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

[ Vol. 17 , Issue. 1 ]

Author(s):

Irina Il'ina*, Ekaterina Morozova, Dina Korсhagina, Konstantin Volсho, Tat'yana Tolstikova and Nariman Salakhutdinov   Pages 68 - 78 ( 11 )

Abstract:


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.

Keywords:

Monoterpenoid aldehyde, isopulegol, chromene, analgesia, acetic acid-induced writhing test, hot-plate test.

Affiliation:

N.N. Vorozhtsov Novosibirsk Institute of Organiс Сhemistry, Siberian Branсh, Russian Aсademy of Sсienсes, Lavrentjev Avenue, 9, 630090 Novosibirsk, N.N. Vorozhtsov Novosibirsk Institute of Organiс Сhemistry, Siberian Branсh, Russian Aсademy of Sсienсes, Lavrentjev Avenue, 9, 630090 Novosibirsk, N.N. Vorozhtsov Novosibirsk Institute of Organiс Сhemistry, Siberian Branсh, Russian Aсademy of Sсienсes, Lavrentjev Avenue, 9, 630090 Novosibirsk, N.N. Vorozhtsov Novosibirsk Institute of Organiс Сhemistry, Siberian Branсh, Russian Aсademy of Sсienсes, Lavrentjev Avenue, 9, 630090 Novosibirsk, N.N. Vorozhtsov Novosibirsk Institute of Organiс Сhemistry, Siberian Branсh, Russian Aсademy of Sсienсes, Lavrentjev Avenue, 9, 630090 Novosibirsk, N.N. Vorozhtsov Novosibirsk Institute of Organiс Сhemistry, Siberian Branсh, Russian Aсademy of Sсienсes, Lavrentjev Avenue, 9, 630090 Novosibirsk

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