Derivatives of acetylformamide oxime and their cytostatic properties

Poplavskaya, I. A.; Kurmangalieva, R. G.; Khalilova, S. F.; Абдуллин, Х.А.; Kudrina, I. K.

doi:10.1007/bf00762893

Cited by 2 publications

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“…Thus, a desulfurization reaction of 256 with O-substituted hydroxylamines in the presence of mercury(II) acetate and/or mercury(II) chloride and N,N-diisopropylethylamine (DIEA) in acetonitrile afforded the Nmethylated amidoxime analogues (258)(259)(260)(261)(262)(263)(264)(265)(266)(267)(268)(269)(270)(271)(272)(273)(274)(275)(276) [254]. The N-methylated amidoxime derivative 257 was prepared directly from 256 and hydroxylamine in the same manner as above or alternatively was synthesized by simple removal of the benzyl group (Bn) of the Obenzyl N-methylamidoxime 266 by palladium-charcoal catalyzed hydrogenation in the presence of hydrochloric acid.…”

Section: Iv5 Anthelminthicidesmentioning

confidence: 99%

“…Detailed investigation of N-substituted amidoximes and related compounds confirmed the critical role of the bis(2-chlorethyl)amino group in controlling tumors. Indeed, absence of the latter caused a dramatic decrease in activity, only -4-(ethoxy)phenylamino--isonitrosoacetone hydrochloride 294 reaching 67% against Guerin carcinoma [271] The presence of a glyoxime moiety along with the amidoximic one did not improve the properties [272].…”

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

Fylaktakidou¹,

Hadjipavlou‐Litina

Litinas³

et al. 2008

CPD

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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.

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Section: Iv5 Anthelminthicidesmentioning

confidence: 99%

mentioning

confidence: 99%

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

Fylaktakidou¹,

Hadjipavlou‐Litina

Litinas³

et al. 2008

CPD

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“…648 Thiobenzamides have been condensed with anilines to afford amidines (315).648 Thioamides can be converted to amidines, e.g. (316), by treatment with ammonia in the presence of mercury acetate. 31 ?…”

Section: Ohc-nmezmentioning

confidence: 99%

Synthesis of Iminium Salts, Orthoesters and Related Compounds

Kantlehner

1991

Comprehensive Organic Synthesis

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Derivatives of acetylformamide oxime and their cytostatic properties

Cited by 2 publications

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

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

Synthesis of Iminium Salts, Orthoesters and Related Compounds

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