Derivatives of pyrazinecarboxylic acid: 1H, 13C and 15N NMR spectroscopic investigations

Hölzer, W.; Eller, Gernot A.; Datterl, Barbara; Habicht, D.

doi:10.1002/mrc.2437

Cited by 9 publications

(6 citation statements)

References 34 publications

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“…Peaks for the pyrazine hydrogens were in the range of 8.99–8.86 in DMSO- d 6 and 8.82–8.68 in CDCl 3 . They were detected as one peak or as two peaks with coupling constant J ranging between 2.2–2.7 Hz, which is in accordance with the literature [ 28 ]. The IR spectroscopy confirmed the presence of the expected characteristic functional groups.…”

Section: Resultssupporting

confidence: 91%

Design, Synthesis, Antimycobacterial Evaluation, and In Silico Studies of 3-(Phenylcarbamoyl)-pyrazine-2-carboxylic Acids

et al. 2017

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Pyrazinamide, the first-line antitubercular drug, has been regarded the basic component of tuberculosis treatment for over sixty years. Researchers have investigated its effect on Mycobacterium tuberculosis for this long time, and as a result, new potential targets of pyrazinamide or its active form, pyrazinoic acid, have been found. We have designed and prepared 3-(phenyl-carbamoyl)pyrazine-2-carboxylic acids as more lipophilic derivatives of pyrazinoic acid. We also prepared methyl and propyl derivatives as prodrugs with further increased lipophilicity. Antimycobacterial, antibacterial and antifungal growth inhibiting activity was investigated in all prepared compounds. 3-[(4-Nitrophenyl)carbamoyl]pyrazine-2-carboxylic acid (16) exerted high antimycobacterial activity against Mycobacterium tuberculosis H37Rv with MIC = 1.56 μg·mL−1 (5 μM). Propyl 3-{[4-(trifluoromethyl)phenyl]carbamoyl}pyrazine-2-carboxylate (18a) showed also high antimycobacterial activity against Mycobacterium tuberculosis H37Rv with MIC = 3.13 μg·mL−1. In vitro cytotoxicity of the active compounds was investigated and no significant cytotoxic effect was observed. Based to structural similarity to known inhibitors of decaprenylphosphoryl-β-d-ribose oxidase, DprE1, we performed molecular docking of the prepared acids to DprE1. These in silico experiments indicate that modification of the linker connecting aromatic parts of molecule does not have any negative influence on the binding.

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Section: Resultssupporting

confidence: 91%

Design, Synthesis, Antimycobacterial Evaluation, and In Silico Studies of 3-(Phenylcarbamoyl)-pyrazine-2-carboxylic Acids

et al. 2017

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“…In the 1 H-NMR spectra (in DMSO-d 6 ), the signal of the amidic hydrogen appeared as a singlet at 10.93-9.84 ppm. The two signals of pyrazine hydrogens H3 and H6 appeared as doublets at 7.92-8.66 ppm with coupling constant J in the range of 1.3-1.4 Hz which is in accordance with literature [20]. The signal of the 5-amino hydrogen appeared usually as triplet at 7.98-7.76 ppm with coupling constant J in the range 5.5-5.9 Hz.…”

Section: Synthesis Of Variously Substituted 5-alkylamino-n-phenylpyrasupporting

confidence: 90%

5-Alkylamino-N-phenylpyrazine-2-carboxamides: Design, Preparation, and Antimycobacterial Evaluation

et al. 2020

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According to the World Health Organization, tuberculosis is still in the top ten causes of death from a single infectious agent, killing more than 1.7 million people worldwide each year. The rising resistance developed by Mycobacterium tuberculosis against currently used antituberculars is an imperative to develop new compounds with potential antimycobacterial activity. As a part of our continuous research on structural derivatives of the first-line antitubercular pyrazinamide, we have designed, prepared, and assessed the in vitro whole cell growth inhibition activity of forty-two novel 5-alkylamino-N-phenylpyrazine-2-carboxamides with various length of the alkylamino chain (propylamino to octylamino) and various simple substituents on the benzene ring. Final compounds were tested against Mycobacterium tuberculosis H37Ra and four other mycobacterial strains (M. aurum, M. smegmatis, M. kansasii, M. avium) in a modified Microplate Alamar Blue Assay. We identified several candidate molecules with micromolar MIC against M. tuberculosis H37Ra and low in vitro cytotoxicity in HepG2 cell line, for example, N-(4-hydroxyphenyl)-5-(pentylamino)pyrazine-2-carboxamide (3c, MIC = 3.91 µg/mL or 13.02 µM, SI > 38) and 5-(heptylamino)-N-(p-tolyl)pyrazine-2-carboxamide (4e, MIC = 0.78 µg/mL or 2.39 µM, SI > 20). In a complementary screening, we evaluated the in vitro activity against bacterial and fungal strains of clinical importance. We observed no antibacterial activity and sporadic antifungal activity against the Candida genus.

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“…40 3 and 4) indicated a nitrogen heterocyclic skeleton consistent with 1 H-NMR. 41 3 and 4) indicated an alkaloid skeleton consistent with 1 H-NMR. 42 The 1 H-NMR data (600 MHz, CD 3 OD) showed one imino group proton conrmed at [d H 7.29 (1H, d, J = 7.6, H-1)] and one methyne hydrogen proton [d H 5.51 (1H, d, J = 7.6, H-5)].…”

Section: Phytochemical Extraction and Puricationmentioning

confidence: 61%

“…The NMR data of 22 (Tables 3 and 4) indicated a nitrogen heterocyclic skeleton consistent with 1 H-NMR. 41 The 1 H-NMR data (600 MHz, CD 3 OD) showed two characteristic aromatic protons confirmed at [ δ H 8.39 (1H, s, H-5), and 8.34 (1H, s, H-6)].…”

Section: Resultsmentioning

confidence: 98%

Bioactive substances inhibiting COX-2 and cancer cells isolated from the fibrous roots of Alangium chinense (Lour.) Harms

et al. 2023

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Derivatives of pyrazinecarboxylic acid: ¹H, ¹³C and ¹⁵N NMR spectroscopic investigations

Cited by 9 publications

References 34 publications

Design, Synthesis, Antimycobacterial Evaluation, and In Silico Studies of 3-(Phenylcarbamoyl)-pyrazine-2-carboxylic Acids

Design, Synthesis, Antimycobacterial Evaluation, and In Silico Studies of 3-(Phenylcarbamoyl)-pyrazine-2-carboxylic Acids

5-Alkylamino-N-phenylpyrazine-2-carboxamides: Design, Preparation, and Antimycobacterial Evaluation

Bioactive substances inhibiting COX-2 and cancer cells isolated from the fibrous roots of Alangium chinense (Lour.) Harms

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