1-Substitution in 2-methyl-4(5)-nitroimidazole. I. Synthesis of compounds with potential antitrichomonal activity

Kajfež, F.; Šunjić, Vitomir; Kolbah, D.; Fajdiga, T.; Oklobdzija, M.

doi:10.1021/jm00307a044

Cited by 28 publications

(14 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

“…The organic layers were dried (MgSO 4 ) and evaporated under reduced pressure to give 0.75 g (47%) of 41 as a white solid. 40: mp: 63.5-641C (MeOH/H 2 O) (62.5-63.5 [Kajfez et al, 1968] [Kajfez et al, 1968] …”

Section: -(2-ethoxyethyl)-2-methyl-5-nitro-1h-imidazole (40)mentioning

confidence: 99%

“…The two products were separated making use of the greater basicity of 41 with respect to 40. Both these compounds were previously described in the literature in higher yield but from different starting materials and through a different pathway [Kajfez et al, 1968]. Structural identification of isomeric 40 and 41 was obtained both on the basis of 13 C NMR data and of their melting points reported in literature [McKillop et al, 1983;Kajfez et al, 1968].…”

mentioning

confidence: 99%

“…Both these compounds were previously described in the literature in higher yield but from different starting materials and through a different pathway [Kajfez et al, 1968]. Structural identification of isomeric 40 and 41 was obtained both on the basis of 13 C NMR data and of their melting points reported in literature [McKillop et al, 1983;Kajfez et al, 1968]. Derivatives 42, 43 (Table 2) were synthesised according to published procedure [Kawashima et al, 1993;Dunstan et al, 1965]; they were stable in 50 mM phosphate buffer-1% DMSO solution at 371C for more than 72 h (HPLC detection).…”

mentioning

confidence: 99%

See 3 more Smart Citations

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

Bertinaria

Galli

Sorba

et al. 2003

Drug Development Research

View full text Add to dashboard Cite

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.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: -(2-ethoxyethyl)-2-methyl-5-nitro-1h-imidazole (40)mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

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

Bertinaria

Galli

Sorba

et al. 2003

Drug Development Research

View full text Add to dashboard Cite

show abstract

“…amino-7a-methoxy-3-[(1-methyl-lH-tetrazol-5-yl) thiomethyl]-3-cephem-4-carboxylic acid (10) Method D. To a cold solution of diphenylmethyl 7/3-amino-7a-methoxy-3-[ (1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate221 (1.1 g, 2.1 mmole) in 30 ml of 1,2-dichloroethane were added dropwise 0.35 ml of N,N-diethylaniline in 10 ml of 1,2-dichloroethane and 3.15 mmole of 1-methyl-4-nitro-1H-imidazol-5-ylthioacetyl chloride (see preparation under method A) in 10 ml of the same solvent. The mixture was stirred for 20 minutes under cooling and then washed with water, buffer solution pH 7.8, and water successively.…”

Section: A-methoxy Cephalosporinsmentioning

confidence: 99%

New cephalosporins and 7.ALPHA.-methoxy cephalosporins chemistry and biological activities.

Elitropi¹,

Pantò²,

Tricerri³

et al. 1979

J. Antibiot.

View full text Add to dashboard Cite

Nucleophilic substitutions in some derivatives of 4‐ and 5‐nitroimidazoles

Šunjić¹,

Fajdiga²,

Japelj³

et al. 1969

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

Hydrogen, as well as the halogen atom, at the 4 or 5 position in some 5‐ and 4‐nitroimidazoles were displaced by various nucleophiles such as the amino, cyano, hydroxy, and alkoxy groups. The greater reactivity of the departing group in the 4 position, which was regularly observed, is ascribed to the double activating effect of the azo and nitro groups. Cyanide ion in alcoholic solution reacted peculiarly with both 4‐ and 5‐nitroimidazoles giving o‐cyanoazoxyimidazoles as the only products. In some of the nucleophilic displacements at the 4 position of 5‐nitroimidazoles the formation of intermediate S̀‐complexes was observed.

show abstract

1-Substitution in 2-methyl-4(5)-nitroimidazole. I. Synthesis of compounds with potential antitrichomonal activity

Cited by 28 publications

References 5 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

New cephalosporins and 7.ALPHA.-methoxy cephalosporins chemistry and biological activities.

Nucleophilic substitutions in some derivatives of 4‐ and 5‐nitroimidazoles

Contact Info

Product

Resources

About