Coumarin substituted pyrrolo-fused heterocyclic systems by 1,3-dipolar cycloadditon reactions

Popa, Marcel Mirel; Georgescu, Emilian; Drăghici, Constantin; Georgescu, Florentina; Dumitraşcu, Florea; Dumitrescu, Dan

doi:10.1007/s00706-015-1563-z

Cited by 10 publications

(11 citation statements)

References 45 publications

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“…The hydrogen atoms H-4 and H-5 from the pyridazinone core appear as two doublets with a coupling constant of 9.6 Hz, as expected. In the 13 C-NMR spectra, the two types of carbonyl groups appear at δ between 159.7-160.1 ppm for the pyridazine moiety and 169.5-169.7 ppm for the ester group. The carbon signals of methyl from CO 2 C 2 H 5 and -CHC 2 H 5 groups appeared at 14 ppm and 10 ppm, respectively.…”

Section: Chemistrymentioning

confidence: 99%

“…The IR spectra were registered on a Vertex 70 spectrometer (Bruker Optik GmbH, Ettlingen, Germany) in ATR modes. The NMR spectra were recorded on a Varian Gemini 300BB spectrometer (Varian, Palo Alto, CA, USA) operating at 300 MHz for 1 H and 75 MHz for 13 C in CDCl 3 or CDCl 3 and TFA mixture as solvents, using TMS as the internal standard. The chemical shifts (δ) are reported in parts per million (ppm) and all coupling constants values J are given in hertz (Hz).…”

Section: Chemistrymentioning

confidence: 99%

“…The compound was purified by crystallization from ethanol as colorless crystals with mp 59-61 1 H-NMR (300 MHz, CDCl 3 ) δ ppm: 0.98, (t, 3H, J = 7.4, Hz, CH 3 ), 1.23 (t, 3H, J = 7.1 Hz, CH 3 ), 2.23-2.36 (m, 2H, CH 2 ), 4.13-4.26 (m, 2H, CH 2 O), 5.49, 5.54 (2d, 1H, J = 6.8 Hz, CH), 7.05 (d, 1H, J = 9.7, H-4), 7.14 (t, 2H, J = 8.9 Hz, H-3 , H-5 ), 7.67 (d, 1H, J = 9.7 Hz, H-5), 7.77 (dd, 2H, J = 8.9, 5.2 Hz, H-2 , H-6 ). 13 Ethyl 2-[6-oxo-3-(4-chlorophenyl)pyridazin-1-yl]butanoate (1c). The compound was purified by crystallization from 2-propanol as colorless crystals with mp 49-51 The acids 2a-c were obtained from alkaline hydrolysis of the corresponding esters by a procedure described in the literature by McMillan and King [44,45].…”

Section: General Procedures For the Synthesis Of Esters 1a-cmentioning

confidence: 99%

“…The compound was purified by crystallization from methanol as fluorescent yellow crystals with mp 98-100 1 H-NMR (300 MHz, CDCl 3 ) δ ppm: 1.42 (t, 6H, J = 7.5 Hz, 2CH 3 ), 3.07 (q, 2H, J = 7.5 Hz, CH 2 ), 4.39 (q, 2H, J = 7.1 Hz, CH 2 O), 7.14-7.26 (m, 4H, H-3, H-6, H-3 , H-5 ), 7.99 (dd, 2H, J = 8.8, 5.3 Hz, H-2 , H-6 ), 8.49 (d, 1H, J = 9.4 Hz, H-4). 13…”

Section: General Procedures For the Synthesis Of Esters 1a-cmentioning

confidence: 99%

“…The chemistry and applications of pyrrolo [1,2-b]pyridazines have been reviewed extensively in 1977 [9] and then in 2008 [11]. Subsequently, new developments in the synthetic aspects [12][13][14][15] and applications of pyrrolo [1,2-b]pyridazines regarding their pharmacological potentials such as antitumor [16][17][18], antibacterial [19], anti-inflammatory [20][21][22], antidepressant [23], antimetabolic [24] actions and their optical properties were reported [25,26].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Cytotoxic Evaluation of New Pyrrolo[1,2-b]pyridazines Obtained via Mesoionic Oxazolo-Pyridazinones

Ivan

Bărbuceanu

Hotnog

et al. 2023

IJMS

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New pyrrolo[1,2-b]pyridazines were synthesized by 3 + 2 cycloaddition reaction between mesoionic oxazolo-pyridazinones and methyl/ethyl propiolate. The mesoionic compounds were generated in situ by action of acetic anhydride on 3(2H)pyridazinone acids obtained from corresponding esters by alkaline hydrolysis followed by acidification. The structures of the compounds were confirmed by elemental analyses and IR, 1H-NMR, 13C-NMR, and X-ray diffraction data. The regioselectivity of cycloaddition was evidenced by NMR spectroscopy and confirmed by X-ray analysis. The compounds were evaluated for their cytotoxicity on plant cells (Triticum aestivum L.) and crustacean animal cells (Artemia franciscana Kellogg and Daphnia magna Straus). The results indicated that the tested compounds exhibited low toxicity on the plant cell (IC50 values higher than 200 µM), while on Artemia nauplii no lethality was observed. Daphnia magna assay showed that pyrrolo[1,2-b]pyridazines 5a and 5c could exhibit toxic effects, whereas, for the other compounds, toxicity was low to moderate. Also, the cytotoxic effects of the compounds were tested on three human adenocarcinoma-derived adherent cell lines (colon LoVo, ovary SK-OV-3, breast MCF-7). The in vitro compound-mediated cytotoxicity assays, performed by the MTS technique, demonstrated dose- and time-dependent cytotoxic activity for several compounds, the highest anti-tumor activity being observed for 5a, 2c, and 5f, especially against colon cancer cells.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: General Procedures For the Synthesis Of Esters 1a-cmentioning

confidence: 99%

Section: General Procedures For the Synthesis Of Esters 1a-cmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Cytotoxic Evaluation of New Pyrrolo[1,2-b]pyridazines Obtained via Mesoionic Oxazolo-Pyridazinones

Ivan

Bărbuceanu

Hotnog

et al. 2023

IJMS

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ChemInform Abstract: Coumarin Substituted Pyrrolo‐Fused Heterocyclic Systems by 1,3‐Dipolar Cycloadditon Reactions.

Popa

Georgescu²,

Drăghici

et al. 2016

ChemInform

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Coumarin Substituted Pyrrolo-Fused Heterocyclic Systems by 1,3-Dipolar Cycloadditon Reactions. -The title heterocyclic systems are obtained by 1,3-dipolar cycloaddition of in situ from several N-heterocycles and chromenone (II) generated cycloimmonium-ylides with electron-deficient alkynes. -(POPA*, M. M.; GEORGESCU, E.; DRAGHICI, C.; GEORGESCU, F.; DUMITRASCU, F.; DUMITRESCU, D.; Monatsh. Chem. 146 (2015) 12, 2029-2040, http://dx.doi.org/10.1007/s00706-015-1563-z ; Nenitzescu Cent. Org. Chem., Roum. Acad., RO-060023 Bucharest, Rom.; Eng.) -Toeppel 14-175

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Greener Synthesis of Pyrroloquinazoline Derivatives: Recent Advances

Moreira¹,

Santos

Corrêa³

2022

Eur J Org Chem

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Quinazoline derivatives draw attention from a synthetic and medicinal chemistry point of view, given the wide range of biological activities already described. This class of fused Nheterocyclic compounds has also shown its importance and potential pharmacological application. This Review covers the contributions reported in the last ten years for the synthesis of pyrroloquinazoline derivatives, focusing on greener protocols to obtain these adducts, such as multicomponent reactions, photocatalysis, microwaves, electrosynthesis among others.

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Coumarin substituted pyrrolo-fused heterocyclic systems by 1,3-dipolar cycloadditon reactions

Cited by 10 publications

References 45 publications

Synthesis, Characterization and Cytotoxic Evaluation of New Pyrrolo[1,2-b]pyridazines Obtained via Mesoionic Oxazolo-Pyridazinones

Synthesis, Characterization and Cytotoxic Evaluation of New Pyrrolo[1,2-b]pyridazines Obtained via Mesoionic Oxazolo-Pyridazinones

ChemInform Abstract: Coumarin Substituted Pyrrolo‐Fused Heterocyclic Systems by 1,3‐Dipolar Cycloadditon Reactions.

Greener Synthesis of Pyrroloquinazoline Derivatives: Recent Advances

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