Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents. / Motawia, Mohammed Saddik; Jørgensen, Per T.; Larnkjær, Anni; Pedersen, Erik B.; Nielsen, Claus.

In: Monatshefte für Chemie Chemical Monthly, Vol. 124, No. 1, 1993, p. 55-64.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Motawia, MS, Jørgensen, PT, Larnkjær, A, Pedersen, EB & Nielsen, C 1993, 'Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents', Monatshefte für Chemie Chemical Monthly, vol. 124, no. 1, pp. 55-64. https://doi.org/10.1007/BF00808509

APA

Motawia, M. S., Jørgensen, P. T., Larnkjær, A., Pedersen, E. B., & Nielsen, C. (1993). Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents. Monatshefte für Chemie Chemical Monthly, 124(1), 55-64. https://doi.org/10.1007/BF00808509

Vancouver

Motawia MS, Jørgensen PT, Larnkjær A, Pedersen EB, Nielsen C. Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents. Monatshefte für Chemie Chemical Monthly. 1993;124(1):55-64. https://doi.org/10.1007/BF00808509

Author

Motawia, Mohammed Saddik ; Jørgensen, Per T. ; Larnkjær, Anni ; Pedersen, Erik B. ; Nielsen, Claus. / Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents. In: Monatshefte für Chemie Chemical Monthly. 1993 ; Vol. 124, No. 1. pp. 55-64.

Bibtex

@article{81ec679f674848df87741ced81c6afb2,
title = "Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents",
abstract = "Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylamino-methyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3′-fluoro-2′,3′-dideoxynucleosides 13a-f and 3′-azido-2′,3′-dideoxy nucleosides 16d, f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d, f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2′,3′-dideoxy-3′-fluorouridines 14a-f and 15a-f and 2′,3′-dideoxy-3′-azidouridines 17d, f and 18d, f.",
keywords = "AZT analogues, Herpes simplex virus, Human immunodeficiency virus, Nucleosides, convergent synthesis of, Uridines, 3′-azido-2′,3′-dideoxy, Uridines, 3′-fluoro-2′,3′-dideoxy",
author = "Motawia, {Mohammed Saddik} and J{\o}rgensen, {Per T.} and Anni Larnkj{\ae}r and Pedersen, {Erik B.} and Claus Nielsen",
note = "(Ekstern)",
year = "1993",
doi = "10.1007/BF00808509",
language = "English",
volume = "124",
pages = "55--64",
journal = "Monatshefte fuer Chemie",
issn = "0026-9247",
publisher = "Springer Wien",
number = "1",

}

RIS

TY - JOUR

T1 - Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents

AU - Motawia, Mohammed Saddik

AU - Jørgensen, Per T.

AU - Larnkjær, Anni

AU - Pedersen, Erik B.

AU - Nielsen, Claus

N1 - (Ekstern)

PY - 1993

Y1 - 1993

N2 - Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylamino-methyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3′-fluoro-2′,3′-dideoxynucleosides 13a-f and 3′-azido-2′,3′-dideoxy nucleosides 16d, f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d, f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2′,3′-dideoxy-3′-fluorouridines 14a-f and 15a-f and 2′,3′-dideoxy-3′-azidouridines 17d, f and 18d, f.

AB - Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylamino-methyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3′-fluoro-2′,3′-dideoxynucleosides 13a-f and 3′-azido-2′,3′-dideoxy nucleosides 16d, f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d, f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2′,3′-dideoxy-3′-fluorouridines 14a-f and 15a-f and 2′,3′-dideoxy-3′-azidouridines 17d, f and 18d, f.

KW - AZT analogues

KW - Herpes simplex virus

KW - Human immunodeficiency virus

KW - Nucleosides, convergent synthesis of

KW - Uridines, 3′-azido-2′,3′-dideoxy

KW - Uridines, 3′-fluoro-2′,3′-dideoxy

UR - http://www.scopus.com/inward/record.url?scp=0002885074&partnerID=8YFLogxK

U2 - 10.1007/BF00808509

DO - 10.1007/BF00808509

M3 - Journal article

AN - SCOPUS:0002885074

VL - 124

SP - 55

EP - 64

JO - Monatshefte fuer Chemie

JF - Monatshefte fuer Chemie

SN - 0026-9247

IS - 1

ER -

ID: 249247215