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Journal articles on the topic 'Pyrrolo pyrimidinone'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

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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2

B, S. a. l. i. e. v. a. G., J. u. m. a. e. v. a. M. E, K. h. o. l. i. k. o. v. T. S, A. i. s. a. H. A, and B. o. z. o. r. o. v. K. h. A. "SYNTHESIS, ACETYLCHOLINESTERASE AND BUTYRYLCHOLINESTERASE INHIBITORY ACTIVITY OF NOVEL TRICYCLIC 1-PHENYL-1,6,7,8-TETRAHYDRO-4H- PYRAZOLO[3,4-d]PYRROLO[1,2-a]PYRIMIDIN-4-ONE." 2022-yil, 3-son (133/1) ANIQ FANLAR SERIYASI 1, no. 125/2 (2021): 1–7. http://dx.doi.org/10.59251/2181-1296.v1.1252.948.

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A convenient synthesis of novel tricyclic annulated pyrimidinone, namely 1-phenyl- 1,6,7,8-tetrahydro-4 H -pyrazolo[3,4- d ]pyrrolo[1,2- a ]pyrimidin-4-one was described herein. Cyclization was provided via A-ring modification of deoxyvasicinone (natural product). Biological activities of this compound reveal promising acetylcholinesterase inhibitory activity of 82.48±0.76 %, while showed moderate butyrylcholinesterase inhibitory activity

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3

Huynh, Van Truong, and Huu Hiep Nguyen. "Bioactive Compounds of Bacillus subtilis strain B237 isolated from the endophytic bacteria in Houttuynia cordata Thunb by Gas Chromatography-Mass Spectrometry." Pharmaceutical and Chemical Journal 7, no. 4 (2020): 1–7. https://doi.org/10.5281/zenodo.13955164.

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To identify some compounds by GC-MS from the biologically active compounds have been identified in hexane-acetone, acetone-methanol and ethyl acetate organic solvents. The determination of bioactive chemical compounds is based on peak area, retention time, molecular weight and molecular formula. From the endophytic bacteria of <em>Houttuynia cordata </em>Thunb from <em>Bacillus subtilis </em>strain B237 having antibacterial activity against <em>Staphylococcus aureus</em> from people’s furuncles. <em>Houttuynia cordata </em>Thunb was collected in Kien Giang province, bacteria were isolate

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4

Panda, Ashish Kumar, Ruchi Bharti, Ajay Thakur, Monika Verma, and Renu Sharma. "Microwave-Assisted Multicomponent Synthesis of Pyrrolo [2, 3-d] Pyrimidinone Derivatives and Their DFT Calculations." Der Pharma Chemica 15, no. 3 (2023): 10. https://doi.org/10.5281/zenodo.13318888.

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Herein we have reported a green and environmentally benign methodology for synthesizing novel pyrrolo[2,3-d] pyrimidine derivatives under microwave-assisted reaction conditions. The desired product was obtained with an excellent yield (80-90%) within 30 minutes only. The characteristic features of this protocol were the use of green reaction conditions, high atom economy, less reaction time, excellent yields, no use of specific purification processes, no column chromatography, etc. Later, theoretical studies like DFT were also performed on each newly synthesized product (4a-e) using B3LYP (Bec

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5

Ruchi, Bharti, and Ashish Kumar Panda. "Microwave-Assisted Multicomponent Synthesis of Pyrrolo [2, 3-d] Pyrimidinone Derivatives and Their DFT Calculations." DER PHARMA CHEMICA 15, no. 3 (2023): 10. https://doi.org/10.4172/0975-413X.15.3.52-61.

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Herein we have reported a green and environmentally benign methodology for synthesizing novel pyrrolo[2,3-d] pyrimidine derivatives under microwave-assisted reaction conditions. The desired product was obtained with an excellent yield (80-90%) within 30 minutes only. The characteristic features of this protocol were the use of green reaction conditions, high atom economy, less reaction time, excellent yields, no use of specific purification processes, no column chromatography, etc. Later, theoretical studies like DFT were also performed on each newly synthesized product (4a-e) using B3LYP (Bec

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6

Panda, Ashish Kumar, Bharti Ruchi, Ajay Thakur, Monika Verma, and Renu Sharma. "Microwave-Assisted Multicomponent Synthesis of Pyrrolo [2, 3-d] Pyrimidinone Derivatives and Their DFT Calculations." Der Pharma Chemica 15, no. 3 (2023): 10. https://doi.org/10.5281/zenodo.10951900.

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Herein we have reported a green and environmentally benign methodology for synthesizing novel pyrrolo[2,3-d] pyrimidine derivatives under microwave-assisted reaction conditions. The desired product was obtained with an excellent yield (80-90%) within 30 minutes only. The characteristic features of this protocol were the use of green reaction conditions, high atom economy, less reaction time, excellent yields, no use of specific purification processes, no column chromatography, etc. Later, theoretical studies like DFT were also performed on each newly synthesized product (4a-e) using B3LYP (Bec

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7

Vaskevych, Alla, Nataliia Savinchuk, and Mykhailo Vov. "Synthesis of pyrrolo(pyrido)[1,2-a]quinazolinones and their benzoannulated analogues: An overview." Current Chemistry Letters 14, no. 3 (2025): 507–32. https://doi.org/10.5267/j.ccl.2025.3.005.

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Angular pyrrolo(pyrido)[1,2-a]quinazolinones, being structurally isomeric to linear pyrrolo(pyrido)[2,1-b]quinazolinone alkaloids, are attractive molecular systems for both synthetic transformations and targeted biomedical research. The pyrrolo(pyrido)[1,2-a]quinazolinone scaffold has proven to be quite effective in the search for compounds with a wide range of pharmacological activities, e.g. anti-inflammatory, antioxidant, antibacterial, antiarrhythmic, and inhibitors of important biotargets. The present review summarises the methods for the synthesis of pyrrolo(pyrido)[1,2-a]quinazolinones

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8

Bernáth, Gábor, Ferenc Csende, Zsolt Böcskei, Pál Sohár, and Géza Stájer. "Preparation of Cycloalkano[c]pyridazinoens and Cycloalkane-condensed Pyrrolo[1,2-a]imidazolone, -pyrimidinone and -[1,3]diazepinone Stereoisomers." HETEROCYCLES 45, no. 2 (1997): 323. http://dx.doi.org/10.3987/com-96-7673.

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9

Tretyakov, N. A., M. V. Dmitriev, and A. N. Maslivets. "Synthesis of spiro(pyrrol-2,5'-pyrrolo[2,3-<i>d</i>]pyrimidine)2',4',5,6'-tetraones by the reaction of pyrrolo[2,1-<i>c</i>][1,4]oxazinetriones with 6-aminopyrimidine-2,4-diones." Журнал органической химии 59, no. 2 (2023): 180–86. http://dx.doi.org/10.31857/s0514749223020039.

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8-Aroyl-3,4-dihydro-1 H -pyrrolo[2,1- c ][1,4]oxazine-1,6,7-triones react with 6-aminopyrimidine-2,4(1 H ,3 H )diones to form 3-aroyl-4-hydroxy-1-(2-hydroxyalkyl)spiro(pyrrole-2,5'-pyrrolo[2,3- d ]pyrimidine)2',4',5,6'(1 H ,1' H ,3' H ,7' H )-tetraones, the structure of which was confirmed by X-ray diffraction analysis.

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10

Song, Buer, Zarifa Murtazaeva, Lifei Nie, et al. "Pyrrolopyrimidines: Design, Synthesis and Antitumor Properties of Novel Tricyclic Pyrrolo [2,3-d]pyrimidine Derivatives." Molecules 30, no. 14 (2025): 2917. https://doi.org/10.3390/molecules30142917.

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The pyrrolo[2,3-d]pyrimidine (7-deazapurine) scaffold is a unique heterocyclic system included in the composition of most nucleotides. In this study, series of the pyrrolo[2,3-d]pyrimidine-imines and 3-halo-substituted pyrrolo[2,3-d]pyrimidines were designed and prepared in high yields. Condensed pyrimidines are obtained via carbonyl-amine condensation and carbon-halogen bond formation. Pyrrolo[2,3-d]pyrimidine-imines containing a bromine substituent at position C-4 of the phenyl ring and azepine side-ring exhibited superior antitumor activity on the colon cancer HT-29 cell line; IC50 values w

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11

Cawrse, Brian M., Nia’mani M. Robinson, Nina C. Lee, Gerald M. Wilson, and Katherine L. Seley-Radtke. "Structural and Biological Investigations for a Series of N-5 Substituted Pyrrolo[3,2-d]pyrimidines as Potential Anti-Cancer Therapeutics." Molecules 24, no. 14 (2019): 2656. http://dx.doi.org/10.3390/molecules24142656.

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Pyrrolo[3,2-d]pyrimidines have been studied for many years as potential lead compounds for the development of antiproliferative agents. Much of the focus has been on modifications to the pyrimidine ring, with enzymatic recognition often modulated by C2 and C4 substituents. In contrast, this work focuses on the N5 of the pyrrole ring by means of a series of novel N5-substituted pyrrolo[3,2-d]pyrimidines. The compounds were screened against the NCI-60 Human Tumor Cell Line panel, and the results were analyzed using the COMPARE algorithm to elucidate potential mechanisms of action. COMPARE analys

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12

Singh, Deepshikha, Praveen M. Parkali, Umme Hani, et al. "Structure-based design, synthesis, computational screening and biological evaluation of novel pyrrole fused pyrimidine derivatives targeting InhA enzyme." RSC Advances 15, no. 32 (2025): 25776–98. https://doi.org/10.1039/d5ra03004h.

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13

CSENDE, F., G. BERNATH, Z. BOECSKEI, P. SOHAR, and G. STAJER. "ChemInform Abstract: Saturated Heterocycles. Part 239. Preparation of Cycloalkano(c) pyridazinones and Cycloalkane-Condensed Pyrrolo(1,2-a)imidazolone, - pyrimidinone and -(1,3)diazepinone Stereoisomers." ChemInform 28, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199734130.

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14

Abu-Hashem, Ameen Ali, Sami A. Al-Hussain, and Magdi E. A. Zaki. "Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives." Molecules 26, no. 7 (2021): 2031. http://dx.doi.org/10.3390/molecules26072031.

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In this article, we showed the synthesis of new polycyclic aromatic compounds, such as thienotriazolopyrimidinones, N-(thienotriazolopyrimidine) acetamide, 2-mercapto-thienotriazolo-pyrimidinones, 2-(((thieno-triazolopyrimidine) methyl) thio) thieno-triazolopyrimidines, thieno-pyrimidotriazolo-thiazines, pyrrolo-triazolo-thienopyrimidines, thienopyrimido-triazolopyrrolo-quinoxalines, thienopyrimido-triazolo-pyrrolo-oxathiino-quinoxalinones, 1,4-oxathiino-pyrrolo- triazolothienopyrimidinones, imidazopyrrolotriazolothienopyrimidines and 1,2,4-triazoloimidazo- pyrrolotriazolothienopyrimidindiones

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15

El-Bayouki, Khairy Abdelhameed Mohsen, Wahid Mohmoud Basyouni, and Eslam Attya Mostafa. "Synthesis of new pyrrole and pyrrolo[2,3-d]pyrimidine derivatives of potential antioxidant activity." Collection of Czechoslovak Chemical Communications 75, no. 8 (2010): 813–34. http://dx.doi.org/10.1135/cccc2009566.

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New 2-amino-3-cyanopyrrole derivatives were prepared and converted to 7-deazapurines. 7-Deazaadenine 6 was synthesized by different methods and alkylated with alkyl iodides to afford the quaternized 3-alkylpyrrolopyrimidinium iodide salts 8. The latter salts were dequaternized to N-alkylpyrrolo[2,3-d]pyrimidin-4-amines 12. Compounds 12 were identical to the products obtained from reactions of 4-chloro-7-(4-fluorophenyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidine 11 with methyl- or ethylamine in the presence of a catalyst. The thione 13 and its related 4-methylthio- and 4-ylcarbonothioate derivative

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16

M.H. Hilmy, Khaled, Fawzya N.M. Kishk, Esmat B.A. Shahen, and Mohamed A. Hawata. "Novel pyrrolo[2,3-b]pyridine and pyrrolo[2,3-d] pyrimidine derivatives: Design, synthesis, and structure elucidation." Bulletin of the Chemical Society of Ethiopia 37, no. 4 (2023): 983–92. http://dx.doi.org/10.4314/bcse.v37i4.14.

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ABSTRACT. A cyclo condensation reaction is an effective method for a two-component reaction of 2-amino-1,5-diphenyl-1H-pyrrole-3-carbonitrile 3a-c and active methylene compounds in acetic acid and catalytic hydrochloric acid to produce new substituted 1H-pyrrolo[2,3-b]pyridine 4a-c, 5a-c, and 6a-c have been established. Additionally, a new series of substituted 1H-pyrrolo[2,3-d]pyrimidines 7a-c and 8a-c could be synthesized utilizing a feasible and efficient approach, including urea and thiourea substrates. Spectroscopic data IR, MS, 1H, and 13C NMR, as well as elemental analyses, elucidated t

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17

Salaheldin, Abdellatif M. "Enaminonitriles in Heterocyclic Synthesis: Novel Synthesis of 3-Aminopyrroles and Pyrrolo[3,2-d]pyrimidine Derivatives." Zeitschrift für Naturforschung B 63, no. 5 (2008): 564–70. http://dx.doi.org/10.1515/znb-2008-0514.

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Several new 3-aminopyrrole derivatives have been synthesized from 3-substituted amino-2-phenylacrylonitriles using Thorpe-Ziegler cyclization. These substituted pyrroles are readily converted into 5H-pyrrolo[3,2-d]pyrimidines (9-deazapurines).

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18

Banfield, JE, GD Fallon, and BM Gatehouse. "Heterocyclic-Derivatives of Guanidine. VI. Formation and X-Ray Structure Determination of 2-Dimethylamino-7,8-diphenyl-4,6-dihydropyrrolo[1,2-a]pyrimidine-4,6-dione." Australian Journal of Chemistry 40, no. 5 (1987): 1003. http://dx.doi.org/10.1071/ch9871003.

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The structure N-(2-dimethylamino-4-oxo-7,8-diphenyl-4,6-dihydropyrrolo [l,2-a]pyrimidi n-6-yl-idene)acetamide (3) is proposed for a compound derived from the action of ketene on 2-(2-imino- 3,4-diphenyl-2H-pyrrol-5-yl)-1,1,3-trimethylguanidine (1; R1 = R2 = R3 = Me) on the basis of the crystal structure of its hydrolysis product, the oxo-compound 2-dimethylamino-7,8-diphenyl-4,6-dihydropyrrolo[l,2-a]pyrimidine-4,6-dione (4), the structure of which was determined by X-ray analysis. A lower homologue of (3), N-(2-methylamino-4-oxo-7,8-diphenyl-4,6-dihydro- pyrrolo[l,2-a]pyrimidin-6-ylidene)aceta

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19

Popa, Marcel Mirel, Emilian Georgescu, Mino R. Caira, et al. "Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively." Beilstein Journal of Organic Chemistry 11 (June 26, 2015): 1079–88. http://dx.doi.org/10.3762/bjoc.11.121.

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The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric h

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20

O. Abdelhamid, Abdou, Fathy M. Abdel-Galil, and Sohair S. Saleh. "Reactions with Heterocyclic Enaminonitriles: Synthesis of Pyrrolo[2,3-b]pyridine, Pyrrolo[2,3-d]pyrimidine and Pyrrole Derivatives." HETEROCYCLES 27, no. 8 (1988): 1861. http://dx.doi.org/10.3987/com-87-4432.

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21

Saalfrank, Rolf W., Bernd Hörner, Stephan Reck, et al. "Synthese und Umsetzungen von 4-Acyl/Carbamoyl-N-aryl-3-chloropyrrol-2,5-dionen: Kristallstruktur eines auf Wasserstoffbrückenbindungen basierenden supramolekularen Bandes [1] / Synthesis and Reactions of 4-Acyl/Carbamoyl-N-aryl-3-chloro-pyrrol-2,5-diones: Crystal Structure of a Supramolecular Ribbon Based on Hydrogen Bonds [ 1]." Zeitschrift für Naturforschung B 51, no. 8 (1996): 1084–98. http://dx.doi.org/10.1515/znb-1996-0806.

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Reaction of malondiamides 1 with oxalyl chloride (2) leads to the formation of 2,3-dioxo-2,3- dihydrofuran hydrochlorides 3 and 2,3-dioxo-2,3-dihydro-furanes 4, respectively. The structure of 3a was established by X-ray diffraction. The β-oxo-dibenzylamides 5 react with 2 regiospecifically to give the 2,3-dioxo-2,3-dihydrofuranes 6. Addition of water in 1,4-position to 6a yields hydroxy-enol 7, which forms bimolecular aggregates via intermolecular hydrogen bonds as shown by X-ray analysis. Intramolecular C,N-bisacylation of β-oxoamides 8 and malondiamides 11 with 2 leads to the pyrrol-2,5-dion

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22

Selvakumar, Balaraman, and Kuppanagounder P. Elango. "Synthesis of Non-Glutamate-Type Pyrrolo[2,3-d]Pyrimidines via Direct Aminocarbonylation of Aryl Halides Using Solid Co2(CO)8 as a CO Source and Their Antibacterial Activity." Journal of Chemical Research 41, no. 4 (2017): 230–34. http://dx.doi.org/10.3184/174751917x14894997017658.

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The synthesis of pyrrolo[2,3-d]pyrimidine derivatives by direct aminocarbonylation was demonstrated using solid Co2(CO)8 as a CO source in an autoclave at elevated temperature by reacting an aryl halide scaffold with a variety of amines. Using this method, 12 non-glutamate-type pyrrolo[2,3-d]pyrimidine analogues were prepared. Some compounds exhibited antibacterial activity against both Gram-positive and Gram-negative bacteria.

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23

Rogerio, Kamilla Rodrigues, Cedric Stephan Graebin, Luiza Helena Pinto Domingues, et al. "Novel Quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione Derivatives Against Chloroquine-resistant Plasmodium falciparum." Current Topics in Medicinal Chemistry 20, no. 2 (2020): 99–110. http://dx.doi.org/10.2174/1568026619666191019100711.

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Introduction: In this work DHPMs were combined with the quinoline nucleus to obtain new quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione compounds with improved antiplasmodial activity as well as decreased cytotoxicity. Nineteen quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione derivatives connected by a linker group to quinolone ring moieties with different substituents were synthesized and assayed against P. falciparum. Materials and Methods: Nineteen quinolinyl-pyrrolo[3,4-d]pyrimidine-2,5-dione derivatives connected by a linker group to quinoline ring moieties with different substituents were syn

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24

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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25

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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Shevchenko, Nadiya М., Oleksandr O. Severin, Maryna V. Kachaeva, Oleksandr Р. Kozachenko, Yevheniia S. Velihina, and Volodymyr S. Brovarets. "Synthesis of new pyrrolo[2,3-d]pyrimidine and thieno[2,3-d]pyrimidine derivatives of piperazin-1-yl-1,3-oxazole-4-carbonitriles, prediction and evaluation of their ADMET properties." Ukrainica Bioorganica Acta 19, no. 2 (2024): 21–32. https://doi.org/10.15407/bioorganica2024.02.021.

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The discovery of nucleoside antibiotics gave impetus to the development of the chemistry of pyrrolo[2,3-d]pyrimidines and thieno[2,3-d]pyrimidines as biologically active compounds. This work describes a universal and efficient approach to the synthesis of new pyrrolo[2,3-d]pyrimidine and thieno[2,3-d]pyrimidine derivatives of piperazin-1-yl-1,3-oxazole-4-carbonitriles. Their potential as biologically active compounds is considered and ADMET-score is predicted to assess their further application as pharmaceutical substances

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27

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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Kouhkan, Maryam, Ramin Javahershenas, and Jabbar Khalafy. "Biological Evaluation of Pyrrolo [3, 2-d] pyrimidine Derivatives as Antibacterial Agents against Pathogenic Bacteria." Biotechnology and Bioprocessing 2, no. 9 (2021): 01–05. http://dx.doi.org/10.31579/2766-2314/054.

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Background: Pyrimidine molecules' biological and chemotherapeutic importance in the medicinal world has been overlooked in many reports. We have previously synthesized new series of pyrrolo [3,2-d]pyrimidine derivatives (4a-4f) and here, we evaluate the antibacterial activity of these derivatives against Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and Salmonella bacteria. Materials and Methods: The agar well diffusion and agar dilution methods were used for determining inhibition zone diameter and minimum inhibitory concentration during preliminary evaluation of antimicrobi

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29

El-Ablak, F. Z., N. S. Abu-Elenein, and M. A. Sofan. "Synthesis of New Pyrrolo Heterocycles (I): Novel Synthesis of Pyrano[2,3-c]pyrrole, Isoindoline, Pyrrolo[3,4-b]pyridine, and Pyrrolo[3,4-d]pyrimidine Derivatives." Journal of Heterocyclic Chemistry 53, no. 6 (2015): 1999–2006. http://dx.doi.org/10.1002/jhet.2520.

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30

Latif, Muhammad, Byung Jin Byun, and Kwangho Lee. "Synthesis of 4‐(3,4‐dicarboxamido‐1H‐pyrrole)pyrimidines as Anaplastic Lymphoma Kinase Inhibitors." Bulletin of the Korean Chemical Society 36, no. 2 (2015): 520–25. http://dx.doi.org/10.1002/bkcs.10097.

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To explore non‐aniline aromatic substitution on the pyrimidine C4 position, novel 4‐(N,N′‐di‐n‐propyl‐3,4‐dicarboxamido‐1H‐pyrrole)pyrimidines are designed and synthesized as anaplastic lymphoma kinase inhibitors for non‐small cell lung cancer treatment. To overcome the unexpected cleavage between the C‐N linkage of pyrrole nitrogen and C4‐pyrimidine during hydrolysis and inaccessibility of the desired diamide formation through coupling agent‐mediated conditions, the 4‐(N,N′‐di‐n‐propyl‐3,4‐dicarboxamido‐1H‐pyrrole)pyrimidine was assembled through direct nucleophilic substitution under microwa

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31

Bakhale, Sunil C., and Pushpendra Tiwari. "Microwave-assisted synthesis and biological evaluation of some new 4-(2-phenylhydrazinyl)-7H-pyrrolo[2,3-d]pyrimidine derivatives." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 517. https://doi.org/10.59467/ijhc.2025.35.517.

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The present study details with the design, synthesis, and biological evaluation of 4-(2-phenylhydrazinyl)-7H-pyrrolo[2,3-d]pyrimidine derivatives (SB1-SB10). An optimized microwave-assisted synthesis protocol using ethanol as the solvent was developed, achieving 70-82% yields in 10-15 min at 150°C due to ethanol. The derivatives' biological potential was evaluated through in vitro antimicrobial assays, demonstrating promising antimicrobial activity. These findings suggest that SB1-SB10 derivatives could serve as model structures for developing new bioactive substances, supporting potential app

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32

Muzychka, Lyubov, Iryna Yaremchuk, Iryna Yaremchuk, and Oleg Smolii. "7-Substituted pyrrolo[2,3-d]pyrimidines for the synthesis of new 1-deazapyrimido[1,2,3-cd]purines." French-Ukrainian Journal of Chemistry 5, no. 2 (2017): 15–23. http://dx.doi.org/10.17721/fujcv5i2p15-23.

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Few examples of new heterocyclic 1-deazapyrimido[1,2,3-cd]purine derivatives were synthesized by intramolecular cyclization of methyl 7-(oxiran-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylates. The latter were obtained by iodolactonization of 7-allylpyrrolo[2,3-d]pyrimidine-6-carboxylic acids.

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33

Bandaru, Praveen Kumar, N. S. Kameswara Rao, and P. Shyamala. "Novel Pyrrolo-Pyrimidine Derivatives Bearing Amide Functionality as Potential Anticancer Agents: Synthesis and Molecular Docking Studies." Asian Journal of Chemistry 36, no. 12 (2024): 2827–36. https://doi.org/10.14233/ajchem.2024.32677.

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Current investigation presents the synthesis, molecular docking and anticancer evaluation of novel pyrrolo-pyrimidine derivatives designed to target Janus kinase 1 (JAK1), Janus kinase 2 (JAK2) and cyclin-dependent kinase 4 (CDK4). The synthesis route commenced with 2-amino-4,6-dichloropyrimidine-5-carbaldehyde, proceeding through sequential steps involving intermediate formations and coupling reactions to yield a diverse array of pyrrolo-pyrimidine derivatives. Characterization using spectroscopic techniques (1H NMR, 13C NMR and HRMS) confirmed the chemical structures of the synthesized compo

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34

Yadav, Vijay B., Pragati Rai, Hozeyfa Sagir, Akhilesh Kumar та I. R. Siddiqui. "A green route for the synthesis of pyrrolo[2,3-d]pyrimidine derivatives catalyzed by β-cyclodextrin". New Journal of Chemistry 42, № 1 (2018): 628–33. http://dx.doi.org/10.1039/c7nj03577b.

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35

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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36

Baumann, Marcus, Antonio M. Rodriguez Garcia, and Ian R. Baxendale. "Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines." Organic & Biomolecular Chemistry 13, no. 14 (2015): 4231–39. http://dx.doi.org/10.1039/c5ob00245a.

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Avasthi, Kamlakar, Lakshmi Shukla, Ruchir Kant, and Krishnan Ravikumar. "Folded conformations due to arene interactions in dissymmetric and symmetric butylidene-linker models based on pyrazolo[3,4-d]pyrimidine, purine and 7-deazapurine." Acta Crystallographica Section C Structural Chemistry 70, no. 6 (2014): 555–61. http://dx.doi.org/10.1107/s2053229614009449.

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The butylidene-linker models 1-[2-(2,6-dimethylsulfanyl-9H-purin-9-yl)-2-methylidenepropyl]-4,6-bis(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine, C18H20N8S4, (XI), 7,7′-(2-methylidenepropane-1,3-diyl)bis[3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one], C20H22N6O2S2, (XIV), and 7-[2-(4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-methylidenepropyl]-3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one, C19H21N7OS3, (XV), show folded conformations in solution, as shown by1H NMR analysis. This folding carries over to the crystalline state. Intramolecular π–π int

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Mounir, Salem, Magda Marzouk, and Naglaa Mahmoud. "Synthesis of various fused pyrimidine rings with their pharmacological and antimicrobial evaluation." Journal of the Serbian Chemical Society 79, no. 9 (2014): 1059–73. http://dx.doi.org/10.2298/jsc130528016m.

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Various fused pyrimidine such as furo[2,3-d]pyrimidine, triazolo[1,5-a]pyrimidine, tetrazolo[1,5-a]pyrimidine were synthesized from the reactions of thioxopyrimidine-6(1H)-ones with ethyl chloroacetate (under different reaction conditions), thiourea, and sodium nitrite. Pyrimidine thiones reacted with POCl3/PCl5 to give the chloro derivatives which reacted with sodium azide, and thiourea to give the tetrazolo[1,5-c]pyrimidine, pyrimido pyrimidine. Thioxopyrimidine-6(1H)-ones reacted with benzyl amine to give pyrrolo[2,3-d]pyrimidinethione. Theoretical calculation using MIDO/3, Fukui indices an

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39

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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40

Gaybullayev, Sh, A. Nasrullayev, R. Kuryazov, H. A. Aisa, N. Chao, and Kh Bozorov Bozorov. "IMPLEMENTATION OF THE TARGETED SYNTHESIS OF 6-SUBSTITUTED-4 AMINO-7H-PYRROLO[2,3-d]PYRIMIDINES AS JANUS KINASE INHIBITORS." 2022-yil 3-son (133/1) ANIQ FANLAR SERIYASI 1, no. 1 (2025): 41–45. https://doi.org/10.59251/2181-1296.2025.v1.149.2.3278.

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7H-Pyrrolo[2,3-d]pyrimidines or 7-deazapurines are analogs of purines, which are part of DNA and RNA found in the human body, and therefore exhibit a high level of biological activity. There are also several approved drugs containing the 7H-pyrrolo[2,3 d]pyrimidine nucleus, and most of them are used as Janus kinase inhibitors. This research work focuses on the synthesis of targeted compounds using molecular docking.

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41

El-Gaby, M. S. A., A. M. Gaber, A. A. Atalla, and K. A. Abd Al-Wahab. "Novel synthesis and antifungal activity of pyrrole and pyrrolo[2,3-d]pyrimidine derivatives containing sulfonamido moieties." Il Farmaco 57, no. 8 (2002): 613–17. http://dx.doi.org/10.1016/s0014-827x(01)01178-8.

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42

El-Bayouki, Khairy Abdelhameed Mohsen, Wahid Mohmoud Basyouni, and Eslam Attya Mostafa. "ChemInform Abstract: Synthesis of New Pyrrole and Pyrrolo[2,3-d]pyrimidine Derivatives of Potential Antioxidant Activity." ChemInform 42, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.201102179.

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Agarwal, Anshu, Meenakshi Sharma, Meenakshi Agrawal, and D. Kishore. "Expedient Protocols for the Installation of Pyrimidine Based Privileged Templates on 2-Position of Pyrrolo[2,1-c][1,4]-benzodiazepine Nucleus Linked Through a p-phenoxyl Spacer." E-Journal of Chemistry 9, no. 3 (2012): 1305–12. http://dx.doi.org/10.1155/2012/629414.

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Exceedingly facile single step expedient protocols based on the versatility and reactivity of corresponding intermediates : [2-(dimethylaminomethylene) ketone] (5) and chalcone (6), derived from 2-(p-acetyl phenoxyl) substituted analogue of pyrrolo[2,1-c][1,4]-benzodiazepine (4), have been developed to provide an easy installation of the pyrimidine based privileged templates at 2-position of pyrrolo[2,1-c][1,4]-benzodiazepine through a p-phenoxyl spacer, by utilizing the synthetic strategy depicted in schemes-1and2.

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44

Sim, MinHwi, Yong-Guy Kim, Jin-Hyung Lee, and Jintae Lee. "Antibiofilm Activities of Multiple Halogenated Pyrimidines Against Staphylococcus aureus." International Journal of Molecular Sciences 25, no. 23 (2024): 12830. http://dx.doi.org/10.3390/ijms252312830.

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Staphylococcus aureus, prevalent in hospital and community settings, forms biofilms that are highly resistant to antibiotics and immune responses, complicating treatment and contributing to chronic infections. These challenges underscore the need for novel treatments that target biofilm formation and effectively reduce bacterial virulence. This study investigates the antibiofilm and antimicrobial efficacy of novel halogenated pyrimidine derivatives against S. aureus, focusing on three compounds identified as potent biofilm inhibitors: 2,4-dichloro-5-fluoropyrimidine (24DC5FP), 5-bromo-2,4-dich

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45

Dommaraju, Yuvaraj, Somadrita Borthakur, Nimmakuri Rajesh, and Dipak Prajapati. "An efficient catalyst-free chemoselective multicomponent reaction for the synthesis of pyrimidine functionalized pyrrolo-annelated derivatives." RSC Advances 5, no. 31 (2015): 24327–35. http://dx.doi.org/10.1039/c5ra00796h.

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An efficient catalyst-free, one-pot multicomponent reaction has been developed for the synthesis of pyrimidine functionalized pyrrolo-annelated derivatives. The method offers easy and column free separation, mild reaction conditions and high yields.

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46

Bhusari, Nilesh, Abhay Bagul, Vipin Kumar Mishra, Aisha Tufail, Digambar Gaikwad, and Amit Dubey. "Sustainable synthesis of Schiff base derivatives via an ionic liquid and a microwave-assisted approach: structural, biological, and computational evaluation." RSC Advances 15, no. 28 (2025): 22764–88. https://doi.org/10.1039/d5ra02622a.

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A microwave-assisted method was developed for synthesizing novel 4-amino-pyrrolo[2,3-d]pyrimidine-based Schiff bases (APR1a–d), using ionic liquid [HMIM][TFSI] as both catalyst and solvent, offering a green and efficient approach.

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47

Tsupak, E. B., and M. A. Shevchenko. "[3,4]-annulated pyrroles 1. Polynuclear heterocyclic systems based on pyrrolo[3,4-d]pyrimidine-2,4-dione." Russian Chemical Bulletin 55, no. 12 (2006): 2265–70. http://dx.doi.org/10.1007/s11172-006-0581-8.

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48

Alzahrani, Abdullah Y. A., Wesam S. Shehab, Asmaa H. Amer, et al. "Correction: Design, synthesis, pharmacological evaluation, and in silico studies of the activity of novel spiro pyrrolo[3,4-d]pyrimidine derivatives." RSC Advances 14, no. 49 (2024): 36351. http://dx.doi.org/10.1039/d4ra90128b.

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Correction for ‘Design, synthesis, pharmacological evaluation, and in silico studies of the activity of novel spiro pyrrolo[3,4-d]pyrimidine derivatives’ by Abdullah Y. A. Alzahrani et al., RSC Adv., 2024, 14, 995–1008, https://doi.org/10.1039/D3RA07078F.

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Shaker, Raafat M., Kamal U. Sadek, Ebtisam A. Hafez, and Mohamed Abd Elrady. "5-Aminouracil as a Building Block in Heterocyclic Synthesis: Part IV. One-pot Synthesis of 1H-Pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione Derivatives Using Controlled Microwave Heating." Zeitschrift für Naturforschung B 66, no. 8 (2011): 843–49. http://dx.doi.org/10.1515/znb-2011-0810.

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An efficient and direct procedure for the synthesis of pyrrolo[2,3-d]pyrimidine-2,4-dione derivatives using controlled microwave heating has been described. The products were characterized by elemental analyses, IR, 1H NMR, 13C NMR and MS spectra.

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50

El Kaïm, Laurent, Laurence Grimaud, and Simon Wagschal. "Toward Pyrrolo[2,3-d]pyrimidine Scaffolds." Journal of Organic Chemistry 75, no. 15 (2010): 5343–46. http://dx.doi.org/10.1021/jo100759b.

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