) was used in this study.

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Name: 2,6-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem