Category: 591-54-8

Synthetic Route of C4H5N3. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Probing the effects of pyrimidine functional group switches on acyclic fleximer analogues for antiviral activity. Author is Yates, Mary K.; Chatterjee, Payel; Flint, Mike; Arefeayne, Yafet; Makuc, Damjan; Plavec, Janez; Spiropoulou, Christina F.; Seley-Radtke, Katherine L..

Due to their ability to inhibit viral DNA or RNA replication, nucleoside analogs have been used for decades as potent antiviral therapeutics. However, one of the major limitations of nucleoside analogs is the development of antiviral resistance. In that regard, flexible nucleoside analogs known as “”fleximers”” have garnered attention over the years due to their ability to survey different amino acids in enzyme binding sites, thus overcoming the potential development of antiviral resistance. Acyclic fleximers have previously demonstrated antiviral activity against numerous viruses including Middle East Respiratory Syndrome coronavirus (MERS-CoV), Ebola virus (EBOV), and, most recently, flaviviruses such as Dengue (DENV) and Yellow Fever Virus (YFV). Due to these interesting results, a Structure Activity Relationship (SAR) study was pursued in order to analyze the effect of the pyrimidine functional group and acyl protecting group on antiviral activity, cytotoxicity, and conformation. The results of those studies are presented herein.

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Pyrazine | C4H4N2 – PubChem

SDS of cas: 591-54-8. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Energetic and Geometric Characteristics of the Substituents: Part 2: The Case of NO2, Cl, and NH2 Groups in Their Mono-Substituted Derivatives of Simple Nitrogen Heterocycles. Author is Wieczorkiewicz, Pawel A.; Szatylowicz, Halina; Krygowski, Tadeusz M..

Variously substituted N-heterocyclic compounds are widespread across bio- and medicinal chem. The work aims to computationally evaluate the influence of the type of N-heterocyclic compound and the substitution position on the properties of three model substituents: NO2, Cl, and NH2. For this reason, the energetic descriptor of global substituent effect (Erel), geometry of substituents, and electronic descriptors (cSAR, pEDA, sEDA) are considered, and interdependences between these characteristics are discussed. Furthermore, the existence of an endocyclic N atom may induce proximity effects specific for a given substituent. Therefore, various quantum chem. methods are used to assess them: the quantum theory of atoms in mols. (QTAIM), anal. of non-covalent interactions using reduced d. gradient (RDG) function, and electrostatic potential maps (ESP). The study shows that the energetic effect associated with the substitution is highly dependent on the number and position of N atoms in the heterocyclic ring. Moreover, this effect due to interaction with more than one endo N atom (e.g., in pyrimidines) can be assessed with reasonable accuracy by adding the effects calculated for interactions with one endo N atom in substituted pyridines. Finally, all possible cases of proximity interactions for the NO2, Cl, and NH2 groups are thoroughly discussed.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 591-54-8, is researched, Molecular C4H5N3, about Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability, the main research direction is dialkylbiaryl monosphosphine ligand preparation amination coupling catalyst.Computed Properties of C4H5N3.

The authors have developed a new dialkylbiaryl monophosphine ligand, GPhos, that supports a palladium catalyst capable of promoting carbon-nitrogen cross-coupling reactions between a variety of primary amines and aryl halides; in many cases, these reactions can be carried out at room temperature The reaction development was guided by the idea that the productivity of catalysts employing BrettPhos-like ligands is limited by their lack of stability at room temperature Specifically, it was hypothesized that primary amine and N-heteroaromatic substrates can displace the phosphine ligand, leading to the formation of catalytically dormant palladium complexes that reactivate only upon heating. This notion was supported by the synthesis and kinetic study of a putative off-cycle Pd complex. Consideration of this off-cycle species, together with the identification of substrate classes that are not effectively coupled at room temperature using previous catalysts, led to the design of a new dialkylbiaryl monophosphine ligand. An Ot-Bu substituent was added ortho to the dialkylphosphino group of the ligand framework to improve the stability of the most active catalyst conformer. To offset the increased size of this substituent, the authors also removed the para i-Pr group of the non-phosphorus-containing ring, which allowed the catalyst to accommodate binding of even very large α-tertiary primary amine nucleophiles. In comparison to previous catalysts, the GPhos-supported catalyst exhibits better reactivity both under ambient conditions and at elevated temperatures Its use allows for the coupling of a range of amine nucleophiles, including (1) unhindered, (2) five-membered-ring N-heterocycle-containing, and (3) α-tertiary primary amines, each of which previously required a different catalyst to achieve optimal results.

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Related Products of 591-54-8. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Design, synthesis, molecular docking and cytotoxic activity of novel urea derivatives of 2-amino-3-carbomethoxythiophene. Author is Vikram, Venugopalarao; Penumutchu, Srinivasa R.; Vankayala, Raviraj; Thangudu, Suresh; Amperayani, Karteek Rao; Parimi, Umadevi.

An efficient feasible route for the one-pot synthesis of novel series of urea derivatives (2a-2j) from 2-amino-3-carbomethoxythiophene (1) via in situ isocyanate has been developed, and their corresponding anticancer activities were accomplished. The series of urea derivatives were characterized by using 1H, 13C NMR and mass spectroscopic anal. The cytotoxic activities were evaluated against human cervical (HeLa) and human lung (NCI-H23) cancer cell lines. These studies revealed satisfactory activity for some of the compounds, which could potentially serve as lead compounds for drug discovery and development. Furthermore, mol. docking studies supported in identifying the potential binding sites between the urea derivatives and eukaryotic ribonucleotidereductase (RR). High ambiguity driven docking (HADDOCK) modeling was specifically employed to determine the model complex of RR and urea derivatives The proposed model has provided a deep insight into the mol. level interactions of RR-urea model complexes in understanding the exact pharmacophore for designing highly potent RR inhibitors. Overall, the present work has shed light in developing a feasible and robust approach for the synthesis of novel urea derivatives of 2-amino-3-carbomethoxythiophene and identified a part of mol. structure that is responsible for a specific biol. interaction leading to potential anticancer activities. Graphic abstract: We report herein, the exptl. design, synthesis and characterization of a novel series of urea derivatives of 2-amino-3carbomethoxythiophene with pyrimidine amine and benzyl amine analogs as both derivatives which exhibited potential antitumor activity via one pot synthesis and subsequently studied the structure activity relationships (SAR), and anticancer activities. The docking studies identified a part of molecularstructure that is responsible for a specific biol. interaction leading to the destruction of cancer cells.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Synthesis of 2-guanidinyl pyridines and their trypsin inhibition and docking, published in 2020-08-15, which mentions a compound: 591-54-8, mainly applied to guanidinylpyridine synthesis trypsin inhibition docking; safety allergic reaction aminomethoxymethylnicotinamide; Enzymology; Halogen bonding; Hydrogen bonding; Inhibitor; Molecular docking; Pyridin-2-yl guanidine; Serine protease, Recommanded Product: 4-Aminopyrimidine.

A range of guanidine-based pyridines, and related compounds, have been prepared (19 examples). These compounds were evaluated in relation to their competitive inhibition of bovine pancreatic trypsin. Results demonstrate that compounds in which the guanidinyl substituent can form an intramol. hydrogen bond (IMHB) with the pyridinyl nitrogen atom are better trypsin inhibitors than their counterparts that are unable to form an IMHB. Among the compounds 6a-p, examples containing a 5-halo substituent were, generally, found to be better trypsin inhibitors. This trend was inversely related to electronegativity, thus, 1-(5-iodopyridin-2-yl)guanidinium ion 6e (I.TFA) (Ki = 0.0151 mM) was the optimum inhibitor in the 5-halo series. Amongst the isomeric Me substituted compounds, 1-(3-methylpyridin-2-yl)guanidinium ion 6h (II.TFA) demonstrated optimum levels of trypsin inhibition (Ki = 0.0140 mM). In order to rationalize the measured enzyme inhibition, selected compounds were docked with bovine and human trypsin with a view to understanding active site occupancy and taken together with the Ki values the order of inhibitory ability suggests that the 5-halo 2-guanidinyl pyridine inhibitors form a halogen bond with the catalytically active serine hydroxy group. Safety: severe allergic reactions have been reported with 6-amino-N-methoxy-N-methylnicotinamide.

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Pyrazine – Wikipedia,
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Recommanded Product: 4-Aminopyrimidine. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Exploring the Influence of Intermolecular Interactions in Prebiotic Chemistry Using Laser Spectroscopy and Calculations. Author is Camiruaga, Ander; Usabiaga, Imanol; Calabrese, Camilla; Lamas, Iker; Basterretxea, Francisco J.; Fernandez, Jose A..

One of the most fascinating questions in chem. is why nature chose CGAT as the alphabet of life. Very likely, such selection was the result of multiple factors and a long period of refinement. Here, we explore how the intermol. interactions influenced such process, by characterizing the formation of dimers between adenine, theobromine and 4-aminopyrimidine. Using a combination of mass-resolved excitation spectroscopy and DFT calculations, we determined the structure of adenine-theobromine and 4-aminopyrimidine-theobromine dimers. The binding energy of these dimers is very close to the canonical adenine-thymine nucleobases. Likewise, the dimers are able to adopt Watson-Crick conformations. These findings seem to indicate that there were many options available to build the first versions of the informational polymers, which also had to compete with other mols., such as 4-aminopyrimidine, which does not have a valid attaching point for a saccharide. For some reason, nature did not select the most strongly-bonded partners or if it did, such proto-bases were later replaced by the nowadays canonical CGAT.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Formula: C4H5N3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Recent developments of RET protein kinase inhibitors with diverse scaffolds as hinge binders. Author is Jia, Cong-Cong; Chen, Wang; Feng, Zi-Li; Liu, Zhao-Peng.

A review. RET is a proto-oncogene encoding a receptor tyrosine kinase. RET regulates key aspects of cellular proliferation, differentiation and survival. The activation of RET via gene fusions or point mutations is closely related to lung, thyroid and other cancers. This review summarizes the developments of a diversity of small mol. RET protein kinase inhibitors in the past 10 years. These RET inhibitors are classified according to their hinge binder chemotypes as: pyrimidines, including the pyrazolopyrimidines, pyrimidine oxazines, quinazolines, 4-aminopyrimidines and 4-aminopyridines; indolinones; 5-aminopyrazole-4-carboxamides; 3-trifluoromethylanilines; imidazopyridines, imidazopyridazines and pyrazopyridines; nicotinonitriles; pyridones and 1,2,4-triazoles. In each section, the biol. activities of the inhibitors, their structure-activity relationships and possible binding modes with the RET kinase are introduced.

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Pyrazine – Wikipedia,
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Computed Properties of C4H5N3. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Discovery of Potent, Selective, and State-Dependent NaV1.7 Inhibitors with Robust Oral Efficacy in Pain Models: Structure-Activity Relationship and Optimization of Chroman and Indane Aryl Sulfonamides. Author is Ramdas, Vidya; Talwar, Rashmi; Kanoje, Vijay; Loriya, Rajesh M.; Banerjee, Moloy; Patil, Pradeep; Joshi, Advait Arun; Datrange, Laxmikant; Das, Amit Kumar; Walke, Deepak Sahebrao; Kalhapure, Vaibhav; Khan, Talha; Gote, Ganesh; Dhayagude, Usha; Deshpande, Shreyas; Shaikh, Javed; Chaure, Ganesh; Pal, Ravindra R.; Parkale, Santosh; Suravase, Sachin; Bhoskar, Smita; Gupta, Rajesh V.; Kalia, Anil; Yeshodharan, Rajesh; Azhar, Mahammad; Daler, Jagadeesh; Mali, Vinod; Sharma, Geetika; Kishore, Amitesh; Vyawahare, Rupali; Agarwal, Gautam; Pareek, Himani; Budhe, Sagar; Nayak, Arun; Warude, Dnyaneshwar; Gupta, Praveen Kumar; Joshi, Parag; Joshi, Sneha; Darekar, Sagar; Pandey, Dilip; Wagh, Akshaya; Nigade, Prashant B.; Mehta, Maneesh; Patil, Vinod; Modi, Dipak; Pawar, Shashikant; Verma, Mahip; Singh, Minakshi; Das, Sudipto; Gundu, Jayasagar; Nemmani, Kumar; Bock, Mark G.; Sharma, Sharad; Bakhle, Dhananjay; Kamboj, Rajender Kumar; Palle, Venkata P..

Voltage-gated sodium channel NaV1.7 is a genetically validated target for pain. Identification of NaV1.7 inhibitors with all of the desired properties to develop as an oral therapeutic for pain has been a major challenge. Herein, we report systematic structure-activity relationship (SAR) studies carried out to identify novel sulfonamide derivatives as potent, selective, and state-dependent NaV1.7 inhibitors for pain. Scaffold hopping from benzoxazine to chroman and indane bicyclic system followed by thiazole replacement on sulfonamide led to identification of lead mols. with significant improvement in solubility, selectivity over NaV1.5, and CYP2C9 inhibition. The lead mols. 13, 29, 32, 43, and 51 showed a favorable pharmacokinetics (PK) profile across different species and robust efficacy in veratridine and formalin-induced inflammatory pain models in mice. Compound 51 also showed significant effects on the CCI-induced neuropathic pain model. The profile of 51 indicated that it has the potential for further evaluation as a therapeutic for pain.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 591-54-8, is researched, Molecular C4H5N3, about Nanoscale, automated, high throughput synthesis and screening for the accelerated discovery of protein modifiers, the main research direction is protein modifier preparation combinatorial nanoscale; cyclic aromatic amidine aldehyde isocyanide Groebke Blackburn Bienayme reaction.Reference of 4-Aminopyrimidine.

Hit finding in early drug discovery is often based on high throughput screening (HTS) of existing and historical compound libraries, which can limit chem. diversity, is time-consuming, very costly, and environmentally not sustainable. On-the-fly compound synthesis and in situ screening in a highly miniaturized and automated format has the potential to greatly reduce the medicinal chem. environmental footprint. Here, acoustic dispensing technol. has been used to synthesize a library in a 1536 well format based on the Groebke-Blackburn-Bienayme’ reaction (GBB-3CR) on a nanomole scale. The unpurified library was screened by differential scanning fluorimetry (DSF) and cross-validated using microscale thermophoresis (MST) against the oncogenic protein-protein interaction menin-MLL. Several GBB reaction products were found as μM menin binder, and the structural basis of the interactions with menin was elucidated by co-crystal structure anal. Miniaturization and automation of the organic synthesis and screening process can lead to an acceleration in the early drug discovery process, which is an alternative to classical HTS and a step towards the paradigm of continuous manufacturing

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Pyrazine – Wikipedia,
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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Structure-Guided Discovery of Silicon-Containing Subnanomolar Inhibitor of Hydroxyphenylpyruvate Dioxygenase as a Potential Herbicide.Recommanded Product: 591-54-8.

4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been recognized as one of the most promising targets in the field of herbicide innovation considering the severity of weed resistance currently. In a persistent effort to develop effective HPPD-inhibiting herbicides, a structure-guided strategy was carried out to perform the structural optimization for triketone-quinazoline-2,4-diones, a novel HPPD inhibitor scaffold first discovered in our laboratory Herein, starting from the crystal structure of Arabidopsis thaliana (At)HPPD complexed with 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(o-tolyl)quinazoline-2,4(1H,3H)-dione (MBQ), three subseries of quinazoline-2,4-dione derivatives were designed and prepared by optimizing the hydrophobic interactions between the side chain of the core structure at the R1 position and the hydrophobic pocket at the active site entrance of AtHPPD. 6-(2-Hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(3-(trimethylsilyl)prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione (I) with the best inhibitory activity against AtHPPD was identified to be the first subnanomolar-range AtHPPD inhibitor (Ki = 0.86 nM), which significantly outperformed that of the lead compound MBQ (Ki = 8.2 nM). Further determination of the crystal structure of AtHPPD in complex with compound 60 (1.85 Å) and the binding energy calculation provided a mol. basis for the understanding of its high efficiency. Addnl., the greenhouse assay indicated that 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-propylquinazoline-2,4(1H,3H)-dione (II) and compound I showed acceptable crop safety against peanut and good herbicidal activity with a broad spectrum. Moreover, compound II also showed superior selectivity for wheat at the dosage of 120 g ai/ha and favorable herbicidal efficacy toward the gramineous weeds at the dosage of as low as 30 g ai/ha. We believe that compounds II and I have promising prospects as new herbicide candidates for wheat and peanut fields.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem