Methods for the synthesis of pyrrolo[1,2-b]pyridazine and pyrrolo[1,2-b]cinnoline derivatives (microreview)

Plieva, Anastasiya T.

doi:10.1007/s10593-019-02441-5

Cited by 4 publications

(1 citation statement)

References 20 publications

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“…The interest in heterocyclic condensed systems with bridgehead nitrogen from pyrroloazines class has been growing for several decades, both for the versatility of their chemistry and especially for their pharmaceutical potential. From this class, pyrrolo [1,2-b]pyridazines, have particular interest owing to their biological activities and significant optical properties [9][10][11]. The chemistry and applications of pyrrolo [1,2-b]pyridazines have been reviewed extensively in 1977 [9] and then in 2008 [11].…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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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Copper‐Mediated Oxidative [3+2]‐Annulation of Nitroalkenes and Ylides of 1,2‐Diazines: Assembly of Functionalized Pyrrolo[1,2‐b]pyridazines

et al. 2021

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Oxidative [3 + 2]-annulation reactions between nitroalkenes and pyridazinium ylides mediated by Cu(OAc) 2 ⋅H 2 O were investigated. Functionalized pyrrolo[1,2-b]pyridazines and pyrrolo[1,2-a]phthalazines were accessed via this route. Starting from α-fluoronitroalkenes the reaction provides the first preparative synthesis of a broad scope of 5-fluoro-pyrrolo[1,2-b]pyridazines. The substrate scope in the case of α-unsubstituted nitroalkenes was investigated. Mechanistic features of the oxidative annulation reaction were studied to support the stepwise [3 + 2]-cycloaddition/oxidation/HNO 2 elimination mechanism. Partially saturated primary [3 + 2]-adducts were isolated and characterized as key intermediates.

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Desymmetrization of meso-Dicarbonatecyclohexene with β-Hydrazino Carboxylic Esters via a Pd-Catalyzed Allylic Substitution Cascade

Zheng

et al. 2020

Org. Lett.

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The desymmetrization of meso-dicarbonatecyclohexene with β-hydrazino carboxylic esters has been achieved via a RuPHOX/Pd-catalyzed allylic substitution cascade for the construction of chiral hexahydrocinnoline derivatives with high performance. Mechanistic studies reveal that the reaction exploits a pathway different from that of our previous work and that the first nitrogen nucleophilic process is the rate-determining step. The protocol could be conducted on a gram scale without any loss of catalytic behavior, and the corresponding chiral hexahydrocinnolines can undergo diverse transformations.

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Methods for the synthesis of pyrrolo[1,2-b]pyridazine and pyrrolo[1,2-b]cinnoline derivatives (microreview)

Cited by 4 publications

References 20 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

Copper‐Mediated Oxidative [3+2]‐Annulation of Nitroalkenes and Ylides of 1,2‐Diazines: Assembly of Functionalized Pyrrolo[1,2‐b]pyridazines

Desymmetrization of meso-Dicarbonatecyclohexene with β-Hydrazino Carboxylic Esters via a Pd-Catalyzed Allylic Substitution Cascade

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