Synthesis and study of the pharmacologic properties of derivatives of 1,2,3,4-tetrahydro-5-nitropyrimidine

Remennikov, G. Ya.; Shavaran, S. S.; Boldyrev, I. V.; Kurilenko, L. K.; Klebanov, Boris; Kukhar, V. P.

doi:10.1007/bf00772019

Cited by 4 publications

(4 citation statements)

References 9 publications

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“…); 1339 (NO 2 , sym.). 1 From the methanol-pyridine filtrate we isolated 0.65 g (64%) of compound IId, mp 269-271°C (from dioxane).…”

Section: -(3-bromo-4-methoxyphenyl)-5-nitro-6-phenylpyrimidin-2(1h)-mentioning

confidence: 99%

“…), 1356 (NO 2 , sym.). 1 By diluting the dioxane mother liquor with water we isolated a mixture of mono-and dibromo-substituted compounds (according to the mass spectral data).…”

Section: -(3-bromo-4-methoxyphenyl)-5-nitro-6-phenylpyrimidin-2(1h)-mentioning

confidence: 99%

“…Some 4-aryl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones exhibit an appreciable biological activity, specifically as calcium channel modulators [1]. We recently found that several 4-aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-one derivatives show a high antiarrhythmic activity [2].…”

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confidence: 98%

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Bromination-Dehydrobromination of 4-Aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-ones

2005

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Depending on the conditions, bromination of 4-aryl-5-nitro-6-phenyl-3,4-dihydropyrimidine-2(1H)-ones and subsequent dehydrobromination gives either 4-aryl-5-nitro-6-phenylpyrimidin-2(1H)-ones or their mixtures with the corresponding 4-aryl-5-bromo-6-methoxy-5-nitro-6-phenyltetrahydropyrimidin-2-ones which are formed as two diastereoisomers.Some 4-aryl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones exhibit an appreciable biological activity, specifically as calcium channel modulators [1]. We recently found that several 4-aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-one derivatives show a high antiarrhythmic activity [2]. According to the data of [3], the stability of the heterocyclic fragment in 1,4(or 3,4)-dihydropyrimidines and structurally related 1,4-dihydropyridines to aromatization is important for their biological activity. Therefore, it seemed to be reasonable to examine the behavior of 4-aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-ones I in dehydrogenation and oxidation reactions which could result in aromatization of the heteroring.The present communication reports on the bromination and subsequent dehydrobromination of dihydropyrimidinones Ia-Ic. This two-step technique is widely used for aromatization of dihydropyrimidinones [4]. Here, the first step (i.e., bromination) is usually determining. It was shown that the ease of bromination of 4,6-diphenyldihydropyrimidin-2-ones depends on the substituent in position 5 of the heteroring. The bromination of 4,6-diphenyldihydropyrimidin-2-ones having such substituent in position 5 as ethoxycarbonyl, aroxy, or nitro group requires more severe conditions as compared to the corresponding 5-unsubstituted and 5-alkyl derivatives [4][5][6]. For example, compound Ia undergoes bromination with bromine in boiling acetic acid, and the subsequent dehydrobromination yields pyrimidinone IIa [5].Taking into account these findings, we performed bromination of 3-chlorophenyl derivative Ib on heating in acetic acid, and the bromination product was isolated and treated with pyridine in boiling methanol. As a result, we obtained 4-(3-chlorophenyl)-5-nitro-6-phenylpyrimidin-2(1H)-one (IIb) in good yield (Scheme 1). Unlike compounds Ia and Ib, 4-(4-methoxyphenyl)-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-one (Ic) readily reacted with an equimolar amount of bromine both in acetic acid and in chloroform at room temperature. However, the reaction involved only the methoxyphenyl group to give 4-(3-bromo-4-methoxyphenyl)-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-one (Id). This is consistent with published data on ready bromination of para-substituted anisoles [7]. The subsequent bromination of compound Id with an equimolar amount of bromine in acetic acid on heating, followed by dehydrobromination, afforded a mixture of products containing 4-(3-bromo-4-methoxyphenyl)-5-nitro-6-phenylpyrimidin-2(1H)-one (IId) and dibromo derivatives (according to the data of elemental analysis and mass spectrometry). We succeeded in isolating compound IId and a mixture of dibromo derivatives, but ...

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“…); 1339 (NO 2 , sym.). 1 From the methanol-pyridine filtrate we isolated 0.65 g (64%) of compound IId, mp 269-271°C (from dioxane).…”

Section: -(3-bromo-4-methoxyphenyl)-5-nitro-6-phenylpyrimidin-2(1h)-mentioning

confidence: 99%

“…), 1356 (NO 2 , sym.). 1 By diluting the dioxane mother liquor with water we isolated a mixture of mono-and dibromo-substituted compounds (according to the mass spectral data).…”

Section: -(3-bromo-4-methoxyphenyl)-5-nitro-6-phenylpyrimidin-2(1h)-mentioning

confidence: 99%

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Bromination-Dehydrobromination of 4-Aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-ones

2005

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“…The substitution of nitro group for ester group in the dihydropyrimidines may alter their biological action. Some 4-aryl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones exhibit an appreciable biological activity, specifically as calcium channel modulators [8]. Moreover, nitro functionalized DHPMs were synthesized and found as pyrimidine nucleoside analogues [9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Crystal, and Molecular Structure Analysis of 3,4-dihydro-6-(2-hydroxyphenyl)-5-nitro-4-phenylpyrimidin-2(1H)-one

Savant¹,

Gowda

Anandalwar

et al. 2015

Molecular Crystals and Liquid Crystals

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A novel nitro and 2-hydroxyphenyl functionalized pyrimidinone at C5 and C6, respectively, has been synthesized using 1-(2-hydroxyphenyl)-2-nitroethanone, benzaldehyde, urea, and etidronic acid as a catalyst is described. The synthesized compound characterized by spectroscopic techniques and finally confirmed by X-ray diffraction studies. The molecule crystallizes in the monoclinic crystal class in the space group P2 1 /c with cell parameters a = 11.1070(10) Å, b = 8.8210(4)Å, c = 15.1110(13)Å, β = 106.193(2) • , and Z = 4. The pyrimidine ring adopts flattened boat conformation.

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Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers

2016

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Synthesis and study of the pharmacologic properties of derivatives of 1,2,3,4-tetrahydro-5-nitropyrimidine

Cited by 4 publications

References 9 publications

Bromination-Dehydrobromination of 4-Aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-ones

Bromination-Dehydrobromination of 4-Aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-ones

Synthesis, Characterization, Crystal, and Molecular Structure Analysis of 3,4-dihydro-6-(2-hydroxyphenyl)-5-nitro-4-phenylpyrimidin-2(1H)-one

Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers

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