Discovery of 4 '-azido-2 '-deoxy-2 '-C-methyl cytidine and prodrugs thereof: A potent inhibitor of Hepatitis C virus replication

Genadiy Kalayanov; Anna Winqvist; Pedro Pinho; Christian Sund; Xiao-Xiong Zhou; Horst Wahling; Anna-Karin Belfrage; Michael Pelcman; Tatiana Agback; Kurt Benckestock; Kristina Wikstrom; Mirva Boothee; Anneli Lindqvist; Christina Rydegard; Tim H. M. Jonckers; Koen Vandyck; Pierre Raboisson; Tse-I Lin; Sophie Lachau-Durand; Herman de Kock; David B. Smith; Joseph A. Martin; Klaus Klumpp; Kenneth Simmen; Lotta Vrang; Ylva Terelius; Bertil Samuelsson; Asa Rosenquist; Nils Gunnar Johansson

doi:10.1016/j.bmcl.2012.03.021

Discovery of 4 '-azido-2 '-deoxy-2 '-C-methyl cytidine and prodrugs thereof: A potent inhibitor of Hepatitis C virus replication

Genadiy Kalayanov
, Anna Winqvist
, Pedro Pinho
, Christian Sund
, Xiao-Xiong Zhou
, Horst Wahling
, Anna-Karin Belfrage
, Michael Pelcman
, Tatiana Agback
, Kurt Benckestock
, Kristina Wikstrom
, Mirva Boothee
, Anneli Lindqvist
, Christina Rydegard
, Tim H. M. Jonckers
, Koen Vandyck
, Pierre Raboisson
, Tse-I Lin
, Sophie Lachau-Durand
, Herman de Kock

David B. Smith, Joseph A. Martin, Klaus Klumpp, Kenneth Simmen, Lotta Vrang, Ylva Terelius, Bertil Samuelsson, Asa Rosenquist, Nils Gunnar Johansson

Publikation: Bidrag till tidskrift › Artikel i vetenskaplig tidskrift › Peer review

Sammanfattning

4'-Azido-2'-deoxy-2'-methylcytidine (14) is a potent nucleoside inhibitor of the HCV NS5B RNA-dependent RNA polymerase, displaying an EC50 value of 1.2 mu M and showing moderate in vivo bioavailability in rat (F = 14%). Here we describe the synthesis and biological evaluation of 4'-azido-2'-deoxy-2'-methylcytidine and prodrug derivatives thereof. (C) 2012 Elsevier Ltd. All rights reserved.

Originalspråk	Engelska
Sidor (från-till)	3265-3268
Antal sidor	4
Tidskrift	Bioorganic and Medicinal Chemistry Letters
Volym	22
Nummer	9
DOI	https://doi.org/10.1016/j.bmcl.2012.03.021
Status	Publicerad - 2012
Externt publicerad	Ja

Nyckelord

Hepatitis C virus
NS5B polymerase
Antivirals
Nucleoside
Prodrug
Phosphoramidate

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10.1016/j.bmcl.2012.03.021

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Kalayanov, G., Winqvist, A., Pinho, P., Sund, C., Zhou, X.-X., Wahling, H., Belfrage, A.-K., Pelcman, M., Agback, T., Benckestock, K., Wikstrom, K., Boothee, M., Lindqvist, A., Rydegard, C., Jonckers, T. H. M., Vandyck, K., Raboisson, P., Lin, T.-I., Lachau-Durand, S., ... Johansson, N. G. (2012). Discovery of 4 '-azido-2 '-deoxy-2 '-C-methyl cytidine and prodrugs thereof: A potent inhibitor of Hepatitis C virus replication. Bioorganic and Medicinal Chemistry Letters, 22(9), 3265-3268. https://doi.org/10.1016/j.bmcl.2012.03.021

@article{935cce546da244eea63fb642bee4c55e,

title = "Discovery of 4 '-azido-2 '-deoxy-2 '-C-methyl cytidine and prodrugs thereof: A potent inhibitor of Hepatitis C virus replication",

abstract = "4'-Azido-2'-deoxy-2'-methylcytidine (14) is a potent nucleoside inhibitor of the HCV NS5B RNA-dependent RNA polymerase, displaying an EC50 value of 1.2 mu M and showing moderate in vivo bioavailability in rat (F = 14\%). Here we describe the synthesis and biological evaluation of 4'-azido-2'-deoxy-2'-methylcytidine and prodrug derivatives thereof. (C) 2012 Elsevier Ltd. All rights reserved.",

keywords = "Hepatitis C virus, NS5B polymerase, Antivirals, Nucleoside, Prodrug, Phosphoramidate, Hepatitis C virus, NS5B polymerase, Antivirals, Nucleoside, Prodrug, Phosphoramidate",

author = "Genadiy Kalayanov and Anna Winqvist and Pedro Pinho and Christian Sund and Xiao-Xiong Zhou and Horst Wahling and Anna-Karin Belfrage and Michael Pelcman and Tatiana Agback and Kurt Benckestock and Kristina Wikstrom and Mirva Boothee and Anneli Lindqvist and Christina Rydegard and Jonckers, \{Tim H. M.\} and Koen Vandyck and Pierre Raboisson and Tse-I Lin and Sophie Lachau-Durand and \{de Kock\}, Herman and Smith, \{David B.\} and Martin, \{Joseph A.\} and Klaus Klumpp and Kenneth Simmen and Lotta Vrang and Ylva Terelius and Bertil Samuelsson and Asa Rosenquist and Johansson, \{Nils Gunnar\}",

year = "2012",

doi = "10.1016/j.bmcl.2012.03.021",

language = "English",

volume = "22",

pages = "3265--3268",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "9",

}

Kalayanov, G, Winqvist, A, Pinho, P, Sund, C, Zhou, X-X, Wahling, H, Belfrage, A-K, Pelcman, M, Agback, T, Benckestock, K, Wikstrom, K, Boothee, M, Lindqvist, A, Rydegard, C, Jonckers, THM, Vandyck, K, Raboisson, P, Lin, T-I, Lachau-Durand, S, de Kock, H, Smith, DB, Martin, JA, Klumpp, K, Simmen, K, Vrang, L, Terelius, Y, Samuelsson, B, Rosenquist, A & Johansson, NG 2012, 'Discovery of 4 '-azido-2 '-deoxy-2 '-C-methyl cytidine and prodrugs thereof: A potent inhibitor of Hepatitis C virus replication', Bioorganic and Medicinal Chemistry Letters, vol. 22, nr. 9, s. 3265-3268. https://doi.org/10.1016/j.bmcl.2012.03.021

TY - JOUR

T1 - Discovery of 4 '-azido-2 '-deoxy-2 '-C-methyl cytidine and prodrugs thereof: A potent inhibitor of Hepatitis C virus replication

AU - Kalayanov, Genadiy

AU - Winqvist, Anna

AU - Pinho, Pedro

AU - Sund, Christian

AU - Zhou, Xiao-Xiong

AU - Wahling, Horst

AU - Belfrage, Anna-Karin

AU - Pelcman, Michael

AU - Agback, Tatiana

AU - Benckestock, Kurt

AU - Wikstrom, Kristina

AU - Boothee, Mirva

AU - Lindqvist, Anneli

AU - Rydegard, Christina

AU - Jonckers, Tim H. M.

AU - Vandyck, Koen

AU - Raboisson, Pierre

AU - Lin, Tse-I

AU - Lachau-Durand, Sophie

AU - de Kock, Herman

AU - Smith, David B.

AU - Martin, Joseph A.

AU - Klumpp, Klaus

AU - Simmen, Kenneth

AU - Vrang, Lotta

AU - Terelius, Ylva

AU - Samuelsson, Bertil

AU - Rosenquist, Asa

AU - Johansson, Nils Gunnar

PY - 2012

Y1 - 2012

N2 - 4'-Azido-2'-deoxy-2'-methylcytidine (14) is a potent nucleoside inhibitor of the HCV NS5B RNA-dependent RNA polymerase, displaying an EC50 value of 1.2 mu M and showing moderate in vivo bioavailability in rat (F = 14%). Here we describe the synthesis and biological evaluation of 4'-azido-2'-deoxy-2'-methylcytidine and prodrug derivatives thereof. (C) 2012 Elsevier Ltd. All rights reserved.

AB - 4'-Azido-2'-deoxy-2'-methylcytidine (14) is a potent nucleoside inhibitor of the HCV NS5B RNA-dependent RNA polymerase, displaying an EC50 value of 1.2 mu M and showing moderate in vivo bioavailability in rat (F = 14%). Here we describe the synthesis and biological evaluation of 4'-azido-2'-deoxy-2'-methylcytidine and prodrug derivatives thereof. (C) 2012 Elsevier Ltd. All rights reserved.

KW - Hepatitis C virus

KW - NS5B polymerase

KW - Antivirals

KW - Nucleoside

KW - Prodrug

KW - Phosphoramidate

KW - Hepatitis C virus

KW - NS5B polymerase

KW - Antivirals

KW - Nucleoside

KW - Prodrug

KW - Phosphoramidate

UR - https://res.slu.se/id/publ/99459

U2 - 10.1016/j.bmcl.2012.03.021

DO - 10.1016/j.bmcl.2012.03.021

M3 - Journal article

SN - 0960-894X

VL - 22

SP - 3265

EP - 3268

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 9

ER -