β-Lactam derivatives as enzyme inhibitors: halogenated β-lactams and related compounds

Elriati, Ali; Loose, Jutta; Mayrhofer, Roswitha; Bergmann, Hans‐Joachim; Otto, Hans‐Hartwig

doi:10.1007/s00706-007-0837-5

Cited by 11 publications

(9 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Substituted imines were synthesized (Figure 1) by the reaction of equimolar amounts of aldehydes, namely, 2,4-dichlorobenzaldehyde, 3-nitrobenzaldehyde, 2,6-dichlorobenzaldehyde, and amines such as 2/3/4-fluoroaniline, 2-furfurylamine, 2,4,5-trichloroaniline, 1,2,3,4,5-pentafluoroaniline in dry methanol to afford substituted imines. All the imines (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) were characterized on the basis of spectral data and microanalysis.…”

Section: Resultsmentioning

confidence: 99%

Schiff Bases as Potential Fungicides and Nitrification Inhibitors

Aggarwal¹,

Kumar²,

Dureja³

et al. 2009

J. Agric. Food Chem.

View full text Add to dashboard Cite

A number of substituted Schiff bases were synthesized and characterized by (1)H NMR and mass spectrometry. These compounds were screened for antifungal activity in vitro against pathogenic fungi, namely, Sclerotium rolfsii and Rhizoctonia bataticola, and for their effect on nitrification inhibition under laboratory conditions. Maximum antifungal activity was exhibited by (2,4-dichlorobenzylidene)-(2,4,5-trichlorophenyl)-amine and (3-nitrobenzylidene)-(2,4,5-trichlorophenyl)-amine against both fungi (ED(50) with range from 3 to 24 microg/mL). Maximum nitrification inhibition (NI) was exhibited by (2,4-dichlorobenzylidene)-(2-fluorophenyl)-amine, (4-fluorophenyl)-(3-nitrobenzylidene)-amine, (2,6-dichlorobenzylidene)-(4-fluorophenyl)-amine, and (2,6-dichlorobenzylidene)-(3 fluorophenyl)-amine (NI in the range 91-96%).

show abstract

Section: Resultsmentioning

confidence: 99%

Schiff Bases as Potential Fungicides and Nitrification Inhibitors

Aggarwal¹,

Kumar²,

Dureja³

et al. 2009

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…Machanochemical approach to fluorine-containing imines formed in the reactions of fluorinated aldehydes with various aromatic amines or chiral benzylamines. [32], 100 [33]] 4a 78% [92 [34]] [34]] d 1d 97% [78 [18]] 2d 95% [66 [35]] 3d 99% [99 [32]] 4d 98% [80 [36], 92 [37], 97 [38,39], 98 [40]] 3a 91% [99 [32], 100 [33]]…”

Section: Aldehyde Aminementioning

confidence: 99%

“…Here, a few examples are presented. The condensation of α-keto ester, ethyl [32], 100 [33]] 4a 78% [92 [34]] [34]] d 1d 97% [78 [18]] 2d 95% [66 [35]] 3d 99% [99 [32]] 4d 98% [80 [36], 92 [37], 97 [38,39], 98 [40]]…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis of Fluorinated Imines

et al. 2022

View full text Add to dashboard Cite

A number of imines, including 12 new compounds, previously not reported in the literature, derived from variously fluorinated benzaldehydes and different anilines or chiral benzylamines were synthesized by a solvent-free mechanochemical method, which was based on the manual grinding of equimolar amounts of the substrates at the room temperature. In a very short reaction time of only 15 min, the method produced the expected products with good-to-excellent yields. The yields were comparable or significantly higher than those reported in the literature for the imines synthesized by other methods. Importantly, the conditions used for the reactions with aniline derivatives also resulted in the high yields of imines obtained from chiral benzylamines, and can be extended to the synthesis with other similar amines. Structures of all imines were confirmed by NMR spectroscopy: 1H, 13C and 19F. For four compounds, X-ray structures were also obtained. The synthetic approach presented in this paper contributes to the prevention of environmental pollution and can be easily extended for larger-scale syntheses. The mechanochemical solvent-free method provides a convenient strategy particularly useful for the preparation of fluorinated imines being versatile intermediates or starting material in the synthesis of drugs and other fine chemicals.

show abstract

“…Elriati et al reported the synthesis of new β‐lactams, namely a set of compounds with no substituents at C‐3 and others with mono‐ and di‐halogenation at C‐3; however, when tested for PPE inhibition they showed very weak inhibition and no further tests with HNE were performed. These results are in agreement with the suggestion of S1 subsite specificity of elastase toward small hydrophobic substituents.…”

Section: Acylating Inhibitorsmentioning

confidence: 99%

Targeting COPD: advances on low‐molecular‐weight inhibitors of human neutrophil elastase

Lucas

Costa

Guedes

et al. 2011

Medicinal Research Reviews

View full text Add to dashboard Cite

Chronic obstructive pulmonary disease (COPD) is a major increasing health problem and the World Health Organization (WHO) reports COPD as the fifth leading cause of death worldwide. COPD refers to a condition of inflammation and progressive weakening of the structure of the lung as well as irreversible narrowing of the airways. Current treatment is only palliative and no available drug halts the progression of the disease. Human neutrophil elastase (HNE) is a serine protease, which plays a major role in the COPD inflammatory process. The protease/anti-protease imbalance leads to an excess of extracellular HNE hydrolyzing elastin, the structural protein that confers elasticity to the lung tissue. Although HNE was identified as a therapeutic target for COPD more than 30 years ago, only Sivelestat (ONO-5046), an HNE inhibitor from Ono Pharmaceutical, has been approved for clinical use. Nevertheless, Sivelestat is only approved in Japan and its development in the USA was terminated in 2003. Other inhibitors in pre-clinical or phase I trials were discontinued for various reasons. Hence, there is an urgent need for low-molecular-weight synthetic elastase inhibitors and the present review discusses the recent advances on this field covering acylating agents, transition-state inhibitors, mechanism-based inhibitors, relevant natural products, and major patent disclosures.

show abstract

β-Lactam derivatives as enzyme inhibitors: halogenated β-lactams and related compounds

Cited by 11 publications

References 27 publications

Schiff Bases as Potential Fungicides and Nitrification Inhibitors

Schiff Bases as Potential Fungicides and Nitrification Inhibitors

Mechanochemical Synthesis of Fluorinated Imines

Targeting COPD: advances on low‐molecular‐weight inhibitors of human neutrophil elastase

Contact Info

Product

Resources

About