Sonogashira cross-coupling in the synthesis of acyclic nucleoside phosphonates:: Preparation of 6-[(phosphonomethoxy)alkynyl]- and 6-[(phosphonomethoxy)alkyl]pyrimidines

被引：6

作者：

Hocková, D ^{[1
]}

Masojídková, M ^{[1
]}

Holy, A ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CZ-16610 Prague, Czech Republic

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2005年 / 70卷 / 02期

关键词：

nucleotide analogues; acyclic nucleoside phosphonates; pyrimidines; Sonogashira reaction; cross-coupling reactions; nucleosides; alkynes; hydrogenation; antivirals;

D O I：

10.1135/cccc20050247

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several 6-[(phosphonomethoxy) alkyl] pyrimidines and 6-[( phosphonomethoxy) alkynyl]pyrimidines were prepared as saturated and unsaturated carba-analogues of antivirally active 2,4-diamino-6-[ 2-(phosphonomethoxy) ethoxy] pyrimidine. As the key step of their synthesis the Sonogashira cross-coupling reaction was successfully applied. The replacement of the C - O moiety by the C - C bond resulted in the loss of biological activity.

引用

页码：247 / 258

页数：12

共 10 条

[1] 6-[2-phosphonomethoxy)alkoxy]-2,4-diaminopyrimidines:: A new class of acyclic pyrimidine nucleoside phosphonates with antiviral activity
Balzarini, J
Pannecouque, C
Naesens, L
Andrei, G
Snoeck, R
De Clercq, E
Hocková, D
Holy, A
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (8-9) : 1321 - 1327
[2] The efficient synthesis of 2-arylpyrimidine acyclic nucleoside phosphonates using Liebeskind-Srogl cross-coupling reaction
Brehova, Petra
Cesnek, Michal
Dracinsky, Martin
Holy, Antonin
Janeba, Zlatko
TETRAHEDRON, 2011, 67 (38) : 7379 - 7385
[3] Synthesis of acyclic nucleotide analogues derived from 6-(sec- or tert-alkyl)purines via coupling of 6-chloropurine derivatives with organocuprates
Dvoráková, H
Dvorák, D
Holy, A
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1998, 63 (12) : 2065 - 2074
[4] Synthesis and cytostatic activity of nucleosides and acyclic nucleoside analogues derived from 6-(trifluoromethyl)purines
Hocková, D
Hocek, M
Dvoráková, H
Votruba, I
TETRAHEDRON, 1999, 55 (36) : 11109 - 11118
[5] Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions
Cooke, G
de Cremiers, HA
Rotello, VM
Tarbit, B
Vanderstraeten, PE
TETRAHEDRON, 2001, 57 (14) : 2787 - 2789
[6] Synthesis of C-6-substituted uridine phosphonates through aerobic ligand-free Suzuki-Miyaura cross-coupling
Nencka, Radim
Sinnaeve, Davy
Karalic, Izet
Martins, Jose C.
Van Calenbergh, Serge
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (22) : 5234 - 5246
[7] Synthesis of Fluorescent 2-Substituted 6-(Het)aryl-7-deazapurine Bases {4-(Het)aryl-pyrrolo[2,3-d]pyrimidines} by Aqueous Suzuki-Miyaura Cross-Coupling Reactions
Sabat, Nazarii
Naus, Petr
Matyasovsky, Jan
Dziuba, Dmytro
Slavetinska, Lenka Postova
Hocek, Michal
SYNTHESIS-STUTTGART, 2016, 48 (07): : 1029 - 1045
[8] Synthesis of acyclic nucleotide analogues derived from 6-hetarylpurines via cross-coupling reactions of 9-[2-(diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with hetaryl organometallic reagents
Hocek, M
Masojidkova, M
Holy, A
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1997, 62 (01) : 136 - 146
[9] Synthesis of acyclic nucleotide analogues derived from 2-amino-6-C-substituted purines via cross-coupling reactions of 2-amino-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-6-halopurines with diverse organometallic reagents
Cesnek, M
Hocek, M
Holy, A
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2000, 65 (08) : 1357 - 1373
[10] Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: Palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides [1]
Hassan, Abdalla E. A.
Abou-Elkhair, Reham A. I.
Riordan, James M.
Allan, Paula W.
Parker, William B.
Khare, Rashmi
Waud, William R.
Montgomery, John A.
Secrist, John A., III
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 47 : 167 - 174

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