Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity

Oleg I. Artyushin; Elena V. Sharova; Natalya M. Vinogradova; Galina K. Genkina; Aleksandra A. Moiseeva; Zinaida S. Klemenkova; Iana R. Orshanskaya; Anna A. Shtro; Renata A. Kadyrova; Vladimir V. Zarubaev; Olga I. Yarovaya; Nariman F. Salakhutdinov; Valery K. Brel

doi:10.1016/j.bmcl.2017.03.051

Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity

Oleg I. Artyushin, Elena V. Sharova, Natalya M. Vinogradova, Galina K. Genkina, Aleksandra A. Moiseeva, Zinaida S. Klemenkova, Iana R. Orshanskaya, Anna A. Shtro, Renata A. Kadyrova, Vladimir V. Zarubaev, Olga I. Yarovaya, Nariman F. Salakhutdinov, Valery K. Brel

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.

Original language	English
Pages (from-to)	2181-2184
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	27
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2017.03.051
Publication status	Published - 15 May 2017

Keywords

Acetylenes
Antivirals
Azides
Camphor
Click chemistry
Imine derivatives
Influenza
Triazoles
AZIDE-ALKYNE CYCLOADDITION
DESIGN
DISCOVERY
1,2,3-TRIAZOLES
INHIBITORS
INFLUENZA-VIRUS ENTRY
Antiviral Agents/chemical synthesis
Click Chemistry
Humans
Structure-Activity Relationship
Ethanolamines/chemical synthesis
Animals
Influenza A Virus, H1N1 Subtype/drug effects
Camphor/analogs & derivatives
Dogs
Madin Darby Canine Kidney Cells

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Artyushin, O. I., Sharova, E. V., Vinogradova, N. M., Genkina, G. K., Moiseeva, A. A., Klemenkova, Z. S., Orshanskaya, I. R., Shtro, A. A., Kadyrova, R. A., Zarubaev, V. V., Yarovaya, O. I., Salakhutdinov, N. F., & Brel, V. K. (2017). Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity. Bioorganic and Medicinal Chemistry Letters, 27(10), 2181-2184. https://doi.org/10.1016/j.bmcl.2017.03.051

Artyushin, Oleg I. ; Sharova, Elena V. ; Vinogradova, Natalya M. ; Genkina, Galina K. ; Moiseeva, Aleksandra A. ; Klemenkova, Zinaida S. ; Orshanskaya, Iana R. ; Shtro, Anna A. ; Kadyrova, Renata A. ; Zarubaev, Vladimir V. ; Yarovaya, Olga I. ; Salakhutdinov, Nariman F. ; Brel, Valery K. / Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity. In: Bioorganic and Medicinal Chemistry Letters. 2017 ; Vol. 27, No. 10. pp. 2181-2184.

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title = "Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity",

abstract = "A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.",

keywords = "Acetylenes, Antivirals, Azides, Camphor, Click chemistry, Imine derivatives, Influenza, Triazoles, AZIDE-ALKYNE CYCLOADDITION, DESIGN, DISCOVERY, 1,2,3-TRIAZOLES, INHIBITORS, INFLUENZA-VIRUS ENTRY, Antiviral Agents/chemical synthesis, Click Chemistry, Humans, Structure-Activity Relationship, Ethanolamines/chemical synthesis, Animals, Influenza A Virus, H1N1 Subtype/drug effects, Camphor/analogs & derivatives, Dogs, Madin Darby Canine Kidney Cells",

author = "Artyushin, {Oleg I.} and Sharova, {Elena V.} and Vinogradova, {Natalya M.} and Genkina, {Galina K.} and Moiseeva, {Aleksandra A.} and Klemenkova, {Zinaida S.} and Orshanskaya, {Iana R.} and Shtro, {Anna A.} and Kadyrova, {Renata A.} and Zarubaev, {Vladimir V.} and Yarovaya, {Olga I.} and Salakhutdinov, {Nariman F.} and Brel, {Valery K.}",

note = "Copyright {\textcopyright} 2017. Published by Elsevier Ltd.",

year = "2017",

month = may,

day = "15",

doi = "10.1016/j.bmcl.2017.03.051",

language = "English",

volume = "27",

pages = "2181--2184",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "10",

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Artyushin, OI, Sharova, EV, Vinogradova, NM, Genkina, GK, Moiseeva, AA, Klemenkova, ZS, Orshanskaya, IR, Shtro, AA, Kadyrova, RA, Zarubaev, VV, Yarovaya, OI , Salakhutdinov, NF & Brel, VK 2017, 'Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity', Bioorganic and Medicinal Chemistry Letters, vol. 27, no. 10, pp. 2181-2184. https://doi.org/10.1016/j.bmcl.2017.03.051

Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity. / Artyushin, Oleg I.; Sharova, Elena V.; Vinogradova, Natalya M.; Genkina, Galina K.; Moiseeva, Aleksandra A.; Klemenkova, Zinaida S.; Orshanskaya, Iana R.; Shtro, Anna A.; Kadyrova, Renata A.; Zarubaev, Vladimir V.; Yarovaya, Olga I.; Salakhutdinov, Nariman F.; Brel, Valery K.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 27, No. 10, 15.05.2017, p. 2181-2184.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity

AU - Artyushin, Oleg I.

AU - Sharova, Elena V.

AU - Vinogradova, Natalya M.

AU - Genkina, Galina K.

AU - Moiseeva, Aleksandra A.

AU - Klemenkova, Zinaida S.

AU - Orshanskaya, Iana R.

AU - Shtro, Anna A.

AU - Kadyrova, Renata A.

AU - Zarubaev, Vladimir V.

AU - Yarovaya, Olga I.

AU - Salakhutdinov, Nariman F.

AU - Brel, Valery K.

PY - 2017/5/15

Y1 - 2017/5/15

N2 - A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.

AB - A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.

KW - Acetylenes

KW - Antivirals

KW - Azides

KW - Camphor

KW - Click chemistry

KW - Imine derivatives

KW - Influenza

KW - Triazoles

KW - AZIDE-ALKYNE CYCLOADDITION

KW - DESIGN

KW - DISCOVERY

KW - 1,2,3-TRIAZOLES

KW - INHIBITORS

KW - INFLUENZA-VIRUS ENTRY

KW - Antiviral Agents/chemical synthesis

KW - Click Chemistry

KW - Humans

KW - Structure-Activity Relationship

KW - Ethanolamines/chemical synthesis

KW - Animals

KW - Influenza A Virus, H1N1 Subtype/drug effects

KW - Camphor/analogs & derivatives

KW - Dogs

KW - Madin Darby Canine Kidney Cells

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U2 - 10.1016/j.bmcl.2017.03.051

DO - 10.1016/j.bmcl.2017.03.051

M3 - Article

C2 - 28366530

AN - SCOPUS:85016578082

VL - 27

SP - 2181

EP - 2184

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 10

ER -