A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-<i>a</i>]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

Piltan, Mohammad; Moradi, Loghman; Abasi, Golaleh; Zarei, Seyed Amir

doi:10.3762/bjoc.9.55

Cited by 29 publications

(20 citation statements)

References 27 publications

(20 reference statements)

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“…Quinoxaline derivatives have promising biological properties because of their privileged scaffold (13)(14)(15). Several biological effects have been reported, including anticancer (14,16,17), antimicrobial (18)(19)(20)(21)(22), antiviral (23), and anti-inflammatory and antioxidant (24,25) effects.…”

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confidence: 99%

In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis

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Sangi

et al. 2016

Antimicrob Agents Chemother

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Leishmaniasis is endemic in 98 countries and territories worldwide. The therapies available for leishmaniasis have serious side effects, thus prompting the search for new therapies. The present study investigated the antileishmanial activities of 2,3-diarylsubstituted quinoxaline derivatives against Leishmania amazonensis. The antiproliferative activities of 6,7-dichloro-2,3-diphenylquinoxaline (LSPN329) and 2,3-di-(4-methoxyphenyl)-quinoxaline (LSPN331) against promastigotes and intracellular amastigotes were assessed, and the cytotoxicities of LSPN329 and LSPN331 were determined. Morphological and ultrastructural alterations were examined by electron microscopy, and biochemical alterations, reflected by the mitochondrial membrane potential (⌬⌿m), mitochondrial superoxide anion (O 2 · ؊ ) concentration, the intracellular ATP concentration, cell volume, the level of phosphatidylserine exposure on the cell membrane, cell membrane integrity, and lipid inclusions, were evaluated. In vivo antileishmanial activity was evaluated in a murine cutaneous leishmaniasis model. Compounds LSPN329 and LSPN331 showed significant selectivity for promastigotes and intracellular amastigotes and low cytotoxicity. In promastigotes, ultrastructural alterations were observed, including an increase in lipid inclusions, concentric membranes, and intense mitochondrial swelling, which were associated with hyperpolarization of ⌬⌿m, an increase in the O 2 · ؊ concentration, decreased intracellular ATP levels, and a decrease in cell volume. Phosphatidylserine exposure and DNA fragmentation were not observed. The cellular membrane remained intact after treatment. Thus, the multifactorial response that was responsible for the cellular collapse of promastigotes was based on intense mitochondrial alterations. BALB/c mice treated with LSPN329 or LSPN331 showed a significant decrease in lesion thickness in the infected footpad. Therefore, the antileishmanial activity and mitochondrial mechanism of action of LSPN329 and LSPN331 and the decrease in lesion thickness in vivo brought about by LSPN329 and LSPN331 make them potential candidates for new drug development for the treatment of leishmaniasis.

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confidence: 99%

In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis

Kaplum

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Sangi

et al. 2016

Antimicrob Agents Chemother

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“…It was reported that electron-withdrawing Scheme 128 One-pot synthesis of quinazolino [1,2,3]triazolo [1,4] A nitro group at the 3-position of 1,2-diamino benzene 418 was not favorable as the desired product was not obtained even after 24 h of heating [243].…”

Section: Synthesis Of Quinoxalinesmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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“…In contrast, when acetylenedicarboxylates were used, they underwent the cyclization and elimination to generate quinoxalines 4.5 [Eq. (4‐2) (Scheme ).…”

Section: Nitrogen‐containing Nucleophilesmentioning

confidence: 99%

Tandem Reactions of Ynones: via Conjugate Addition of Nitrogen‐, Carbon‐, Oxygen‐, Boron‐, Silicon‐, Phosphorus‐, and Sulfur‐Containing Nucleophiles

et al. 2019

Adv Synth Catal

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Scheme 12. Enamines:T BAF-catalyzed cyclization.Scheme 13. Intramolecular cyclization.Scheme14. Intramolecular cyclizations.Scheme15. CÀNa nd OÀNb ond cleavage. Scheme 16. Applications of RNH-Nu. Scheme 17. NH-sulfoximines and NH-sulfondiimines. Scheme18. Radical cyclizationf or the synthesis of indoles. Scheme 22. 2H-Azirines:[3 + +2] cycloadditions. Scheme 23. Visible light-induced cycloaddition for pyrrole synthesis. Scheme24. Cyclization and sulfonyl migration. Scheme 25. NR 2 -E strategy analysis. Scheme 57. Several arenes for annulations. Scheme 58. Conjugateaddition. Scheme 59. Asymmetric conjugate addition.Scheme60. Conjugatea ddition andcyclization.

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A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

Cited by 29 publications

References 27 publications

In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis

In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

Tandem Reactions of Ynones: via Conjugate Addition of Nitrogen‐, Carbon‐, Oxygen‐, Boron‐, Silicon‐, Phosphorus‐, and Sulfur‐Containing Nucleophiles

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