Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. X-ray Analysis
2.3. Biological Assay
3. Materials and Methods
3.1. General Information
3.2. Methyl (Z)-4-(4-cyanophenyl)-2-hydroxy-4-oxobut-2-enoate 2
3.3. (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzonitrile 3
3.4. (Z)-4-(3-Hydroxy-4-methoxy-4-oxobut-2-enoyl)benzoic Acid 4
3.5. (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid 1
3.6. Biological Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
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Compound | D–H···A | D–H, Å | H···A, Å | D···A, Å | Angle D–H···A, ° |
---|---|---|---|---|---|
Piron | N1—H1···O1 * | 0.877(19) | 1.99(2) | 2.8649(16) | 173.0(16) |
Piron | N2—H2···O2 | 0.90(2) | 1.96(2) | 2.6529(16) | 132.8(17) |
Compound 3 | N1A—H1A···O1 ** | 0.91(2) | 2.03(2) | 2.915(2) | 163(2) |
Compound 3 | N2A—H2A···O2A | 0.92(3) | 2.02(2) | 2.697(2) | 129(2) |
Compound 3 | O1W—H1WA···O1 | 0.85 | 2.09 | 2.866(3) | 152 |
Compound 3 | O1W—H1WB···O1A | 0.85 | 2.25 | 2.873(3) | 131 |
Compound 3 | N1—H1···O1A *** | 0.89(3) | 2.08(3) | 2.884(2) | 150(2) |
Compound 3 | N2—H2···O2 | 0.88(2) | 2.05(2) | 2.707(2) | 130(2) |
Group | Edema Inhibition, % | ||
---|---|---|---|
1 h | 3 h | 5 h | |
Compound 1 5 mg/kg | 19.5 | 14.2 | −61.6 |
Compound 1 25 mg/kg | 63.1 1 | 61.5 1 | 16.2 |
Compound 1 125 mg/kg | 48.9 2 | 58.3 1 | 20.0 |
Diclofenac 10 mg/kg | 77.2 1 | 73.1 2 | 59.2 2 |
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Dmitriev, M.V.; Khramtsova, E.E.; Apuskin, D.Y.; Andreev, A.I.; Kovalenko, I.I.; Mashevskaya, I.V.; Maslivets, A.N. Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid. Molbank 2024, 2024, M1772. https://doi.org/10.3390/M1772
Dmitriev MV, Khramtsova EE, Apuskin DY, Andreev AI, Kovalenko II, Mashevskaya IV, Maslivets AN. Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid. Molbank. 2024; 2024(1):M1772. https://doi.org/10.3390/M1772
Chicago/Turabian StyleDmitriev, Maksim V., Ekaterina E. Khramtsova, Danila Y. Apuskin, Alexander I. Andreev, Ilya I. Kovalenko, Irina V. Mashevskaya, and Andrey N. Maslivets. 2024. "Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid" Molbank 2024, no. 1: M1772. https://doi.org/10.3390/M1772