Synthesis of [<sup>14</sup>C]imidazole ring labeled metiamide, cimetidine and impromidine

Villani, A. J.; Petka, L.; Blackburn, D. W.; Saunders, D.; White, G. R.; Winster, J.

doi:10.1002/jlcr.2580271206

Cited by 7 publications

(3 citation statements)

References 13 publications

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“…Synthesis of [ 13 C 2 ]cimetidine. Double 13 C-labeled cimetidine (Figure A) was synthesized using a modification of a previous route . Briefly, potassium [ 13 C]thiocyanate was prepared from commercially available potassium [ 13 C]cyanide and condensed with ethyl 2-aminoacetoacetate hydrochloride to give [2- 13 C]4-ethylaceto-5-methyl-2-thioimidazole.…”

Section: Methodsmentioning

confidence: 99%

“…Briefly, potassium [ 13 C]thiocyanate was prepared from commercially available potassium [ 13 C]cyanide and condensed with ethyl 2-aminoacetoacetate hydrochloride to give [2- 13 C]4-ethylaceto-5-methyl-2-thioimidazole. All remaining steps were carried out as described in ref , except that [ 13 C]methylamine hydrochloride was substituted for natural abundance isotope methylamine in the final reaction to afford pure [ 13 C 2 ]cimetidine after normal-phase gravity column purification.…”

Section: Methodsmentioning

confidence: 99%

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Molecular Conformations of the Polymorphic Forms of Cimetidine from ¹³C Solid-State NMR Distance and Angle Measurements

et al. 2000

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The polymorphic drug compound cimetidine, a histamine H2 receptor antagonist, was synthesized containing sites of 13C enrichment at the imidazolium methine carbon C2 and at the guanidinium methyl carbon C16. The structures of four crystalline forms of double 13C-labeled cimetidine, three anhydrates (A, B, and C) and a monohydrate (M1), were examined using 13C cross polarization magic angle spinning (CP-MAS) NMR methods. Rotational resonance magnetization exchange curves obtained for forms A and M1 were consistent with C2−C16 interatomic distances of 3.78 and 3.82 Å as measured from their crystal structures. Exchange curves for forms B and C, for which crystal structures have not been obtained, indicated that in both cases the C2−C16 interatomic distance lies between 5.2 and 5.8 Å, suggesting that cimetidine adopts a partially extended conformation in these forms. In addition, double quantum heteronuclear local field (2Q-HLF) NMR was used to determine the relative orientations of the 13C−H bonds at the two 13C-labeled sites. The experimental data were consistent with the known geometry of forms A and M1 and, in the case of form C, with a limited number of possible structures. Energetically favorable molecular conformations of form C, which were in agreement with the distance and angle measurements, fell into just six distinct clusters. These results demonstrate the feasibility of determining the complete solid-state structures of pharmaceutical compounds, and other materials not amenable to crystallography, using CP-MAS NMR combined with a minimal isotope labeling strategy.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Molecular Conformations of the Polymorphic Forms of Cimetidine from ¹³C Solid-State NMR Distance and Angle Measurements

et al. 2000

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“…Imidazole core, as one of the most notable five‐member azaheterocycles, has formed the structure of some drug molecules, such as, cimetidine, azomycin, and metronidazole [1] . There are lots of reports focused on imidazole derivatives ascribe to the electron‐rich imidazole ring possessing extensive pharmacological activities [2–10] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Fluorinated Imidazole[4,5f][1,10]phenanthroline Derivatives as Potential Inhibitors of Liver Cancer Cell Proliferation by Inducing Apoptosis via DNA Damage

et al. 2021

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Phenanthroline derivatives containing fluorinated imidazole ring are effective anti‐neoplastic agents. Herein, a series of four fluorinated imidazole[4,5f][1,10]phenanthroline derivatives were synthesized and investigated as potential inhibitors to fight against the growth of liver cancer cells. The in vitro antitumor activity of targeted compounds have been evaluated by using MTT assay, and results showed that compound 4 (2‐(2,3‐difluorophenyl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline) exhibited excellent inhibitory effect against the growth of various tumor cells, particularly for HepG2 cells, with IC50 value of approximately 0.29 μM. This result has been further confirmed by colony formation assay, showing that compound 4 suppressed the proliferation of HepG2 cells. Moreover, cell apoptosis (AO/PI dual staining and flow cytometry) analyses as well as comet assay showed that compound 4 may induce apoptosis of HepG2 cells through triggering DNA damage. Furthermore, the in vivo anti‐tumor activity were evaluated on zebrafish bearing HepG2 cells showed that compound 4 can observably block the growth of liver cancer cells. All in together, these compounds, particularly compound 4, may be developed as a potential agent to treat liver cancer in the future.

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Synthesis of isotopically labelled pyridoindolone 5‐HT₃ receptor antagonists (1)

Prakash

Cable

Correa

et al. 1995

Labelled Comp Radiopharmac

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SummarySyntheses of labelled versions of 5-HT3 receptor antagonists, Alosetron and Lurosetron, are described. [14C]Alosetron was prepared by routes utilizing either Fischer indolisation of an amidohydrazine or palladium-mediated cyclisation of an aryl enaminone as key steps. 2H and 13C versions of Alosetron were prepared from suitably labelled imidazoles.Lurosetron was labelled in either the methylene bridge carbon or carbonyl carbon, using 14C-labelled paraformaldehyde or phosgene, respectively.

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Synthesis of [¹⁴C]imidazole ring labeled metiamide, cimetidine and impromidine

Cited by 7 publications

References 13 publications

Molecular Conformations of the Polymorphic Forms of Cimetidine from ¹³C Solid-State NMR Distance and Angle Measurements

Molecular Conformations of the Polymorphic Forms of Cimetidine from ¹³C Solid-State NMR Distance and Angle Measurements

Synthesis of Fluorinated Imidazole[4,5f][1,10]phenanthroline Derivatives as Potential Inhibitors of Liver Cancer Cell Proliferation by Inducing Apoptosis via DNA Damage

Synthesis of isotopically labelled pyridoindolone 5‐HT₃ receptor antagonists (1)

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Synthesis of [14C]imidazole ring labeled metiamide, cimetidine and impromidine

Cited by 7 publications

References 13 publications

Molecular Conformations of the Polymorphic Forms of Cimetidine from 13C Solid-State NMR Distance and Angle Measurements

Molecular Conformations of the Polymorphic Forms of Cimetidine from 13C Solid-State NMR Distance and Angle Measurements

Synthesis of Fluorinated Imidazole[4,5f][1,10]phenanthroline Derivatives as Potential Inhibitors of Liver Cancer Cell Proliferation by Inducing Apoptosis via DNA Damage

Synthesis of isotopically labelled pyridoindolone 5‐HT3 receptor antagonists (1)

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Synthesis of [¹⁴C]imidazole ring labeled metiamide, cimetidine and impromidine

Molecular Conformations of the Polymorphic Forms of Cimetidine from ¹³C Solid-State NMR Distance and Angle Measurements

Molecular Conformations of the Polymorphic Forms of Cimetidine from ¹³C Solid-State NMR Distance and Angle Measurements

Synthesis of isotopically labelled pyridoindolone 5‐HT₃ receptor antagonists (1)