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Journal articles on the topic 'Pyrrolo[2,3-d]pyrimidines'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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1

Dodonova, Jelena, and Sigitas Tumkevicius. "Fused Pyrrolo[2,3-d]pyrimidines (7-Deazapurines) by Palladium-Catalyzed Direct N–H and C–H Arylation Reactions." Synthesis 49, no. 11 (2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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Palladium-catalyzed intramolecular direct C–H arylations for the synthesis of hitherto unknown fused hetero systems containing an incorporated pyrrolo[2,3-d]pyrimidine scaffold are described. Pyrimido[5′,4′:4,5]pyrrolo[2,1-a]isoindoles were synthesized from 2,4-diarylpyrrolo[2,3-d]pyrimidines and o-bromobenzyl bromides by using a cascade N-benzylation/C–H arylation reaction sequence. A series of pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines were successfully assembled via a domino process involving the palladium-catalyzed direct double C–H arylation reactions of 2,4,7-triarylpyrrolo[2,3-d]

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2

Zhou, Jing, Zhengtong Mao, Haokun Pan, and Xingxian Zhang. "Pd-Catalyzed highly selective and direct ortho C–H arylation of pyrrolo[2,3-d]pyrimidine derivatives." Organic Chemistry Frontiers 7, no. 2 (2020): 324–28. http://dx.doi.org/10.1039/c9qo01312a.

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Pd-Catalyzed one-pot direct ortho C–H arylation of pyrrolo[2,3-d]pyrimidine derivatives is reported. This protocol provides a variety of biphenyl-containing pyrrolo[2,3-d]pyrimidines in good to excellent yields.

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3

Mao, Zhengtong, Min Liu, Gaoyang Zhu, Jing Zhou, and Xingxian Zhang. "Transition-metal-free highly regioselective C–H acetoxylation of pyrrolo[2,3-d]pyrimidine derivatives." Organic Chemistry Frontiers 7, no. 18 (2020): 2696–702. http://dx.doi.org/10.1039/d0qo00702a.

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Transition-metal-free catalyzed direct C(sp<sup>2</sup>)–H acetoxylation of pyrrolo[2,3-d]pyrimidine derivatives is reported. This protocol provides a variety of acetoxylated pyrrolo[2,3-d]pyrimidines in good to excellent yields.

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4

Soto-Acosta, Ruben, Eunkyung Jung, Li Qiu, Daniel J. Wilson, Robert J. Geraghty, and Liqiang Chen. "4,7-Disubstituted 7H-Pyrrolo[2,3-d]pyrimidines and Their Analogs as Antiviral Agents against Zika Virus." Molecules 26, no. 13 (2021): 3779. http://dx.doi.org/10.3390/molecules26133779.

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Discovery of compound 1 as a Zika virus (ZIKV) inhibitor has prompted us to investigate its 7H-pyrrolo[2,3-d]pyrimidine scaffold, revealing structural features that elicit antiviral activity. Furthermore, we have demonstrated that 9H-purine or 1H-pyrazolo[3,4-d]pyrimidine can serve as an alternative core structure. Overall, we have identified 4,7-disubstituted 7H-pyrrolo[2,3-d]pyrimidines and their analogs including compounds 1, 8 and 11 as promising antiviral agents against flaviviruses ZIKV and dengue virus (DENV). While the molecular target of these compounds is yet to be elucidated, 4,7-di

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5

Mohamed, Mosaad, Ramdan El-Domany, and Rania Abd El-Hameed. "Synthesis of certain pyrrole derivatives as antimicro-bial agents." Acta Pharmaceutica 59, no. 2 (2009): 145–58. http://dx.doi.org/10.2478/v10007-009-0016-9.

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Synthesis of certain pyrrole derivatives as antimicro-bial agentsIn an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis andin vitromicrobiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-dto5a-d) and pyrrolo[2,3-d]pyrimidines (6a-dto10a, d) were synthesized. Thein vitroantimicrobial testing of the synthesized compounds

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6

Devine, Shane M., San Sui Lim, Indu R. Chandrashekaran, et al. "A critical evaluation of pyrrolo[2,3-d]pyrimidine-4-amines as Plasmodium falciparum apical membrane antigen 1 (AMA1) inhibitors." Med. Chem. Commun. 5, no. 10 (2014): 1500–1506. http://dx.doi.org/10.1039/c4md00090k.

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7

Melik-Ogandzhanyan, R. G., V. E. Khachatryan, and A. S. Gapoyan. "Furo-, Thieno-, and Pyrrolo-[2,3-d]pyrimidines." Russian Chemical Reviews 54, no. 3 (1985): 262–76. http://dx.doi.org/10.1070/rc1985v054n03abeh003026.

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8

Sajadikhah, Seyed Sajad, and Abdolkarim Zare. "Synthesis of pyrrolo[2,3-d]pyrimidines (microreview)." Chemistry of Heterocyclic Compounds 55, no. 12 (2019): 1168–70. http://dx.doi.org/10.1007/s10593-019-02595-2.

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9

Evers, David L., Julie M. Breitenbach, Katherine Z. Borysko, Leroy B. Townsend, and John C. Drach. "Inhibition of Cyclin-Dependent Kinase 1 by Purines and Pyrrolo[2,3-d]Pyrimidines Does Not Correlate with Antiviral Activity." Antimicrobial Agents and Chemotherapy 46, no. 8 (2002): 2470–76. http://dx.doi.org/10.1128/aac.46.8.2470-2476.2002.

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ABSTRACT We have previously shown that a series of nonnucleoside pyrrolo[2,3-d]pyrimidines selectively inhibit the replication of herpes simplex virus type 1 (HSV-1) and human cytomegalovirus (HCMV). These compounds act at the immediate-early or early stage of HCMV replication and have antiviral properties somewhat similar to those of roscovitine and olomoucine, specific inhibitors of cyclin-dependent kinases (cdks). In the present study we examine the hypothesis that pyrrolo[2,3-d]pyrimidines exert their antiviral effects by inhibition of cellular cdks. Much higher concentrations of a panel o

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10

Zhang, Furen, and Chunmei Li. "l-Proline-Catalyzed Cyclization of 6-Aminopyrimidine-4(3H)-ones with Nitroolefins: Synthesis of Polysubstituted 5-Arylpyrrolo[2,3-d]pyrimidin-4-ones." Synlett 28, no. 11 (2017): 1315–20. http://dx.doi.org/10.1055/s-0036-1588757.

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A simple and efficient one-pot procedure for the synthesis of new pyrrolo[2,3-d]pyrimidine derivatives has been established through an l-proline-catalyzed cyclization of 6-aminopyrimidine-4(3H)-one with nitroolefins in water. The reaction at 80 °C in water gives various highly substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. This procedure has the advantages of environmental friendliness, good yields, and convenient operation.

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11

Bucevicius, Jonas, Lina Skardziute, Jelena Dodonova, et al. "2,4-Bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines: synthesis and tuning of optical properties by polar substituents." RSC Advances 5, no. 48 (2015): 38610–22. http://dx.doi.org/10.1039/c5ra05482f.

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Novel D–π–A–π–D type chromophores – 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines were prepared and their photophysical, electrochemical properties in conjunction with quantum chemical calculations were investigated.

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12

Bayomi, Said M. "Synthesis and Ring Transformation of Pyrrolo[2,3-d][1,3]oxazine to Pyrrolo[2,3-d]Pyrimidines." Journal of the Chinese Chemical Society 39, no. 1 (1992): 101–4. http://dx.doi.org/10.1002/jccs.199200015.

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13

Bayomi, Said M. "Synthesis and ring transformation of pyrrolo[2,3-d][1,3]oxazine to pyrrolo[2,3-d]pyrimidines." Archives of Pharmacal Research 13, no. 1 (1990): 97–100. http://dx.doi.org/10.1007/bf02857841.

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14

SAKAMOTO, Takao, Chisato SATOH, Yoshinori KONDO, and Hiroshi YAMANAKA. "Condensed Heteroaromatic Ring Systems. XXI. Synthesis of Pyrrolo(2,3-d)pyrimidines and Pyrrolo(3,2-d)pyrimidines." CHEMICAL & PHARMACEUTICAL BULLETIN 41, no. 1 (1993): 81–86. http://dx.doi.org/10.1248/cpb.41.81.

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15

Musumeci, Francesca, Monica Sanna, Chiara Greco, et al. "Pyrrolo[2,3-d]pyrimidines active as Btk inhibitors." Expert Opinion on Therapeutic Patents 27, no. 12 (2017): 1305–18. http://dx.doi.org/10.1080/13543776.2017.1355908.

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16

Sznaidman, Marcos L., Eric A. Meade, Lilia M. Beauchamp, Stuart Russell, and Margaret Tisdale. "The antiinfluenza activity of pyrrolo[2,3-d]pyrimidines." Bioorganic & Medicinal Chemistry Letters 6, no. 5 (1996): 565–68. http://dx.doi.org/10.1016/0960-894x(96)00070-4.

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17

C. Taylor, Edward, and Baihua Hu. "A Fischer-Indole Approach to Pyrrolo[2,3-d]pyrimidines." HETEROCYCLES 43, no. 2 (1996): 323. http://dx.doi.org/10.3987/com-95-7260.

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18

Bundy, Gordon L., Robert S. Gremban, Lee S. Banitt, John R. Palmer, Stephen A. Mizsak, and Fusen Han. "Chemical Oxidation of 2,4-Diamino-pyrrolo[2,3-d]pyrimidines." Journal of Organic Chemistry 63, no. 21 (1998): 7542–46. http://dx.doi.org/10.1021/jo9810664.

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19

Kidwai, Mazaahir, Kavita Singhal, and Shweta Rastogi. "Paal knorr reaction for novel pyrrolo[2,3-d]pyrimidines." Journal of Heterocyclic Chemistry 43, no. 5 (2006): 1231–36. http://dx.doi.org/10.1002/jhet.5570430514.

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20

Prieur, Vanessa, Jaime Rubio-Martínez, Mercè Font-Bardia, Gérald Guillaumet, and M. Dolors Pujol. "Microwave-Assisted Synthesis of Substituted Pyrrolo[2,3-d]pyrimidines." European Journal of Organic Chemistry 2014, no. 7 (2014): 1514–24. http://dx.doi.org/10.1002/ejoc.201301496.

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21

Lee, Ji Hoon, and Hyun-Suk Lim. "Solid-phase synthesis of tetrasubstituted pyrrolo[2,3-d]pyrimidines." Organic & Biomolecular Chemistry 10, no. 21 (2012): 4229. http://dx.doi.org/10.1039/c2ob06899k.

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22

Klumpp, Susanne, Martina Frey, Gertrud Kleefeld, Armin Sauer, and Kurt Eger. "Pyrrolo[2,3-d]pyrimidines as inhibitors of cAMP-phosphodiesterase." Biochemical Pharmacology 38, no. 6 (1989): 949–53. http://dx.doi.org/10.1016/0006-2952(89)90285-2.

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23

BISTRYAKOVA, I. D., N. M. SMIRNOVA, and T. S. SAFONOVA. "ChemInform Abstract: Pyrido(2,3-d)pyrimidines. Part 8. Synthesis of Pyrrolo(2′,3′:4,5) pyrido(2,3-d)pyrimidines." ChemInform 25, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199415204.

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24

Kuyper, Lee F., Janice M. Garvey, David P. Baccanari, John N. Champness, David K. Stammers, and Christopher R. Beddell. "Pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines as conformationally restricted analogues of the antibacterial agent trimethoprim." Bioorganic & Medicinal Chemistry 4, no. 4 (1996): 593–602. http://dx.doi.org/10.1016/0968-0896(96)00045-4.

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25

BASYOUNI, W. M., H. M. HOSNI, and K. A. M. EL-BAYOUKI. "ChemInform Abstract: Pyrrolo[2,3-d]pyrimidines. Part 3. Synthesis of Some Novel 4-Substituted Pyrrolo[2,3-d]pyrimidines and Their Related Triazolo Derivatives." ChemInform 29, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.199819160.

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26

Itoh, Tsuneo, Ikuko Fujii, Yasuo Tomii, et al. "A Novel and Facile Synthesis of Pyrrolo[2,3-d]pyrimidines." HETEROCYCLES 24, no. 4 (1986): 927. http://dx.doi.org/10.3987/r-1986-04-0927.

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27

Rashad, Aymn E., Mosaad S. Mohamed, Magdy E. A. Zaki, and Samar S. Fatahala. "Synthesis and Biological Evaluation of Some Pyrrolo[2,3-d]pyrimidines." Archiv der Pharmazie 339, no. 12 (2006): 664–69. http://dx.doi.org/10.1002/ardp.200600055.

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28

SZNAIDMAN, M. L., E. A. MEADE, L. M. BEAUCHAMP, S. RUSSELL, and M. TISDALE. "ChemInform Abstract: The Antiinfluenza Activity of Pyrrolo(2,3-d)pyrimidines." ChemInform 27, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199628196.

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29

Quijano, M. Luisa, Manuel Nogueras, Aldolfo Sánchez, Gerardo Alvarez De Cienfuegos, and Miguel Melgarejo. "Synthesis, anticancer and antimicrobiological activities of pyrrolo[2,3-d]pyrimidines." Journal of Heterocyclic Chemistry 27, no. 4 (1990): 1079–83. http://dx.doi.org/10.1002/jhet.5570270449.

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30

Ghorab, Moustafa, Eman Noaman, Magda Ismail, Helmy Heiba, Yousry Ammar, and Marwa Sayed. "Novel Antitumor and Radioprotective Sulfonamides Containing Pyrrolo[2,3-d]pyrimidines." Arzneimittelforschung 56, no. 06 (2011): 405–13. http://dx.doi.org/10.1055/s-0031-1296742.

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31

EL-BAYOUKI, K. A. M., W. M. BASYOUNI, H. HOSNI, and A. S. EL-DEEN. "ChemInform Abstract: Pyrrolo(2,3-d)pyrimidines. Part 1. Synthesis of Novel Pyrrolo(2,3-d) pyrimidine Derivatives with Antimicrobial Activity." ChemInform 26, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199549191.

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32

North, Thomas W., Getachew Sequar, Leroy B. Townsend, John C. Drach та Peter A. Barry. "Rhesus Cytomegalovirus Is Similar to Human Cytomegalovirus in Susceptibility to Βenzimidazole Nucleosides". Antimicrobial Agents and Chemotherapy 48, № 7 (2004): 2760–65. http://dx.doi.org/10.1128/aac.48.7.2760-2765.2004.

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ABSTRACT Rhesus and human cytomegalovirus (RhCMV and HCMV, respectively) exhibit comparable inhibition by benzimidazole nucleosides, including 2,5,6-trichloro-(1-β-d-ribofuranosyl)benzimidazole (TCRB), and pyrrolo[2,3-d]pyrimidines. The two HCMV protein targets of TCRB, UL89 and UL56, are highly conserved with their RhCMV homologues. These data indicate that infection of rhesus macaques with RhCMV represents a useful model to test novel anti-HCMV drugs.

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33

Klimenko, Anna, Elena Matyugina, Evgeniya Logashenko, et al. "Novel 5′-Norcarbocyclic Derivatives of Bicyclic Pyrrolo- and Furano[2,3-d]Pyrimidine Nucleosides." Molecules 23, no. 10 (2018): 2654. http://dx.doi.org/10.3390/molecules23102654.

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Here we report the synthesis and biological activity of new 5′-norcarbocyclic derivatives of bicyclic pyrrolo- and furano[2,3-d]pyrimidines with different substituents in the heterocyclic ring. Lead compound 3i, containing 6-pentylphenyl substituent, displays inhibitory activity with respect to a number of tumor cells with a moderate selectivity index value. Compound 3i induces cell death by the apoptosis pathway with the dissipation of mitochondrial potential.

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34

Bystryakova, I. D., N. M. Smirnova, and T. S. Safonova. "Pyrido[2,3-d]dipyrimidines 8. Synthesis of pyrrolo(2?,3??4,5)pyrido[2,3-d]pyrimidines." Chemistry of Heterocyclic Compounds 29, no. 6 (1993): 687–90. http://dx.doi.org/10.1007/bf00531548.

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35

Tumkevicius, Sigitas, та Jelena Dodonova. "Pyrrolo[2,3-d]pyrimidine-Core-Extended π-Systems: Synthesis of 2,4,7-Triarylpyrrolo[2,3-d]pyrimidines". Synlett 2011, № 12 (2011): 1705–8. http://dx.doi.org/10.1055/s-0030-1260931.

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36

Abdel-Mohsen, Shawkat A., and Ahmed A. Geies. "A convenient synthesis of pyrrolo[2,3-b]pyridines and pyrido[2′,3′:5,4]pyrrolo[2,3-d]pyrimidines." Monatshefte für Chemie - Chemical Monthly 139, no. 10 (2008): 1233–40. http://dx.doi.org/10.1007/s00706-007-0839-3.

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37

Mohamed, Mosaad S., Aymn E. Rashad, Mostafa Adbel-Monem, and Samar S. Fatahalla. "New Anti-Inflammatory Agents." Zeitschrift für Naturforschung C 62, no. 1-2 (2007): 27–31. http://dx.doi.org/10.1515/znc-2007-1-205.

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The pyrrole derivatives 1a, b and 2a, b were used as precursors for the preparation of N-substituted pyrrole derivatives 3a, b-9a, b and pyrrolo[2,3-d]pyrimidines 13-16. Also, all the newly prepared products were tested for anti-inflammatory activity as analogues to fenamates, and some of them revealed moderate anti-inflammatory activity compared to the standard drug indomethacin.

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38

Tumkevicius, Sigitas, and Jonas Bucevicius. "Efficient Synthesis of (Arylethynyl)pyrrolo[2,3-d]pyrimidines by Stille Coupling." Synlett 26, no. 06 (2015): 810–14. http://dx.doi.org/10.1055/s-0034-1380153.

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39

TAYLOR, E. C., and B. HU. "ChemInform Abstract: A Fischer-Indole Approach to Pyrrolo(2,3-d)pyrimidines." ChemInform 27, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199625146.

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40

Kumar, Vidya P., Kathleen M. Frey, Yiqiang Wang, Hitesh K. Jain, Aleem Gangjee, and Karen S. Anderson. "Substituted pyrrolo[2,3-d]pyrimidines as Cryptosporidium hominis thymidylate synthase inhibitors." Bioorganic & Medicinal Chemistry Letters 23, no. 19 (2013): 5426–28. http://dx.doi.org/10.1016/j.bmcl.2013.07.037.

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41

Frank, Annika, Francisco Meza-Arriagada, Cristian O. Salas, Christian Espinosa-Bustos, and Holger Stark. "Nature-inspired pyrrolo[2,3-d]pyrimidines targeting the histamine H3 receptor." Bioorganic & Medicinal Chemistry 27, no. 14 (2019): 3194–200. http://dx.doi.org/10.1016/j.bmc.2019.05.042.

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42

Prieur, Vanessa, Jaime Rubio-Martinez, Merce Font-Bardia, Gerald Guillaumet, and M. Dolors Pujol. "ChemInform Abstract: Microwave-Assisted Synthesis of Substituted Pyrrolo[2,3-d]pyrimidines." ChemInform 45, no. 49 (2014): no. http://dx.doi.org/10.1002/chin.201449171.

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43

Park, Jun Hyung, Hee Myeong Wang, Min Hyeon Shin, and Hyun‐Suk Lim. "Synthesis of a DNA‐Encoded Library of Pyrrolo[2,3 ‐d ]pyrimidines." Bulletin of the Korean Chemical Society 42, no. 4 (2021): 691–98. http://dx.doi.org/10.1002/bkcs.12243.

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44

Marchalín, Štefan, Františka Pavlíková, and Dušan Ilavský. "Synthesis and spectral properties of pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidine derivatives." Collection of Czechoslovak Chemical Communications 54, no. 5 (1989): 1336–45. http://dx.doi.org/10.1135/cccc19891336.

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The starting 2-amino-5-ethoxycarbonyl-6-chloromethyl-4-(2-furyl)-3-cyano-4H-pyran (I) afforded on condensation with triethoxymethane 2-ethoxymethylenamino-4H-pyran II; treatment of the latter with ammonia yielded 2-formamidino-3-cyano-4H-pyran III, which, when heated in dilute ethanol, cyclized to 4-amino-6-ethoxycarbonyl-5-(2-furyl)-7-chloromethyl-4H-pyrano[2,3-d]pyrimidine (IV). Compound IV reacted with alkyl- or arylamines to give substituted 5H,6H,8H-pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidines VI, one of which (VIb, R = p-CH3C6H4) was alternatively obtained from 2-formamidino-4H-pyrano

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45

Hilmy, Khaled M. H., Hanan G. Abdul-Wahab, Dalia H. Soliman, Maha M. A. Khalifa та Amany M. Hegab. "Novel pyrrolo[2,3-d]pyrimidines and pyrrolo[2,3-b]pyridines: design, synthesis, and in vivo TNF-α inhibitory activity". Medicinal Chemistry Research 24, № 5 (2014): 2097–110. http://dx.doi.org/10.1007/s00044-014-1281-9.

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46

Tumkevicius, Sigitas, та Jelena Dodonova. "ChemInform Abstract: Pyrrolo[2,3-d]pyrimidine-Core-Extended π-Systems: Synthesis of 2,4,7-Triarylpyrrolo[2,3-d]pyrimidines." ChemInform 42, № 51 (2011): no. http://dx.doi.org/10.1002/chin.201151156.

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47

Aziz, Jessy, and Sandrine Piguel. "An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles." Synthesis 49, no. 20 (2017): 4562–85. http://dx.doi.org/10.1055/s-0036-1590859.

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This report highlights the recent advances in direct C–H bond functionalization of 5,5- and 6,5-fused heterocycles containing at least two nitrogen atoms. Besides C–C bond formation, C–N, C–S, C–P, and C–Si bonds can also be created via a metal-catalyzed process. Some examples, where a C–H functionalization approach was applied for the synthesis of drug candidates, will be presented as well.1 Introduction2 C–H Functionalization Reactions of N-Containing Heterocycles2.1 Imidazo[1,2-a]pyridines2.2 Pyrrolo[1,2-a]pyrazines2.3 Imidazo[1,2-b]pyrazoles2.4 Imidazo[1,2-a]pyrimidines2.5 Imidazo[1,2-a]py

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48

Bakhite, E. A., A. A. Geies, and H. S. El-Kashef. "Synthesis of Novel Pyrrylthieno[2,3-d]Pyrimidines and Related Pyrrolo[1″,2″:1″,6″]Pyrazino[2″,3″:4,5]Thieno[2,3-d]Pyrimidines." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 2 (2002): 303–23. http://dx.doi.org/10.1080/10426500210243.

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49

Edmont, Dolorès, and David M. Williams. "A new and versatile synthesis of 5-substituted pyrrolo[2,3-d]pyrimidines." Tetrahedron Letters 41, no. 44 (2000): 8581–85. http://dx.doi.org/10.1016/s0040-4039(00)01491-x.

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Muzychka, L. V., E. V. Verves, I. O. Yaremchuk, and O. B. Smolii. "Synthesis of pyrrolo[2,3-d]pyrimidines with 3-amino-2-hydroxypropyl substituents." Chemistry of Heterocyclic Compounds 48, no. 3 (2012): 481–87. http://dx.doi.org/10.1007/s10593-012-1019-x.

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