Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters

Sandham, David A.; Barker, Lucy; Beattie, David T.; Beer, David; Bidlake, Louise; Bentley, David; Butler, K.D.; Craig, Sarah; Farr, David; Ffoulkes-Jones, Claire; Fozard, John R.; Haberthuer, Sandra; Howes, Colin; Hynx, Deborah; Jeffers, Sarah; Keller, Thomas H.; Kirkham, Paul; Maas, Janet; Mazzoni, Lazzaro; Nicholls, Andrew; Pilgrim, Gaynor E.; Schaebulin, Elisabeth; Spooner, Gillian; Stringer, Rowan; Tranter, Pamela; Turner, Katharine L.; Tweed, Morris; Walker, Christoph; Watson, Simon J.; Cuenoud, Bernard

doi:10.1016/j.bmc.2004.06.027

Cited by 22 publications

(13 citation statements)

References 17 publications

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“…1). Chemical study on secondary metabolites in 10% NaCl resulted in the isolation and identification of a new cyclopentanopyridine alkaloid, 3-hydroxy-5-methyl-5,6-dihydro-7H-cyclopenta [b]pyridin-7-one (1), together with 11 aromatic compounds, (2S,3S)-1-(4-hydroxyphenyl) butane-2,3-diol (2) (Thornton and Jones, 1964), (2R,3S)-1-(4-hydroxyphenyl)butane-2,3-diol (3) (Thornton and Jones, 1964), (S)-3-hydroxy-4-(4-hydroxyphenyl)-2-one (4) (Yuki et al, 2009), 3-(hydroxyacetyl)indole (5) (Yang and Cordell, 1997), 1H-indole-3-carboxylic acid (6) (Burton et al, 1986), 5-hydroxy-3-coumaranone (7) (Lee et al, 2010), 4-methylfuran-2-carboxylic acid (8) (Sandham et al, 2004), 3-methylfuran (9) (Hiraoka, 1970), 5-methyluracil (10) (Ellis et al, 1973), 2,5-furandimethanol (11) (Katritzky and Law, 1988), and 5-methylpyridin-3-ol (12) (Boux et al, 1988). The absolute configurations of compounds 2-4 were determined for the first time.…”

Section: Introductionmentioning

confidence: 99%

Aromatic compounds from the halotolerant fungal strain of Wallemia sebi PXP-89 in a hypersaline medium

Peng

Wang

et al. 2011

Arch. Pharm. Res.

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A new cyclopentanopyridine alkaloid, 3-hydroxy-5-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one (1), together with 11 known aromatic compounds were isolated from the secondary metabolites of the halotolerant fungal strain Wallemia sebi PXP-89 in 10% NaCl. Their structures including the absolute configurations of (2S,3S)-1-(4-hydroxyphenyl)butane-2,3-diol (2), (2R,3S)-1-(4-hydroxyphenyl)butane-2,3-diol (3), and (S)-3-hydroxy-4-(4-hydroxyphenyl)-2-one (4) were elucidated by spectroscopic analysis and a modified Mosher's method. Compound 1 exhibited antimicrobial activity against Enterobacter aerogenes with a MIC of 76.7 μM. The absolute configurations of compounds 2-4 were determined for the first time.

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Section: Introductionmentioning

confidence: 99%

Aromatic compounds from the halotolerant fungal strain of Wallemia sebi PXP-89 in a hypersaline medium

Peng

Wang

et al. 2011

Arch. Pharm. Res.

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“…17) as a promising lead with minimal oral absorption as well as superior efficacy and duration of action and similar intratracheal (i.t.) side effect profile compared to budesonide [210]. Compound 51 showed complete inhibition of eosinophilia 24 h after 1 mg/kg dosing without any significant oral side effects.…”

Section: Softmentioning

confidence: 90%

“…Nevertheless, development of these series for asthma has been discontinued, most likely because too rapid enzymatic inactivation at the desired site of action resulted in reduced anti-inflammatory efficacy [209]. Soft 17-Furoate Androstadienes A SD design approach aiming toward a safe, inhaled corticosteroid has also been recently reported by a group at Novartis [210]. The starting point of this design was essentially a 6a-F substituted mometasone furoate (58) analog with a 17b acid inactive metabolite.…”

Section: Softmentioning

confidence: 97%

Retrometabolism‐Based Drug Design and Targeting

Bodor

Buchwald

2010

Burger's Medicinal Chemistry and Drug Discovery

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Retrometabolic drug design (RMDD) approaches are systematic methodologies aimed to design safe compounds with an improved therapeutic index. RMDDs thoroughly integrate structure– activity and structure‐metabolism considerations into the entire design process and incorporate two major concepts aimed to design soft drugs and chemical delivery systems, respectively. Soft drugs (SDs) are new, active therapeutic agents designed to undergo predictable metabolism resulting in inactive metabolites after exerting their desired therapeutic effect(s). Chemical delivery systems (CDSs) are biologically inert molecules that provide enhanced and targeted delivery of an active drug to a particular organ or site through a designed sequential metabolism that involves several steps. Here, we present a comprehensive review including a general overview of the RMDD principles and a large number of specific examples from various pharmacological areas, including many recent developments, to illustrate RMDD concepts. Whenever possible, the rationale for the design as well as the pharmacokinetic and pharmacodynamic properties of the new therapeutic agents are briefly summarized and compared to those of the other compounds used in the same field.

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“…[13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] One of the important transformations includes the selective oxidation of furfurala nd its derivatives to obtain important chemicals such as 2-furoic acid, 2,5-furandicarboxylica cid (FDCA)a nd 2,5-diformylfuran (DFF) (Scheme1), for diverse applications in the food, pharmaceuticals andp olymer industries. [31][32][33][34][35][36][37] For example, 2-furoic acid is widely used as ap reservative and flavouringa gent. [32][33][34] FDCA, obtained from the selective oxidation of 5-HMF,h as been identified as the top-12v alue-added chemicals from biomass.…”

Section: Introductionmentioning

confidence: 99%

“…[31][32][33][34][35][36][37] For example, 2-furoic acid is widely used as ap reservative and flavouringa gent. [32][33][34] FDCA, obtained from the selective oxidation of 5-HMF,h as been identified as the top-12v alue-added chemicals from biomass. [35] FDCA has shown potentialt os erve as ab io-based polymer buildingb lock by replacing petroleum-derived terephthalic acid for the production of crucial polymers such as poly(ethylene terephthalate) (PET) and poly(butylene terephthalate) (PBT).…”

Section: Introductionmentioning

confidence: 99%

Catalytic Aerial Oxidation of Biomass‐Derived Furans to Furan Carboxylic Acids in Water over Bimetallic Nickel–Palladium Alloy Nanoparticles

et al. 2016

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Bimetallic Ni1−xPdx (0.10≤x≤0.75) alloy nanoparticle catalysts were synthesised and successfully employed for the catalytic aerial oxidation of biomass‐derived furans, such as 2‐furfuraldehyde (furfural), 2‐furfuryl alcohol (furfuryl alcohol), 5‐hydroxymethyl‐2‐furfural (5‐HMF), 5‐methyl‐2‐furfural (MF) and 5‐methyl‐2‐furfuryl alcohol (MFA), to selectively afford the corresponding furan carboxylic acids (2‐furoic acid, furan‐2,5‐dicarboxylic acid (FDCA) and 5‐methyl‐2‐furoic acid (MFCA)) in water at 80 °C. Among the studied Ni1−xPdx nanoparticle catalysts, Ni0.90Pd0.10 nanoparticle catalyst outperformed the others, achieving high yields of the corresponding furan carboxylic acid products. The presence of Ni in the Ni1−xPdx nanoparticle catalysts was advantageous, because it not only enhanced the catalytic activity for the facile oxidation of biomass‐derived furans using aerial oxygen to achieve high catalytic turnover, but also provided excellent stability to the Ni0.90Pd0.10 nanoparticle catalyst towards air and water and thus significantly enhanced its recyclability (up to 10 catalytic runs). The experiments revealed that the catalytic oxidation of 5‐HMF proceeded by the initial oxidation of the formyl group to carboxylic acid, and, subsequently, the conversion of alcohol to carboxylic acid via the formyl group to form FDCA. Moreover, the one‐pot direct transformation of fructose to furan carboxylic acid products (such as FDCA) was also achieved by using the Ni0.90Pd0.10 nanoparticle catalyst.

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Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters

Cited by 22 publications

References 17 publications

Aromatic compounds from the halotolerant fungal strain of Wallemia sebi PXP-89 in a hypersaline medium

Aromatic compounds from the halotolerant fungal strain of Wallemia sebi PXP-89 in a hypersaline medium

Retrometabolism‐Based Drug Design and Targeting

Catalytic Aerial Oxidation of Biomass‐Derived Furans to Furan Carboxylic Acids in Water over Bimetallic Nickel–Palladium Alloy Nanoparticles

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