Article Sidebar

Submitted
August 11, 2024
Published
August 20, 2024
Download
PDF
Statistic
Read Counter : 521 Download : 1

Main Article Content

Abstract

Administration of non-steroidal anti-inflammatory drugs (NSAIDs) is the first therapeutic choice for the treatment of pain and inflammation. Several existing amide derivatives show their properties as anti-inflammatory, antidegenerative, anticancer, antimicrobial and analgesic, one of which is salicylanilide. The precursor for salicylanilide synthesis is carboxylic acid, using natural methyl salicylate from gondopuro oil and amines sonochemically with the help of Decyclocarbodiimide (DCC) coupling reagent. The research aims to carry out the synthesis of amide derivatives using DCC coupling reagent with the sonochemical method in 7 hours. Identification of synthetic compounds by spectrum elucidation using infrared spectrophotometry (FTIR-ATR), GC-MS and in-vivo anti-inflammatory and analgesic activity tests. In this study, the mixture was sonicated for 7 hours at a temperature of ±0oC, then left in the refrigerator overnight, evaporated at a temperature of 65oC. The precipitate formed was filtered using Buchner, washed using cold distilled water and washed again using methanol. The crystals obtained were then dried in an oven at 40ºC until dry, then the % yield of the synthesized compound was determined. Tests include organoleptic tests, melting point, solubility, FTIR, GC-MS In vivo anti-inflammatory and analgesic activity tests. The research results showed that salicylanilide compounds could be synthesized in 7 hours with a % yield of 27.55%. The resulting synthesis can melt from a temperature of 218-222°C and can dissolve in methanol, ethanol, chloroform and ether but does not dissolve in distilled water. FTIR testing on salicylanilide compounds showed the presence of phenolic -OH, aromatic C-H, C=O amide and aromatic C=C groups. The synthesized compound produced an abundance of 2.43%. The highest percentage of anti-inflammatory power was at dose 3 synthesis (7.56 mg/ 200 grams of rat body weight) at 44.46% and the highest analgesic effect was at dose 4 synthesis (10.08 mg/ 200 grams Rat BW)

Article Details

Author Biography

Erwin Indriyanti

Sekolah Tinggi Ilmu Farmasi (STIFAR) Yayasan Pharmasi Semarang

References

  1. Arshad, M. A., Khurshid, U., Ahmad, S., Ijaz, S., Rashid, F., & Azam, R. (2014). Review on methods used to determine Antioxidant activity. Jezs, 1(1), 41–46. https://www.researchgate.net/publication/313845805
  2. Babu, P. N. K., Devi, B. R., & Dubey, P. K. (2013). Ultrasound assisted convenient, rapid and environmentally benign synthesis of N-alkylbenzimidazoles. Der Chemica Sinica, 4(1), 105–110.
  3. Devica, S. (2015).No Title No Title. In Pengaruh Harga Diskon Dan Persepsi Produk Terhadap Nilai Belanja Serta Perilaku Pembelian Konsumen (Vol. 7, Issue 9).
  4. Doulgkeris, C. M., Galanakis, D., Kourounakis, A. P., Tsiakitzis, K. C., Gavalas, A. M., Eleftheriou, P. T., Victoratos, P., Rekka, E. A., & Kourounakis, P. N. (2006). Synthesis and pharmacochemical study of novel polyfunctional molecules combining anti-inflammatory, antioxidant, and hypocholesterolemic properties. Bioorganic and Medicinal Chemistry Letters, 16(4), 825–829. https://doi.org/10.1016/j.bmcl.2005.11.027
  5. Draye, M., Chatel, G., & Duwald, R. (2020). Ultrasound for drug synthesis: A green approach. Pharmaceuticals, 13(2). https://doi.org/10.3390/ph13020023
  6. Farshori, N. N., Banday, M. R., Zahoor, Z., & Rauf, A. (2010). DCC/DMAP mediated esterification of hydroxy and non-hydroxy olefinic fatty acids with β-sitosterol: In vitro antimicrobial activity. Chinese Chemical Letters, 21(6), 646–650. https://doi.org/10.1016/j.cclet.2010.01.003
  7. Gunathilake, K. D. P. P., Ranaweera, K. K. D. S., & Rupasinghe, H. P. V. (2018). In vitro anti-inflammatory properties of selected green leafy vegetables. Biomedicines, 6(4), 1–10. https://doi.org/10.3390/biomedicines6040107
  8. Hendrata, F. D. (2014). Sintesis Metil 2-Asetoksibenzoat Dari Minyak Gandapura Dan Uji Aktivitasnya Sebagai Antiinflamasi the Synthesis of Methyl 2-Acetoxybenzoate From Wintergreen Oil and the Test As Antiinflammatory. 1–13.
  9. Indriyanti, E., & Prahasiwi, M. S. (2020). SYNTHESIS OF CINNAMIC ACID BASED ON PERKIN REACTION USING SONOCHEMICAL METHOD AND ITS POTENTIAL AS PHOTOPROTECTIVE AGENT. 5(1), 54–61.
  10. Karadag, A., Ozcelik, B., & Saner, S. (2009). Review of methods to determine antioxidant capacities. Food Analytical Methods, 2(1), 41–60. https://doi.org/10.1007/s12161-008-9067-7
  11. Li, J. T., Zang, H. J., Feng, J. Y., Li, L. J., & Li, T. S. (2001). Synthesis of cinnamic acids catalyzed by expansive graphite under ultrasound. Synthetic Communications, 31(5), 653–656. https://doi.org/10.1081/SCC-100103251
  12. Li, Z., Zhuang, T., Dong, J., Wang, L., Xia, J., Wang, H., Cui, X., & Wang, Z. (2021). Sonochemical fabrication of inorganic nanoparticles for applications in catalysis. Ultrasonics Sonochemistry, 71. https://doi.org/10.1016/j.ultsonch.2020.105384
  13. Ma’mun. (2015). Penyulingan Dan Analisis Beberapa Jenis Minyak Gandapura. Buletin Penelitian Tanaman Rempah Dan Obat, 16(2), 82–89.
  14. Mehta, N., Aggarwal, S., Thareja, S., Malla, P., Misra, M., Bhardwaj, T. R., & Kumar, M. (2010). Synthesis, pharmacological and toxicological evaluation of amide derivatives of ibuprofen. International Journal of ChemTech Research, 2(1), 233–238.
  15. Of, S., Activity, A., Mucuna, O. F., On, E., & Albino, S. (2015). Study of Analgetik Activity of Mucuna Pruriens. 4(5), 1124–1132.
  16. Oleracea, B., & Italica, L. V. A. R. (2015). A Preliminary Report On Antihyperglycemic And Analgetik Properties Of Methanol Extract Of. 4(09), 225–234.
  17. Patel, B. R., Desai, D. H., Raval, J. P., & Patel, B. R. (2014). Green Efficient Synthesis of Aryl Thioamides Using Ultrasound: A Comparative Study. Journal of Pharmacy And Applied Sciences, 1(1), 29–33.
  18. Priambodo, W. S., Saleh, C., Kimia, J., & Mulawarman, U. (2019). Pembuatan Metil Salisilat Menggunakan Katalis Asam Dengan Metode Tanpa Pelarut. Atomik, 04(1), 41–44.
  19. Retnowati, R., & Azzuhro, D. (2013). Sintesis N , N-dietil-2-hidroksibenzamida Menggunakan Metil Salisilat dari Minyak Gandapura. Natural B, 2(1), 94–102.
  20. Ripa, F. A., Dash, P. R., & Faruk, M. O. (2015). CNS depressant, analgetik and anti-inflammatory activities of methanolic seed extract of Calamus rotang Linn. fruits in rat. J Pharmacog Phytochem, 3(5), 121–125.
  21. Robb, C. T., Goepp, M., Rossi, A. G., & Yao, C. (2020). Non-steroidal anti-inflammatory drugs, prostaglandins, and COVID-19. British Journal of Pharmacology, July, 4899–4920. https://doi.org/10.1111/bph.15206
  22. Ruan, B. F., Ge, W. W., Cheng, H. J., Xu, H. J., Li, Q. S., & Liu, X. H. (2017). Resveratrol-based cinnamic ester hybrids: synthesis, characterization, and anti-inflammatory activity. Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 1282–1290. https://doi.org/10.1080/14756366.2017.1381090
  23. Sondhi, S. M., Singh, J., Kumar, A., Jamal, H., & Gupta, P. P. (2009). Synthesis of amidine and amide derivatives and their evaluation for anti-inflammatory and analgetik activities. European Journal of Medicinal Chemistry, 44(3), 1010–1015. https://doi.org/10.1016/j.ejmech.2008.06.029
  24. Sulistyo, R., Suratmo, & Retnowati, R. (2015). Sintesis salisilanilida dari komponen utama minyak gandapura. Kimia Student Journal, 1(1), 805–811.
  25. Umar, M. I., Asmawi, M. Z., Sadikun, A., Majid, A. M. S. A., Al-Suede, F. S. R., Hassan, L. E. A., Altaf, R., & Ahamed, M. B. K. (2014). Ethyl-p-methoxycinnamate isolated from kaempferia galanga inhibits inflammation by suppressing interleukin- 1, tumor necrosis factor-α, and angiogenesis by blocking endothelial functions. Clinics, 69(2), 134–144. https://doi.org/10.6061/clinics/2014(02)10
  26. Yadav, A., Kumari, R., Yadav, A., Mishra, J. P., Seweta, S., & Prabha, S. (2016). Antioxidants and its functions in human body. Research in Environment and Life Sciences, 9(11), 1328–1331.
  27. Siswandono, dan Soekardjo, Bambang, 1995, Kimia Medisinal, Airlangga University Press, Surabaya.