New NO‐Donors with Antithrombotic and Vasodilating Activities, Part 17. Arylazoamidoximes and 3‐Arylazo‐1,2,4‐oxadiazol‐5‐ones

Rehse, Klaus; Bade, S.; Harsdorf, Angela; Clement, Bernd

doi:10.1002/ardp.19973301207

Cited by 11 publications

(5 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An arylazo group directly linked to the amidoxime group yielded compounds with considerable antithrombotic and antihypertensive activities via NO generation [132]. The same team has extended the study to amidoximes with other electron withdrawing substituents [133] as well, and the results in terms of structure-activity relationships are given below.…”

Section: Iv14 No Donors Aromatic and Aliphatic Amidoximes As Thrommentioning

confidence: 97%

See 1 more Smart Citation

Recent Developments in the Chemistry and in the Biological Applications of Amidoximes

Fylaktakidou¹,

Hadjipavlou‐Litina

Litinas³

et al. 2008

CPD

View full text Add to dashboard Cite

Amidoximes are compounds bearing both a hydroxyimino and an amino group at the same carbon atom which makes them versatile building blocks for the synthesis of various heterocycles. Their importance in chemistry along with their rich biology, make amidoximes an attractive target for medicinal chemists, biochemists and biologists. Amidoximes and simple O-substituted derivatives possess very important biological activities functioning as antituberculotic, antibacterial, bacteriostatic, insecticidal, elminthicidal, antiviral, herbicidal, fungicidal, antineoplastic, antiarrythmic, antihypertensive, antihistaminic, anxiolytic-antidepressant, anti-inflammatory/antioxidant, antiaggregatory (NO donors) or plant growth regulatory agents. A number of amidoximes has already been used as drugs, or currently being in clinical trials. Their numerous pharmaceutical applications have been recently enriched, due to the fact that some mechanistic pathways, concerning their conversion to amidines, as well as their ability to release NO were clarified, giving a new insight to their mode of action and allowing the design of new therapeutic agents. The main subject of the present review paper is to highlight aspects concerning chemical and biological questions on this interesting class of compounds. Some new synthetic methodologies as well as improvements of previously reported general reactions involving amidoximes, acylated amidoximes, and amidines are presented. The biological applications of amidoximes over the end of 2006 are also extensively reviewed.

show abstract

Section: Iv14 No Donors Aromatic and Aliphatic Amidoximes As Thrommentioning

confidence: 97%

“…The oxidative formation of nitric oxide from amidoximes by liver cells [132] was mimicked in vitro by the addition of a Fe 3+ -porphyrin complex (as cytochrome surrogate) and an oxygen donor, i.e. (bis-trifluoroacetoxy)-iodo-benzene to the ethanolic solution of selected compounds.…”

Section: Iv14 No Donors Aromatic and Aliphatic Amidoximes As Thrommentioning

confidence: 99%

Recent Developments in the Chemistry and in the Biological Applications of Amidoximes

Fylaktakidou¹,

Hadjipavlou‐Litina

Litinas³

et al. 2008

CPD

View full text Add to dashboard Cite

show abstract

“…Due to their NO-donating capacities, some oxime derivatives have also been shown to offer therapeutic potential for the treatment of erectile dysfunction, as well as cardiovascular diseases [ 203 , 204 ]. Likewise, a number of oxime derivatives have been shown to exhibit antithrombogenic, hypotensive, and cardiotonic activity [ 198 , 205 , 206 ]. For example, amidoximes and oximes have been shown to inhibit platelet aggregation, decrease thrombus formation, induce vasodilation, and lower intraocular pressure [ 192 , 197 , 199 , 207 , 208 , 209 ].…”

Section: Metabolism Of Oximes and No Productionmentioning

confidence: 99%

Oximes: Novel Therapeutics with Anticancer and Anti-Inflammatory Potential

et al. 2021

View full text Add to dashboard Cite

Oximes have been studied for decades because of their significant roles as acetylcholinesterase reactivators. Over the last twenty years, a large number of oximes have been reported with useful pharmaceutical properties, including compounds with antibacterial, anticancer, anti-arthritis, and anti-stroke activities. Many oximes are kinase inhibitors and have been shown to inhibit over 40 different kinases, including AMP-activated protein kinase (AMPK), phosphatidylinositol 3-kinase (PI3K), cyclin-dependent kinase (CDK), serine/threonine kinases glycogen synthase kinase 3 α/β (GSK-3α/β), Aurora A, B-Raf, Chk1, death-associated protein-kinase-related 2 (DRAK2), phosphorylase kinase (PhK), serum and glucocorticoid-regulated kinase (SGK), Janus tyrosine kinase (JAK), and multiple receptor and non-receptor tyrosine kinases. Some oximes are inhibitors of lipoxygenase 5, human neutrophil elastase, and proteinase 3. The oxime group contains two H-bond acceptors (nitrogen and oxygen atoms) and one H-bond donor (OH group), versus only one H-bond acceptor present in carbonyl groups. This feature, together with the high polarity of oxime groups, may lead to a significantly different mode of interaction with receptor binding sites compared to corresponding carbonyl compounds, despite small changes in the total size and shape of the compound. In addition, oximes can generate nitric oxide. This review is focused on oximes as kinase inhibitors with anticancer and anti-inflammatory activities. Oximes with non-kinase targets or mechanisms of anti-inflammatory activity are also discussed.

show abstract

“…The first major works that appeared on that topic were published by Rehse et al in 1997 and 1998 [66,67]. Seven aryl azoamidoximes and their effects on thrombosis inhibition, blood pressure and inhibition of platelet aggregation were investigated [66]. Five of the seven amidoximes inhibited the formation of thrombus in mesenteric rat vessels and even two of these amidoximes inhibited the thrombus formation by more than 20% (Figure 10).…”

Section: Oxidation Of Amidoximes/oximes and No Releasementioning

confidence: 99%

Amidoximes and Oximes: Synthesis, Structure, and Their Key Role as NO Donors

2019

View full text Add to dashboard Cite

Nitric oxide (NO) is naturally synthesized in the human body and presents many beneficial biological effects; in particular on the cardiovascular system. Recently; many researchers tried to develop external sources to increase the NO level in the body; for example by using amidoximes and oximes which can be oxidized in vivo and release NO. In this review; the classical methods and most recent advances for the synthesis of both amidoximes and oximes are presented first. The isomers of amidoximes and oximes and their stabilities will also be described; (Z)-amidoximes and (Z)-oximes being usually the most energetically favorable isomers. This manuscript details also the biomimetic and biological pathways involved in the oxidation of amidoximes and oximes. The key role played by cytochrome P450 or other dihydronicotinamide-adenine dinucleotide phosphate (NADPH)-dependent reductase pathways is demonstrated. Finally, amidoximes and oximes exhibit important effects on the relaxation of both aortic and tracheal rings alongside with other effects as the decrease of the arterial pressure and of the thrombi formation

show abstract

New NO‐Donors with Antithrombotic and Vasodilating Activities, Part 17. Arylazoamidoximes and 3‐Arylazo‐1,2,4‐oxadiazol‐5‐ones

Cited by 11 publications

References 16 publications

Recent Developments in the Chemistry and in the Biological Applications of Amidoximes

Recent Developments in the Chemistry and in the Biological Applications of Amidoximes

Oximes: Novel Therapeutics with Anticancer and Anti-Inflammatory Potential

Amidoximes and Oximes: Synthesis, Structure, and Their Key Role as NO Donors

Contact Info

Product

Resources

About