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Kul'magambetova, E. A.; Yamovoi, V. I.; Kusainova, D. D.; Pak, R. N.; Kulyyasov, A. T.; Турдыбеков, К. М.; Адекенов, С. М.; Gatilov, Yu. V.

doi:10.1023/a:1022622301506

Cited by 7 publications

(3 citation statements)

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“…Yield 2.6 g (55%) of 99% pure product (according to HPLC). The analytical and spectral characteristics agreed with those reported [8].…”

Section: -Hydrazono-7-methoxy-2-phenylchroman-5-ol (2)supporting

confidence: 87%

“…Hydrazone 2 reacted readily with substituted aromatic aldehydes (anisaldehyde, 4-fluorobenzaldehyde, 4-hydroxybenzaldehyde, 4-nitrobenzaldehyde, 2-chlorobenzaldehyde, 5-bromosalicylaldehyde, 2,4-dimethoxybenzaldehyde, 4-hydroxy-3-nitrobenzaldehyde, and 2-hydroxy-6-nitrosobenzaldehyde) to form the corresponding pinostrobin N-arylidenehydrazones (3)(4)(5)(6)(7)(8)(9)(10)(11) (68-95% yields) (Scheme 2).…”

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confidence: 99%

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Synthesis and Cytotoxicity of Pinostrobin Hydrazone Derivatives

Жанымханова¹,

Turysbaeva²,

Покровский

et al. 2015

Chem Nat Compd

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The corresponding hydrazones and thiosemicarbazones were synthesized via the reaction of pinostrobin hydrazone with carbonyl compounds (aromatic aldehydes, acetone) or alkyl(aryl)isothiocyanates, respectively. The new pinostrobin derivatives showed significant cytotoxicity (MTT-assay) against human tumor cell models.Keywords: pinostrobin hydrazone, (4E)-benzylidenehydrazones, thiosemicarbazones, cytotoxic activity.Flavonoids comprise flavones, flavanones, flavonols, and isoflavones and constitute a large and important group of plant polyphenolic compounds. Available flavanones include pinostrobin (1), which was isolated from Populus balsamifera L.[1]. Pinostrobin exhibits antiproliferative [2], antimicrobial [3], neuroprotective [4], and anti-inflammatory [5] properties. The ointment Topolin and tincture Efmatol were formulated from extracts of P. balsamifera buds as antiperiodontitis and antiinflammatory agents, the active ingredient of which was the flavonoid 1 [6,7]. Considering the availability of 1, the preparation of new derivatives with high specific biological activity is critical.The preparation of pinostrobin oxime, for which hepatoprotective activity was found [8], has been reported. Halosubstituted pinostrobin derivatives were synthesized [9]. Also, prenylation of 1 was described and the cytotoxicity of new derivatives against human tumor cells was studied [10].The goals of our work were to develop a method for producing pinostrobin hydrazone; to study its reactions with aromatic aldehydes, phenylisothiocyanate, alkylisothiocyanates, and acetone; and also to study the cytotoxic activity of several derivatives against human tumor cell models.Treatment of 1 with an excess of hydrazine hydrate was reported [8] to give pinostrobin hydrazone (2). Our experiments showed that 2 was readily formed via the reaction of 1 with hydrazine hydrate in EtOH. Pyrazole 2a that could be produced by cleavage of the pyrone ring was not observed (Scheme 1).

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“…Yield 2.6 g (55%) of 99% pure product (according to HPLC). The analytical and spectral characteristics agreed with those reported [8].…”

Section: -Hydrazono-7-methoxy-2-phenylchroman-5-ol (2)supporting

confidence: 87%

mentioning

confidence: 99%

Synthesis and Cytotoxicity of Pinostrobin Hydrazone Derivatives

Жанымханова¹,

Turysbaeva²,

Покровский

et al. 2015

Chem Nat Compd

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“…7 Flavanones possess strong antioxidant and antibacterial activity but only scant data on their chemical modification is available in the literature. 8 The reactions of flavanone with simple hydrazines have been reported [9][10][11] but no such investigation with hydrazino heterocycles has been carried out. The chemistry of 4-thiazolidinones has been reviewed 12 and found to exhibit antibacterial, herbicidal, anti-inflammatory, and analgesic activities, 13 while some derivatives are potent anti-HIV agents 14 and evaluated as selective human immunodeficiency virus type-1 reverse transcriptase (HIV-1 RT) enzyme inhibitors.…”

Section: Introductionmentioning

confidence: 99%