Dergiler / Marmara Pharmaceutical Journal / 2018 / Cilt: 22 - Sayı: 4

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-Naproxen as anticancer agents

Sayfa
559–569
DOI
—
🏛️Bu makalenin bibliyografik verileri ve tam metin bağlantısı DergiPark üzerinden sağlanmıştır.
DergiPark Kaydı ↗
✨

Yapay Zeka Hızlı Bakış & Çıkarımlar

AI Insight
⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

Compounds (7a-m) exhibited anticancer activity with IC50 values of 87.2-400 µM against prostate cancer cell lines.

📌 3 Maddede Bu Makale

🎯
Amaç & Hipotez:A novel series of new naproxen derivatives (S)-ethyl{[4-(4-fluorophenyl)-5-[(1-(6-methoxynaphtalen-2- yl)ethyl)]-4H-1,2,4-triazole-3-yl]sulphanyl}acetate (5), (S)-2-({5-[1-(6-methoxynaphtalen-1-yl)ethyl]-4-fluorophenyl-4H1,2,4-triazole-3-yl}sulphanyl)acetohydrazide (6), 2-{[5-[1-(6-methoxynaphtalen-2-yl)ethyl]-4-(4-fluorophenyl)-4H-1,2,4- triazole-3-yl]sulphanyl}-N'-[(substituted)methylidene]acetohydrazides (7a-m) were synthesized, in this study.
📊
Temel Bulgular & Veri:The structures of compounds 5, 6 and 7a-m were defined by spectral (1H-NMR, 13C-NMR, HR-MS and FT-IR) methods and their purity was proven by elemental analysis, thin layer chromatography and high pressure liquid chromatography.
💡
Sonuç & Katkı:Compounds (7a-m) exhibited anticancer activity with IC50 values of 87.2-400 µM against prostate cancer cell lines.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri

Özet

A novel series of new naproxen derivatives (S)-ethyl{[4-(4-fluorophenyl)-5-[(1-(6-methoxynaphtalen-2- yl)ethyl)]-4H-1,2,4-triazole-3-yl]sulphanyl}acetate (5), (S)-2-({5-[1-(6-methoxynaphtalen-1-yl)ethyl]-4-fluorophenyl-4H1,2,4-triazole-3-yl}sulphanyl)acetohydrazide (6), 2-{[5-[1-(6-methoxynaphtalen-2-yl)ethyl]-4-(4-fluorophenyl)-4H-1,2,4- triazole-3-yl]sulphanyl}-N'-[(substituted)methylidene]acetohydrazides (7a-m) were synthesized, in this study. The structures of compounds 5, 6 and 7a-m were defined by spectral (1H-NMR, 13C-NMR, HR-MS and FT-IR) methods and their purity was proven by elemental analysis, thin layer chromatography and high pressure liquid chromatography. These compounds were evaluated for in vitro anticancer activity by using MTS method against PC-3 and DU-143 (androgen-independent human prostate cancer cell lines) and LNCaP (androgen-sensitive human prostate adenocarcinoma) prostate cancer cell lines. Cisplatin was used as the positive sensitivity reference standard. Compounds (7a-m) exhibited anticancer activity with IC50 values of 87.2-400 µM against prostate cancer cell lines.

🔖

Bu Makaleye Atıf Yap

HAN, M. İ., BEKÇİ, H., CUMAOĞLU, A., KÜÇÜKGÜZEL, Ş. G. (2018). Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-Naproxen as anticancer agents. Marmara Pharmaceutical Journal, Cilt: 22 - Sayı: 4, 559–569. https://ajindex.com/articles/283621

📄 Tam Metin PDF Okuyucu

📄

PDF görüntüleyici hazırlanıyor...

Kaynakça (3)

  1. Hawkey CJ. COX-2 inhibitors. The Lancet 1999; 353: 307-314
  2. Ammar YA, Salem MA, Fayed EA, Helal MH, El-Gaby MSA, Thabet HK. Naproxen derivatives: Synthesis, reactions, and biological applications. Synth Commun. 2017; 47; 1341-1367. [CrossRef] [3] Harris RE, Donk JB, Alshafie GA. Similar reductions in the risk of human colon cancer by selective and nonselective cyclooxygenase-2 (COX-2) inhibitors. BMC Cancer. 2008; 8: 237-242. [CrossRef] [4] Kim MS, Kim JE, Lim DY, Huang Z, Chen H, Langfald A, Lubet RA, Grubbs CJ, Dong Z, Bode AM. Naproxen induces cell-cycle arrest and apoptosis in human urinary bladder cancer cell lines and chemically induced cancers by targeting PI3K. Cancer Prev Res. 2014; 7(2): 237-245. [CrossRef] [5] Lubet RA, Scheiman JM, Bode A, White J, Minasian L, Juliana MM, Boring DL, Steele VE, Grubbs CJ. Prevention of chemically induced urinary bladder cancers by naproxen: protocols to reduce gastric toxicity in humans do not alter preventive efficacy. Cancer Prev Res. 2015; 8(4): 297-302. [CrossRef] [6] Kömürcü ŞG, Rollas S, Ulgen M, Gorrod JW, Cevikbaş A. Evaluation of some arylhydrazones of p-aminobenzoic acid hydrazide as antimicrobial agents and their in-vitro hepatic microsomal metabolism. Boll Chim Farmaceutico. 1995; 134: 375-379
  3. Küçükgüzel ŞG, Oruc EE, Rollas S, Şahin F, Ozbek A. Synthesis, characterization and biological activity of novel 4- thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem. 2002; 37: 197-206. [CrossRef] [8] Küçükgüzel ŞG, Mazı A, Şahin F, Ozturk S, Stables J. Synthesis and biological activities of diflunisal hydrazidehydrazones. Eur J Med Chem. 2003; 38: 1005-1013. [CrossRef] [9] Rollas S, Küçükgüzel ŞG. Biological activities of hydrazone derivatives. Molecules. 2007; 12: 1910-1939. [CrossRef] [10] Çıkla P, Özsavcı D, Bingöl Özakpınar Ö, Şener A, Çevik O, Özbaş Turan S, Akbuğa J, Şahin F, Küçükgüzel ŞG. Synthesis, cytotoxicity and pro-apoptosis of etodolac hydrazide derivatives as anticancer agents. Arch Pharm. 2013; 346: 367-379. [CrossRef] [11] Çıkla P, Tatar E, Küçükgüzel İ, Şahin F, Yurdakul D, Basu A, Krishnan R, Nichols DB, Basu NK, Küçükgüzel ŞG. Synthesis and characterization of flurbiprofen hydrazide derivatives as potential anti-HCV, anticancer, antimicrobial agents. Med Chem Res. 2013; 22: 5685-5699. [CrossRef] [12] Aydın S, Basu NK, Arora P, Basu A, Nichols DB, Talele TT, Akkurt M, Celik İ, Buyukgungor O, Küçükgüzel ŞG. Microwave assisted synthesis of some novel fl