Scale-Up Synthesis of 1-Methyladamantane and Its Functionalization as a Key Point for Promising Antiviral Agents
Alexander E Pashenko
1, 2, 3
,
Alexandr Gaidai
1, 3, 4
,
Nazar Hryhoriev
1, 4
,
Olesia Volovenko
1
,
Olesia B. Volovenko
1
,
Igor Levandovskiy
4
,
Igor A. Levandovskiy
4
,
Olga Maksymenko
1
,
Dmitriy M. Volochnyuk
1, 2, 3
,
Sergey V. Ryabukhin
1, 2, 3
1
Enamine Ltd., 78 Chervonotkatska Street, 02660 Kyiv, Ukraine
|
2
Taras Shevchenko National University of Kyiv, 60 Volodymyrska Street, 01033 Kyiv, Ukraine
|
3
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska Street, 02660 Kyiv, Ukraine
|
4
National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”, 37 Peremohy Avenue, 03056 Kyiv, Ukraine
|
Publication type: Journal Article
Publication date: 2023-02-24
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Methyladamantane and its derivatives are rare chemotypes for industrial and even wide research use. The proposed scalable and inexpensive approach to such compounds opens the door to further extensive study of biologically active derivatives based on this uncommon core. Optimized synthesis of the key precursor, the chiral (1S,3R,5R,7S)-3-methyl-5-phenyladamantane-1-carboxylic acid, showcases some significant innovations. The main one is very effective and cost-efficient stacked injections in preparative chiral chromatography and showed potential for enantioresolution of chiral cage compounds. Scaling the preparation of (1S,3R,5R,7S)-trans-N-(4-aminocyclohexyl)-3-methyl-5-phenyladamantane-1-carboxamide, which was recently shown to have notable activity against the Ebola virus, to multigram levels is an excellent example of our elaboration significance. It may push forward further biological investigation of this promising antiviral agent.
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GOST
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Pashenko A. E. et al. Scale-Up Synthesis of 1-Methyladamantane and Its Functionalization as a Key Point for Promising Antiviral Agents // Organic Process Research and Development. 2023. Vol. 27. No. 3. pp. 477-487.
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Pashenko A. E., Gaidai A., Hryhoriev N., Volovenko O., Volovenko O. B., Levandovskiy I., Levandovskiy I. A., Maksymenko O., Volochnyuk D. M., Ryabukhin S. V. Scale-Up Synthesis of 1-Methyladamantane and Its Functionalization as a Key Point for Promising Antiviral Agents // Organic Process Research and Development. 2023. Vol. 27. No. 3. pp. 477-487.
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RIS
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TY - JOUR
DO - 10.1021/acs.oprd.2c00305
UR - https://pubs.acs.org/doi/10.1021/acs.oprd.2c00305
TI - Scale-Up Synthesis of 1-Methyladamantane and Its Functionalization as a Key Point for Promising Antiviral Agents
T2 - Organic Process Research and Development
AU - Pashenko, Alexander E
AU - Gaidai, Alexandr
AU - Hryhoriev, Nazar
AU - Volovenko, Olesia
AU - Volovenko, Olesia B.
AU - Levandovskiy, Igor
AU - Levandovskiy, Igor A.
AU - Maksymenko, Olga
AU - Volochnyuk, Dmitriy M.
AU - Ryabukhin, Sergey V.
PY - 2023
DA - 2023/02/24
PB - American Chemical Society (ACS)
SP - 477-487
IS - 3
VL - 27
SN - 1083-6160
SN - 1520-586X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2023_Pashenko,
author = {Alexander E Pashenko and Alexandr Gaidai and Nazar Hryhoriev and Olesia Volovenko and Olesia B. Volovenko and Igor Levandovskiy and Igor A. Levandovskiy and Olga Maksymenko and Dmitriy M. Volochnyuk and Sergey V. Ryabukhin},
title = {Scale-Up Synthesis of 1-Methyladamantane and Its Functionalization as a Key Point for Promising Antiviral Agents},
journal = {Organic Process Research and Development},
year = {2023},
volume = {27},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.oprd.2c00305},
number = {3},
pages = {477--487},
doi = {10.1021/acs.oprd.2c00305}
}
Cite this
MLA
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Pashenko, Alexander E., et al. “Scale-Up Synthesis of 1-Methyladamantane and Its Functionalization as a Key Point for Promising Antiviral Agents.” Organic Process Research and Development, vol. 27, no. 3, Feb. 2023, pp. 477-487. https://pubs.acs.org/doi/10.1021/acs.oprd.2c00305.
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