6
MOGHADDAM-MANESH AND HOSSEINZADEGAN
ethanol:water (1:1) was added to the mixture and stirred for
MCF-7 breast cancer cells. Concentrations of 6.25, 12.5,
25, 75, 150, and 300 μM/mL of derivatives for 48 h were
tested to evaluate the anticancer activity.
0.5 h at room temperature then sediments were separated
and recrystallized in acetonitrile.
ACKNOWLEDGMENTS
5
.4 | Selected spectral data [9]
We gratefully thank Dr. Majid Mohebi, General Manager
of General Bureau of Standard Sistan and Baluchestan
Province, Iranian National Standards Organization.
0
0
5
.4.1 | 6 -Amino-7,8-dimethyl-2 -
(
2,4,6-trioxotetrahydropyrimidin-5[2H]-ylidene)
0
spiro[indeno[1,2-b]quinoxaline-11,4 -[1,3]
dithiine]-5 -carbonitrile (7a)
DATA AVAILABILITY STATEMENT
The data that supports the findings of this study are avail-
able in the supplementary material of this article.
0
–1
IR (KBr, cm ): 3352, 3275 (NH ), 2164 (CN), 1718, 1673
2
1
ORCID
(CO); H NMR (250 MHz, DMSO-d ) δ 0.99 (3H, s, Me),
6
1
.05 (3H, s, Me), 2.01–2.25 (4H, m, 2CH ), 6.65 (1H, d,
2
J = 7.5 Hz, H-Ar), 6.80–7.01 (3H, m, H-Ar), 7.24 (2H, br
s, NH2); C NMR (75 MHz, DMSO-d ) δ 27.8, 27.9, 33.7,
13
6
REFERENCES
4
1
7.6, 51.3, 58.1, 110.4, 111.5, 117.1, 122.7, 123.6, 129.1,
35.3, 143.4, 160.1, 173.9, 177.9, 193.4, 194.6. Anal. Calcd
[1] P. Xu, G. W. Zheng, M.-H. Zong, N. Li, W. Y. Lou, Bioresour
Bioprocess 2017, 4, 34.
for C H N O S : C, 59.42; H, 3.79; N, 6.59; S, 15.11.
Found: C, 59.37; H, 3.83; N, 6.62; S, 15.15.
21
16 2 4 2
[
[
[
2] H. Beyzaei, M. K. Deljoo, R. Aryan, B. Ghasemi, M. M. Zahedi,
M. Moghaddam-Manesh, Chem Central J 2018, 12, 114.
3] R. Aryan, H. Beyzaei, M. Nojavan, M. Rezaei, Res Chem Inter-
med 2017, 43, 4731.
4] H. Beyzaei, Z. Motraghi, R. Aryan, M. M. Zahedi, A.
Samzadeh-Kermani, Acta Chim Slov 2017, 64, 911.
0
0
5
2
.4.2 | 6 -Amino-2 -(4,4-dimethyl-
,6-dioxocyclohexylidene) spiro[indeno[1,2-b]
0
0
quinoxaline-11,4 -[1,3]dithiine]-5 -
carbonitrile (10a)
[5] H. Mehrabi, Z. Esfandiarpour, T. Davodian, J Sulfur Chem
018, 39, 164.
2
[6] K. Chaiseeda, W. Chavasiri, Phosphorus Sulfur Silicon Relat
Elem 2017, 192, 1034.
–1
IR (KBr, cm ): 3222 and 3218 (NH ), 2162 (CN), 1672
2
[
7] H. R. Shaterian, H. R. Ahmadian, M. Ghashang, R.
Doostmohammadi, H. Yarahmadi, Phosphorus Sulfur Silicon
Relat Elem 2008, 183, 1099.
1
(CO); H NMR (DMSO-d ) δ 0.99 (s, 3H, CH ), 1.01 (s,
6 3
3
H, CH ), 1.99–2.05 (m, 2H, CH ), 2.57–2.75 (m, 2H,
3
2
CH ), 7.30 (br s, 2H, NH ), 7.49–7.59 (m, 3H, H-Ar), 7.78
2
2
[8] M. Moghaddam-Manesh, D. Ghazanfari, E. Sheikhhosseini,
M. Akhgar, ChemistrySelect 2019, 4, 9247.
[9] M. Moghaddam-Manesh, D. Ghazanfari, E. Sheikhhosseini,
M. Akhgar, Acta Chim Slov 2020, 67, 276.
13
(
t, J = 7.75 Hz, 2H, H-Ar), 8.01–8.16 (m, 3H, H-Ar).
C
NMR (DMSO-d ) δ 27.4, 28.0, 32.4, 47.5, 50.5, 59.0, 112.3,
6
1
1
17.9, 121.9, 124.9, 129.3, 129.5, 129.8, 130.1, 132.8, 136.6,
41.4, 142.1, 152.3, 154.6, 159.3, 165.3, 159.9.185.4. Anal.
[
[
[
10] M. Moghaddam-Manesh, E. Sheikhhosseini, D. Ghazanfari,
M. Akhgar, Bioorg Chem 2020, 98, 103751.
11] M. Yamashita, T. Tahara, S. Hayakawa, H. Matsumoto, S. I.
Wada, K. Tomioka, A. Iida, Bioorg Med Chem 2018, 26, 1920.
12] J. K. DeMartino, I. Hwang, S. Connelly, I. A. Wilson, D. L.
Boger, J Med Chem 2008, 51, 5441.
Calcd for C H N O S : C, 65.30; H, 4.06; N, 11.28; S,
1
27
20 4 2 2
2.91. Found: C, 65.34; H, 4.08; N, 11.31; S, 12.95.
5
.5 | Antibacterial activity
[13] L. Santos, F. Ramos, Trends Food Sci Technol 2016, 52, 16.
[
[
[
[
14] C. Y. C. Wang, H. S. Shie, S. C. Chen, J. P. Huang, I. C. Hsieh,
M. S. Wen, F. C. Lin, D. Wu, Int J Clin Pract 2007, 61, 68.
15] K. Rantsiou, R. Urso, L. Iacumin, C. Cantoni, P. Cattaneo, G.
Comi, L. Cocolin, Appl Environ Microbiol 2005, 71, 1977.
16] C. Ravelo, B. Magarinos, S. L ꢀo pez-Romalde, A. E. Toranzo,
J. L. Romalde, J Clin Microbiol 2003, 41, 751.
According to the clinical and laboratory standards institute
CLSI) guidelines M07-A9, M26-A, M02-A11, M44-A, and
(
M27-A2, broth microdilution, and time-kill susceptibility
based on the inhibition zone diameter, MIC, and MBC
values against L. garvieae (IBRC-M 10900) and E. tarda
17] S. C. Maria Da Gl oꢀ ria, E. V. Maria Da Conceiç ~a o, J. A. Elliott, M.
(IBRC-M 10718) were measured [8–10,21,22].
Reeves, R. R. Facklam, L. M. Teixeira, Molecular analysis of
Lactococcus garvieae and Enterococcus gallinarum isolated from water
buffalos with subclinical mastitis, Springer, Nature Switzerland 1997.
5.6 | Anticancer activity
[18] L. Devriese, J. Hommez, H. Laevens, B. Pot, P. Vandamme, F.
Haesebrouck, Vet Microbiol 1999, 70, 87.
[
19] W. Ewing, A. McWhorter, M. Escobar, A. Lubin, Int J Systemat
MTT method and previous reports [23,24] were used to
evaluate the anticancer properties of derivatives against
Evol Microbiol 1965, 15, 33.