The Convenient Way for Obtaining Geranial by Acid‐Catalyzed Kinetic Resolution of Citral

Ильина, И. В.; Волчо, К. П.; Корчагина, Д. В.; Salakhutdinov, N. F.

doi:10.1002/hlca.201500266

Cited by 4 publications

(1 citation statement)

References 14 publications

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“…A similar situation was observed for the reaction of 15 with bromide 19d; in this case the ratio between 20d and 20c was 9.5:0.5 (Scheme 2). This ratio can be explained by a partial isomerization process of bromides or target products as described previously [35]. In order to modify amine 17, carboxylic acids 23a,c,d were obtained by applying previously reported procedures [36][37][38].…”

Section: Chemistrymentioning

confidence: 99%

Novel Tdp1 Inhibitors Based on Adamantane Connected with Monoterpene Moieties via Heterocyclic Fragments

et al. 2021

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Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising target for anticancer therapy due to its ability to counter the effects topoisomerase 1 (Top1) poison, such as topotecan, thus, decreasing their efficacy. Compounds containing adamantane and monoterpenoid residues connected via 1,2,4-triazole or 1,3,4-thiadiazole linkers were synthesized and tested against Tdp1. All the derivatives exhibited inhibition at low micromolar or nanomolar concentrations with the most potent inhibitors having IC50 values in the 0.35–0.57 µM range. The cytotoxicity was determined in the HeLa, HCT-116 and SW837 cancer cell lines; moderate CC50 (µM) values were seen from the mid-teens to no effect at 100 µM. Furthermore, citral derivative 20c, α-pinene-derived compounds 20f, 20g and 25c, and the citronellic acid derivative 25b were found to have a sensitizing effect in conjunction with topotecan in the HeLa cervical cancer and colon adenocarcinoma HCT-116 cell lines. The ligands are predicted to bind in the catalytic pocket of Tdp1 and have favorable physicochemical properties for further development as a potential adjunct therapy with Top1 poisons.

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Section: Chemistrymentioning

confidence: 99%

Novel Tdp1 Inhibitors Based on Adamantane Connected with Monoterpene Moieties via Heterocyclic Fragments

et al. 2021

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Synthesis of oxygen-containing heterocyclic compounds based on monoterpenoids

Patrusheva¹,

Волчо²,

Salakhutdinov³

2018

Russ. Chem. Rev.

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The review integrates data on the synthesis of chiral oxygen-containing heterocycles of various structural types by reactions of monoterpenoids with carbonyl compounds. Depending on the structure of the monoterpene and carbonyl components and the catalyst used, these reactions lead to mono-, bi-, tri- or tetracyclic products. The possible reaction mechanisms are discussed and data on the biological activities of the products are given. The bibliography includes 125 references.

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Synthesis and Analgesic Activity of Monoterpenoid Aldehyde-derived Hydro-2H-chromeneols

Ильина¹,

Морозова²,

Korсhagina³

et al. 2019

LDDD

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Background: Despite a variety of drugs used to stop acute pain, problems related to their insufficient efficacy and undesirable side effects have remained unresolved. Therefore, the search for analgesics of new structural types, which combine high activity with low toxicity, is a topical issue. It is known that a number of compounds with a hydrogenated 2H-chromene skeleton exhibit significant analgesic activity in in vivo tests. Methods: New hydro-2H-chromenols containing monoterpenoid moieties were obtained via one-pot synthesis by the interaction between para-menthane alcohols and commercially available monoterpene aldehydes: Citral, hydroxycitronellal, myrtenal, and perillaldehyde. The analgesic activity of these compounds wаs studied in the acetic acid-induced writhing test and hot plate test. Results: The target compounds were characterized using NMR and HR-MS. Most of them exhibited pronounced analgesic activity. Conclusion: Due to high analgesic activity, (2S,4aR,8R,8aR)-2-((E)-2,6-dimethylhepta-1,5-dien-1- yl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol is considered as candidate compound to participate in further research.

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The Convenient Way for Obtaining Geranial by Acid‐Catalyzed Kinetic Resolution of Citral

Cited by 4 publications

References 14 publications

Novel Tdp1 Inhibitors Based on Adamantane Connected with Monoterpene Moieties via Heterocyclic Fragments

Novel Tdp1 Inhibitors Based on Adamantane Connected with Monoterpene Moieties via Heterocyclic Fragments

Synthesis of oxygen-containing heterocyclic compounds based on monoterpenoids

Synthesis and Analgesic Activity of Monoterpenoid Aldehyde-derived Hydro-2H-chromeneols

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