Pyrimidopyridazine

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Joanna Wietrzyk - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and investigation of the antitumor properties of novel bicyclic furopyrimidine pyrrolopyrimidine and Pyrimidopyridazine nucleoside analogues
    Synthesis, 2015
    Co-Authors: Adam Mieczkowski, Ewelina Tomczyk, Malgorzata Makowska, Anna Nasulewiczgoldeman, Roman Gajda, Krzysztof Woźniak, Joanna Wietrzyk
    Abstract:

    A series of nine hitherto unknown bicyclic pyrimidine nucleoside analogues (BCNAs) bearing bicyclic furo[2,3- d ]pyrimidin-2(3 H )-one, 3 H -pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and 5,6-dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one bases were prepared in a straightforward approach. Each of the synthesized compounds possesses a β- d -ribofuranose, β- d -2-deoxyribofuranose or β- d -arabinofuranose moiety attached to the heterocyclic ring system. This is one of few examples of the synthesis of pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one nucleosides, and the first example of such nucleosides possessing an arabinose moiety. A key synthetic step involved a Sonogashira coupling reaction. For the coupling with 4-phenyl-1-butyne, deprotected 5-iodouridine, 5-iodo-2′-deoxyuridine and 5-iodoarabinouridine were used, and this reaction was followed by cycloisomerization and subsequent conversion of the furan ring into a pyrrole or a pyridazine ring. This approach resulted in the creation of a small library of compounds, which were evaluated for their antiproliferative properties against HL-60 and Jurkat E6.1 cell lines. Of all tested compounds, only 6-(2-phenylethyl)-3-(β- d -ribofuranosyl)furo[2,3- d ]pyrimidin-2(3 H )-one exhibited weak antiproliferative activity, with IC 50 values of 54 and 81 μM for HL-60 and Jurkat E6.1 cells, respectively.

Ewelina Tomczyk - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and investigation of the antitumor properties of novel bicyclic furopyrimidine pyrrolopyrimidine and Pyrimidopyridazine nucleoside analogues
    Synthesis, 2015
    Co-Authors: Adam Mieczkowski, Ewelina Tomczyk, Malgorzata Makowska, Anna Nasulewiczgoldeman, Roman Gajda, Krzysztof Woźniak, Joanna Wietrzyk
    Abstract:

    A series of nine hitherto unknown bicyclic pyrimidine nucleoside analogues (BCNAs) bearing bicyclic furo[2,3- d ]pyrimidin-2(3 H )-one, 3 H -pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and 5,6-dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one bases were prepared in a straightforward approach. Each of the synthesized compounds possesses a β- d -ribofuranose, β- d -2-deoxyribofuranose or β- d -arabinofuranose moiety attached to the heterocyclic ring system. This is one of few examples of the synthesis of pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one nucleosides, and the first example of such nucleosides possessing an arabinose moiety. A key synthetic step involved a Sonogashira coupling reaction. For the coupling with 4-phenyl-1-butyne, deprotected 5-iodouridine, 5-iodo-2′-deoxyuridine and 5-iodoarabinouridine were used, and this reaction was followed by cycloisomerization and subsequent conversion of the furan ring into a pyrrole or a pyridazine ring. This approach resulted in the creation of a small library of compounds, which were evaluated for their antiproliferative properties against HL-60 and Jurkat E6.1 cell lines. Of all tested compounds, only 6-(2-phenylethyl)-3-(β- d -ribofuranosyl)furo[2,3- d ]pyrimidin-2(3 H )-one exhibited weak antiproliferative activity, with IC 50 values of 54 and 81 μM for HL-60 and Jurkat E6.1 cells, respectively.

Adam Mieczkowski - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and investigation of the antitumor properties of novel bicyclic furopyrimidine pyrrolopyrimidine and Pyrimidopyridazine nucleoside analogues
    Synthesis, 2015
    Co-Authors: Adam Mieczkowski, Ewelina Tomczyk, Malgorzata Makowska, Anna Nasulewiczgoldeman, Roman Gajda, Krzysztof Woźniak, Joanna Wietrzyk
    Abstract:

    A series of nine hitherto unknown bicyclic pyrimidine nucleoside analogues (BCNAs) bearing bicyclic furo[2,3- d ]pyrimidin-2(3 H )-one, 3 H -pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and 5,6-dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one bases were prepared in a straightforward approach. Each of the synthesized compounds possesses a β- d -ribofuranose, β- d -2-deoxyribofuranose or β- d -arabinofuranose moiety attached to the heterocyclic ring system. This is one of few examples of the synthesis of pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one nucleosides, and the first example of such nucleosides possessing an arabinose moiety. A key synthetic step involved a Sonogashira coupling reaction. For the coupling with 4-phenyl-1-butyne, deprotected 5-iodouridine, 5-iodo-2′-deoxyuridine and 5-iodoarabinouridine were used, and this reaction was followed by cycloisomerization and subsequent conversion of the furan ring into a pyrrole or a pyridazine ring. This approach resulted in the creation of a small library of compounds, which were evaluated for their antiproliferative properties against HL-60 and Jurkat E6.1 cell lines. Of all tested compounds, only 6-(2-phenylethyl)-3-(β- d -ribofuranosyl)furo[2,3- d ]pyrimidin-2(3 H )-one exhibited weak antiproliferative activity, with IC 50 values of 54 and 81 μM for HL-60 and Jurkat E6.1 cells, respectively.

Roman Gajda - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and investigation of the antitumor properties of novel bicyclic furopyrimidine pyrrolopyrimidine and Pyrimidopyridazine nucleoside analogues
    Synthesis, 2015
    Co-Authors: Adam Mieczkowski, Ewelina Tomczyk, Malgorzata Makowska, Anna Nasulewiczgoldeman, Roman Gajda, Krzysztof Woźniak, Joanna Wietrzyk
    Abstract:

    A series of nine hitherto unknown bicyclic pyrimidine nucleoside analogues (BCNAs) bearing bicyclic furo[2,3- d ]pyrimidin-2(3 H )-one, 3 H -pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and 5,6-dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one bases were prepared in a straightforward approach. Each of the synthesized compounds possesses a β- d -ribofuranose, β- d -2-deoxyribofuranose or β- d -arabinofuranose moiety attached to the heterocyclic ring system. This is one of few examples of the synthesis of pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one nucleosides, and the first example of such nucleosides possessing an arabinose moiety. A key synthetic step involved a Sonogashira coupling reaction. For the coupling with 4-phenyl-1-butyne, deprotected 5-iodouridine, 5-iodo-2′-deoxyuridine and 5-iodoarabinouridine were used, and this reaction was followed by cycloisomerization and subsequent conversion of the furan ring into a pyrrole or a pyridazine ring. This approach resulted in the creation of a small library of compounds, which were evaluated for their antiproliferative properties against HL-60 and Jurkat E6.1 cell lines. Of all tested compounds, only 6-(2-phenylethyl)-3-(β- d -ribofuranosyl)furo[2,3- d ]pyrimidin-2(3 H )-one exhibited weak antiproliferative activity, with IC 50 values of 54 and 81 μM for HL-60 and Jurkat E6.1 cells, respectively.

Krzysztof Woźniak - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and investigation of the antitumor properties of novel bicyclic furopyrimidine pyrrolopyrimidine and Pyrimidopyridazine nucleoside analogues
    Synthesis, 2015
    Co-Authors: Adam Mieczkowski, Ewelina Tomczyk, Malgorzata Makowska, Anna Nasulewiczgoldeman, Roman Gajda, Krzysztof Woźniak, Joanna Wietrzyk
    Abstract:

    A series of nine hitherto unknown bicyclic pyrimidine nucleoside analogues (BCNAs) bearing bicyclic furo[2,3- d ]pyrimidin-2(3 H )-one, 3 H -pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and 5,6-dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one bases were prepared in a straightforward approach. Each of the synthesized compounds possesses a β- d -ribofuranose, β- d -2-deoxyribofuranose or β- d -arabinofuranose moiety attached to the heterocyclic ring system. This is one of few examples of the synthesis of pyrrolo[2,3- d ]pyrimidin-2(7 H )-one and dihydropyrimido[4,5- c ]pyridazin-7(8 H )-one nucleosides, and the first example of such nucleosides possessing an arabinose moiety. A key synthetic step involved a Sonogashira coupling reaction. For the coupling with 4-phenyl-1-butyne, deprotected 5-iodouridine, 5-iodo-2′-deoxyuridine and 5-iodoarabinouridine were used, and this reaction was followed by cycloisomerization and subsequent conversion of the furan ring into a pyrrole or a pyridazine ring. This approach resulted in the creation of a small library of compounds, which were evaluated for their antiproliferative properties against HL-60 and Jurkat E6.1 cell lines. Of all tested compounds, only 6-(2-phenylethyl)-3-(β- d -ribofuranosyl)furo[2,3- d ]pyrimidin-2(3 H )-one exhibited weak antiproliferative activity, with IC 50 values of 54 and 81 μM for HL-60 and Jurkat E6.1 cells, respectively.