Efficient Synthesis of 2-Amino-6-Arylbenzothiazoles via Pd(0) Suzuki Cross Coupling Reactions: Potent Urease Enzyme Inhibition and Nitric Oxide Scavenging Activities of the Products
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Entry | Aryl Boronic Acid/Aryl Boronic Pinacol Ester | Product | Solvent/H2O (4:1) | Yield% [a] |
---|---|---|---|---|
1 | 3a | Toluene | 65 | |
2 | 3a | Dioxane | 75 | |
3 | 3b | Toluene | 61 | |
4 | 3c | DMF | 64 | |
5 | 3c | Dioxane | 71 | |
6 | 3d | Dioxane | 67 | |
7 | 3e | Dioxane | 78 |
2.2. Pharmacology
2.2.1. Antiurease Activity
Compound | Percentage inhibition at 25 µg/mL | Percentage inhibition at 50 µg/mL | IC50 (µg/mL) |
---|---|---|---|
2 | 43 ± 0.0034 | 95 ± 0.005 | 28.4 |
4 | 39 ± 0.001 | 89 ± 0.009 | 30.5 |
3a | 46 ± 0.005 | 90.49 ± 0.002 | 27.27 |
3b | 39 ± 0.0012 | 88.19 ± 0.007 | 30.6 |
3c | 44 ± 0.005 | 86.24 ± 0.001 | 28.57 |
3d | 43 ± 0.007 | 88.6 ± 0.002 | 28.88 |
3e | 48 ± 0.005 | 85 ± 0.002 | 26.35 |
Standard | 33 ± 0.04 | 77 ± 0.01 | 34.65 |
2.2.2. Nitric Acid (NO) Scavenging Percentage (Antioxidant Activity)
Compound | Nitric Oxide Percentage Scavenging Activity at 25 µg/mL | Nitric Oxide Percentage Scavenging Activity at 50 µg/mL | Nitric Oxide Percentage Scavenging Activity at 100 µg/mL | IC50 (µg/mL) |
---|---|---|---|---|
1 2 | 20 ± 0.004 | 48 ± 0.0007 | 90 ± 0.0007 | 57.8 |
2 4 | 25 ± 0.001 | 54 ± 0.002 | 92 ± 0.002 | 46.5 |
3 3a | 24 ± 0.003 | 56 ± 0.001 | 95 ± 0.001 | 68.3 |
4 3b | 17 ± 0.006 | 34 ± 0.005 | 66 ± 0.005 | 75 |
5 3c | 31 ± 0.022 | 67 ± 0.002 | 98 ± 0.002 | 38.19 |
6 3d | 10 ± 0.01 | 23 ± 0.009 | 63 ± 0.009 | 83.75 |
7 3e | 9 ± 0.007 | 22 ± 0.001 | 52 ± 0.001 | 96.66 |
Standard | 40.5 ± 0.01 | 70.5 ± 0.91 | 99.5 ± 0.91 | 66.66 |
3. Experimental
3.1. General
3.2. General Procedure for the Synthesis of 2-Amino-6-arylbenzothiazoles
3.3. Preparation of N-(6-bromobenzo[d]thiazol-2-yl)acetamide (4)
3.4. Characterization Data
3.5. NO Scavenging Activity
3.6. Antiurease Activity
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Gull, Y.; Rasool, N.; Noreen, M.; Nasim, F.-u.-H.; Yaqoob, A.; Kousar, S.; Rashid, U.; Bukhari, I.H.; Zubair, M.; Islam, M.S. Efficient Synthesis of 2-Amino-6-Arylbenzothiazoles via Pd(0) Suzuki Cross Coupling Reactions: Potent Urease Enzyme Inhibition and Nitric Oxide Scavenging Activities of the Products. Molecules 2013, 18, 8845-8857. https://doi.org/10.3390/molecules18088845
Gull Y, Rasool N, Noreen M, Nasim F-u-H, Yaqoob A, Kousar S, Rashid U, Bukhari IH, Zubair M, Islam MS. Efficient Synthesis of 2-Amino-6-Arylbenzothiazoles via Pd(0) Suzuki Cross Coupling Reactions: Potent Urease Enzyme Inhibition and Nitric Oxide Scavenging Activities of the Products. Molecules. 2013; 18(8):8845-8857. https://doi.org/10.3390/molecules18088845
Chicago/Turabian StyleGull, Yasmeen, Nasir Rasool, Mnaza Noreen, Faiz-ul-Hassan Nasim, Asma Yaqoob, Shazia Kousar, Umer Rashid, Iftikhar Hussain Bukhari, Muhammad Zubair, and Md. Saiful Islam. 2013. "Efficient Synthesis of 2-Amino-6-Arylbenzothiazoles via Pd(0) Suzuki Cross Coupling Reactions: Potent Urease Enzyme Inhibition and Nitric Oxide Scavenging Activities of the Products" Molecules 18, no. 8: 8845-8857. https://doi.org/10.3390/molecules18088845