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Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction.

Organic letters

Galeta J, Šála M, Dračínský M, Vrábel M, Havlas Z, Nencka R.
PMID: 27391276
Org Lett. 2016 Aug 05;18(15):3594-7. doi: 10.1021/acs.orglett.6b01601. Epub 2016 Jul 08.

A straightforward synthesis of pyrimido[4,5-d]pyridazines from pyrimidines and tetrazines under basic conditions is reported. Deprotonated, substituted 5-halopyrimidines readily react with variously substituted tetrazines in a highly regioselective manner via a complex reaction pathway, which was supported by DFT calculations....

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Galeta J, Šála M, Dračínský M, et al. Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction. Org Lett. 2016;18(15):3594-7doi: 10.1021/acs.orglett.6b01601.
Galeta, J., Šála, M., Dračínský, M., Vrábel, M., Havlas, Z., & Nencka, R. (2016). Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction. Organic letters, 18(15), 3594-7. https://doi.org/10.1021/acs.orglett.6b01601
Galeta, Juraj, et al. "Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction." Organic letters vol. 18,15 (2016): 3594-7. doi: https://doi.org/10.1021/acs.orglett.6b01601
Galeta J, Šála M, Dračínský M, Vrábel M, Havlas Z, Nencka R. Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction. Org Lett. 2016 Aug 05;18(15):3594-7. doi: 10.1021/acs.orglett.6b01601. Epub 2016 Jul 08. PMID: 27391276.
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Bis-pyrimidine acetamides: design, synthesis and biological evaluation.

Chemistry Central journal

Kumar S, Lim SM, Ramasamy K, Vasudevan M, Shah SAA, Narasimhan B.
PMID: 29086907
Chem Cent J. 2017 Aug 08;11(1):80. doi: 10.1186/s13065-017-0312-2.

BACKGROUND: In the past few years, increased resistance of microorganisms towards antimicrobial agents become a serious health problem, so there is a need for the discovery of new antimicrobial agents. On the other hand, bis-pyrimidines possess various types of...

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Kumar S, Lim SM, Ramasamy K, et al. Bis-pyrimidine acetamides: design, synthesis and biological evaluation. Chem Cent J. 2017;11(1):80doi: 10.1186/s13065-017-0312-2.
Kumar, S., Lim, S. M., Ramasamy, K., Vasudevan, M., Shah, S. A. A., & Narasimhan, B. (2017). Bis-pyrimidine acetamides: design, synthesis and biological evaluation. Chemistry Central journal, 11(1), 80. https://doi.org/10.1186/s13065-017-0312-2
Kumar, Sanjiv, et al. "Bis-pyrimidine acetamides: design, synthesis and biological evaluation." Chemistry Central journal vol. 11,1 (2017): 80. doi: https://doi.org/10.1186/s13065-017-0312-2
Kumar S, Lim SM, Ramasamy K, Vasudevan M, Shah SAA, Narasimhan B. Bis-pyrimidine acetamides: design, synthesis and biological evaluation. Chem Cent J. 2017 Aug 08;11(1):80. doi: 10.1186/s13065-017-0312-2. PMID: 29086907; PMCID: PMC5548699.
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Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers.

Angewandte Chemie (International ed. in English)

Feng GS, Chen MW, Shi L, Zhou YG.
PMID: 29575705
Angew Chem Int Ed Engl. 2018 May 14;57(20):5853-5857. doi: 10.1002/anie.201801485. Epub 2018 Apr 17.

A facile access to optically active cyclic ureas was developed through palladium-catalyzed asymmetric hydrogenation of pyrimidines containing tautomeric hydroxy group with up to 99 % ee. Mechanistic studies indicated that reaction pathway proceed through hydrogenation of C=N of the...

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Feng GS, Chen MW, Shi L, et al. Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers. Angew Chem Int Ed Engl. 2018;57(20):5853-5857doi: 10.1002/anie.201801485.
Feng, G. S., Chen, M. W., Shi, L., & Zhou, Y. G. (2018). Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers. Angewandte Chemie (International ed. in English), 57(20), 5853-5857. https://doi.org/10.1002/anie.201801485
Feng, Guang-Shou, et al. "Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers." Angewandte Chemie (International ed. in English) vol. 57,20 (2018): 5853-5857. doi: https://doi.org/10.1002/anie.201801485
Feng GS, Chen MW, Shi L, Zhou YG. Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1H)-one Tautomers. Angew Chem Int Ed Engl. 2018 May 14;57(20):5853-5857. doi: 10.1002/anie.201801485. Epub 2018 Apr 17. PMID: 29575705.
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Catalytic asymmetric hydrogenation of pyrimidines.

Angewandte Chemie (International ed. in English)

Kuwano R, Hashiguchi Y, Ikeda R, Ishizuka K.
PMID: 25565291
Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2393-6. doi: 10.1002/anie.201410607. Epub 2015 Jan 07.

The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99% ee) using an iridium catalyst composed of [IrCl(cod)]2, a ferrocene-containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf)3 (cod = 1,5-cyclooctadiene). The chiral catalyst converted various 4-substituted pyrimidines...

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Kuwano R, Hashiguchi Y, Ikeda R, et al. Catalytic asymmetric hydrogenation of pyrimidines. Angew Chem Int Ed Engl. 2015;54(8):2393-6doi: 10.1002/anie.201410607.
Kuwano, R., Hashiguchi, Y., Ikeda, R., & Ishizuka, K. (2015). Catalytic asymmetric hydrogenation of pyrimidines. Angewandte Chemie (International ed. in English), 54(8), 2393-6. https://doi.org/10.1002/anie.201410607
Kuwano, Ryoichi, et al. "Catalytic asymmetric hydrogenation of pyrimidines." Angewandte Chemie (International ed. in English) vol. 54,8 (2015): 2393-6. doi: https://doi.org/10.1002/anie.201410607
Kuwano R, Hashiguchi Y, Ikeda R, Ishizuka K. Catalytic asymmetric hydrogenation of pyrimidines. Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2393-6. doi: 10.1002/anie.201410607. Epub 2015 Jan 07. PMID: 25565291.
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New Pyrano[2,3-d:6,5-d']dipyrimidine Derivatives-Synthesis, in vitro Cytotoxicity and Computational Studies.

Anti-cancer agents in medicinal chemistry

Maddila S, Naicker K, Gorle S, Rana S, Yalagala K, Maddila SN, Singh M, Singh P, Jonnalagadda SB.
PMID: 26592746
Anticancer Agents Med Chem. 2016;16(8):1031-1037. doi: 10.2174/1871520616666151123095932.

A new series of pyrano[2,3-d:6,5-d']dipyrimidine derivatives were synthesized and evaluated for their in vitro anticancer activity. The structures of all the synthesized compounds were confirmed by 1H NMR, 13C NMR, 15N NMR, HR-MS and FT-IR spectral analyses. The cytotoxic...

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Maddila S, Naicker K, Gorle S, et al. New Pyrano[2,3-d:6,5-d']dipyrimidine Derivatives-Synthesis, in vitro Cytotoxicity and Computational Studies. Anticancer Agents Med Chem. 2016;16(8):1031-1037doi: 10.2174/1871520616666151123095932.
Maddila, S., Naicker, K., Gorle, S., Rana, S., Yalagala, K., Maddila, S. N., Singh, M., Singh, P., & Jonnalagadda, S. B. (2016). New Pyrano[2,3-d:6,5-d']dipyrimidine Derivatives-Synthesis, in vitro Cytotoxicity and Computational Studies. Anti-cancer agents in medicinal chemistry, 16(8), 1031-1037. https://doi.org/10.2174/1871520616666151123095932
Maddila, Suresh, et al. "New Pyrano[2,3-d:6,5-d']dipyrimidine Derivatives-Synthesis, in vitro Cytotoxicity and Computational Studies." Anti-cancer agents in medicinal chemistry vol. 16,8 (2016): 1031-1037. doi: https://doi.org/10.2174/1871520616666151123095932
Maddila S, Naicker K, Gorle S, Rana S, Yalagala K, Maddila SN, Singh M, Singh P, Jonnalagadda SB. New Pyrano[2,3-d:6,5-d']dipyrimidine Derivatives-Synthesis, in vitro Cytotoxicity and Computational Studies. Anticancer Agents Med Chem. 2016;16(8):1031-1037. doi: 10.2174/1871520616666151123095932. PMID: 26592746.
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Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization.

Organic letters

Parthasarathy K, Azcargorta AR, Cheng Y, Bolm C.
PMID: 24720665
Org Lett. 2014 May 02;16(9):2538-41. doi: 10.1021/ol500918t. Epub 2014 Apr 11.

Rhodium-catalyzed C-H functionalizations have been used for ortho-directed additions of 2-arylpyridines and (hetero)aryl-substituted pyrimidines, isoquinolines, and benzo[h]quinolones to cyclic imines. The resulting amino-functionalized products are formed in good to high yields.

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Parthasarathy K, Azcargorta AR, Cheng Y, et al. Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization. Org Lett. 2014;16(9):2538-41doi: 10.1021/ol500918t.
Parthasarathy, K., Azcargorta, A. R., Cheng, Y., & Bolm, C. (2014). Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization. Organic letters, 16(9), 2538-41. https://doi.org/10.1021/ol500918t
Parthasarathy, Kanniyappan, et al. "Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization." Organic letters vol. 16,9 (2014): 2538-41. doi: https://doi.org/10.1021/ol500918t
Parthasarathy K, Azcargorta AR, Cheng Y, Bolm C. Directed additions of 2-arylpyridines and related substrates to cyclic imines through rhodium-catalyzed C-H functionalization. Org Lett. 2014 May 02;16(9):2538-41. doi: 10.1021/ol500918t. Epub 2014 Apr 11. PMID: 24720665.
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Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines.

Chemistry Central journal

Zaki YH, Sayed AR, Elroby SA.
PMID: 27042207
Chem Cent J. 2016 Apr 01;10:17. doi: 10.1186/s13065-016-0163-2. eCollection 2016.

BACKGROUND: Isoxazoles exhibit interesting biological activities, and the 1,3-dipolar cycloaddition(13DC) reactions play an important role in both mechanistic and synthetic organic chemistry. Pyrazoles and annulated pyrazoles exhibit some diverse biological activities. They are used as antipyretic, analgesic drugs, tranquilizing,...

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Zaki YH, Sayed AR, Elroby SA. Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chem Cent J. 2016;10:17doi: 10.1186/s13065-016-0163-2.
Zaki, Y. H., Sayed, A. R., & Elroby, S. A. (2016). Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chemistry Central journal, 1017. https://doi.org/10.1186/s13065-016-0163-2
Zaki, Yasser Hassan, et al. "Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines." Chemistry Central journal vol. 10 (2016): 17. doi: https://doi.org/10.1186/s13065-016-0163-2
Zaki YH, Sayed AR, Elroby SA. Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines. Chem Cent J. 2016 Apr 01;10:17. doi: 10.1186/s13065-016-0163-2. eCollection 2016. PMID: 27042207; PMCID: PMC4818429.
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1,N6-ethenoadenine and other Fluorescent Nucleobase Analogues as Substrates for Purine-Nucleoside Phosphorylases: Spectroscopic and Kinetic Studies.

Current pharmaceutical design

Wierzchowski J, Stachelska-Wierzchowska A, Wielgus-Kutrowska B, Bzowska A.
PMID: 29022509
Curr Pharm Des. 2017 Oct 11; doi: 10.2174/1381612823666171011103551. Epub 2017 Oct 11.

BACKGROUND: Purine-nucleoside phosphorylase (PNP) is known as a tool for the synthesis of various nucleosides and nucleoside analogues. Mechanism, properties, molecular diversity and inhibitors of PNP, particularly these of pharmacological significance, are briefly characterized.METHODS: UV and fluorescence spectroscopy was...

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Wierzchowski J, Stachelska-Wierzchowska A, Wielgus-Kutrowska B, et al. 1,N6-ethenoadenine and other Fluorescent Nucleobase Analogues as Substrates for Purine-Nucleoside Phosphorylases: Spectroscopic and Kinetic Studies. Curr Pharm Des. 2017;doi: 10.2174/1381612823666171011103551.
Wierzchowski, J., Stachelska-Wierzchowska, A., Wielgus-Kutrowska, B., & Bzowska, A. (2017). 1,N6-ethenoadenine and other Fluorescent Nucleobase Analogues as Substrates for Purine-Nucleoside Phosphorylases: Spectroscopic and Kinetic Studies. Current pharmaceutical design, . https://doi.org/10.2174/1381612823666171011103551
Wierzchowski, Jacek, et al. "1,N6-ethenoadenine and other Fluorescent Nucleobase Analogues as Substrates for Purine-Nucleoside Phosphorylases: Spectroscopic and Kinetic Studies." Current pharmaceutical design vol. (2017). doi: https://doi.org/10.2174/1381612823666171011103551
Wierzchowski J, Stachelska-Wierzchowska A, Wielgus-Kutrowska B, Bzowska A. 1,N6-ethenoadenine and other Fluorescent Nucleobase Analogues as Substrates for Purine-Nucleoside Phosphorylases: Spectroscopic and Kinetic Studies. Curr Pharm Des. 2017 Oct 11; doi: 10.2174/1381612823666171011103551. Epub 2017 Oct 11. PMID: 29022509.
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Synthesis, characterization and in silico biological activity of some 2-(N,N-dimethyl guanidinyl)-4,6-diaryl pyrimidines.

Journal of pharmacy & bioallied sciences

Kumarachari RK, Peta S, Surur AS, Mekonnen YT.
PMID: 27413345
J Pharm Bioallied Sci. 2016 Jul-Sep;8(3):181-7. doi: 10.4103/0975-7406.171678.

INTRODUCTION: As pyrimidine is a basic nucleus in DNA and RNA, it has been found to be associated with diverse biological activities. Pyrimidine derivatives were reported to possess anticonvulsant, antimicrobial, anti-inflammatory, antitumor, and antihistaminic. Recently, our team reported the...

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Kumarachari RK, Peta S, Surur AS, et al. Synthesis, characterization and in silico biological activity of some 2-(N,N-dimethyl guanidinyl)-4,6-diaryl pyrimidines. J Pharm Bioallied Sci. 2016;8(3):181-7doi: 10.4103/0975-7406.171678.
Kumarachari, R. K., Peta, S., Surur, A. S., & Mekonnen, Y. T. (2016). Synthesis, characterization and in silico biological activity of some 2-(N,N-dimethyl guanidinyl)-4,6-diaryl pyrimidines. Journal of pharmacy & bioallied sciences, 8(3), 181-7. https://doi.org/10.4103/0975-7406.171678
Kumarachari, Rajasekhar Komarla, et al. "Synthesis, characterization and in silico biological activity of some 2-(N,N-dimethyl guanidinyl)-4,6-diaryl pyrimidines." Journal of pharmacy & bioallied sciences vol. 8,3 (2016): 181-7. doi: https://doi.org/10.4103/0975-7406.171678
Kumarachari RK, Peta S, Surur AS, Mekonnen YT. Synthesis, characterization and in silico biological activity of some 2-(N,N-dimethyl guanidinyl)-4,6-diaryl pyrimidines. J Pharm Bioallied Sci. 2016 Jul-Sep;8(3):181-7. doi: 10.4103/0975-7406.171678. PMID: 27413345; PMCID: PMC4929956.
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A unified model of the standard genetic code.

Royal Society open science

José MV, Zamudio GS, Morgado ER.
PMID: 28405378
R Soc Open Sci. 2017 Mar 01;4(3):160908. doi: 10.1098/rsos.160908. eCollection 2017 Mar.

The Rodin-Ohno (RO) and the Delarue models divide the table of the genetic code into two classes of aminoacyl-tRNA synthetases (aaRSs I and II) with recognition from the minor or major groove sides of the tRNA acceptor stem, respectively....

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José MV, Zamudio GS, Morgado ER. A unified model of the standard genetic code. R Soc Open Sci. 2017;4(3):160908doi: 10.1098/rsos.160908.
José, M. V., Zamudio, G. S., & Morgado, E. R. (2017). A unified model of the standard genetic code. Royal Society open science, 4(3), 160908. https://doi.org/10.1098/rsos.160908
José, Marco V, et al. "A unified model of the standard genetic code." Royal Society open science vol. 4,3 (2017): 160908. doi: https://doi.org/10.1098/rsos.160908
José MV, Zamudio GS, Morgado ER. A unified model of the standard genetic code. R Soc Open Sci. 2017 Mar 01;4(3):160908. doi: 10.1098/rsos.160908. eCollection 2017 Mar. PMID: 28405378; PMCID: PMC5383835.
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CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines.

Organic letters

Huo C, Tang J, Xie H, Wang Y, Dong J.
PMID: 26882001
Org Lett. 2016 Mar 04;18(5):1016-9. doi: 10.1021/acs.orglett.6b00137. Epub 2016 Feb 16.

The carbon tetrabromide mediated oxidative carbon-nitrogen bond formation of 2-aminopyridines or 2-aminopyrimidines with β-keto esters or 1,3-diones, leading to a variety of complex imidazo[1,2-α]pyridines or imidazo[1,2-α]pyrimidines, is reported. The reactions were realized under mild and metal-free conditions.

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Huo C, Tang J, Xie H, et al. CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines. Org Lett. 2016;18(5):1016-9doi: 10.1021/acs.orglett.6b00137.
Huo, C., Tang, J., Xie, H., Wang, Y., & Dong, J. (2016). CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines. Organic letters, 18(5), 1016-9. https://doi.org/10.1021/acs.orglett.6b00137
Huo, Congde, et al. "CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines." Organic letters vol. 18,5 (2016): 1016-9. doi: https://doi.org/10.1021/acs.orglett.6b00137
Huo C, Tang J, Xie H, Wang Y, Dong J. CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines. Org Lett. 2016 Mar 04;18(5):1016-9. doi: 10.1021/acs.orglett.6b00137. Epub 2016 Feb 16. PMID: 26882001.
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A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines.

Chemical communications (Cambridge, England)

Hang Z, Zhu J, Lian X, Xu P, Yu H, Han S.
PMID: 26498376
Chem Commun (Camb). 2016 Jan 04;52(1):80-3. doi: 10.1039/c5cc07880f.

An efficient self-assembled methanoproline-thiourea organocatalyst for the synthesis of optically active 6-isopropyl-3,4-dihydro-pyrimidines via an asymmetric Biginelli reaction was developed, which is superior to the individual precatalyst. A wide range of optically active 6-isopropyl-3,4-dihydropyrimidines with remarkable pharmacological interest was obtained...

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Hang Z, Zhu J, Lian X, et al. A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines. Chem Commun (Camb). 2016;52(1):80-3doi: 10.1039/c5cc07880f.
Hang, Z., Zhu, J., Lian, X., Xu, P., Yu, H., & Han, S. (2016). A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines. Chemical communications (Cambridge, England), 52(1), 80-3. https://doi.org/10.1039/c5cc07880f
Hang, Zhijun, et al. "A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines." Chemical communications (Cambridge, England) vol. 52,1 (2016): 80-3. doi: https://doi.org/10.1039/c5cc07880f
Hang Z, Zhu J, Lian X, Xu P, Yu H, Han S. A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines. Chem Commun (Camb). 2016 Jan 04;52(1):80-3. doi: 10.1039/c5cc07880f. PMID: 26498376.
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