Synthesis, Characterization, Antimicrobial Evaluation and QSAR Studies of Organotin(IV)

Synthesis, characterization, antimicrobial evaluation and QSAR studies of organotin(IV) complexes of Schiff base ligands of 2-amino-6-substituted-benzothiazole derivatives

1Aarti Ahlawat, 2Vikramjeet Singh, 1Sonika Asija*

1Department of Chemistry, G.J. University of Science &Technology, Hisar-125001 (Haryana), India

2Department of Pharmaceutical Sciences, G.J. University of Science & Technology, Hisar- 125001 (Haryana), India

Corresponding Author E-mail ID: [email protected]

Supplementary materials:

1H NMR of compound 1 (L1) 1 H NMR of compound 6 (Bu2SnL1Cl) 13 C NMR Spectra of compound 1 (Bu2SnL1Cl) 13 C NMR Spectra of compound 6 (Bu2SnL1Cl) 119 Sn NMR Spectra of compound 6 (Bu2SnL1Cl) Table 3. Correlation matrix for antifungal activity of synthesized derivatives against A. flavus

E le 0 0 v 1 1 v 2 2 v 3 3 v χ χ χ χ χ χ χ χ 1 2 3 R J Te HOMO μ pMICaf . E - 0. 1.00 0.94 0.97 0.68 0.42 0.30 0.99 0.96 0.90 0.99 - 0χ 0.991 0.785 -0.125 9 0.322 0.179 0.835 0 8 6 1 9 8 4 8 5 1 0.989 9 8 - 0. 1.00 0.91 0.86 0.58 0.53 0.95 0.92 0.93 0.91 - 0χv 0.910 0.931 0.123 9 0.496 0.094 0.952 0 5 3 7 4 8 4 6 0 0.928 5 1 - 0. 0.97 0.59 0.33 0.21 0.97 0.95 0.85 1.00 - 1χ 1.000 0.713 -0.240 9 0.327 0.127 0.772 4 5 9 2 7 6 7 0 0.971 8 8 - 0. 0.77 0.98 0.80 0.79 0.80 0.74 0.84 0.71 - 1χv 1.000 0.339 7 0.486 0.182 0.991 7 4 8 7 4 0 9 3 0.780 8 5 2χ 1.00 0.67 0.51 0.37 0.95 0.89 0.83 0.97 -0.244 - - 0.262 0.265 0.831 0. 9 0 2 7 3 2 8 5 4 0.963 6 4 - 0. 1.00 0.84 0.85 0.70 0.62 0.76 0.59 - 2χv 0.440 6 0.467 0.196 0.969 0 4 1 3 8 3 5 0.681 8 0 - 0. 1.00 0.95 0.42 0.30 0.48 0.33 - 3χ 0.300 4 0.100 0.525 0.782 0 6 5 0 7 9 0.461 0 6 - 0. 1.00 0.32 0.21 0.44 0.21 - 3χv 0.448 2 0.294 0.315 0.743 0 1 9 2 2 0.325 9 6 - 0. 1.00 0.98 0.94 0.97 - 1 -0.032 9 0.345 0.156 0.844 0 5 2 7 0.986 9 8

2 1.00 0.95 0.95 0.000 - - 0.379 0.052 0.772 0 1 6 0.955 0. 9 7 9 - 0. 1.00 0.85 - 3 0.247 9 0.382 0.122 0.844 0 7 0.905 2 0 - 0. 1.00 - R -0.240 9 0.327 0.127 0.772 0 0.971 8 8 0. 0 J 1.000 0.095 0.186 -0.056 0.247 9 2 0. 9 Te 1.000 -0.228 -0.290 -0.830 8 5 1. 0 Ele.E -0.348 -0.143 -0.831 0 0 HOMO 1.000 -0.712 0.457 μ 1.000 0.212 pMICaf 1.000 Table 4. Correlation of structural descriptors with antimicrobial activity of synthesized compounds

Mol. Descriptor pMICaf pMICbc pMICsa pMICpa pMICan pMICec 0χ 0.835 0.958 0.948 0.852 0.780 0.602 0χv 0.952 0.987 0.847 0.918 0.764 0.567 1χ 0.772 0.925 0.949 0.801 0.774 0.586 1χv 0.991 0.901 0.674 0.905 0.668 0.484 2χ 0.831 0.936 0.958 0.847 0.791 0.589 2χv 0.969 0.818 0.560 0.858 0.593 0.424 3χ 0.782 0.576 0.411 0.682 0.431 0.308 3χv 0.743 0.502 0.238 0.606 0.342 0.214

1 0.844 0.967 0.928 0.860 0.765 0.603

2 0.772 0.936 0.889 0.803 0.722 0.584

3 0.844 0.948 0.815 0.853 0.683 0.570 R 0.772 0.925 0.949 0.801 0.774 0.586 J 0.247 0.081 -0.246 0.160 -0.132 -0.022 W 0.737 0.907 0.952 0.778 0.765 0.584 Te -0.830 -0.937 -0.942 -0.841 -0.760 -0.608 Ele.E -0.831 -0.962 -0.938 -0.847 -0.773 -0.598 NuE 0.830 0.962 0.937 0.847 0.774 0.597 LUMO -0.349 -0.384 -0.588 -0.399 -0.408 -0.389 HOMO 0.457 0.428 0.143 0.359 0.307 0.079 Μ 0.212 0.129 0.306 0.221 0.147 0.191 Table 5. Comparison of observed and predicted antibacterial and antifungal activity obtained by QSAR models.

Comp pMICaf pMICbc pMICpa pMICan . Obs Pre Res Obs Pre Res Obs Pre Res Obs Pre Res Obs Pre Res 1 - 1.75 0.00 1.46 1.70 1.74 - 2.04 1.746 5 9 1.445 4 -0.019 1.746 1 0.045 6 1.793 0.047 8 2.075 -0.027 2 1.72 0.01 1.39 1.75 1.74 - 2.04 1.747 9 8 1.446 8 0.048 1.747 4 -0.007 7 1.750 0.003 9 2.107 -0.058 3 - 1.73 0.00 1.41 1.64 1.72 - 2.03 1.728 0 2 1.427 0 0.017 1.728 3 0.085 8 1.757 0.029 0 2.040 -0.010 4 - 1.72 0.01 1.37 1.61 1.70 - 2.00 1.707 5 8 1.406 8 0.028 1.707 7 0.090 7 1.736 0.029 9 2.024 -0.015 5 2.29 0.03 2.34 2.63 2.32 - 2.62 2.323 2 1 2.323 1 -0.018 2.624 6 -0.012 3 2.367 0.044 4 2.641 -0.017 6 - 2.33 0.03 2.30 2.30 2.29 - 2.59 2.295 4 9 2.295 0 -0.005 2.278 9 -0.031 5 2.340 0.045 6 2.443 0.153 7 2.24 0.00 2.08 2.08 2.25 2.25 2.254 9 5 1.952 1 -0.129 1.952 1 -0.129 4 2.197 0.057 4 2.305 -0.051 8 - 2.27 0.04 1.97 2.08 2.23 2.23 2.231 3 2 1.930 1 -0.041 1.930 8 -0.158 1 2.125 0.106 1 2.309 -0.078 9 2.26 0.05 2.27 2.68 2.32 - 2.62 2.323 6 7 2.323 5 0.048 2.624 9 -0.065 3 2.324 0.001 4 2.673 -0.049 10 2.296 2.30 - 2.296 2.23 0.062 2.597 2.36 0.235 2.29 2.297 - 2.59 2.475 0.122 0.01 8 2 4 2 6 0.001 7 11 2.22 0.03 2.01 2.13 2.25 2.25 2.255 3 2 1.953 5 -0.062 2.237 4 0.103 5 2.153 0.102 5 2.337 -0.082 12 - 2.24 0.01 1.90 2.14 2.23 2.23 2.232 7 5 1.931 5 0.026 2.215 1 0.074 2 2.082 0.150 2 2.341 -0.109 13 2.26 0.04 2.28 2.57 2.31 - 2.61 2.313 7 6 2.313 6 0.027 2.614 9 0.035 3 2.331 0.018 4 2.606 0.008 14 - 2.30 0.02 2.24 2.25 2.28 - 1.98 2.285 9 4 2.285 5 0.040 2.268 1 0.017 5 2.304 0.019 4 2.408 -0.424 15 2.22 0.01 2.02 2.02 1.94 - 2.54 2.243 4 9 1.941 6 -0.085 1.941 3 -0.082 1 2.161 0.220 4 2.270 0.274 16 - 2.24 0.02 1.91 2.03 1.91 - 2.52 2.220 8 8 1.918 6 0.002 1.918 0 -0.112 8 2.089 0.171 1 2.274 0.247 17 2.26 0.04 2.25 2.55 2.30 - 2.60 2.302 2 0 2.302 4 0.048 2.603 3 0.050 2 2.310 0.008 3 2.591 0.012 18 - 2.30 0.03 2.21 2.22 2.27 - 2.57 2.274 4 0 2.274 3 0.061 2.256 5 0.031 4 2.283 0.009 5 2.392 0.183 19 2.21 0.01 1.99 1.99 2.23 2.23 2.230 9 1 1.928 4 -0.066 1.928 8 -0.070 0 2.140 0.090 0 2.255 -0.025 20 - 2.24 0.03 1.88 2.00 2.20 2.20 2.206 4 8 1.904 5 0.019 1.904 4 -0.100 6 2.068 0.138 6 2.259 -0.052 Fig.1 XRD pattern of organotin complex 5 (Ph2SnL1Cl)

Fig. 2 Plot of observed pMICaf (μM/mL) against the predicted pMICaf (μM/mL) for the linear regression model developed by Eq. 1

Fig 3. Plot of residual pMICaf (μM/mL) against the observed pMICaf (μM/mL) for the linear regression model developed by Eq. 1 Fig 4. XRD pattern of organotin complex 6 (Bu2SnL1Cl)

Fig 5. XRD pattern of organotin complex 7 (Et2SnL1Cl) Fig 6. XRD pattern of organotin complex 8 (Me2SnL1Cl)