Synthesis and analgesic activity of monoterpenoid aldehyde-derived hydro-2H-chromeneols. / Il'ina, Irina; Morozova, Ekaterina; Korсhagina, Dina et al.
In: Letters in Drug Design and Discovery, Vol. 17, No. 1, 01.01.2020, p. 68-78.Research output: Contribution to journal › Article › peer-review
}
TY - JOUR
T1 - Synthesis and analgesic activity of monoterpenoid aldehyde-derived hydro-2H-chromeneols
AU - Il'ina, Irina
AU - Morozova, Ekaterina
AU - Korсhagina, Dina
AU - Volсho, Konstantin
AU - Tolstikova, Tat'yana
AU - Salakhutdinov, Nariman
PY - 2020/1/1
Y1 - 2020/1/1
N2 - 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.
AB - 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.
KW - Acetic acid-induced writhing test
KW - Analgesia
KW - Chromene
KW - Hot-plate test
KW - Isopulegol
KW - Monoterpenoid aldehyde
KW - isopulegol
KW - chromene
KW - analgesia
KW - ESTERS
KW - acetic acid-induced writhing test
KW - hot-plate test
UR - http://www.scopus.com/inward/record.url?scp=85078714444&partnerID=8YFLogxK
U2 - 10.2174/1570180816666181114131220
DO - 10.2174/1570180816666181114131220
M3 - Article
AN - SCOPUS:85078714444
VL - 17
SP - 68
EP - 78
JO - Letters in Drug Design and Discovery
JF - Letters in Drug Design and Discovery
SN - 1570-1808
IS - 1
ER -
ID: 23328360