Synthesis of adenine and hypoxanthine from 3-methylxanthine

Gutorov, L. A.; Nikolaeva, L. A.; Ovcharova, I. M.; Golovchinskaya, E. S.

doi:10.1007/bf00777993

Cited by 2 publications

(3 citation statements)

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“…Introduction of ethyl acetoacetate to AU2 in an S N Ar manner followed by decarboxylation and deacetoxylation furnished a methylated compound 3b in low yield . Hydroxylation of AU2 proceeded to afford 3c in 78% yield .…”

Section: Resultsmentioning

confidence: 99%

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Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H⁺-ATPase Phosphorylation Pathway

et al. 2023

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Stomata are pores in the leaf epidermis of plants and their opening and closing regulate gas exchange and water transpiration. Stomatal movements play key roles in both plant growth and stress responses. In recent years, small molecules regulating stomatal movements have been used as a powerful tool in mechanistic studies, as well as key players for agricultural applications. Therefore, the development of new molecules regulating stomatal movement and the elucidation of their mechanisms have attracted much attention. We herein describe the discovery of 2,6-dihalopurines, AUs, as a new stomatal opening inhibitor, and their mechanistic study. Based on biological assays, AUs may involve in the pathway related with plasma membrane H + -ATPase phosphorylation. In addition, we identified leucine-rich repeat extensin proteins (LRXs), LRX3, LRX4 and LRX5 as well as RALF, as target protein candidates of AUs by affinity based pull down assay and molecular dynamics simulation. The mechanism of stomatal movement related with the LRXs−RALF is an unexplored pathway, and therefore further studies may lead to the discovery of new signaling pathways and regulatory factors in the stomatal movement.

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Section: Resultsmentioning

confidence: 99%

“…31 Hydroxylation of AU2 proceeded to afford 3c in 78% yield. 32 3d was synthesized by halogen exchange using CsF in 53% yield. 33 In addition, 6chloroadenine was reacted with benzyl bromide to obtain 3e in 63% yield.…”

Section: Sar Study Of Au Derivativesmentioning

confidence: 99%

Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H⁺-ATPase Phosphorylation Pathway

et al. 2023

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“…New methods for the synthesis of purine, adenine, hypoxanthine, and guanine 46-49 (yields 73, 77, 85, and 95% respectively) from xanthine 40 were developed according to a combined scheme through the intermediate compounds 42-45 (yields 87, 95, 95, and 81% respectively) [9][10][11][12][13][14].…”

Section: Koh Kohmentioning

confidence: 99%

The use of protecting groups in the synthesis of purine derivatives (review)

Александрова

Кочергин²

2009

Chem Heterocycl Comp

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During the synthesis of derivatives of purine from amino-, hydroxy-, thio-, or chloropurines there is often a need at position 2, 6, 7, or 9 of the purine ring to insert a protecting group that can be removed after the necessary chemical operations and retained or replaced by another pharmacophoric group during the search for biologically active substances. ALKYL (ARALKYL) PROTECTION OF POSITION 7(9)The following basic rules were established on the basis of experimental data from a large number of papers and patents relating to the nucleophilic substitution of chloropurines, reported in the monographs [1, 2]: In the series of chloro-, dichloro-, and trichloropurines the most reactive is the chlorine atom at position 6, in second place is the chlorine atom at position 8, and in third place the chlorine atom at position 2 of the purine bicycle. This rule persists in the series of 7(9)-alkyl-2,6-, -2,8-, and -6,8-dichloropurines.In the series of 7(9)-alkyl-2,6,8-trichloropurines the order of nucleophilic substitution of the chlorine atoms changes. In these compounds, unlike 2,6,8-trichloropurine, the most vulnerable center for nucleophilic attack is the chlorine atom at position 8 and then the chlorine atom at position 6 of the purine ring. The chlorine atom at position 2 was and remains the most inert in the series of 7(9)-alkyl-2,6,8-trichloropurines.In the synthesis of 8-substituted purines from 2,6,8-trichloro-7-methylpurine (1) the founder of purine chemistry E. Fischer used the methyl group as protection. Thus, 2,6-dichloro-7-methylpurin-8-one (2) was obtained by the reaction of the trichloride 1 with KOH in aqueous solution at 20°C [3].

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Synthesis of adenine and hypoxanthine from 3-methylxanthine

Cited by 2 publications

References 3 publications

Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H⁺-ATPase Phosphorylation Pathway

Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H⁺-ATPase Phosphorylation Pathway

The use of protecting groups in the synthesis of purine derivatives (review)

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Synthesis of adenine and hypoxanthine from 3-methylxanthine

Cited by 2 publications

References 3 publications

Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H+-ATPase Phosphorylation Pathway

Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H+-ATPase Phosphorylation Pathway

The use of protecting groups in the synthesis of purine derivatives (review)

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Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H⁺-ATPase Phosphorylation Pathway

Discovery of 2,6-Dihalopurines as Stomata Opening Inhibitors: Implication of an LRX-Mediated H⁺-ATPase Phosphorylation Pathway