Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Biological Activities
2.2.1. Anticancer Screening (In Vitro Cytotoxicity)
2.2.2. Structural Activity Relationship (SAR)
3. Experimental Section
3.1. General Information
3.2. Synthesis of 2,3-Diamino-6-Benzoyl-5-Methylthieno[2,3-d]Pyrimidin-4(3H)-One (3)
3.3. Synthesis of 2-(4-Aminophenyl)-6-Benzoyl-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (4)
3.4. Synthesis of N-(4-(3-Acetyl-6-Benzoyl-7-Methyl-8-oxo-3,8-Dihydrothieno[2,3-d][1,2,4] Triazolo[1,5-a]Pyrimidin-2-yl)Phenyl) Acetamide (5)
3.5. General Procedure for Synthesis of 6-Benzoyl-2-(4-Substituted-Phenyl)-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (6a–c)
3.6. Synthesis of 6-Benzoyl-7-Methyl-2-Phenylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (6a)
3.7. Synthesis of 6-Benzoyl-2-(4-Chlorophenyl)-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (6b)
3.8. Synthesis of 6-Benzoyl-2-(4-Methoxyphenyl)-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (6c)
3.9. Synthesis of 6-Benzoyl-7-Methyl-2-(Phenylamino)Thieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (7)
3.10. Synthesis of 6-Benzoyl-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidine-2,8(1H,3H)-Dione (8)
3.11. Synthesis of 6-Benzoyl-2-Mercapto-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (9)
3.12. Synthesis of 6-Benzoyl-2-(Chloromethyl)-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (10)
3.13. Synthesis of 6-Benzoyl-2-(((6-Benzoyl-7-Methyl-8-oxo-3,8-Dihydrothieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-2-yl)Methyl)thio)-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(3H)-One (11)
3.14. Synthesis of 6-Benzoyl-2-(Mercaptomethyl)-7-Methylthieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidin-8(1H)-One (12)
3.15. Synthesis of 2-Benzoyl-3-Methylthieno[2″,3″:4′,5′]Pyrimido[1′,2′:2,3][1,2,4]Triazolo [5,1-c][1,4] Thiazine-4,7(8H,10H)-Dione (13)
3.16. Synthesis of 6-Benzoyl-7-Methyl-8-oxo-3,8-Dihydrothieno[2,3-d][1,2,4]Triazolo[1,5-a]Pyrimidine-2-Carbox-ylic Acid (14)
3.17. Synthesis of 2-Benzoyl-8-Hydroxy-9-Mercapto-3-Methylpyrrolo[1′,2′:2,3][1,2,4]Triazolo[1,5-a]Thieno[2,3-d]Pyrimidine-4,7-Dione (15)
3.18. Synthesis of 2-Benzoyl-3-Methyl-8,13-Dihydrothieno[2‴,3‴:4″,5″]Pyrimido[1″,2″:2′,3′][1,2,4]triazolo[1′,5′:1,2]Pyrrolo[3,4-b]Quinoxaline-4,7-Dione (16)
3.19. Synthesis of 2-Benzoyl-3-Methylthieno[2⁗,3⁗:4‴,5‴]Pyrimido[1‴,2‴:2″,3″][1,2,4]Triazolo[1″,5″:1′,2′]Pyrrolo[3′,4′:5,6][1,4]Oxathiino[2,3-b]Quinoxaline-4,7-Dione (17)
3.20. Synthesis of 8-Benzoyl-9-Methyl-[1,4]Oxathiino[3″,2″:3′,4′]Pyrrolo[1′,2′:2,3][1,2,4]Triazolo[1,5-a]Thieno[2,3-d]Pyrimidine-3,10,13(2H)-Trione (18)
3.21. Synthesis of 7-Benzoyl-2-Mercapto-8-Methyl-1H-Imidazo[4″,5″:3′,4′]Pyrrolo[1′,2′:2,3][1,2,4]Triazolo[1,5-a]Thieno[2,3-d]Pyrimidine-9,12-Dione (19)
3.22. Synthesis of 10-Benzoyl-9-Methyl-3-Phenyl-1H-[1,2,4]Triazolo[4‴,3‴:1″,2″]Imidazo[4″,5″:3′,4′]Pyrrolo[1′,2′:2,3][1,2,4]Triazolo[1,5-a]Thieno[2,3-d]Pyrimidine-5,8-Dione (20)
3.23. Pharmacological Screening
3.23.1. Ethics Approval and Consent to Participate
3.23.2. Human and Animal Rights
3.23.3. Chemicals and Drugs
3.23.4. Materials and Methods (In Vitro Cytotoxicity)
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compounds | In Vitro Cytotoxicity IC50 (µM) | |||
---|---|---|---|---|
CNE2 a | KB a | MCF-7 a | MGC-803 a | |
1 | >50 | >50 | >50 | >50 |
2 | >50 | >50 | >50 | >50 |
3 | 33.5 ± 1.8 | 32.2 ± 1.2 | 34.1 ± 1.3 | 35.7 ± 1.5 |
4 | 21.3 ± 1.1 | 20.5 ± 1.3 | 20.9 ± 1.2 | 21.5 ± 1.4 |
5 | 13.1 ± 1.1 | 12.3 ± 1.4 | 12.5 ± 1.3 | 12.8 ± 1.2 |
6a | 26.3 ± 1.4 | 25.8 ± 1.7 | 26.9 ± 1.9 | 27.5 ± 1.3 |
6b | 24.5 ± 1.5 | 23.1 ± 1.2 | 24.2 ± 1.4 | 25.2 ± 1.1 |
6c | 25.1 ± 1.2 | 24.2 ± 1.3 | 25.5 ± 1.5 | 26.8 ± 1.8 |
7 | 14.2 ± 1.7 | 13.5 ± 1.5 | 13.7 ± 1.1 | 13.9 ± 1.4 |
8 | 29.1 ± 1.2 | 28.7 ± 1.1 | 29.5 ± 1.8 | 30.2 ± 1.6 |
9 | 18.3 ± 1.7 | 17.2 ± 1.5 | 17.8 ± 1.4 | 18.5 ± 1.3 |
10 | 19.1 ± 1.6 | 18.4 ± 1.2 | 18.7 ± 1.3 | 19.2 ± 1.5 |
11 | 12.1 ± 1.2 | 11.1 ± 1.3 | 11.8 ± 1.5 | 11.7 ± 1.4 |
12 | 16.1 ± 1.4 | 15.3 ± 1.3 | 15.9 ± 1.2 | 16.5 ± 1.1 |
13 | 15.4 ± 1.3 | 14.1 ± 1.2 | 14.8 ± 1.1 | 15.7 ± 1.2 |
14 | 20.5 ± 1.8 | 19.8 ± 1.5 | 19.8 ± 1.4 | 20.4 ± 1.6 |
15 | 12.7 ± 1.2 | 11.7 ± 1.6 | 12.1 ± 1.2 | 12.2 ± 1.4 |
16 | 11.9 ± 1.5 | 10.9 ± 1.2 | 11.6 ± 1.1 | 11.5 ± 1.3 |
17 | 11.8 ± 1.4 | 10.8 ± 1.1 | 11.5 ± 1.4 | 11.3 ± 1.5 |
18 | 12.4 ± 1.5 | 11.3 ± 1.4 | 11.9 ± 1.3 | 11.9 ± 1.1 |
19 | 11.7 ± 1.3 | 10.7 ± 1.5 | 11.4 ± 1.1 | 11.1 ± 1.2 |
20 | 11.6 ± 1.1 | 10.5 ± 1.5 | 11.3 ± 1.2 | 10.9 ± 1.4 |
5-Fluorouracil | 11.8 ± 1.4 | 10.7 ± 1.2 | 11.5 ± 1.3 | 11.1 ± 1.1 |
Compounds/Chemical Structures | In Vitro Cytotoxicity IC50 (µM) | |||
---|---|---|---|---|
CNE2 a | KB a | MCF-7 a | MGC-803 a | |
12.1 ± 1.2 | 11.1 ± 1.3 | 11.8 ± 1.5 | 11.7 ± 1.4 | |
11.9 ± 1.5 | 10.9 ± 1.2 | 11.6 ± 1.1 | 11.5 ± 1.3 | |
11.8 ± 1.4 | 10.8 ± 1.1 | 11.5 ± 1.4 | 11.3 ± 1.5 | |
12.4 ± 1.5 | 11.3 ± 1.4 | 11.9 ± 1.3 | 11.9 ± 1.1 | |
11.7 ± 1.3 | 10.7 ± 1.5 | 11.4 ± 1.1 | 11.1 ± 1.2 | |
11.6 ± 1.1 | 10.5 ± 1.5 | 11.3 ± 1.2 | 10.9 ± 1.4 | |
11.8 ± 1.4 | 10.7 ± 1.2 | 11.5 ± 1.3 | 11.1 ± 1.1 |
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Abu-Hashem, A.A.; Al-Hussain, S.A.; Zaki, M.E.A. Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives. Molecules 2021, 26, 2031. https://doi.org/10.3390/molecules26072031
Abu-Hashem AA, Al-Hussain SA, Zaki MEA. Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives. Molecules. 2021; 26(7):2031. https://doi.org/10.3390/molecules26072031
Chicago/Turabian StyleAbu-Hashem, Ameen Ali, Sami A. Al-Hussain, and Magdi E. A. Zaki. 2021. "Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives" Molecules 26, no. 7: 2031. https://doi.org/10.3390/molecules26072031