The structure–activity relationships of mansonone F, a potent anti-MRSA sesquiterpenoid quinone: SAR studies on the C6 and C9 analogs

Suh, Young‐Ger; Kim, Sun Nam; Shin, Dongyun; Hyun, Soonsil; Lee, Do-Sang; Min, Kyung Hoon; Han, Sae Mi; Li, Fu-Nan; Choi, Eung‐Chil; Choi, Seong-Hak

doi:10.1016/j.bmcl.2005.09.024

Cited by 26 publications

(11 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…IR spectrum, ν, cm -1 : 1767 (C=O, ester), 1693 (C=O, ketone), 1588. 1 6-Acetylacenaphthen-5-yl benzoate (III). Freshly distilled benzoyl chloride, 0.6 ml (4 mmol), was added to a solution of 0.67 g (3 mmol) of 1-(6-hydroxyacenaphthen-5-yl)ethanone (I) in 3 ml of anhydrous pyridine, and the mixture was kept for 2 h at 0°C.…”

Section: Methodsmentioning

confidence: 99%

“…IR spectrum, ν, cm -1 : 1735 (C=O, ester), 1711, 1678 (C=O, ketone), 1599. 1 6-(Acetoxyacetyl)acenaphthen-5-yl benzoate (VII) and 6-(hydroxyacetyl)acenaphthen-5-yl benzoate (VIII). Ammonium acetate, 0.12 g (1.6 mmol), was added to a solution of 0.2 g (0.5 mmol) of compound V in 3 ml of ethanol.…”

Section: -(Bromoacetyl)acenaphthen-5-yl Benzoate (V)mentioning

confidence: 99%

“…IR spectrum, ν, cm -1 : 1740 (C=O, ester), 1721 (PhC=O), 1697 (C=O, ketone). 1 The mixture was heated for 1 h under reflux and cooled, the precipitate of piperidinium bromide was filtered off, the filtrate was evaporated, and the residue was purified by chromatography on aluminum oxide using chloroform as eluent; a fraction with R f 0.8 was…”

Section: -(Bromoacetyl)acenaphthen-5-yl Benzoate (V)mentioning

confidence: 99%

“…Yield 0.27 g (72%), orange powder, mp 161-162°C (from ethanol). IR spectrum, ν, cm -1 : 2609 (OH), 1627 (C=O) 1. H NMR spectrum (CDCl 3 ), δ, ppm: 2.80 s (3H, CH 3 ), 3.38 m (4H, CH 2 CH 2 ), 7.26 br.d (1H, 3-H, J 3, 4 = 7.55 Hz), 7.57 br.s (1H, 8-H), 8.22 d (1H, 4-H, J 3, 4 = 7.55 Hz), 12.60 s (1H, OH).…”

mentioning

confidence: 99%

“…Heating of the latter in acetic anhydride produced 3-acetoxyacenaphtho[5,6-bc]pyran which was subjected to dehydrogenation to obtain a new heteroaromatic system.Compounds possessing pronounced antibacterial properties comparable with those of strong antibiotics were found among peri-fused pyran derivatives [1, 2]. peri-Fused bis-pyran systems like 1,6-and 1,8-dioxapyrenes exhibited unusual photobiological and genotoxic activity [3,4], readily formed charge-transfer complexes [5], and were used as building blocks for the synthesis of so-called organic metals [6].…”

mentioning

confidence: 99%

See 4 more Smart Citations

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

2011

View full text Add to dashboard Cite

peri-Acyloxyacenaphthenyl bromomethyl ketones prepared by bromination of peri-acyloxyacenaphthenyl methyl ketones reacted with sodium methoxide to give 2-acyl-3-hydroxyacenaphtho[5,6-bc]pyran derivatives, while their reaction with piperidine afforded acenaphtho[5,6-bc]pyran-3-on. Heating of the latter in acetic anhydride produced 3-acetoxyacenaphtho[5,6-bc]pyran which was subjected to dehydrogenation to obtain a new heteroaromatic system.Compounds possessing pronounced antibacterial properties comparable with those of strong antibiotics were found among peri-fused pyran derivatives [1, 2]. peri-Fused bis-pyran systems like 1,6-and 1,8-dioxapyrenes exhibited unusual photobiological and genotoxic activity [3,4], readily formed charge-transfer complexes [5], and were used as building blocks for the synthesis of so-called organic metals [6]. We previously synthesized 2-acylnaphtho[1,8-bc]pyran-3-ones and coordination compounds based thereon, which showed strong yellow-orange fluorescence and were proposed as effective chemosensors and highly sensitive analytical reagents for qualitative and quantitative determination of heavy metals [7]. Naphtho[1,8-bc]-pyran-3-ones were obtained by bromination of periacyloxynaphthyl alkyl ketones at the side alkyl chain OH Ac I OAc Ac II Ac 2 O, NaOAc OBz Ac III PhCOCl, pyridine OAc COCH 2 Br VI 1,4-Dioxane · Br 2 OH Ac IV CuBr 2 , EtOAc-CHCl 3 , Δ Br CuBr 2 , EtOAc-CHCl 3 , Δ OBz COCH 2 Br V Scheme 1.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: -(Bromoacetyl)acenaphthen-5-yl Benzoate (V)mentioning

confidence: 99%

Section: -(Bromoacetyl)acenaphthen-5-yl Benzoate (V)mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

2011

View full text Add to dashboard Cite

show abstract

Simple Strategy for Benzo[de]chromene‐7,8‐dione Synthesis via Tandem Sonogashira Coupling and Intramolecular Cyclization Reactions

et al. 2022

View full text Add to dashboard Cite

Benzo[de]chromene‐7,8‐dione derivatives are known to have important biological and pharmacological properties. Thus, a novel and efficient method was developed for the synthesis of benzo[de]chromene‐7,8‐dione derivatives via the tandem reaction of 5‐bromo‐2‐hydroxynaphthalene‐1,4‐dione and terminal alkynes, which proceeds under the typical reaction conditions for Sonogashira coupling using Pd and Cu catalysts. The process likely occurs via a tandem reaction due to the synthesized Sonogashira coupling product undergoing intramolecular cyclization in the presence of a Cu catalyst. This method is superior to existing synthesis methods in that it can access benzo[de]chromene‐7,8‐dione compounds without the post‐oxidation of benzo[de]chromenes. Furthermore, it enables the direct supply of several biologically active compounds. The minimum inhibitory concentrations (MICs) of the synthesized compounds against multidrug efflux pump‐deficient strains of S. aureus, E. coli, and P. aeruginosa and their parent strains were determined. Certain synthesized compounds exhibited strong antimicrobial activity, indicating that they are substrates for multidrug efflux pumps.

show abstract

Construction of 4‐Isochromanones through Cu(OTf)₂‐Catalysed Sequential C=O and C–O Bond Formation

Xing

Qin

et al. 2018

Eur J Org Chem

View full text Add to dashboard Cite

A new strategy for the facile and efficient synthesis of 4‐isochromanones has been developed. The reaction involves a Cu(OTf)2‐catalysed sequential reaction of epoxides carrying electron‐deficient alkenes using the solvent DMSO as the oxidant. The single‐step process involves a sequential oxidative ring opening of epoxides and an oxa‐Michael addition where one new C=O bond and one new C–O bond are created. The advantages of this approach include high efficiency, a broad substrate scope, and mild conditions.

show abstract

The structure–activity relationships of mansonone F, a potent anti-MRSA sesquiterpenoid quinone: SAR studies on the C6 and C9 analogs

Cited by 26 publications

References 7 publications

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

Simple Strategy for Benzo[de]chromene‐7,8‐dione Synthesis via Tandem Sonogashira Coupling and Intramolecular Cyclization Reactions

Construction of 4‐Isochromanones through Cu(OTf)₂‐Catalysed Sequential C=O and C–O Bond Formation

Contact Info

Product

Resources

About

The structure–activity relationships of mansonone F, a potent anti-MRSA sesquiterpenoid quinone: SAR studies on the C6 and C9 analogs

Cited by 26 publications

References 7 publications

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

Simple Strategy for Benzo[de]chromene‐7,8‐dione Synthesis via Tandem Sonogashira Coupling and Intramolecular Cyclization Reactions

Construction of 4‐Isochromanones through Cu(OTf)2‐Catalysed Sequential C=O and C–O Bond Formation

Contact Info

Product

Resources

About

Construction of 4‐Isochromanones through Cu(OTf)₂‐Catalysed Sequential C=O and C–O Bond Formation