ChemInform Abstract: ANTIMICROBIAL PROPERTIES OF SOME FURAZAN AND FUROXAN DERIVATIVES

Calvino, R.; Mortarini, V.; Gasco, Alberto; Sanfilippo, A.; Ricciardi, M.

doi:10.1002/chin.198105225

Cited by 8 publications

(19 citation statements)

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“…Commercially available metronidazole (1) and 2-methyl-5-nitro imidazole (39) from Aldrich Chemical (Milwaukee, WI) were used. Compounds 2 [Calvino et al, 1980], 3, 31, 33 [Sorba et al, 1996], 4 [Boschi et al, 1997], 5 [Farrar, 1964], 12 [Kenley et al, 1984], 13-15 [Di Stilo et al, 1998], 17 [Rolando et al, 2003], and 34 [Kajfez et al, 1968] were synthesised according to the reported methods. The calculated log P (CLOGP) of the compounds was calculated using a CLOGP for Windows 4.0 software from the BioByte Corporation.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and anti‐Helicobacter pylori properties of NO‐donor/metronidazole hybrids and related compounds

Bertinaria

Galli

Sorba

et al. 2003

Drug Development Research

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Two series (A, B) of 2-(2-methyl-5-nitro-1H-imidazolyl)ethyl derivatives (6-9, 18-23) conjugated through an oxygen or an aminomethyl bridge with either a furoxan NO-donor moiety or a furazan substructure, devoid of NO-donor properties, were synthesised. A third group (C) of 2-(2-methyl-5-nitro-1H-imidazolyl)ethyl derivatives conjugated with nitrooxy and dinitrooxy NO-donor functions (35, 38) as well as the corresponding analogue without these functions (40) were prepared. All the compounds were evaluated in vitro for their activity against a number of Helicobacter pylori strains. Metronidazole (1) and its amino analogue (11) were taken as reference compounds. All the synthesised hybrids and their analogues exhibited good anti-H. pylori activity with MIC 50 in the range less than 0.0039-1, resulting in compounds more active than metronidazole. Derivatives 6-9 displayed good potency also against metronidazole-resistant strains. Compounds lacking the 5-nitroimidazole moiety (24-29, 30-33) proved to be inactive against H. pylori with the exception of 33. The lack of significant differences in the antibacterial potency between furoxan and furazan hybrids in both series (A, B) suggest that the role of the N-oxide moiety of the furoxan system either as an inductor of oxidative stress or as a promoter of NO-donor properties is marginal. The substitution of the furoxan substructures with nitrooxy moieties (35, 38) afforded active compounds. In view of their NO-donor properties, NO-metronidazole hybrids could represent potential therapeutic tools both in the treatment of gastric ulcer and in a number of extragastrointestinal disorders such as ischaemic heart diseases and atherosclerosis-related to some H. pylori strains. Drug Dev. Res. 60:225-239, 2003.

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Section: Methodsmentioning

confidence: 99%

Synthesis and anti‐Helicobacter pylori properties of NO‐donor/metronidazole hybrids and related compounds

Bertinaria

Galli

Sorba

et al. 2003

Drug Development Research

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“…Analysis (C, H, N) of the target compounds was performed by REDOX (Monza) and the results were within ±0.4% of the theoretical unless otherwise stated. Products 5 [17], 7 [19], 9 [20], 11 [21], 14 [16], 15 [17], 25 [18], 41 [22] were synthesized as described elsewhere; product 6 was a gift from Sanofi‐Aventis Deutschland GmbH. 43 was synthesized by the reaction of ethyl glycolate and 30 at reflux and its mp was in accordance with literature (mp 142–143°C (EtOAc), Ref.…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis (Scheme 1) of NO-donor melatonins [16][17][18][19] obtained by modification of the 5-methoxy group of melatonin required the preliminary preparation of the intermediates 10, 13 and the use of the previously described furoxans 14 [16], 15 [17]. The nitric ester 10 was easily obtained by the action of p-toluensulfonyl chloride (TsCl) in pyridine on 3-hydroxypropyl nitrate (9).…”

Section: Chemistrymentioning

confidence: 99%

NO‐donor melatonin derivatives: synthesis and in vitro pharmacological characterization

Chegaev

Lazzarato

Rolando

et al. 2007

Journal of Pineal Research

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Numerous studies document that melatonin possesses a broad-spectrum antioxidant activity. It traps a number of reactive oxygen species (ROS) such as hydroxyl and peroxyl radicals, singlet oxygen and hypochlorous acid. It also inhibits peroxynitrite-induced reactions. It is known that atherosclerosis progression involves ROS-induced oxidation of low-density lipoproteins in sub-endothelial space and the depletion of nitric oxide (NO) in blood vessels, as well as a decreased sensitivity of the vessels to the actions of NO. Considering this, a series of new NO-donor antioxidants were designed and synthesized by joining melatonin with NO-donor nitrooxy and furoxan moieties as polyvalent agents potentially useful for the treatment of cardiovascular diseases involving atherosclerotic vascular changes. The in vitro antioxidant properties of the resulting products were assessed in the thiobarbituric acid reactive substances assay (TBARS), the ABTS(+.) as well as in the alkaline phosphatase (ALP) assay. The antioxidant capacities of NO-donor melatonins to inhibit lipoperoxidation (TBARS-IC(50)) was predominantly dependent on their lipophilicity, and therefore on their partitioning process into membranes. On the other hand, their comparable capacity to inhibit protein oxidation (ALP-IC(50)) was independent of their lipophilicity and was consistent with their similar ability to participate in electron transfer reactions. All the NO-donor melatonins were also evaluated for their ability to relax rat aorta strips precontracted with 1 microM phenylephrine. Finally, binding affinities and intrinsic activity studies, carried out at MT(1) and MT(2) receptor subtypes, showed a rather complex picture in need of further investigation.

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“…Elemental analyses of the new compounds were performed by REDOX (Cologno M.) and are reported below for each compound. Compounds 5, 12 7, 5c 8, 13 9, 5c 10 14 were synthesised according to literature methods.…”

Section: Methodsmentioning

confidence: 99%

Unsymmetrically substituted furoxans. Part 18. Smiles rearrangement in furoxan systems and in related furazans

Boschi¹,

Sorba²,

Bertinaria³

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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ChemInform Abstract: ANTIMICROBIAL PROPERTIES OF SOME FURAZAN AND FUROXAN DERIVATIVES

Abstract: Das Aminofurazan (Ia) bzw. das Aminofuroxan (Ib) werden mit CF3‐CO3H zu den Nitro‐Derivaten (IIa) bzw. (IIb) oxidiert; unter analogen Bedingungen liefert das (Ib)‐Isomere (III) überwiegend das Nitrofurazan (IIa) und nur in geringer Menge das gewünschte Furoxan (IV).

Cited by 8 publications

References 0 publications

Synthesis and anti‐Helicobacter pylori properties of NO‐donor/metronidazole hybrids and related compounds

Synthesis and anti‐Helicobacter pylori properties of NO‐donor/metronidazole hybrids and related compounds

NO‐donor melatonin derivatives: synthesis and in vitro pharmacological characterization

Unsymmetrically substituted furoxans. Part 18. Smiles rearrangement in furoxan systems and in related furazans

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