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Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments. / Ponomarev, Konstantin; Morozova, Ekaterina; Pavlova, Alla et al.

In: Medicinal Chemistry, Vol. 13, No. 8, 01.12.2017, p. 773-779.

Research output: Contribution to journalArticlepeer-review

Harvard

Ponomarev, K, Morozova, E, Pavlova, A, Suslov, E, Korchagina, D, Nefedov, A, Tolstikova, T, Volcho, K & Salakhutdinov, N 2017, 'Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments', Medicinal Chemistry, vol. 13, no. 8, pp. 773-779. https://doi.org/10.2174/1573406413666170525124316

APA

Ponomarev, K., Morozova, E., Pavlova, A., Suslov, E., Korchagina, D., Nefedov, A., Tolstikova, T., Volcho, K., & Salakhutdinov, N. (2017). Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments. Medicinal Chemistry, 13(8), 773-779. https://doi.org/10.2174/1573406413666170525124316

Vancouver

Ponomarev K, Morozova E, Pavlova A, Suslov E, Korchagina D, Nefedov A et al. Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments. Medicinal Chemistry. 2017 Dec 1;13(8):773-779. doi: 10.2174/1573406413666170525124316

Author

Ponomarev, Konstantin ; Morozova, Ekaterina ; Pavlova, Alla et al. / Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments. In: Medicinal Chemistry. 2017 ; Vol. 13, No. 8. pp. 773-779.

BibTeX

@article{98a3b37709234545b3ce7bb66529db89,
title = "Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments",
abstract = "Background: It was found earlier that compounds combining diazaadamantane and monoterpene moieties possessed promising analgesic activity along with low acute toxicity and the lack of ulcerogenic activity. Objective: In this paper, new structural analogues of the most active compounds were synthesized and evaluated for their analgesic activity. Methods: Their structures were confirmed by various analytical methods, such as 1H and13C NMR, HRMS. All of them were evaluated for analgesic activity at a dose of 20 mg/kg or less using acetic acid-induced writhing test and hot plate test. Results: Some compounds showed analgesic activity in acetic acid-induced writhing test. One of the synthesized compounds demonstrated high analgesic activity in both tests with 46% effect in acetic acid-induced writhing test and 89% effect in hot plate test. Both structural fragments of this compound did not possess any analgesic effect at a dose of 20 mg/kg. Conclusion: Structure-activity relationships indicated that the most active compound combines fragments of (–)-myrtenal and 6-amino-5,7-dimethyl-1,3-diazaadamantane. Both parts of the molecule are important for demonstrating analgesic activity.",
keywords = "Acetic acid-induced writhing test, Adamantane, Analgesic activity, Azaadamantane, Heterocyclic compounds, Hot plate test, Monoterpene, Administration, Oral, Monoterpenes/administration & dosage, Pain/chemically induced, Adamantane/administration & dosage, Structure-Activity Relationship, Amines/administration & dosage, Dose-Response Relationship, Drug, Acetic Acid, Analgesics/administration & dosage, Animals, Mice, Molecular Structure, Pain Measurement, azaadamantane, PEPTIDASE-IV INHIBITOR, adamantane, analgesic activity, DERIVATIVES, POTENT, acetic acid-induced writhing test, hot plate test, heterocyclic compounds",
author = "Konstantin Ponomarev and Ekaterina Morozova and Alla Pavlova and Evgeniy Suslov and Dina Korchagina and Andrej Nefedov and Tat'yana Tolstikova and Konstantin Volcho and Nariman Salakhutdinov",
note = "Copyright{\textcopyright} Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.",
year = "2017",
month = dec,
day = "1",
doi = "10.2174/1573406413666170525124316",
language = "English",
volume = "13",
pages = "773--779",
journal = "Medicinal Chemistry",
issn = "1573-4064",
publisher = "BENTHAM SCIENCE PUBL LTD",
number = "8",

}

RIS

TY - JOUR

T1 - Synthesis and analgesic activity of amines combining diazaadamantane and monoterpene fragments

AU - Ponomarev, Konstantin

AU - Morozova, Ekaterina

AU - Pavlova, Alla

AU - Suslov, Evgeniy

AU - Korchagina, Dina

AU - Nefedov, Andrej

AU - Tolstikova, Tat'yana

AU - Volcho, Konstantin

AU - Salakhutdinov, Nariman

N1 - Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - Background: It was found earlier that compounds combining diazaadamantane and monoterpene moieties possessed promising analgesic activity along with low acute toxicity and the lack of ulcerogenic activity. Objective: In this paper, new structural analogues of the most active compounds were synthesized and evaluated for their analgesic activity. Methods: Their structures were confirmed by various analytical methods, such as 1H and13C NMR, HRMS. All of them were evaluated for analgesic activity at a dose of 20 mg/kg or less using acetic acid-induced writhing test and hot plate test. Results: Some compounds showed analgesic activity in acetic acid-induced writhing test. One of the synthesized compounds demonstrated high analgesic activity in both tests with 46% effect in acetic acid-induced writhing test and 89% effect in hot plate test. Both structural fragments of this compound did not possess any analgesic effect at a dose of 20 mg/kg. Conclusion: Structure-activity relationships indicated that the most active compound combines fragments of (–)-myrtenal and 6-amino-5,7-dimethyl-1,3-diazaadamantane. Both parts of the molecule are important for demonstrating analgesic activity.

AB - Background: It was found earlier that compounds combining diazaadamantane and monoterpene moieties possessed promising analgesic activity along with low acute toxicity and the lack of ulcerogenic activity. Objective: In this paper, new structural analogues of the most active compounds were synthesized and evaluated for their analgesic activity. Methods: Their structures were confirmed by various analytical methods, such as 1H and13C NMR, HRMS. All of them were evaluated for analgesic activity at a dose of 20 mg/kg or less using acetic acid-induced writhing test and hot plate test. Results: Some compounds showed analgesic activity in acetic acid-induced writhing test. One of the synthesized compounds demonstrated high analgesic activity in both tests with 46% effect in acetic acid-induced writhing test and 89% effect in hot plate test. Both structural fragments of this compound did not possess any analgesic effect at a dose of 20 mg/kg. Conclusion: Structure-activity relationships indicated that the most active compound combines fragments of (–)-myrtenal and 6-amino-5,7-dimethyl-1,3-diazaadamantane. Both parts of the molecule are important for demonstrating analgesic activity.

KW - Acetic acid-induced writhing test

KW - Adamantane

KW - Analgesic activity

KW - Azaadamantane

KW - Heterocyclic compounds

KW - Hot plate test

KW - Monoterpene

KW - Administration, Oral

KW - Monoterpenes/administration & dosage

KW - Pain/chemically induced

KW - Adamantane/administration & dosage

KW - Structure-Activity Relationship

KW - Amines/administration & dosage

KW - Dose-Response Relationship, Drug

KW - Acetic Acid

KW - Analgesics/administration & dosage

KW - Animals

KW - Mice

KW - Molecular Structure

KW - Pain Measurement

KW - azaadamantane

KW - PEPTIDASE-IV INHIBITOR

KW - adamantane

KW - analgesic activity

KW - DERIVATIVES

KW - POTENT

KW - acetic acid-induced writhing test

KW - hot plate test

KW - heterocyclic compounds

UR - http://www.scopus.com/inward/record.url?scp=85029551777&partnerID=8YFLogxK

U2 - 10.2174/1573406413666170525124316

DO - 10.2174/1573406413666170525124316

M3 - Article

C2 - 28545384

AN - SCOPUS:85029551777

VL - 13

SP - 773

EP - 779

JO - Medicinal Chemistry

JF - Medicinal Chemistry

SN - 1573-4064

IS - 8

ER -

ID: 9409327