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Journal articles on the topic '4-dihydropyrimidines'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

C. Heda, L. C., Rashmi Sharma, C. Pareek, and P. B. Chaudhari. "Synthesis and Antimicrobial Activity of Some Derivatives of 5-Substituted Indole Dihydropyrimidines." E-Journal of Chemistry 6, no. 3 (2009): 770–74. http://dx.doi.org/10.1155/2009/893812.

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P. Biginelli reported the synthesis of functionalized 3, 4 dihydropyrimidine-2 (1H)-ones via three component condensation of an aromatic aldehyde, urea and ethylacetoacetate. This multicomponent reaction is of much importance due to excellent pharmacological properties of dihydropyrimidines. In this account, we synthesized some halo substituted indole dihydropyrimidines and evaluated their antimicrobial activity. The minimum inhibitory concentration (MIC) was determined by micro dilution technique in Mueller-Hinton broth. The MICs were recorded after 24 hours of incubation at 37 °C. These results are promising, showing these compounds are biologically active.

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2

Cho, Hidetsura, Yoshio Nishimura, Yoshizumi Yasui, Satoshi Kobayashi, Shin-ichiro Yoshida, Eunsang Kwon, and Masahiko Yamaguchi. "Synthesis of 4-unsubstituted dihydropyrimidines. Nucleophilic substitution at position-2 of dihydropyrimidines." Tetrahedron 67, no. 14 (April 2011): 2661–69. http://dx.doi.org/10.1016/j.tet.2011.01.092.

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3

Vedernikova, Irina V., Achiel Haemers, and Yuryi I. Ryabukhin. "Synthesis of 4-oxopyrimidinium and 4-oxo-1,4-dihydropyrimidines." Journal of Heterocyclic Chemistry 36, no. 1 (January 1999): 97–104. http://dx.doi.org/10.1002/jhet.5570360115.

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4

Povstyanoy, V. M., T. A. Yuyrova, A. N. Retchitskiy, and A. A. Krysko. "ALTERNATIVE METHODS OF SYNTHESIS OF NOVEL HETEROSYNTHONES – FUNCTIONALIZED HYPOXANTHINE PYRIMIDINES." Odesa National University Herald. Chemistry 26, no. 2(78) (July 31, 2021): 32–39. http://dx.doi.org/10.18524/2304-0947.2021.2(78).233823.

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It has been known that derivatives of dihydropyrimidine and xanthine possess the physiological activity of the wide spectrum of action. The combination of the specified heterocyclic fragments within one molecule can lead to the increase of its known types of biological activity as well as to the discovery of novel types of activity. We have previously reported the synthesis of intermediates, which consist of functionalized dihydropyrimidines, connected via a methylene bridge with the halogen substituted derivatives of the ophylline, 3-methylxanthine and imidazole. It was also observed that these compounds would react with N‑nucleophiles with the formation of various branched and cyclic products. The aim of this work was to determine the optimal conditions for obtaining heterocyclic products as a result of conjugation of bromomethyldihydropyrimidine and hypoxanthine at the positions C6 and C1 via a methylene bridge. It is important to note, that the latter can be widely modified by using structurally diverse aromatic aldehydes during the synthesis of dihydropyrimidine core by using Biginelli reaction, which explains structural diversity of the reaction products. After having tried various reaction conditions, we have concluded that the optimal method for obtaining the products entailed keeping equimolar ratios of bromomethyl substituted dihydropyrimidines and 1-potassium‑2-chloro‑7-methylhypoxanthine in dry ethanol for 4 hours. The ester group at the C5 of dihydropyrimidine ring and a chlorine leaving group at C2 of hypoxanthine fragments of the molecule allow to consider these structures as pro missing synthons for farther synthesis of condensed pyrimidine and xanthine systems. The structures of novel compounds have been confirmed with the methods such as HPLC/MS, 1H, and 13C NMR spectroscopy.

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5

Cho, Hidetsura, Yoshio Nishimura, Yoshizumi Yasui, Satoshi Kobayashi, Shin-ichiro Yoshida, Eunsang Kwon, and Masahiko Yamaguchi. "ChemInform Abstract: Synthesis of 4-Unsubstituted Dihydropyrimidines. Nucleophilic Substitution at Position-2 of Dihydropyrimidines." ChemInform 42, no. 33 (July 22, 2011): no. http://dx.doi.org/10.1002/chin.201133157.

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6

Lin, Yun, Jin-Tao Liu, and Xian-Jin Yang. "One-pot Synthesis of 4-Trifluoromethyl-1,2-dihydropyrimidines." Chinese Journal of Chemistry 25, no. 1 (January 2007): 113–15. http://dx.doi.org/10.1002/cjoc.200790003.

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7

Vedernikova, Irina V., Achiel Haemers, and Yuryi I. Ryabukhin. "ChemInform Abstract: Synthesis of 4-Oxopyrimidinium and 4-Oxo-1,4-dihydropyrimidines." ChemInform 30, no. 32 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199932155.

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8

Khan, M. Wahab, and Nitya G. Kundu. "An Expeditious Synthesis of 4-Acyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidines (6-acyl uracils) and 4-Acyl-6-aryl-2-oxo-2,3-dihydropyrimidines." Journal of Chemical Research 23, no. 1 (January 1999): 20–21. http://dx.doi.org/10.1177/174751989902300116.

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A facile synthesis of 4-acyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidines (6-acyl uracils) and 4-acyl-6-aryl-2-oxo-2,3-dihydropyrimidines is described where the Friedel–Crafts reaction on 2,6-dichloropyrimidine-4-carbonyl chloride plays a crucial role.

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9

Mehrabi, Hossein, Tayebeh Yarahmadi, and Farzaneh Alizadeh Bami. "Synthesis of 4-aryl-2-Thioxo-3,4-Dihydropyrimidines Using a Three-Component Reaction of Meldrum's Acid with Arylaldehydes and Acetylthiourea." Journal of Chemical Research 42, no. 6 (June 2018): 326–28. http://dx.doi.org/10.3184/174751918x15293155829494.

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A one-pot method for the preparation of new 4-aryl-2-thioxo-3,4-dihydropyrimidines via a three-component reaction of Meldrum's acid with arylaldehydes and acetylthiourea in the presence of p-toluenesulfonic acid as catalyst in CH3CN under reflux is reported.

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10

Yavari, Issa, Asiyeh Amirahmadi, and Mohammad Halvagar. "A Synthesis of Functionalized Thiazoles and Pyrimidine-4(3H)-thiones from 1,1,3,3-Tetramethylguanidine, Acetylenic Esters, and Aryl Isothiocyanates." Synlett 28, no. 19 (August 25, 2017): 2629–32. http://dx.doi.org/10.1055/s-0036-1590862.

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Aryl isothiocyanates react with dialkyl 2-{[bis(dimethylamino)methylene]amino}maleates, generated from 1,1,3,3-tetramethylguanidine and acetylenic esters, to afford 2-(dimethylamino)-1,3-thiazole derivatives, functionalized 2-(dimethylamino)-6-thioxo-1,6-dihydropyrimidines, and ethyl 2-(dimethylamino)-6-[(4-nitrophenyl)imino]-4-phenyl-6H-1,3-thiazine-5-carboxylate, in moderate to good yields.

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11

Kadysh, V., J. Stradins, H. Khanina, and G. Duburs. "Electrochemical oxidation of 4-aryl-1,4-dihydropyrimidines on a carbon electrode." Electrochimica Acta 34, no. 7 (July 1989): 899–904. http://dx.doi.org/10.1016/0013-4686(89)80014-3.

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12

Kumar, R., V. K. Sehgal, B. Kaur, and R. Kaur. "Cardiodepressant Activity of Newer Dihydropyrimidine Derivative in Comparison to Nifedipine on Perfused Rabbits Heart." International Journal of Medical and Dental Sciences 1, no. 2 (July 1, 2012): 6. http://dx.doi.org/10.18311/ijmds/2012/18695.

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<p><strong>Background</strong>: Substituted dihydropyridine calcium channel blockers are used in the treatment of cardiovascular diseases. Dihydropyridines are considered as analogue of dihydropyrimidines.</p><p><strong>Objectives</strong>: In present study newly synthesized test compound 5- Acyl-6-methyl-4(2',3'-methylenedioxy) phenyl - 2 - S - ethyl - 1, 4- dihydropyrimidine, a dihydropyrimidine derivative was investigated with an aim to get valuable substitute for the well known dihydropyridine, Nifedipine.</p><p><strong>Material & Methods</strong>: The Calcium Channel blocking actiuity of test compound was studied on Rabbit's Heart and its effects were compared with Nifedipine used as control.</p><p><strong>Results</strong>: Test compound has dose-dependent negative chronotropic and negative inotropic effect on Rabbit's heart but these effects appeared at doses higher than those of Nifedipine. Test compound had no significant change in coronary flow however Nifedipine show significant increase in coronary flow at lower doses.</p><p><strong>Conclusion</strong>: Test compound appears to be less potent myocardial depressant compared to Nifedipine. Test compound produced calcium channel blocking activity which was dose related and in order to ascertain the status of this compound as a drug, further studies are needed not only in other animals and tissue models but also in various pathophysiological models.</p>

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13

Sarode, Varsha I., and Ritesh P. Bhole. "Synthesis, Characterization of 2-Methylthio-1, 4-dihydropyrimidines for its Antibacterial potential." Research Journal of Pharmacy and Technology 12, no. 4 (2019): 1585. http://dx.doi.org/10.5958/0974-360x.2019.00263.4.

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14

Kim, Yong Hae, and Byoung Uk Lim. "A novel tautomerism in alkyl dihydropyrimidines : observation of tautomerism by H-D exchange of 2- and/or 4-methyl protons of dihydropyrimidines in CD3OD." Tetrahedron Letters 32, no. 18 (April 1991): 2057–60. http://dx.doi.org/10.1016/s0040-4039(00)78907-6.

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15

Védernikova, I. V., Yu I. Ryabukhin, M. I. Haitin, and Yu N. Simkina. "Synthèse et Identification des 4-OXO-1,4-Dihydropyrimidines en vue des Applications Pharmacologiques." Bulletin des Sociétés Chimiques Belges 100, no. 6 (September 1, 2010): 487–92. http://dx.doi.org/10.1002/bscb.19911000608.

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16

Zhdanov, Yu A., I. V. Vedernikova, Yu N. Simkina, Yu I. Ryabukhin, M. I. Khaitin, G. A. Korol'chenko, I. A. Il'chenko, and E. I. Sadekova. "Synthesis and psychotropic activity of 4-oxo-1-[hydroxy(acetoxy)phenyl]-1,4-dihydropyrimidines." Pharmaceutical Chemistry Journal 23, no. 5 (May 1989): 378–83. http://dx.doi.org/10.1007/bf00758288.

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17

van der Stoel, R. E., H. C. van der Plas, and H. Jongejan. "Photochemical ring contraction of 4-heteroaryl-substituted 1,4(or 3,4)-dihydropyrimidines into imidazoles." Recueil des Travaux Chimiques des Pays-Bas 102, no. 7-8 (September 2, 2010): 364–67. http://dx.doi.org/10.1002/recl.19831020706.

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18

Guo, Yongbiao, Chuanpin Zou, Zhenhua Gao, Xiangyan Meng, Guilan Huang, Hui Zhong, Huilan Yu, Xiaoqin Ding, and Hui Tang. "Highly Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by Chiral Phosphoric Acids." Synlett 28, no. 15 (June 7, 2017): 2041–45. http://dx.doi.org/10.1055/s-0036-1588853.

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Several chiral phosphoric acids were evaluated as organocatalysts for the enantioselective Biginelli reaction of aliphatic aldehydes. With a chiral phosphoric acid derived from 3,3′-bis(3,5-di-tert-butyl-4-methoxyphenyl)-1,1′-binaphthalene-2,2′-diol, and after extensive optimization of the reaction conditions, the corresponding dihydropyrimidines were obtained in moderate to high yields with 73–87% ee by a three-component reaction of an aliphatic aldehyde, urea, and a β-keto ester.

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19

Memarian, H. R., and S. Amini. "Computational Studies on the Rotamers of 4-Aryl-2-Oxo-1,2,3,4-Tetrahydropyrimidines and 4-Aryl-2-Oxo-1,2-Dihydropyrimidines." Journal of Structural Chemistry 60, no. 3 (March 2019): 377–93. http://dx.doi.org/10.1134/s0022476619030053.

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20

Lorente, A., J. L. García Navío, J. J. Vaquero, and J. L. Soto. "Synthesis of heterocyclic compounds. XXXIX. Synthesis of 5-cyano-2-phenyl-4-thioxo-3,4-dihydropyrimidines." Journal of Heterocyclic Chemistry 22, no. 1 (January 1985): 49–51. http://dx.doi.org/10.1002/jhet.5570220113.

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21

Karade, Nandkishor N., Sumit V. Gampawar, Nilesh P. Tale, and Sanjay B. Kedar. "ChemInform Abstract: Mild and Efficient Oxidative Aromatization of 4-Substituted-1,4-dihydropyrimidines Using (Diacetoxyiodo)benzene." ChemInform 41, no. 44 (October 7, 2010): no. http://dx.doi.org/10.1002/chin.201044164.

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22

Ajumeera, Rajanna, Ganapathi Thipparapu, Shireesha Boyapati, Bharath Singh Padya, and Vijayalaxmi Venkatesan. "Synthesis and Evaluation of Triazolyl Dihydropyrimidines as Potential Anticancer Agents." International Journal of Chemistry 10, no. 4 (November 8, 2018): 18. http://dx.doi.org/10.5539/ijc.v10n4p18.

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Novel N – triazolyl 3(a-f) and O-triazolyl (4a-f) derivatives of 4, 6-diaryl-1, 4-dihydropyrimidines were synthesized through mannich reaction. All compounds were characterized by physical and spectral data. These compounds were screened for in vitro efficiency in human breast cancer cell (MCF-7&MDA-MB-231) lines and found to have very good anti-proliferative activity.  Among all compounds of 4b, 3e, 4e endowed with lesser respective IC50 values of 31.94, 55.73, 55.03 µM in MCF-7 cells and 41.50, 35.28, 32.06 µM in MDA-MB 231 cells by MTT assay. In further studies, Compounds 4b, 3e, 4e were found to arrest cell growth at S phase in MCF-7 cells. In MDA-MB 231 cells, 4b, 4e were found to arrest the cells in S phase, and compound 3e found to arrest G2/M phase when compared to the standard drug tamoxifen, arrested S phase in MCF-7 cells and G0/G1 phase in MDA-MB 231 cells.

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23

Mahran, Asma Mohamed, Nasser Abdelhamid Hassan, Dalia Ahmed A. Osman, Sherif Shaban Ragab, and Allam Abdelhamid Hassan. "Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil." Zeitschrift für Naturforschung C 71, no. 5-6 (May 1, 2016): 133–40. http://dx.doi.org/10.1515/znc-2015-0265.

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Abstract Starting from 6-aryl-5-cyano-2-thiouracil derivative 1a–f, a series of novel thiazolo[3,2-a]pyrimidines 4a–f were synthesized. The mechanism and the regioselectivity of the studied reactions are discussed. In addition, a series of tetrahydro-4-H-pyrimido[2,1-b][1,3]thiazines 7a–e and 2-((ethoxymethyl)thio)-4-aryl-1,6-dihydropyrimidines 9b,c,e were synthesized. The anti-microbial activities of some of the prepared compounds were screened, and the results revealed that compounds 3c and 4c were more active than the standard (Ampicillin) against gram positive bacteria (Pseudomonas aeruginosa). Moreover, compounds 4b,e and 3f were found to be good antifungal agents against the studied fungal strains.

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24

Remennikov, G. Ya, I. V. Boldyrev, S. A. Kravchenko, and V. V. Pirozhenko. "Synthesis and some conversions of 4-aryl-6-methyl-2-methoxy(phenyl)-5-nitro-1,4-dihydropyrimidines." Chemistry of Heterocyclic Compounds 29, no. 10 (October 1993): 1200–1205. http://dx.doi.org/10.1007/bf00538068.

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25

Zhu, Jie, Mingjie Zhang, Bo Liu, and Xiaojuan Li. "New Ytterbium Complex-catalyzed Multicomponent Reactions for Synthesis of Dihydropyrimidines: [4+2] Cycloaddition vs. Biginelli Type Reaction." Chemistry Letters 38, no. 1 (January 5, 2009): 56–57. http://dx.doi.org/10.1246/cl.2009.56.

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26

Ivanov, A. S., N. Z. Tugusheva, L. M. Alekseeva, and V. G. Granik. "Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines." Russian Chemical Bulletin 53, no. 4 (April 2004): 873–81. http://dx.doi.org/10.1023/b:rucb.0000037857.07190.75.

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27

Ahmad, Muhammad Jawad, Syed Fahad Hassan, Riffat Un Nisa, Khurshid Ayub, Muhammad Shahid Nadeem, Samina Nazir, Farzana Latif Ansari, Naveeda Akhtar Qureshi, and Umer Rashid. "Synthesis, in vitro potential and computational studies on 2-amino-1, 4-dihydropyrimidines as multitarget antibacterial ligands." Medicinal Chemistry Research 25, no. 9 (July 14, 2016): 1877–94. http://dx.doi.org/10.1007/s00044-016-1613-z.

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28

Khan, M. Wahab, and Nitya G. Kundu. "An Expeditious Synthesis of 4-Acyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidines (6-acyl uracils) and 4-Acyl-6-aryl-2-oxo-2,3-dihydropyrimidines." Journal of Chemical Research, no. 1 (1999): 20–21. http://dx.doi.org/10.1039/a806787b.

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29

Lorente, Antonio, José L. Garcia Navio, Luis Fuentes, and José L. Soto. "Synthesis of 6-Aryl-5-isopropoxycarbonyl-4-thioxo-3,4-dihydropyrimidines from 3-Substituted Alkyl 2-Cyano-3-thiocarboxamidopropenoates." Synthesis 1985, no. 01 (1985): 86–89. http://dx.doi.org/10.1055/s-1985-31120.

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30

Elumalai, Karthikeyan, Mohammed Ashraf Ali, Manogaran Elumalai, Kalpana Eluri, and Sivaneswari Srinivasan. "Design, synthesis and antimycobacterial activity of some novel 3,5-dichloro-2-ethoxy-6-fluoropyridin-4 amine cyclocondensed dihydropyrimidines." Journal of Pharmacy Research 7, no. 3 (March 2013): 241–45. http://dx.doi.org/10.1016/j.jopr.2013.03.016.

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31

Khan, M. Wahab, and Nitya G. Kundu. "ChemInform Abstract: An Expeditious Synthesis of 4-Acyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidines (6-Acyl uracils) and 4-Acyl-6-aryl-2-oxo-2,3-dihydropyrimidines." ChemInform 30, no. 25 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199925146.

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32

Dobosz, Robert, and Ryszard Gawinecki. "Quantum chemical prediction of structure and stability of the benzodihydropyrimidine tautomers." Journal of Theoretical and Computational Chemistry 13, no. 07 (November 2014): 1450056. http://dx.doi.org/10.1142/s0219633614500564.

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B3LYP/maug-cc-pVTZ and MP2/maug-cc-pVTZ calculations show that 3,4-dihydro-quinazoline and its 2- and/or 4-methyl and -phenyl substituted derivatives in solution (chloroform, DMSO, methanol) are only by 0.3 kcal/mol–2.2 kcal/mol more stable than the respective tautomeric 1,4-dihydroquinazolines (the available literature experimental stability data are not coherent). In the gas phase, 2- and/or 4-substituted tautomers of 3,4-dihydroquinazoline are also energetically preferred (B3LYP/maug-cc-pVTZ, MP2/maug-cc-pVTZ and CCSD/cc-pVDZ calculations lead to the same conclusion). In vacuum, 1,4-dihydro tautomer is by 0.1 kcal/mol–0.2 kcal/mol more stable only for unsubstituted dihydro-quinazoline. The observed tautomeric preference was found almost independent on substitution and solvent used. The optimization procedure used shows that the pyrimidine ring in dihydropyrimidines studied is not planar. Noncoplanarity of the 2-phenyl ring and C = N bond in the respective compounds studied is responsible for the weakened conjugation of these two moieties.

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33

E. Ali, Tarik, Mohammed A. Assiri, Mamdouh M. Ali, Abeer E. M. Ali, Ibrahim S. Yahia, and Heba Y. Zahran. "Efficient Synthesis and Anticancer Activities of Some Novel Functionalized (4-Oxo-4H-chromen-3-yl)-2-selenoxo-1,2-dihydropyrimidines." HETEROCYCLES 100, no. 11 (2020): 1831. http://dx.doi.org/10.3987/com-20-14324.

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34

Yu, Han, Peng Xu, Huihong He, Jun Zhu, Hualin Lin, and Sheng Han. "Highly enantioselective Biginelli reactions using methanopyroline/thiourea – based dual organocatalyst systems: asymmetric synthesis of 4-substituted unsaturated aryl dihydropyrimidines." Tetrahedron: Asymmetry 28, no. 2 (February 2017): 257–65. http://dx.doi.org/10.1016/j.tetasy.2016.11.015.

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35

Kappe, C. Oliver. "Highly versatile solid phase synthesis of biofunctional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage." Bioorganic & Medicinal Chemistry Letters 10, no. 1 (January 2000): 49–51. http://dx.doi.org/10.1016/s0960-894x(99)00572-7.

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36

MA, Zhengyue, Guoying YAN, Shiguo ZHU, Gengliang YANG, and Duqiang LUO. "Cyclocondensation Reations of 3-Amino-1,2,4-triazole with 3-(Benzylidene)-6-fluoro-thiochroman-4-ones to Tetracyclically Fused Dihydropyrimidines and Pyrimidines." Chinese Journal of Chemistry 27, no. 5 (May 2009): 987–92. http://dx.doi.org/10.1002/cjoc.200990168.

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37

Tong, Shuo, Qian Wang, Mei-Xiang Wang, and Jieping Zhu. "Switchable [3+2] and [4+2] Heteroannulation of Primary Propargylamines with Isonitriles to Imidazoles and 1,6-Dihydropyrimidines: Catalyst Loading Enabled Reaction Divergence." Chemistry - A European Journal 22, no. 24 (May 3, 2016): 8332–38. http://dx.doi.org/10.1002/chem.201601560.

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38

Nishimura, Yoshio, and Hidetsura Cho. "Synthesis of 4-unsubstituted dihydropyrimidines having acyl and alkoxycarbonyl groups at 5- and 6-positions by cyclization–elimination reactions using 1,3-diaza-1,3-butadienes." Tetrahedron Letters 55, no. 2 (January 2014): 411–14. http://dx.doi.org/10.1016/j.tetlet.2013.11.038.

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39

Nishimura, Yoshio, and Hidetsura Cho. "ChemInform Abstract: Synthesis of 4-Unsubstituted Dihydropyrimidines Having Acyl and Alkoxycarbonyl Groups at 5- and 6-Positions by Cyclization-Elimination Reactions Using 1,3-Diaza-1,3-butadienes." ChemInform 45, no. 25 (June 5, 2014): no. http://dx.doi.org/10.1002/chin.201425177.

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40

Al-Wahaibi, Lamya H., Althaf Shaik, Mohammed A. Elmorsy, Mohammed S. M. Abdelbaky, Santiago Garcia-Granda, Subbiah Thamotharan, Vijay Thiruvenkatam, and Ali A. El-Emam. "Structural Insights of Three 2,4-Disubstituted Dihydropyrimidine-5-carbonitriles as Potential Dihydrofolate Reductase Inhibitors." Molecules 26, no. 11 (May 29, 2021): 3286. http://dx.doi.org/10.3390/molecules26113286.

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In this report, we describe the structural characterization of three 2,4-disubstituted-dihydropyrimidine-5-carbonitrile derivatives, namely 2-{[(4-nitrophenyl)methyl]sulfanyl}-6-oxo-4-propyl-1,6-dihydropyrimidine-5-carbonitrile 1, 4-(2-methylpropyl)-2-{[(4-nitrophenyl)methyl]sulfanyl}-6-oxo-1,6-dihydropyrimidine-5-carbonitrile 2, and 2-[(2-ethoxyethyl)sulfanyl]-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile monohydrate 3. An X-ray diffraction analysis revealed that these compounds were crystallized in the centrosymmetric space groups and adopt an L-shaped conformation. One of the compounds (3) crystallized with a water molecule. A cyclic motif (R22(8)) mediated by N–H···O hydrogen bond was formed in compounds 1 and 2, whereas the corresponding motif was not favorable, due to the water molecule, in compound 3. The crystal packing of these compounds was analyzed based on energy frameworks performed at the B3LYP/6-31G(d,p) level of theory. Various inter-contacts were characterized using the Hirshfeld surface and its associated 2D-fingerprint plots. Furthermore, a molecular docking simulation was carried out to assess the inhibitory potential of the title compounds against the human dihydrofolate reductase (DHFR) enzyme.

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41

Fathima, Nikhath, H. Nagarajaiah, and Noor Shahina Begum. "Methyl 4-(4-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (February 15, 2014): o306. http://dx.doi.org/10.1107/s1600536814002888.

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In the title molecule, C13H14N2O3S, the dihydropyrimidine ring is in a flattened sofa conformation, with the methine C atom forming the flap. The dihedral angle between the mean plane of the five essentially planar atoms of the dihydropyrimidine ring [maximum deviation = 0.056 (4) Å] and the benzene ring is 89.4 (2)°. The O atom of the carbonyl group is in atransconformation with respect to the C=C bond of the dihydropyrimidine ring. In the crystal, N—H...O and O—H...S hydrogen bonds connect molecules, forming a two-dimensional network parallel to (001).

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42

Rovnyak, George C., Karnail S. Atwal, Anders Hedberg, S. David Kimball, Suzanne Moreland, Jack Z. Gougoutas, Brian C. O'Reilly, Joseph Schwartz, and Mary F. Malley. "Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents." Journal of Medicinal Chemistry 35, no. 17 (August 1992): 3254–63. http://dx.doi.org/10.1021/jm00095a023.

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43

Mohamed, Mosaad, Samir Awad, and Naglaa Ahmed. "Synthesis and antimicrobial evaluation of some 6-aryl-5-cyano-2-thiouracil derivatives." Acta Pharmaceutica 61, no. 2 (June 1, 2011): 171–85. http://dx.doi.org/10.2478/v10007-011-0019-1.

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Synthesis and antimicrobial evaluation of some 6-aryl-5-cyano-2-thiouracil derivativesA series of 6-aryl-5-cyano-2-thiouracil derivatives (1a-d) was synthesized by the reaction of ethyl cyanoacetate with thiourea and aldehydes. These products were used as intermediate compounds for the synthesis of a number of thiouracil derivatives (2a-dto10a-d). All compounds were screened for antibacterial and antifungal activities. Some of the prepared compounds, 6-(4-fluorophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide (2a), 4-oxo-2-thioxo-6-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxamide (2d), 6-(4-fluorophenyl)-4-hydrazino-2-thioxo-1,2-dihydropyrimidine-5-cabonitrile (7a) and 4-hydrazino-2-thioxo-6-(3,4,5-trimethoxyphenyl)-1,2-dihydropyrimidine-5-carbonitrile (7d) revealed promising antimicrobial activity.

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44

Suwito, Hery, Noorma Kurnyawaty, Ellyca Susetyo, Yuzkiya Azizah, Kautsar Ul Haq, Alfinda Novi Kristanti, and Indriani Indriani. "(E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxy-phenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one and (E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one." Molbank 2019, no. 2 (June 4, 2019): M1063. http://dx.doi.org/10.3390/m1063.

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Dihydropyrimidine derivatives possess great potential to be used as a precursor for the synthesis of wide diverse dihydropyrimidine-like derivatives. In this research, the title compounds were synthesized through the reaction between 5-acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione and 2,5-dimethoxybenzladehyde under aldol condensation condition. The title compound, (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)]}prop-2-en-1-one (yield 15%), was obtained as major product, whereas (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro pyrimidin-5-yl)]}prop-2-en-1-one (yield 8%) as side product through vinylogous aldol condensation.

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45

Begum, Noor Shahina, and D. E. Vasundhara. "Synthesis, Spectroscopic and Crystal Structure Analysis of Two Dihydropyrimidines." Journal of Chemical Research 2009, no. 4 (April 2009): 201–4. http://dx.doi.org/10.3184/030823409x425064.

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The preparation of two reduced pyrimidine derivatives, ethyl 3-acetyl-4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate and ethyl 4-(3,4-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate, is described, along with details of their crystal structure analysis.

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46

Nizam Mohideen, M., A. Rasheeth, and C. A. M. A. Huq. "Ethyl 2-allylsulfanyl-4-(4-methoxyphenyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate." Acta Crystallographica Section E Structure Reports Online 64, no. 9 (August 23, 2008): o1812. http://dx.doi.org/10.1107/s1600536808026664.

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47

Anuradha, N., A. Thiruvalluvar, K. Pandiarajan, S. Chitra, and R. J. Butcher. "5-Acetyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-thione." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (November 7, 2009): o3036. http://dx.doi.org/10.1107/s160053680904639x.

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48

Anuradha, N., A. Thiruvalluvar, K. Pandiarajan, S. Chitra, and R. J. Butcher. "5-Acetyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyrimidine-2(1H)-thione." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (February 21, 2009): o564—o565. http://dx.doi.org/10.1107/s1600536809005029.

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49

ROVNYAK, G. C., K. S. ATWAL, A. HEDBERG, S. D. KIMBALL, S. MORELAND, J. Z. GOUGOUTAS, B. C. O'REILLY, J. SCHWARTZ, and M. F. MALLEY. "ChemInform Abstract: Dihydropyrimidine Calcium Channel Blockers. Part 4. Basic 3- Substituted 4-Aryl-1,4-dihydropyrimidine-5-carboxylic Acid Esters. Potent Antihypertensive Agents." ChemInform 24, no. 1 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199301205.

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50

Toma, Štefan, Martin Putala, and Marta Sališová. "Ultrasound-accelerated synthesis of ferrocene-containing pyrimidine derivatives." Collection of Czechoslovak Chemical Communications 52, no. 2 (1987): 395–98. http://dx.doi.org/10.1135/cccc19870395.

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The base-catalysed addition of thiourea to ferrocene analogues of chalcones is faster and more selective when the reaction mixture is sonicated than when merely heated. 4-Aryl-6-ferrocenyl- and 6-aryl-4-ferrocenyl-3,4-dihydropyrimidine-2(1H)-tyhiones were isolated in 58-79% yields.

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