Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis

Gundersen, Lise‐Lotte; Charnock, Colin; Negussie, Ayele H.; Rise, Frode; Teklu, Solomon

doi:10.1016/j.ejps.2006.09.006

Cited by 143 publications

(54 citation statements)

References 27 publications

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“…At the concentration of 100 g mL −1 , the growth of S. aureus was fully inhibited. According to the results of previous studies, indolizine derivatives were able to inhibit the growth of mycobacteria (Gundersen et al, 2007), therefore, the acidoresistant rod M. smegmatis was chosen as the model microbe for antimycobacterial activity assay. The best growth inhibition was observed in the presence of derivatives XXI and XX; MIC 100 = 25 g mL −1 (derivative XXI) and MIC 100 = 100 g mL −1 (derivative XX).…”

Section: Resultsmentioning

confidence: 99%

Newly synthesized indolizine derivatives – antimicrobial and antimutagenic properties

Olejníková¹,

Bírošová²,

Švorc

et al. 2015

Chemical Papers

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A series of indolizine derivatives have been synthesized and subjected to antibacterial screening studies. Antibacterial activity of 21 derivatives was investigated against Staphylococcus aureus, Mycobacterium smegmatis, Salmonella typhimurium and Escherichia coli; also, the sensitivity of model yeast Candida parapsilosis and some model filamentous fungi Aspergillus fumigatus, Alternaria alternata, Botrytis cinerea and Microsporum gypseum was tested. Newly synthesized indolizine derivatives have shown selective toxicity to Gram-positive bacteria S. aureus and were also considered to be able to inhibit the acidoresistant rod M. smegmatis. Derivative XXI has shown the highest inhibition effect with the bacteriostatic effect on the cells at the concentration of 25 µg mL −1 . The best antifungal activity has been detected in the presence of derivative XIII. Derivative XIII did also affect the morphology of hyphal tips of B. cinerea, which led to enhanced ramification of hyphae. Finally, the antimutagenic activity of derivatives was investigated. Significant antimutagenic activity was registered in case of derivative VIII. The number of induced revertants by mutagen [2-(5-nitrofuryl)acrylic acid] was decreased almost to the level of spontaneous revertants in the lowest applied concentration (50 µg per plate).

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Section: Resultsmentioning

confidence: 99%

Newly synthesized indolizine derivatives – antimicrobial and antimutagenic properties

Olejníková¹,

Bírošová²,

Švorc

et al. 2015

Chemical Papers

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“…Their uses for different purposes, including their interesting biological activities, were summarized by Wang et al [2]. Recently, Gundersen et al reported the synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis [3]. Indolizine derivatives can be prepared by different routes, including the 1,3-dipolar cycloaddition reaction of pyridylnitrilimines with dimethyl acetylenedicarboxylate [4].…”

Section: Introductionmentioning

confidence: 99%

Reaction of Nitrilimines with 2-Substituted Aza-heterocycles. Synthesis of Pyrrolo[1,2-a]pyridine and Pyrimido[2,1-d]1,2,3,5- tetrazine

Awadallah

Zahra

2008

Molecules

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The reaction of nitrilimine 6a with ethyl pyridine-2-acetate (7) gave the corresponding pyrrolo[1,2-a]pyridine 8, while the reaction of 6b containing an ester moiety afforded the acyclic adduct 9. The reaction of 6a with 2-aminopyrimidine (10) gave the novel unexpected pyrimido[2,1-d]1,2,3,5-tetrazine 11. Acyclic adducts 16 and 17 were obtained from the reaction of 6b with 2-cyanomethylbenzimidazole (14) and 2-aminobenzimidazole (15), respectively.

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“…1-Carbamoylmethylindolizines and 1-oxamoylindolizines were reported to inhibit secretory phospholipase A2 [5]. Functionalized indolizine derivatives are inhibitors of MPtpA/MPtpB phosphatases [6], testosterone 5α-reductase [7], and 15-lipoxygenase [8], and they possess antioxidant [9] and antibacterial activity [10]. Taking into account the above stated, we believed that development of methods for the synthesis of compounds possessing indolizine fragments and exhibiting selective biological activity is an important problem.…”

mentioning

confidence: 98%

“…The goal of the present work was to synthesize pyridinium salts having a 2-(4-amino-3-R-oxycarbonyl-DOI: 10.1134/S1070428011040191 …”

mentioning

confidence: 99%

Alkaloids of Siberia and Altai flora: XVIII. Alkyl 2-acetylamino-5-[2-(pyridin-3-yl)vinyl]benzoates in the synthesis of indolizines containing an anthranilic acid ester moiety

et al. 2011

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Methyl 2-acetylamino-5-[2-(6-methylpyridin-3-yl)vinyl]benzoate reacted with phenacyl bromide to produce quaternary 1-(2-aryl-2-oxoethyl)-2-methyl-5-(4-acetylamino-3-methoxycarbonyl)pyridinium bromides. 1,3-Dipolar cycloaddition of the latter to methyl propynoate and dimethyl but-2-ynedioate gave the corresponding indolizine derivatives containing an anthranilic acid ester moiety. Reactions of acetylenes with N-phenacylpyridinium salts obtained from a diterpene alkaloid derivative, 2-(pyridin-3-yl)vinyl-substituted lappaconitine afforded analogous compounds in which the indolizine fragment is conjugated to the aromatic ring of the alkaloid. 1,3-Dipolar cycloaddition of 1-(2-aryl-2-oxoethyl)-2-methyl-5-(4-acetylamino-3-methoxycarbonyl)pyridinium bromides with methyl propynoate was regioselective.* For communication XVII, see [1].

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Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis

Cited by 143 publications

References 27 publications

Newly synthesized indolizine derivatives – antimicrobial and antimutagenic properties

Newly synthesized indolizine derivatives – antimicrobial and antimutagenic properties

Reaction of Nitrilimines with 2-Substituted Aza-heterocycles. Synthesis of Pyrrolo[1,2-a]pyridine and Pyrimido[2,1-d]1,2,3,5- tetrazine

Alkaloids of Siberia and Altai flora: XVIII. Alkyl 2-acetylamino-5-[2-(pyridin-3-yl)vinyl]benzoates in the synthesis of indolizines containing an anthranilic acid ester moiety

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