Studies on antiallergic agents. I. Synthesis and antiallergic activity of novel pyrazine derivatives.

Makino, Eiichi; Iwasaki, Nobuhiko; Yagi, Noriyuki; Ohashi, Tetsuo; Kato, Hideo; Ito, Yasuo; Azuma, Hiroshi

doi:10.1248/cpb.38.201

Cited by 24 publications

(8 citation statements)

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“…In a very recent study by Panda et al [33], more derivatives of structure presented in Figure 1 were tested on several (myco)bacterial strains showing mild activity at neutral pH. Nevertheless, molecules of the mentioned structure have been tested for their other applications, e.g., as antihistamines [34], insecticides, anthelmintics [35], or proteasome inhibitors [36]. pH.…”

Section: Introductionmentioning

confidence: 99%

“…pH. Nevertheless, molecules of the mentioned structure have been tested for their other applications, e.g., as antihistamines [34], insecticides, anthelmintics [35], or proteasome inhibitors [36]. As a potential drug, PZA core substituted with amino acid (aa) may present numerous advantages in comparison with simple aliphatic or aromatic amides and esters.…”

Section: Introductionmentioning

confidence: 99%

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N-Pyrazinoyl Substituted Amino Acids as Potential Antimycobacterial Agents—the Synthesis and Biological Evaluation of Enantiomers

et al. 2020

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Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 µM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC < 1.95 µg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

N-Pyrazinoyl Substituted Amino Acids as Potential Antimycobacterial Agents—the Synthesis and Biological Evaluation of Enantiomers

et al. 2020

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“…Pyridine and its functional derivative (Pyrazine) are an important class of compound and that exists in several natural flavours, complex organic compounds and is responsible for aroma in food stuffs [2,3] cooked meat, cheese, coffee, tea etc [4]. Recent years various interesting works in pyrazine and their derivatives in medicinal chemistry of their biological significance they are Analgesic, Anti-allergic, Anti-bacterial, Anti-inflammatory, Anti-viral, Anti-cancer, HIV, Antihypertensive, Cardiovascular controlling [5][6][7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Dielectric dispersion, relaxation and molecular interaction of pyrazine binary mixtures

et al. 2018

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The dielectric depressiveness, absorption and orientation behavior is investigated in relation to solution properties of pyrazine with water, methanol and ethanol for varying temperature and mole fraction. This behavior is discussed in terms of inter molecular bonding. Orientation effects and their dielectric properties are indicated by surface dipole potential charges by displacement of oriented solvent. The charge dependence of polar solvents with organic molecular orientation can be qualitatively evolved and can be calculated in terms of its own dielectric properties, relaxation time, and correlation factor and thermodynamical behavior of solvent mixtures. The macroscopic and optical spectroscopic properties of pyrazine+water and pyrazine+alcohol mixtures are also studied.

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“…Pyrazine derivatives have been widely used in the field of medicinal chemistry for the skeleton of biologically active sites . Pyrazine derivatives are important drugs with two nitrogen atoms in the para‐position of the six‐member ring, exhibit a wide range of biological activities like analgesic , antiallergic , antibacterial , anti‐inflammatory , antiviral , diuretic , anticancer , anti‐HIV , hepatitis , antihypertensive , cardiovascular , antidiabetic , antioxidant , and antimycobacterial properties. Pyrazines play an important role as intermediates for perfumes , pharmaceuticals , and agrochemicals , and they are also present in other biological active natural products .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of Pyrazine Containing 1,2,3‐Triazole Derivatives

Ruddarraju¹,

Murugulla²,

Kotla³

et al. 2016

Journal of Heterocyclic Chem

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Here, we demonstrate on the design and synthesis of novel pyrazine containing 1,2,3‐triazole derivatives (7a, 7b, 7c, 7d, 8a, 8b, 8c, 8d, and 12a, 12b, 12c, 12d) using various chemicals, bases, and catalysts synthesized with excellent yields (78–92%) as described in the procedures. The development of this methodology is simple, efficient, and easier to handle; milder reaction conditions and higher selectivity under versatile coupling reagent useful for both amide and ester bond formations have also been developed. The synthesis of amide coupling derivatives prepared by (6a, 6b, 6c, 6d) was coupled with N‐ethylpiperazine to afford (7a, 7b, 7c, 7d) and morpholine to afford (8a, 8b, 8c, 8d) by using 1‐[Bis(dimethylamino)methylene]‐1H‐1,2,3‐triazolo[4,5‐b]pyridinium 3‐oxid hexafluorophosphate (HATU) and N,N‐diisopropylethylamine (DIPEA) in dichloromethane at room temperature for 10 h. The derivatives (6a, 6b, 6c, 6d) were coupled with alcohol (11) by using N,N′‐dicyclohexylcarbodiimide and 4‐dimethylaminopyridine in dichloromethane (DCM) at room temperature for 16 h to give final compounds (12a, 12b, 12c, 12d). In silico docking approach has been applied to these compounds to screen their efficacy against selected drug targets of cancer and diabetes. The docking approach may facilitate the prediction of activity profile for future experimental findings.

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Studies on antiallergic agents. I. Synthesis and antiallergic activity of novel pyrazine derivatives.

Cited by 24 publications

References 0 publications

N-Pyrazinoyl Substituted Amino Acids as Potential Antimycobacterial Agents—the Synthesis and Biological Evaluation of Enantiomers

N-Pyrazinoyl Substituted Amino Acids as Potential Antimycobacterial Agents—the Synthesis and Biological Evaluation of Enantiomers

Dielectric dispersion, relaxation and molecular interaction of pyrazine binary mixtures

Design, Synthesis, and Molecular Docking Studies of Pyrazine Containing 1,2,3‐Triazole Derivatives

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