Synthesis and antimicrobial activity of some novel derivatives of benzofuran: part 1. Synthesis and antimicrobial activity of (benzofuran-2-yl)(3-phenyl-3-methylcyclobutyl) ketoxime derivatives

Koca, Murat; Servi, Süleyman; Kırılmış, Cumhur; Ahmedzade, Misir; Kazaz, Cavit; Özbek, Berna; Ötük, Gülten

doi:10.1016/j.ejmech.2005.07.004

Cited by 113 publications

(48 citation statements)

References 8 publications

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“…These kinds of naturally occurring compounds have attracted much attention from synthetic organic chemists, due to their interesting biological and pharmacological activities. [1][2][3] Several natural products bearing benzofuran and its derivatives as a moiety, [4][5][6] exhibit diverse biological activities such as being potent antibacterial, 7 antimicrobial, 8 antitumor, 9 anticonvulsant antiinammatory, 10 antidiabetic 11 and antineophobic agents.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

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Research on natural products containing benzofuran has remarkably increased during the past few decades.Newly isolated natural products with complex structures are being studied, characterized and screened for possible biological activities. Several of such compounds have exhibited various biological activities, thus their total syntheses have attracted much attention from synthetic organic chemists. In this review, we aim to highlight the origins, structures, biological potencies, and synthetic approaches of those natural products bearing at least one benzofuran in their complex structures. Furthermore, we especially focus on the step in which this key heterocycle is installed during the total synthesis of a natural product as the desired target.

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Section: Introductionmentioning

confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

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“…Oximes can also be synthesized by reacting nitrites with compounds containing an acidic hydrogen atom. Ketoximes can be synthesized from natural products, such as terpenoids (Banerjee & Dureja, 2005; Koca et al ., 2005; Huang et al ., 2008), and methyl ethyl ketoximes are important industrial chemicals, for example, they are used as antioxidant and antiskinning agents in alkyd paints.…”

Section: Introductionmentioning

confidence: 99%

“…Some oximes are beneficial because of antifungal activities, which suppress disease development in plants including the pea (Banerjee & Dureja, 2010), and antimicrobial effects against C. albicans (Koca et al ., 2005). Interestingly, oxime metal chelates exhibit higher antimicrobial activities than the free ligands (Shokrollahi et al ., 2008; Koumousi et al ., 2012).…”

Section: Introductionmentioning

confidence: 99%

Phenyl 2‐pyridyl ketoxime induces cellular senescence‐like alterations via nitric oxide production in human diploid fibroblasts

et al. 2015

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SummaryPhenyl‐2‐pyridyl ketoxime (PPKO) was found to be one of the small molecules enriched in the extracellular matrix of near‐senescent human diploid fibroblasts (HDFs). Treatment of young HDFs with PPKO reduced the viability of young HDFs in a dose‐ and time‐dependent manner and resulted in senescence‐associated β‐galactosidase (SA‐β‐gal) staining and G2/M cell cycle arrest. In addition, the levels of some senescence‐associated proteins, such as phosphorylated ERK1/2, caveolin‐1, p53, p16ink4a, and p21waf1, were elevated in PPKO‐treated cells. To monitor the effect of PPKO on cell stress responses, reactive oxygen species (ROS) production was examined by flow cytometry. After PPKO treatment, ROS levels transiently increased at 30 min but then returned to baseline at 60 min. The levels of some antioxidant enzymes, such as catalase, peroxiredoxin II and glutathione peroxidase I, were transiently induced by PPKO treatment. SOD II levels increased gradually, whereas the SOD I and III levels were biphasic during the experimental periods after PPKO treatment. Cellular senescence induced by PPKO was suppressed by chemical antioxidants, such as N‐acetylcysteine, 2,2,6,6‐tetramethylpiperidinyloxy, and L‐buthionine‐(S,R)‐sulfoximine. Furthermore, PPKO increased nitric oxide (NO) production via inducible NO synthase (iNOS) in HDFs. In the presence of NOS inhibitors, such as L‐NG‐nitroarginine methyl ester and L‐NG‐monomethylarginine, PPKO‐induced transient NO production and SA‐β‐gal staining were abrogated. Taken together, these results suggest that PPKO induces cellular senescence in association with transient ROS and NO production and the subsequent induction of senescence‐associated proteins.

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“…Several benzofurans bearing various substituents at the C-2 position are widely distributed in nature [1]. There are other well known natural products having related benzofuran ring structures, which can get isolated particularly from Machilus glaucescens, Ophryosporus charua, Ophryosporus lorentzii, Krameria ramosissima, and Zanthoxylum ailanthoidol [2].…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis and Antimicrobial Activity of New 3‐Substituted 5‐(Benzofuran‐2‐yl)‐pyrazole Derivatives

Abdel‐Wahab¹,

Abdel‐Aziz

Ahmed

2008

Archiv der Pharmazie

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The reaction of ethyl 4-(benzofuran-2-yl)-2,4-dioxobutanoate 2 with two moles of hydrazine hydrate afforded 5-(benzofuran-2-yl)-1H-pyrazole-3-carbohydrazide 4a, while its reaction with equimolar amount of phenylhydrazine gave ester 3b which then converted to 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide 4b. Various new compounds such as imides 5 and 6, acyl hydrazones 7 and 8, bi-pyrazoles 9-12, and 1,3-thiazole derivatives 14 and 15 were prepared from carbohydrazide derivatives 4a, b. The new compounds are tested for their antimicrobial activity. Compounds 2, 5, 7, and 8 showed antifungal activities against C. albicans. Also, compounds 2, 6, 8, and 15 showed antibacterial activities.

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Synthesis and antimicrobial activity of some novel derivatives of benzofuran: part 1. Synthesis and antimicrobial activity of (benzofuran-2-yl)(3-phenyl-3-methylcyclobutyl) ketoxime derivatives

Cited by 113 publications

References 8 publications

Total synthesis of natural products containing benzofuran rings

Total synthesis of natural products containing benzofuran rings

Phenyl 2‐pyridyl ketoxime induces cellular senescence‐like alterations via nitric oxide production in human diploid fibroblasts

Convenient Synthesis and Antimicrobial Activity of New 3‐Substituted 5‐(Benzofuran‐2‐yl)‐pyrazole Derivatives

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