Compound | Substituent | Melting point (ºC) | Yield (%) |
---|---|---|---|
SP1 | H | 136–137 | 86 |
SP2 | 4-CH3 | 160–162 | 89 |
SP3 | 4-OCH3 | 117–119 | 84 |
SP4 | 4-Cl | 166–168 | 65 |
SP5 | 4-Br | 178–180 | 88 |
SP6 | 4-F | 128–130 | 83 |
SP7 | 4-I | 192–195 | 72 |
SP8 | 4-CH3CO | 144–145 | 64 |
SP9 | 4-OH | 144–146 | 76 |
SP10 | 4-CN | 180–183 | 56 |
SP11 | 3-CN | 165–170 | 61 |
SP12 | 3-Br | 110–113 | 83 |
1H NMR (CDCl3): δ 4.272 (2H, s, Cl-CH2), 7.057–7.130 (1H, t, |
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1H NMR (CDCl3): δ 2.255 (2H, s, CH3), 4.421 (1H, s, Cl-CH2), 7.111–7.153 (2H, d, |
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1H NMR (CDCl3): δ 3.729 (2H, s, OCH3), 4.229 (1H, s, Cl-CH2), 6.886–6.948 (2H, d, |
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1H NMR (CDCl3): δ 4.280 (1H, s, Cl-CH2), 7.358–7.431 (2H, d, |
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1H NMR (CDCl3): δ 4.274 (1H, s, Cl-CH2), 7.495–7.616 (4H, m, Ar-H), 10.447 (1H, s, N-H). 13C NMR (CDCl3): δ 43.742 (Cl-CH2), 115.736 (C4), 121.526 (C2,C6), 131.923 (C3,C5), 138.095 (C1), 165.061 (C=O). | |
1H NMR (CDCl3): δ 4.369 (1H, s, Cl-CH2), 7.122–7.226 (2H, t, |
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1H NMR (CDCl3): δ 4.263 (1H, s, Cl-CH2), 7.425–7.4709 (2H, d, |
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1H NMR (CDCl3): δ 2.544 (3H, s, CH3), 4.328 (1H, s, Cl-CH2), 7,723–7,768 (2H, d, |
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1H NMR (CDCl3): δ 4.280 (2H, s, Cl-CH2), 4.684 (1H, s, OH), 7.139–7.184 (2H, d, |
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1H NMR (CDCl3): δ 4.319 (2H, s, Cl-CH2), 7.552–7.619 (2H, d, |
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1H NMR (CDCl3): δ 4.339 (1H, s, Cl-CH2), 7.552–7.619 (2H, d, |
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1H NMR (CDCl3): δ 4.286 (3H, s, Cl-CH2), 7.285–7.358 (2H, m, Ar-H), 7.470– 7.571 (1H, m, Ar-H), 7.962 (1H, s, Ar-H), 10.489 (1H, s, N-H). 13C NMR (CDCl3): δ 43.688 (Cl-CH2), 118.376 (C2), 121.836 (C5), 121.927 (C6), 126.697 (C4), 131.067 (C3), 140.262 (C1), 165.243 (C=O). |
Compound | log |
log |
log |
log |
---|---|---|---|---|
SP1 | 1.72 | 1.63 | 1.67 | 1.84 |
SP2 | 2.17 | 1.99 | 1.98 | 2.15 |
SP3 | 1.78 | 1.65 | 1.68 | 1.54 |
SP4 | 2.40 | 2.26 | 2.33 | 2.42 |
SP5 | 2.53 | 2.32 | 2.44 | 2.56 |
SP6 | 1.89 | 1.73 | 2.23 | 2.27 |
SP7 | 2.81 | 2.28 | 2.28 | 2.71 |
SP8 | 1.62 | 1.86 | 1.88 | 1.47 |
SP9 | 1.24 | 1.27 | 1.38 | 1.23 |
SP10 | 1.45 | 1.82 | 1.54 | 1.18 |
SP11 | 1.48 | 1.35 | 1.54 | 1.18 |
SP12 | 2.51 | 2.93 | 2.44 | 2.56 |
Levetiracetam | 0.69 | 0.62 | -0.03 | 0.28 |
Piracetam | -1.32 | -1.54 | -1.29 | -0.96 |
Compound | Molecular weight (g/ mol) | Number of atoms | Number of rotatable bonds | Number of hydrogen bond donors | Number of hydrogen bond acceptors | Molar refractivity | Topological polar surface area (Å2) |
---|---|---|---|---|---|---|---|
SP1 | 169.61 | 11 | 3 | 1 | 2 | 45.55 | 29.10 |
SP2 | 183.63 | 12 | 3 | 1 | 2 | 50.52 | 29.10 |
SP3 | 199.63 | 13 | 4 | 1 | 3 | 52.04 | 38.33 |
SP4 | 204.05 | 12 | 3 | 1 | 2 | 50.56 | 29.10 |
SP5 | 248.50 | 12 | 3 | 1 | 2 | 53.25 | 29.10 |
SP6 | 187.60 | 12 | 3 | 1 | 2 | 45.51 | 29.10 |
SP7 | 295.50 | 12 | 3 | 1 | 2 | 58.27 | 29.10 |
SP8 | 211.64 | 14 | 4 | 1 | 3 | 55.75 | 46.17 |
SP9 | 185.61 | 12 | 3 | 2 | 3 | 47.57 | 49.33 |
SP10 | 194.62 | 13 | 3 | 1 | 3 | 50.27 | 52.89 |
SP11 | 194.62 | 13 | 3 | 1 | 3 | 50.27 | 52.89 |
SP12 | 248.50 | 12 | 3 | 1 | 3 | 53.25 | 29.10 |
Levetiracetam | 156.23 | 11 | 3 | 1 | 2 | 48.17 | 46.33 |
Piracetam | 142.16 | 10 | 2 | 1 | 2 | 38.76 | 63.40 |
Prediction tool | SwissADME | pkCSM | Swiss ADME | pkCSM | SwissADME | pkCSM | SwissADME | pkCSM | SwissADME | pkCSM |
---|---|---|---|---|---|---|---|---|---|---|
Compound | Inhibits CYP1A2 | Inhibits CYP1A2 | Inhibits CYP2C19 | Inhibits CYP2C19 | Inhibits CYP2C9 | Inhibits CYP2C9 | Inhibits CYP2D6 | Inhibits CYP2D6 | Inhibits CYP3A4 | Inhibits CYP3A4 |
SP1 | Yes | No | No | No | No | No | No | No | No | No |
SP2 | Yes | Yes | No | No | No | No | No | No | No | No |
SP3 | Yes | Yes | No | No | No | No | No | No | No | No |
SP4 | Yes | Yes | No | No | No | No | No | No | No | No |
SP5 | Yes | Yes | No | No | No | No | No | No | No | No |
SP6 | Yes | Yes | No | No | No | No | No | No | No | No |
SP7 | Yes | Yes | No | No | No | No | No | No | No | No |
SP8 | Yes | Yes | No | No | No | No | No | No | No | No |
SP9 | No | No | No | No | No | No | No | No | No | No |
SP10 | Yes | Yes | No | No | No | No | No | No | No | No |
SP11 | Yes | Yes | No | No | No | No | No | No | No | No |
SP12 | Yes | Yes | No | No | No | No | No | No | No | No |
Levetiracetam | No | No | No | No | No | No | No | No | No | No |
Piracetam | No | No | No | No | No | No | No | No | No | No |
Comp | R | IR (KBr) νmax (cm-1) |
---|---|---|
SP1 | H | 3267 (N-H); 3207, 3145, 3098 (C-H aromatic ring); 2947 (C-H); 1671 (C=O); 1618 (C=C); 1557 (N-H deformation); 1498, (C-H bending); 1443 (C-H bending); 1344 (C-H); 1251 (C-N); 749 (N-H). |
SP2 | 4-CH3 | 3273 (N-H); 3204, 3135, 3090 (C-H aromatic ring); 2954 (C-H); 1673 (C=O); 1616 (C=C); 1554 (N-H); 1402 (C-H); 1343 (C-H); 1251 (C-N); 818 (N-H). |
SP3 | 4-OCH3 | 3295 (N-H); 3139, 3073 (C-H aromatic ring); 2957 (C-H); 2909 2835 (C-H); 1663 (C=O); 1612 (C=C); 1547 (N-H); 1510 (N-H); 1465 (C-H); 1413 (C-H); 1247 (C-N); 830 (N-H). |
SP4 | 4-Cl | 3264(N-H); 3199, 3131, 3082 (C-H aromatic ring); 3005, 2952(C-H); 1669 (C=O); 1614 (C=C); 1551 (N-H); 1490 (C-H); 1400 (C-H); 1248 (C-N); 825 (N-H). |
SP5 | 4-Br | 3263 (N-H); 3194 (C-H); 3125, 3077 (C-H aromatic ring); 3000 2953 (C-H); 1669 (C=O); 1549 (N-H); 1488 (C-H); 1395 (C-H); 1248 (C-N); 822 (N-H). |
SP6 | 4-F | 3275, 3221 (N-H); 3165 (C-H aromatic ring); 2947 (C-H); 1668 (C=O); 1508 (N-H); 1406 (C-H); 1292; 1212 (C-N); 832 (N-H). |
SP7 | 4-I | 3309, 3270 (N-H); 3194, 3077 (C-H aromatic ring); 2936 (C-H); 2953 (C-H); 1672 (C=O); 1610 (N-H); 1543 (C-H); 1392–1089 (CH); 1245 (C-N); 817 (N-H). |
SP8 | 4-COCH3 | 3325, 3286 (N-H); 3196, 3109 (C-H aromatic ring); 2922, 2857 (C-H); 1707 (C=O); 1655 (C=C); 1599 (N-H); 1539 (C-H); 1283 (C-O); 1252 (C-N); 834 (N-H). |
SP9 | 4-OH | 3296 (O-H); 3144 (N-H); 3098 (C-H); 1677 (C=O); 1508 (N-H); 1313 (C-H); 1211 (C-N); 820 (N-H). |
SP10 | 4-CN | 3265 (N-H); 3192, 3119 (C-H); 2946 (C-H); 2226 (C?N); 1681 (C=O); 1603 (C=C); 1539 (N-H); 1408, 1345 (C-H); 1256 (C-N); 839 (N-H). |
SP11 | 3-CN | 3265 (N-H); 3096 (C-H); 2964 C-H); 2232 (C?N); 1678 (C=O); 1610 (C=C); 1561 (N-H); 1485 (C-H); 1293 (C-N); 1089 (C-H); 799 (N-H). |
SP12 | 3-Br | 3268 (N-H); 3193, 3127 (C-H); 2945 (C-H); 1679 (C=O); 1594 (N-H); 1424 (C-H); 1249 (C-N); 779 (N-H). |
Compound | SwissADME | pkCSM | SwissADME | PreADMET | SwissADME | PreADMET |
---|---|---|---|---|---|---|
Gastrointestinal absorption | Intestinal absorption (%) | the compound penetrates the blood-brain barrier | The compound penetrating the blood-brain barrier (cbrain/cblood) | the compound is a P-gp inhibitor | the compound is a P-gp inhibitor | |
SP1 | High | 91.156 | Yes | 0.902206 | No | No |
SP2 | High | 91.692 | Yes | 2.16896 | No | No |
SP3 | High | 93.810 | Yes | 0.612824 | No | No |
SP4 | High | 91.969 | Yes | 1.65555 | No | No |
SP5 | High | 91.902 | Yes | 1.79202 | No | No |
SP6 | High | 91.217 | Yes | 1.07913 | No | No |
SP7 | High | 90.802 | Yes | 1.52595 | No | No |
SP8 | High | 92.635 | Yes | 0.546121 | No | No |
SP9 | High | 90.745 | Yes | 0.975597 | No | No |
SP10 | High | 92.986 | Yes | 0.975597 | No | No |
SP11 | High | 92.817 | Yes | 0.975597 | No | No |
SP12 | High | 92.405 | Yes | 1.79204 | No | No |
Levetiracetam | High | 86.852 | No | 0.440234 | No | No |
Piracetam | High | 86.061 | No | 0.165163 | No | No |
Tested substances | MRSA | ||||
---|---|---|---|---|---|
MIC (μg/mL) | |||||
SP1 | 4-H | 190±40c | 920±80c | 90±20c | 50±0cd |
SP2 | 4-CH3 | 330±110c | 3330±330ab | 60±0c | 60±0cd |
SP3 | 4-OCH3 | 190±40c | 540±110c | 110±10c | 190±40bc |
SP4 | 4-Cl | 60±0c | 3670±330ab | 60±0c | 90±20bcd |
SP5 | 4-Br | 330±80c | 4000±0a | 60±0c | 60±0cd |
SP6 | 4-F | 110±10c | 500±140c | 150±50bc | 110±10bcd |
SP7 | 4-I | 830±170c | 2670±330b | 40±10c | 40±10d |
SP8 | 4-COCH3 | 330±80c | 330±80c | 190±40bc | 90±20bcd |
SP9 | 4-OH | 2660±670a | 270±20c | 130±0c | 40±10d |
SP10 | 3-CN | 290±40c | 190±40c | 40±10c | 90±20bcd |
SP11 | 4-CN | 230±20c | 1000±290c | 750±140a | 220±20ab |
SP12 | 3-Br | 100±20c | 500±140c | 80±20c | 90±20bcd |
Ant/Myc | – | 2000±0ab | 90±10c | 40±10c | 70±20cd |
SP1 | 4-H | 500±0c | 2000±0b | 250±0bcd | 120±0c |
SP2 | 4-CH3 | 670±170c | 4000±0a | 170±40cd | 310±110c |
SP3 | 4-OCH3 | 330±80c | 1000±0c | 250±0bcd | 330±80c |
SP4 | 4-Cl | 2000±0b | Nd | 130±0d | 750±140bc |
SP5 | 4-Br | 4000±0a | Nd | 420±80bcd | 750±140bc |
SP6 | 4-F | 330±80c | 1000±0c | 750±140bc | 250±0c |
SP7 | 4-I | 3000±580ab | 4000±0a | 130±0d | 290±110c |
SP8 | 4-COCH3 | 670±170c | 670±170d | 750±140bc | 330±80c |
SP9 | 4-OH | 4000±0a | 500±0d | 330±80bcd | 170±40c |
SP10 | 3-CN | 500±0c | 420±80d | 130±0d | 250±0c |
SP11 | 4-CN | 500±0c | 2000±0b | 2330±330a | 1330±330ab |
SP12 | 3-Br | 670±170c | 1000±0c | 210±40cd | 330±80c |
Ant/Myc | – | Nd | 130±30e | 100±0d | 100±0c |