Catalyst / Surfactant Free Chemoselective Acylation of Amines in Water

Dulla, Balakrishna; Vijayavardhini, Suryadevara; Rambau, Dandela; Anuradha, V.; Rao, Mandava V. Basaveswara; Pal, Manojit

doi:10.2174/22133461114019990002

Cited by 10 publications

(6 citation statements)

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“…Intermediate compounds were synthesized according to the outlined studies, with slight modifications [ 34 , 35 , 36 , 37 , 38 , 39 ]. Detailed procedures and analysis were shown in Scheme 1 and Supporting Information (Figures S1–S11) .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Fundamental Evaluation of Radioiodinated Rociletinib (CO-1686) as a Probe to Lung Cancer with L858R/T790M Mutations of Epidermal Growth Factor Receptor (EGFR)

Fawwaz

Mishiro

Nishii³

et al. 2020

Molecules

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Rociletinib (CO-1686), a 2,4-diaminopyrimidine derivative, is a highly potent tyrosine kinase inhibitor (TKI) that acts on epidermal growth factor receptor (EGFR) with L858R/T790M mutations. We supposed radioiodinated CO-1686 would function as a useful tool for monitoring EGFR L858R/T790M mutations. To aid in patient selection before therapy with EGFR-TKIs, this study aimed to develop a 125I-labeled derivative of CO-1686, N-{3-[(2-{[4-(4-acetylpiperazin-1-yl)-2-methoxyphenyl]amino}-5-(trifluoromethyl)pyrimidine-4-yl] amino}-5-([125I]iodophenyl)acrylamide ([125I]ICO1686) and evaluate its selectivity toward EGFR L858R/T790M. Radiosynthesis was performed by iododestannylation of the corresponding tributylstannyl precursor with [125I]NaI and N-chlorosuccinimide. The selectivity of the tracer for detecting EGFR L858R/T790M was evaluated using three relevant non-small cell lung cancer (NSCLC) cell lines—H1975, H3255 and H441 overexpressing the dual mutation EGFR L858R/T790M, active mutant EGFR L858R and wild-type EGFR, respectively. The nonradioactive ICO1686 and the precursor compound were successfully synthesized. A novel radiolabeled probe, [125I]ICO1686, was prepared with high radiochemical yield (77%) and purity (>99%). ICO1686 exhibited high cytotoxicity toward H1975 (IC50 0.20 ± 0.05 μM) and H3255 (IC50 0.50 ± 0.21 μM), which is comparable to that of CO-1686. In contrast, the cytotoxicity of ICO1686 toward H441 was 10-fold lower than that toward H1975. In the cell uptake study, the radioactivity uptake of [125I]ICO1686 in H1975 was 101.52% dose/mg, whereas the uptakes in H3255 and H441 were 33.52 and 8.95% dose/mg, respectively. The uptake of [125I]ICO1686 in H1975 was greatly reduced to 45.61% dose/mg protein by treatment with excess CO-1686. In vivo biodistribution study of the radiotracer found that its accumulation in H1975 tumor (1.77 ± 0.43% ID/g) was comparable to that in H3255 tumor (1.63 ± 0.23% ID/g) and the accumulation in H1975 tumor was not reduced by pretreatment with an excess dose of CO-1686. Although this radiotracer exhibited highly specific in vitro uptake in target cancer cells, structural modification is required to improve in vivo biodistribution.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Fundamental Evaluation of Radioiodinated Rociletinib (CO-1686) as a Probe to Lung Cancer with L858R/T790M Mutations of Epidermal Growth Factor Receptor (EGFR)

Fawwaz

Mishiro

Nishii³

et al. 2020

Molecules

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“…We prepared maleimide acid 3 from maleic anhydride 1 by the treatment with amine 2 in the presence of water (Dulla et al, 2014). Thus the obtained 3 was reacted with acetic Scheme 1 Synthesis of halomaleimide 6.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones and functionalization to triazoles

Ali

Vasconcelos

Shamim

et al. 2017

Arabian Journal of Chemistry

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A series of alkynyl maleimides were prepared via one-step cross-coupling reaction using bromomaleimide and acetylenes under the Sonogashira conditions, affording 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones in good to high yields. These products were subsequently converted in the corresponding 1,2,3-triazole using conventional click chemistry approach. The alkynyl maleimide compound (8g) crystallized in the triclinic space group P1 with unit cell parameters a = 5.3692(6), b = 9.2513(10), c = 10.3070(11) Å , a = 85.349(4), b = 86.892(4), c = 86.892(4)°, V = 507.31(10) Å 3 , and Z = 1. In the crystal the molecules are stacked parallel to the c axis and held together through a C-HÁ Á Áp and a C-HÁ Á ÁO interaction. Ó 2016 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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Section: Scheme 2 Synthesis Of Dibenzo[bh][15]naphthyridin-7(12h)-one...mentioning

confidence: 99%

Synthesis of Dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: The Pictet–Spengler Reaction versus a Rearrangement of 4-Phenyl[1,3]oxazolo[4,5-c]quinolines

Fisyuk,

Shatsauskas,

Kirnosov

et al. 2024

Synthesis

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Two approaches were proposed to the synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones. The one-step method based on the Pictet–Spengler reaction of 3-amino-2-phenylquinolin-4(1H)-one with aromatic aldehydes requires heating in a strong acidic media, which leads to significant limitations on the possible products. The second approach is based on the conversion of 3-amino-2-phenylquinolin-4(1H)-one to 4-phenyl[1,3]oxazolo[4,5-c]quinolines followed by rearrangement under the action of AlCl3. A significant advantage of the two-step synthesis is the possibility of obtaining a wider range of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones, including those not available using the Pictet–Spengler reaction.

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Catalyst / Surfactant Free Chemoselective Acylation of Amines in Water

Cited by 10 publications

References 0 publications

Synthesis and Fundamental Evaluation of Radioiodinated Rociletinib (CO-1686) as a Probe to Lung Cancer with L858R/T790M Mutations of Epidermal Growth Factor Receptor (EGFR)

Synthesis and Fundamental Evaluation of Radioiodinated Rociletinib (CO-1686) as a Probe to Lung Cancer with L858R/T790M Mutations of Epidermal Growth Factor Receptor (EGFR)

Synthesis of 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones and functionalization to triazoles

Synthesis of Dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: The Pictet–Spengler Reaction versus a Rearrangement of 4-Phenyl[1,3]oxazolo[4,5-c]quinolines

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