Hydrogenation of plant polyalkoxybenzene derivatives: convenient access to coenzyme Q0 analogues

Varakutin, Alexander E.; Muravsky, Egor A.; Shinkarev, Ilia Yu; Khrustalev, Victor N.; Семенов, В. В.

doi:10.1016/j.mencom.2020.09.015

Cited by 8 publications

(4 citation statements)

References 23 publications

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“…Aldehyde 6 was obtained by the formylation of dihydroapiol 5, according to a previously developed procedure, in the presence of SnCl 4 [8] with a yield of 90% (Scheme 1). The hydrogenation of apiol 1 to dihydroapiol 5 was carried out on highly porous ceramic block Pd-catalyst according to our procedure [9]. The target 6 was obtained during 1 h at 0 • C in high yield with the help of simple separation and crystallization from EtOH.…”

Section: Resultsmentioning

confidence: 99%

“…2. A solution of 4,7-dimethoxy-5-propyl-1,3-benzodioxole 5 [9] (2.1 g, 9.3 mmol) in formylation mixture (12.8 mmol) and dry CH2Cl2 (15 mL) was added dropwise to a solution of SnCl4 (7.0 g, 27 mmol) in dry CH2Cl2 (15 mL) at −10 °C. The reaction mixture was kept for 1 h at 0 °C and poured into water (100 mL).…”

Section: Synthesis Of 47-dimethoxy-6-propyl-2h-13-benzodioxole-5-carb...mentioning

confidence: 99%

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4,7-Dimethoxy-6-propyl-2H-1,3-benzodioxole-5-carbaldehyde

Tsyganov

Семенов

2023

Molbank

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of 47-dimethoxy-6-propyl-2h-13-benzodioxole-5-carb...mentioning

confidence: 99%

4,7-Dimethoxy-6-propyl-2H-1,3-benzodioxole-5-carbaldehyde

Tsyganov

Семенов

2023

Molbank

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“…Methyl-and propyl-substituted derivatives of allylpolyalkoxybenzenes (2a−d and 3a−d, Scheme 1) were prepared from starting natural products 1a− d via the synthetic procedure published earlier. 37 The key step in synthesis of TPP-conjugated polyalkoxyphenyl propanes 7a−d comprised the hydroboration of allylbenzenes 1a−d followed by H 2 O 2 oxidation to afford corresponding tetraalkoxyphenyl-1-propanoles 4a−d in high yields (Scheme 1). However, the detailed examination of hydroboration− oxidation products of apiol (1a) revealed negligible amounts of the concomitant propylbenzene 3a and arylpropan-2-ol 5a, which were isolated from the reaction mixture.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Methyl- and propyl-substituted derivatives of allylpolyalkoxybenzenes ( 2a – d and 3a – d , Scheme ) were prepared from starting natural products 1a – d via the synthetic procedure published earlier . The key step in synthesis of TPP-conjugated polyalkoxyphenyl propanes 7a – d comprised the hydroboration of allylbenzenes 1a – d followed by H 2 O 2 oxidation to afford corresponding tetraalkoxyphenyl-1-propanoles 4a – d in high yields (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of Triphenylphosphonium Derivatives of Natural Allylpolyalkoxybenzenes

et al. 2022

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Derivatives of natural allylpolyalkoxybenzenes conjugated to triphenylphosphonium (TPP) cations by aliphatic linkers of three, six, seven, and eight atoms were synthesized to examine the role of the polyalkoxybenzene pharmacophore, TPP fragment, and linker length in antiproliferative activities. The key synthetic procedures included (i) hydroboration−oxidation of apiol, dillapiol, myristicin, and allyltetramethoxybenzene; (ii) acylation of polyalkoxybenzyl alcohols or amines; and (iii) condensation of polyalkoxybenzaldehydes followed by hydrogenation and cyclopropyl−homoallyl rearrangement. The targeted TPP conjugates as well as the starting allylbenzenes, the corresponding alkylpolyalkoxybenzenes, and the respective alkyl-TPP salts were evaluated for cytotoxicity in a panel of human cancer cell lines using MTT and Click-iT-EdU assays and in a sea urchin embryo model. The linker of three carbon atoms was identified as favorable for selective cancer cell growth inhibition. Although the propyl-TPP salt was cytotoxic at low micromolar concentrations, the introduction of a polyalkoxybenzene moiety significantly potentiated inhibition of both cell growth and de novo DNA synthesis in several human cancer cell lines, HST-116 colon cancer, A375 melanoma, PC-3 prostate cancer, and T-47D breast carcinoma cells, while it failed to produce any developmental abnormalities in the sea urchin embryos.

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Electrooxidative Thiocyanation of Hydroxy‐ and Alkoxybenzenes

Moiseeva,

Sokolov,

Andreev

et al. 2024

Eur J Org Chem

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We developed an original method for thiocyanation of hydroxy‐ and alkoxy‐substituted benzenes (including naturally occurring compounds) using electrogenerated thiocyanogen, (SCN)₂. The presence of zinc chloride as a Lewis acid significantly enhances reaction efficiency by activating thiocyanogen. Cyclic voltammetry of the reactants and their combinations was employed to optimize reaction conditions and investigate the proposed mechanisms. This method demonstrated broad synthetic utility, leading to mono‐ and bis‐thiocyanated arenes and various heterocycles with yields 36–97 %. Notable products include the neuroprotective drug riluzole and precursors for the antiprotozoal drugs toltrazuril and ponazuril.

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Hydrogenation of plant polyalkoxybenzene derivatives: convenient access to coenzyme Q0 analogues

Cited by 8 publications

References 23 publications

4,7-Dimethoxy-6-propyl-2H-1,3-benzodioxole-5-carbaldehyde

4,7-Dimethoxy-6-propyl-2H-1,3-benzodioxole-5-carbaldehyde

Synthesis and Antiproliferative Activity of Triphenylphosphonium Derivatives of Natural Allylpolyalkoxybenzenes

Electrooxidative Thiocyanation of Hydroxy‐ and Alkoxybenzenes

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