Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5

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Standard

Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5. / Petersen, Lene; Hansen, Thomas H.; Khalifa, Nagy M.; Jørgensen, Per T.; Pedersen, Erik B.; Nielsen, Claus.

I: Monatshefte fur Chemie, Bind 133, Nr. 7, 01.01.2002, s. 1031-1043.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Petersen, L, Hansen, TH, Khalifa, NM, Jørgensen, PT, Pedersen, EB & Nielsen, C 2002, 'Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5', Monatshefte fur Chemie, bind 133, nr. 7, s. 1031-1043. https://doi.org/10.1007/s007060200072

APA

Petersen, L., Hansen, T. H., Khalifa, N. M., Jørgensen, P. T., Pedersen, E. B., & Nielsen, C. (2002). Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5. Monatshefte fur Chemie, 133(7), 1031-1043. https://doi.org/10.1007/s007060200072

Vancouver

Petersen L, Hansen TH, Khalifa NM, Jørgensen PT, Pedersen EB, Nielsen C. Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5. Monatshefte fur Chemie. 2002 jan. 1;133(7):1031-1043. https://doi.org/10.1007/s007060200072

Author

Petersen, Lene ; Hansen, Thomas H. ; Khalifa, Nagy M. ; Jørgensen, Per T. ; Pedersen, Erik B. ; Nielsen, Claus. / Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5. I: Monatshefte fur Chemie. 2002 ; Bind 133, Nr. 7. s. 1031-1043.

Bibtex

@article{672e28f8eb944a62bf11f2a0e15f73fc,
title = "Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5",
abstract = "In an effort to obtain more insight into the interaction between HIV-1 reverse transcriptase (RT) and MKC-442 analogues, a new series of compounds was synthesized and evaluated for inhibition of HIV-1 replication. The modifications include bulky alkenyl substituents at the C-5 position of the uracil ring. Analogues with reactive centers (aldehyde and epoxide functionalities) at C-5 were also synthesized in an attempt to develop HIV drugs with improved activity against the Y181C mutants by forming a covalent bond to the mercapto group in cysteine in the hydrophobic pocket of the mutated RT. Difficulties in the syntheses show that the epoxides are chemically reactive, whereas the aldehydes are more stable. One of the alkenyl analogues showed activity against HIV-1 in the same range as MKC-442, whereas the reactive analogues were not active against HIV with the mutation Y181C in RT.",
keywords = "5-Aldehyde or 5-epoxide substituted uracils, 5-Alkenyluracils, HIV-1, MKC-442 analogues, Non-nucleoside reverse transcriptase inhibitors",
author = "Lene Petersen and Hansen, {Thomas H.} and Khalifa, {Nagy M.} and J{\o}rgensen, {Per T.} and Pedersen, {Erik B.} and Claus Nielsen",
year = "2002",
month = jan,
day = "1",
doi = "10.1007/s007060200072",
language = "English",
volume = "133",
pages = "1031--1043",
journal = "Monatshefte fuer Chemie",
issn = "0026-9247",
publisher = "Springer Wien",
number = "7",

}

RIS

TY - JOUR

T1 - Synthesis of new MKC-442 analogues containing alkenyl chains or reactive functionalities at C-5

AU - Petersen, Lene

AU - Hansen, Thomas H.

AU - Khalifa, Nagy M.

AU - Jørgensen, Per T.

AU - Pedersen, Erik B.

AU - Nielsen, Claus

PY - 2002/1/1

Y1 - 2002/1/1

N2 - In an effort to obtain more insight into the interaction between HIV-1 reverse transcriptase (RT) and MKC-442 analogues, a new series of compounds was synthesized and evaluated for inhibition of HIV-1 replication. The modifications include bulky alkenyl substituents at the C-5 position of the uracil ring. Analogues with reactive centers (aldehyde and epoxide functionalities) at C-5 were also synthesized in an attempt to develop HIV drugs with improved activity against the Y181C mutants by forming a covalent bond to the mercapto group in cysteine in the hydrophobic pocket of the mutated RT. Difficulties in the syntheses show that the epoxides are chemically reactive, whereas the aldehydes are more stable. One of the alkenyl analogues showed activity against HIV-1 in the same range as MKC-442, whereas the reactive analogues were not active against HIV with the mutation Y181C in RT.

AB - In an effort to obtain more insight into the interaction between HIV-1 reverse transcriptase (RT) and MKC-442 analogues, a new series of compounds was synthesized and evaluated for inhibition of HIV-1 replication. The modifications include bulky alkenyl substituents at the C-5 position of the uracil ring. Analogues with reactive centers (aldehyde and epoxide functionalities) at C-5 were also synthesized in an attempt to develop HIV drugs with improved activity against the Y181C mutants by forming a covalent bond to the mercapto group in cysteine in the hydrophobic pocket of the mutated RT. Difficulties in the syntheses show that the epoxides are chemically reactive, whereas the aldehydes are more stable. One of the alkenyl analogues showed activity against HIV-1 in the same range as MKC-442, whereas the reactive analogues were not active against HIV with the mutation Y181C in RT.

KW - 5-Aldehyde or 5-epoxide substituted uracils

KW - 5-Alkenyluracils

KW - HIV-1

KW - MKC-442 analogues

KW - Non-nucleoside reverse transcriptase inhibitors

UR - http://www.scopus.com/inward/record.url?scp=57249109794&partnerID=8YFLogxK

U2 - 10.1007/s007060200072

DO - 10.1007/s007060200072

M3 - Journal article

AN - SCOPUS:57249109794

VL - 133

SP - 1031

EP - 1043

JO - Monatshefte fuer Chemie

JF - Monatshefte fuer Chemie

SN - 0026-9247

IS - 7

ER -

ID: 235584416