Synthesis and evaluation of analgesic, anti-inflammatory, and anticancer activities of new pyrazole-3(5)-carboxylic acid derivatives


ÇALIŞKAN B., Yilmaz A., Evren I., Menevse S., Uludag O., BANOĞLU E.

MEDICINAL CHEMISTRY RESEARCH, vol.22, no.2, pp.782-793, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 2
  • Publication Date: 2013
  • Doi Number: 10.1007/s00044-012-0072-4
  • Journal Name: MEDICINAL CHEMISTRY RESEARCH
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.782-793
  • Keywords: Carrageenan, Hind paw edema, Benzoquinone, Writhings, Cell lines, PRELIMINARY BIOLOGICAL EVALUATION, CANCER CELL-GROWTH, PAIN-LIKE BEHAVIOR, AMIDE DERIVATIVES, CYCLOOXYGENASE-2 COX-2, HYDRAZONE DERIVATIVES, PYRAZOLE DERIVATIVES, POTENTIAL AGENTS, BREAST-CANCER, APOPTOSIS
  • Gazi University Affiliated: Yes

Abstract

In this article, we synthesized a series of novel 1-benzyl-5(3)-p-tolyl-1H-pyrazole-3(5)-carboxylic acid derivatives and characterized by IR, H-1 NMR, and mass spectroscopy. Compounds were evaluated for their in vivo analgesic and anti-inflammatory activity using the p-benzoquinone-induced writhing test and the carrageenan-induced paw edema model, respectively. Out of 14 compounds tested, 7a, 7c, 7e, 7f, 7i, 8a-b, and 8f-g exhibited potent analgesic and/or anti-inflammatory activity as compared to reference drugs aspirin and indomethacin. Anticancer activity of these compounds was assessed against five cancer cell lines with the MTT assay (HL-60, human promyelocytic leukemia cells; HeLa, human cervical cancer cells; Raji, human B lymphocyte cell line; MCF7, human breast adenocarcinoma cell line; MDA-MB-231, estrogen-independent human breast cancer cell line). Compounds 7a, 8a, and 8b with high anti-inflammatory activity, and also 7d and 7j with mild anti-inflammatory activity exhibited promising anticancer activity against some selected cell lines.