Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

doi:10.5246/jcps.2017.08.069

中国药学(英文版) ›› 2017, Vol. 26 ›› Issue (8): 611-620.DOI: 10.5246/jcps.2017.08.069

• 【研究论文】 • 上一篇

Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

Syed Misbahul Hasan^1,2, Shah Alam Khan³, Kavita Golani¹, Jaswinder Lamba¹, Aftab Ahmad⁴, Asif Husain^1*

1. Department of Pharmaceutical Chemistry, School of Pharmaceutical Education and Research, Jamia Hamdard (Hamdard University), New Delhi, 110062, India
2. Faculty of Pharmacy, Integral University, Lucknow, UP 226026, India
3. Department of Pharmacy, Oman Medical College, PO Box 620, Postal code-130, Muscat, Sultanate of Oman
4. Health Information Technology Department, Jeddah Community College, King Abdulaziz University, Jeddah, Kingdom of Saudi Arabia

收稿日期:2017-04-28 修回日期:2017-06-11 出版日期:2017-08-31 发布日期:2017-07-05
通讯作者: Tel.: +91-9891116086, E-mail: drasifhusain@yahoo.com

Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

Syed Misbahul Hasan^1,2, Shah Alam Khan³, Kavita Golani¹, Jaswinder Lamba¹, Aftab Ahmad⁴, Asif Husain^1*

1. Department of Pharmaceutical Chemistry, School of Pharmaceutical Education and Research, Jamia Hamdard (Hamdard University), New Delhi, 110062, India
2. Faculty of Pharmacy, Integral University, Lucknow, UP 226026, India
3. Department of Pharmacy, Oman Medical College, PO Box 620, Postal code-130, Muscat, Sultanate of Oman
4. Health Information Technology Department, Jeddah Community College, King Abdulaziz University, Jeddah, Kingdom of Saudi Arabia

Received:2017-04-28 Revised:2017-06-11 Online:2017-08-31 Published:2017-07-05
Contact: Tel.: +91-9891116086, E-mail: drasifhusain@yahoo.com

摘要/Abstract

摘要：

In the present study, synthetic chalcones, flavanones and Schiff bases were prepared starting from paraceamol, and evaluated their anticipated anti-inflammatory activity. Chalcones were synthesized by reacting 3-acetyl-4-hydroxy acetanilide and aromatic aldehydes in alcoholic potassium hydroxide (KOH) solution under Claisen-Schmidt condensation conditions. The chalcones were cyclized in the presence of piperidine in isoamyl alcohol to obtain flavonone derivatives. Schiff bases were synthesized by condensing 3-acetyl-4-hydroxy anilines with aromatic aldehydes in the presence of HCl. These Schiff bases were further reacted with other aromatic aldehydes in alcoholic KOH solution. PASS cheminformatics software was used to predict the anti-inflammatoryactivity of synthesized compounds.PASS software predicted that chalcone-based Schiff bases6a–d contained structural features that can exhibit anti-inflammatory activity. All the prepared derivatives of acetaminophen exhibited moderate to excellent in vivo anti-inflammatory activity in carrageenan-induced edema in rat paw. All the Schiff bases coupled chalcones showed good anti-inflammatory activity compared with the reference drug, diclofenac. Further evaluation of their therapeutic potential and safety profile is required in the future study.

关键词: p-Acetaminophen, Anti-inflammatory, Chalcone, Flavanone

Abstract:

Key words: p-Acetaminophen, Anti-inflammatory, Chalcone, Flavanone

中图分类号:

R916

Supporting:

Syed Misbahul Hasan, Shah Alam Khan, Kavita Golani, Jaswinder Lamba, Aftab Ahmad, Asif Husain. Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases[J]. 中国药学(英文版), 2017, 26(8): 611-620.

参考文献

[1] Serafini, M.; Peluso, I.; Raguzzini, A. Proc. Nutr. Soc. 2010, 69, 273-278.

[2] Middleton, E.Jr.; C. Kandaswami, C. “The impact of plant flavonoids on mammalian biology: Implications for immunity, inflammation and cancer” (J.B. Harborne, ed.), 1st Edition, London: Chapman and Hall, 1994, 619-652.

[3] Moorkoth, S. Chem. Pharm. Bull. 2015, 63, 974-985.

[4] Mostahar, S.; Sayed, A.; Azizul, I. Indian. J. Chem. 2006, 45, 1478-1486.

[5] Ahmad, B.; Khan, S.A.; Tanveer, A. Die Pharmazie. 2003, 58, 173-177.

[6] Cushnie, T.P.; Lamb, A.J. Int. J. Antimicrob. Agents. 2005, 26, 343-356.

[7] Liu, H.L.; Jiang, W.B.; Xie, M.X. Recent. Pat. Anticancer. Drug. Discov. 2010, 5, 152-164.

[8] Bano, S.; Javed, K.; Ahmad, S.; Rathish, I.G.; Singh, S.; Chaitanya, M.; Arunasree, K.M.; Alam, M. Eur. J. Med. Chem. 2013, 65, 51-59.

[9] Chen, C.Y.; Peng, W.H.; Tsai, K.D.; Hsu, S.L. Life. Sci. 2007, 81, 1602-1614.

[10] Khan S.A.; Ahmad, B.; Tanveer, A. Pak. J. Pharm. Sci. 2006, 19, 290-294.

[11] Alcaraz, M.J.; Vicente, A.M.; Araico, A.; Dominguez, J.N.; Terencio, M.C.; Ferra´ndi, M.L. Br. J. Pharmacol. 2004, 142, 1191-1199.

[12] Hwang, T.L.; Yeh, S.H.; Leu, Y.L.; Chern, C.Y.; Hsu, H.C. Br. J. Pharmacol. 2006, 148, 78-87.

[13] Patent pub. No. WO/2003/097575 (2003).

[14] Husain, A.; Varshney, M.M.; Parcha, V.; Ahmad, A.; Khan, S.A. Bangladesh. J. Pharmacol. 2015, 10, 555-561.

[15] Thakare, T.W.S.; Rathod, A.S; Doshi, A.G. Orient. J. Chem. 2010, 26, 717-719.

[16] Sahoo, B.M.; Dinda, S.C.; Ravi Kumar, B.V.V. Lett. Drug. Design. Discov. 2014, 11, 82-89.

[17] Chem, H.; Rhodes, J.J. J. Mol. Med. (Berl). 1996, 74, 497-504.

[18] Kim H.P.; Son, K.H.; Chang, H.W. J. Pharmacol. Sci. 2004, 96, 229-245.

[19] Khan, M.S.Y.; Sharma, S.; Husain, A. Sci. Pharm. 2002, 70, 287-294.

[20] Stepanchikova, A.V.; Lagunin, A.A.; Filimonov, D.A.; Poroikov, V.V. Curr. Med. Chem. 2003, 10, 225-233.

[21] Winter, C.A.; Risley, V.; Nuss, G.W. Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547.

[22] Goel, R.K.; Singh, D.; Lagunin, A.; Poroikov, V. Med. Chem. Res. 2011, 20, 1509-1514.
[23] Nath L.S.; Khan, S.A.; Ahmad, A. Sch. Acad. J. Pharm. 2014, 3, 496-503.

Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 3

编辑推荐

Metrics

本文评价

[1]	Eric Wei Chiang Chan, Ying Ki Ng, Hung Tuck Chan, Siu Kuin Wong. An overview of flavonoids from Sophora flavescens (kushen) with some emphasis on the anticancer properties of kurarinone and sophoraflavanone G[J]. 中国药学(英文版), 2023, 32(8): 603-615.
[2]	Aris Stiawan, Eti Nurwening Sholikhah, Yehezkiel Steven Kurniawan, Yoga Priastomo, Jumina. Synthesis, cytotoxicity assay, and molecular docking study of hydroxychalcone derivatives as potential tyrosinase inhibitors[J]. 中国药学(英文版), 2021, 30(8): 634-644.
[3]	Prajapati Prajesh^*, Vaghela Vipul, Baraiya Dharmendra. Sensitive method for rapid estimation of Lornoxicam in bulk and its dosage form by RP-HPLC[J]. , 2013, 22(1): 110-113.