Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3H)-Quinazolinone-Derived Schiff Base
Abstract
:1. Introduction
2. Results and Discussion
2.1. 1H-NMR Spectral Analysis
2.2. FT-IR Spectral Studies
2.3. UV–Visible Spectroscopy
2.4. Mass Spectral Studies
2.5. Thermal Analysis
X-ray Diffraction (XRD) Analysis
2.6. In Vitro Anticancer Activity Evaluation Using Sulforhodamine-B (SRB) Assay
2.7. Determination of the Descriptors Related to Chemical Reactivity
3. Experimental
3.1. Materials and Methods
3.2. Computational Details
3.3. Chemical Synthesis
3.3.1. Synthesis of 3-[[(E)-(3-Hydroxyphenyl)methylidene]amino]-2-methyl- quinazolin-4(3H)-one (HAMQ)
3.3.2. Synthesis of Metal Complexes (C1–C4)
3.3.3. In Vitro Antiproliferative Activity against Human Cancer Cell Lines
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Not available. |
Compound | Lattice Constants (A˚) | Angles (˚) | FoM | Volume (Å) | Crystallite Size (Å) |
---|---|---|---|---|---|
C1 | a = 4.8 b = 14.1 c = 15.8 | α = 55.11 β = 82.97 ϓ = 41.62 | 1.89 | 1069.34 | 570.62 |
C2 | a = 5.3 b = 7.4 c = 18.4 | α = 56.55 β = 85.65 ϓ = 90.48 | 9.95 | 721.65 | 432.81 |
C3 | a = 4.9 b = 9.4 c = 23.3 | α = 48.20 β = 61 ϓ = 58.99 | 3.76 | 1073.20 | 312.51 |
C4 | a = 2.5 b = 7.3 c = 13.7 | α = 50.80 β = 67.40 ϓ = 69.06 | 2.23 | 250.03 | 1336.94 |
Concentration (µg/mL) | IC50 (µM) | ||||
---|---|---|---|---|---|
C1 (MW 643) | C2 (MW 587) | C3 (MW 631) | C4 (MW 593) | HAMQ (MW 302) | |
0.5 | 77.26 | 36.58 | 35.64 | 50.17 | 16.56 |
0.250 | 74.78 | 35.11 | 31.65 | 42.98 | 8.28 |
0.125 | 73.83 | 27.8 | 29.9 | 31.86 | 4.14 |
0.063 | 67.12 | 14.69 | 28.64 | 30.5 | 2.07 |
0.031 | 59.49 | 9.23 | 21.3 | 22.73 | 1.03 |
0.016 | 49.91 | 7.31 | 17.03 | 22.38 | 0.52 |
0.008 | 24.72 | 3.88 | 15.59 | 22.17 | 0.26 |
0.004 | 150.1 | −0.62 | 12.34 | 8.42 | 0.13 |
0.002 | 13.43 | 0.27 | 10.42 | 4.05 | 0.06 |
0.001 | 7.43 | −2.69 | 8.14 | 2.86 | 0.03 |
Doxorubicin | 18.40 |
Compound | HOMO | LUMO | SOMO | H–L gap | ΔSL | |||
---|---|---|---|---|---|---|---|---|
HAMQ | −6.16 | −2.21 | −2.25 | 3.95 | 0.01 | 0.02 | 0.02 | 0.04 |
C1 | −6.08 | −2.57 | −2.57 | 3.51 | 0.06 | 0.00 | 0.06 | 0.00 |
C2 | −6.16 | −2.62 | −2.61 | 3.54 | 0.02 | 0.00 | 0.02 | 0.01 |
C3 | −5.89 | −2.69 | −2.61 | 3.28 | 0.02 | 0.01 | 0.06 | 0.08 |
C4 | −6.05 | −2.69 | −2.67 | 3.36 | 0.06 | 0.01 | 0.06 | 0.02 |
Compound | ||||||
---|---|---|---|---|---|---|
HAMQ | 4.19 | 3.95 | 2.22 | 6.78 | 2.59 | 9.37 |
C1 | 4.32 | 3.52 | 2.66 | 7.70 | 3.38 | 11.08 |
C2 | 4.39 | 3.54 | 2.72 | 7.85 | 3.46 | 11.31 |
C3 | 4.29 | 3.20 | 2.87 | 8.08 | 3.79 | 11.88 |
C4 | 4.39 | 3.54 | 2.72 | 7.85 | 3.46 | 11.31 |
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Ashok, U.P.; Kollur, S.P.; Anil, N.; Arun, B.P.; Jadhav, S.N.; Sarsamkar, S.; Helavi, V.B.; Srinivasan, A.; Kaulage, S.; Veerapur, R.; et al. Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3H)-Quinazolinone-Derived Schiff Base. Molecules 2020, 25, 5973. https://doi.org/10.3390/molecules25245973
Ashok UP, Kollur SP, Anil N, Arun BP, Jadhav SN, Sarsamkar S, Helavi VB, Srinivasan A, Kaulage S, Veerapur R, et al. Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3H)-Quinazolinone-Derived Schiff Base. Molecules. 2020; 25(24):5973. https://doi.org/10.3390/molecules25245973
Chicago/Turabian StyleAshok, Ubale Panchsheela, Shiva Prasad Kollur, Nishad Anil, Bansode Prakash Arun, Sanjay Namdev Jadhav, Sanjay Sarsamkar, Vasant Baburao Helavi, Asha Srinivasan, Sandeep Kaulage, Ravindra Veerapur, and et al. 2020. "Preparation, Spectroscopic Characterization, Theoretical Investigations, and In Vitro Anticancer Activity of Cd(II), Ni(II), Zn(II), and Cu(II) Complexes of 4(3H)-Quinazolinone-Derived Schiff Base" Molecules 25, no. 24: 5973. https://doi.org/10.3390/molecules25245973