H. O. Foroughi et al.
6‑Amino‑5‑[(3‑chlorophenyl)(4‑hydroxy‑2‑oxo‑2H‑chromen‑
3‑yl)methyl]‑1,3‑dimethylpyrimidine‑2,4(1H,3H)‑dione
(4c, C22H18ClN3O5) White solid; yield 0.396 g (90%); m.p.:
252–254 °C; 1H NMR (250 MHz, DMSO-d6): δ=3.13 (s,
3H, N-CH3), 3.36 (s, 3H, N-CH3), 5.63 (s, 1H, CH), 7.12
(d, 1H, J=7 Hz, Ar–H), 7.19–7.25 (m, 3H, Ar–H and NH2),
7.28–7.36 (m, 3H, Ar–H and NH2), 7.41 (d, 1H, J=8.25 Hz,
Ar–H), 7.62 (dt, 1H, J1 =8.5 Hz, J2 =1.25 Hz, Ar–H), 7.83
(dd, 1H, J1 =8 Hz, J2 =1.25 Hz, Ar–H), 13.97 (br, 1H, OH)
ppm; 13C NMR (62.5 MHz, DMSO-d6): δ=28.18 (N-CH3),
30.50 (N-CH3), 35.90 (CH), 86.31, 104.32, 116.08, 116.84,
123.68, 124.25, 125.20, 125.75, 126.27, 129.78, 132.42,
132.95, 141.25, 149.98, 151.92, 155.17, 163.76 (C = O),
164.01 (C = O), 165.58 (C = O) ppm; IR (KBr): ꢀ = 3386,
3354, 3232, 1701, 1643, 1604, 1562, 1508, 1353, 1203,
1064, 894, 775 cm−1.
References
1. Okuhara T, Noritaka M, Makoto M (1996) Catalytic chemis-
try of heteropoly compounds. Advances in catalysis. Academic
Press, London, p 113
2. Mizuno N, Misono M (1997) CurrOpin Solid State Mater Sci 2:84
3. Dömling A (2002) Curr Opin Chem Biol 6:306
4. Weber L (2002) Curr Med Chem 9:2085
5. Zarenezhad E, Rad MN, Mosslemin MH, Tabatabaee M,
Behrouz S (2014) J Chem Res 38:607
6. Gourdeau H, Leblond L, Hamelin B, Desputeau C, Dong K,
Kianicka I, Custeau D, Boudreau C, Geerts L, Cai SX, Drewe J
(2004) Mol Cancer Ther 3:1375
7. Cheng JF, Ishikawa A, Ono Y, Arrhenius T, Nadzan A (2003)
Bioorg Med Chem Lett 13:3647
8. Sangani CB, Shah NM, Patel MP, Patel RG (2012) J Serbian
Chem Soc 77:1165
9. Thomas N, Zachariah SM (2013) Asian J Pharm Clin Res 6:11
10. Pasunooti KK, Chai H, Jensen CN, Gorityala BK, Wang S, Liu
XW (2011) Tetrahedron Lett 52:80
11. Dansena HA, Dhongade HJ, Chandrakar K (2015) Asian J
Pharm Clin Res 8:171
6‑Amino‑5‑[(4‑hydroxy‑2‑oxo‑2H‑chromen‑3‑yl)(m‑tolyl)‑
methyl]‑1,3‑dimethylpyrimidine‑2,4(1H,3H)‑dione (4g,
C23H21N31O5) White solid; yield 0.377 g (90%); m.p.: 170–
173 °C; H NMR (250 MHz, DMSO-d6): δ = 2.29 (s, 3H,
CH3), 3.33 (s, 3H, N-CH3), 3.56 (s, 3H, N-CH3), 5.71 (s, 1H,
CH), 6.41 (s, 2H, NH2), 7.00 (t, 3H, J=8.75 Hz, Ar–H), 7.17
(t, 1H, J=7.5 Hz, Ar–H), 7.32 (t, 2H, J=8.25 Hz, Ar–H),
7.54–7.60 (m, 1H, Ar–H), 8.00 (d, 1H, J = 8 Hz, Ar–H),
13.42 (s, 1H, OH) ppm; 13C NMR (62.5 MHz, DMSO-d6):
δ = 21.67 (CH3), 28.71 (N-CH3), 29.80 (N-CH3), 36.41
(CH), 86, 104.39, 116.22, 123.33, 124.27, 124.55, 126.86,
127.13, 128.26, 132.21, 133.52, 137.33, 144.69, 150.80,
152.36, 154.41, 164.64 (C = O), 165.11 (C = O), 167.66
(C=O) ppm; IR (KBr): ꢀ =3398, 3332, 3228, 1701, 1616,
1559, 1506, 1205, 1047, 763 cm−1.
12. Rad MN, Behrouz S, Zarenezhad E, Kaviani N (2015) J Iran
Chem Soc 12:1603
13. Gleckman R, Blagg N, Joubert DW (1981) J Human Pharmacol
Drug Ther 1:14
14. Song H, Shin HS, Park KI (1998) Acta Crystallogr Sect C
54:1915
15. Radha S, Mothilal KK, Thamaraichelvan A, Elangovana A
(2016) J Chem Pharm Res 8:202
16 Kaur R, Kaur P, Sharma S, Singh G, Mehndiratta S, Bedi P,
Nepali K (2015) Recent Pat Anti-Cancer Drug Discov 10:23
17. Parker WB (2009) Chem Rev 109:2880
18. Zhi C, Long ZY, Gambino J, Xu WC, Brown NC, Barnes M,
Butler M, LaMarr W, Wright GE (2003) J Med Chem 46:2731
19. Tucci FC, Zhu YF, Struthers RS, Guo Z, Gross TD, Rowbottom
MW, Acevedo O, Gao Y, Saunders J, Xie Q, Reinhart GJ (2005)
J Med Chem 48:1169
20. Afsarian MH, Farjam M, Zarenezhad E, Behrouz S, Rad MN
(2019) Acta ChimSlov 66:874
21. Zarenezhad E, Mosslemin MH, Alborzi A, Anaraki-Ardakani H,
Shams N, Khoshnood MM, Zarenezhad A (2014) J Chem Res 38:337
22. Rad MN, Behrouz S, Zarenezhad E, Moslemin MH, Zaren-
ezhad A, Mardkhoshnood M, Behrouz M, Rostami S (2014)
Med Chem Res 23:3810
6‑Amino‑5‑[(4‑tert‑butylphenyl)(4‑hydroxy‑2‑oxo‑2H‑
c h r o m e n ‑ 3 ‑ y l ) m e t h y l ] ‑ 1 , 3 ‑ d i m e t h y l p y r i m i ‑
dine‑2,4(1H,3H)‑dione (4i, C26H27N3O5) Cream solid; yield
1
0.41 g (89%); m.p.: 245–246 °C; H NMR (250 MHz,
23. Abdolmohammadi A, Balalaie S, Barari M, Rominger F (2013)
Comb Chem High Throughput Screen 16:150
DMSO-d6): δ=1.22 (s, 9H, t-Bu), 3.14 (s, 3H, N-CH3), 3.37
(s, 3H, N-CH3), 5.57 (s, 1H, CH), 7.04 (d, 2H, J=8.25 Hz,
Ar–H), 7.23 (d, 2H, J=8.5 Hz, Ar–H), 7.31 (s, 2H, NH2),
7.35–7.44 (m, 2H, Ar–H), 7.60–7.67 (m, 1H, Ar–H), 7.83
(dd, 1H, J1 =7.87 Hz, J2 =1.5 Hz, Ar–H), 13.96 (s, 1H, OH)
ppm; 13C NMR (62.5 MHz, DMSO-d6): δ=28.18 (N-CH3),
30.51 (N-CH3), 31.12 (3 CH3), 33.92 (C-3CH3), 35.59 (CH),
86.64, 104.73, 116.09, 116.87, 123.65, 124.27, 124.82, 126,
132.37, 135.08, 147.81, 150, 151.87, 155.05, 163.67 (C=O),
164 (C=O), 165.74 (C=O) ppm; IR (KBr): ꢀ =3398, 3244,
2981, 1685, 1639, 1608, 1569, 1504, 1203, 1064, 760 cm−1.
24. Fakheri-Vayeghan S, Abdolmohammadi S, Kia-Kojoori R
(2018) Z Naturforsch B 73:545
25. Bharti R, Parvin T (2015) Synth Commun 45:1442
26. Bharti R, Parvin T (2015) RSC Adv 5:66833
27. Karami B, Eskandari K, Khodabakhshi S, Hoseini SJ,
Hashemian F (2013) RSC Adv 3:23335
28. Lu GP, Cai C (2014) J Heterocycl Chem 51:1595
29. Mosslemin MH, Zarenezhad E, Shams N, Rad MN, Anaraki-
Ardakani H, Fayazipoor R (2014) J Chem Res 38:169
30. Shams N, Mosslemin MH, Anaraki-Ardakani H, Zarenezhad E
(2015) J Chem Res 39:270
31. Khalaf-Nezhad A, Panahi F, Mohammadi S, Foroughi HO
(2013) J Iran Chem Soc 10:189
32. Jay JM, Loessner MJ, Golden DA (2008) Modern food microbiol-
ogy. Springer Science and Business Media, Berlin
Acknowledgements We would like to offer our special thanks
to Islamic Azd University Fasa branch for partial support of this
research work.
Publisher’s Note Springer Nature remains neutral with regard to
jurisdictional claims in published maps and institutional afliations.
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