Indole and Isatin Oximes: Synthesis, Reactions, and Biological Activity.

Абеле, Э.; Абеле, Р.; Dzenitis, O.; Lukevics, É.

doi:10.1002/chin.200332255

Cited by 10 publications

(8 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Researchers investigated the biological activities of derivatives of indole and isatin oximes and observed that compounds that possess a chlorine in the C5 position exhibited high analgesic and anti-inflammatory activities ( 33 ). Furthermore, other studies reported that unsubstituted isatins are 5-10 times less active than halogenated ones at C5 position ( 34 , 35 ).…”

Section: Discussionmentioning

confidence: 99%

Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice

Dantas

Fonseca

Pereira

et al. 2020

Braz J Med Biol Res

View full text Add to dashboard Cite

Several isatin derivatives have shown important biological activities, which have attracted interest from researchers. For this reason, the present study aimed to evaluate the anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide (COPHCT) in mice. Three doses of this compound were tested: 1.0, 2.5, and 5.0 mg/kg. The anti-inflammatory activity was assessed using the carrageenan-induced paw edema model and the zymosan-induced air pouch model. The evaluation of the antinociceptive effect was performed through the formalin test and the acetic acid-induced abdominal writhing test. The paw edema assay demonstrated that all doses of the compound showed a significant reduction of the edema in the second hour evaluated, but a better response was observed in the fourth hour. The zymosan-induced air pouch model indicated that the compound, in all doses, significantly reduced leukocyte migration and total protein concentration levels. In the formalin test, the doses 1.0, 2.5, and 5.0 mg/kg of COPHCT showed activity only in the second phase, with reduction in paw pain time of 73.61, 79.46, and 73.85%, respectively. The number of abdominal writhings decreased with the increasing dose, but only 5.0 mg/kg COPHCT exhibited a significant response, with a reduction of 24.88%. These results demonstrated the ability of this compound to interfere in the anti-inflammatory activity of edema, vascular permeability, and cell migration. In addition, its possible antinociceptive effect may be related to the dose used.

show abstract

Section: Discussionmentioning

confidence: 99%

Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice

Dantas

Fonseca

Pereira

et al. 2020

Braz J Med Biol Res

View full text Add to dashboard Cite

show abstract

“…The indole nucleus possesses a wide range of biological activities being a biologically accepted pharmacophore in medicinal compounds. Antiinflammatory [70], antifungal [71], antimicrobial [72], anticancer [73,74], anti-HIV [75], antioxidant [76], and antiviral [77] activities, among many others, are some examples of the biological potential of indole derivatives. There was only one report concerning the synthesis of indoletype compounds using chalcones as starting materials.…”

Section: Transformation Of Chalcones To Indolesmentioning

confidence: 99%

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Albuquerque¹,

Santos²,

Cavaleiro³

et al. 2014

COC

View full text Add to dashboard Cite

Chalcones belong to the flavonoid family which constitutes one of the major classes of naturally occurring oxygen heterocyclic compounds. The ,-unsaturated carbonyl system of chalcones possesses two electrophilic reactive centers allowing them to participate in addition reactions via attack to the carbonyl group (1,2-addition) or involving the-carbon (1,4-conjugate addition), leading to the synthesis of promising bioactive heterocyclic compounds. The purpose of this review is to present a systematic survey of the most recent literature that uses chalcones in the synthesis of biologically active 5-and 6-membered nitrogen heterocycles such as pyrroles, indoles, isoxazoles, imidazoles, pyrazoles, indazoles, triazoles, tetrazoles, pyridines and pyrimidines. Efficiency, easy-to-handle and cheap reagents, alternative heating conditions and greener protocols will be highlighted. In this review we will cover the literature since the beginning of the 21 st century in more than 400 publications.

show abstract

“…O-ethers of furan amidoximes 303 [284] (Scheme 49), were obtained by the reaction of the corresponding nitriles 302 with Oalkylhydroxylamines in the presence of KOH/EtOH or NaOMe/ MeOH. The products 303 5-phenyl-2-furamidoximes exhibited strong antidepressant activity in mice [285].…”

Section: Iv11 Anxiolytics-antidepressantsmentioning

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

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

Indole and Isatin Oximes: Synthesis, Reactions, and Biological Activity.

Abstract: Organic chemistryOrganic chemistry Z 0200 Indole and Isatin Oximes: Synthesis, Reactions, and Biological Activity. -[218 refs.]. -(ABELE, E.; ABELE, R.; DZENITIS, O.; LUKEVICS, E.; Chem. Heterocycl.

Cited by 10 publications

References 1 publication

Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice

Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

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

Contact Info

Product

Resources

About