A new series of diarylamides possessing quinoline nucleus: Synthesis, in vitro anticancer activities, and kinase inhibitory effect

El‐Gamal, Mohammed I.; Khan, Mohammad Ashrafuddin; Abdel‐Maksoud, Mohammed S.; El-Din, Mahmoud M. Gamal; Oh, Chang‐Hyun

doi:10.1016/j.ejmech.2014.09.068

Cited by 30 publications

(16 citation statements)

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“…Quinoline | 639 ROMERO Et al. alkaloids derived from plants, animals, and micro-organisms have showed remarkable antitumor activity against different cancer cells (Jain, Chandra, Jain, Pathak, & Vaidya, 2016). Also, several examples of synthetic quinolines have been reported by multiple research groups worldwide as promising anticancer agents (Beauchard et al, 2009;Czoch, Pognan, Kaczmarek, & Boraty, 1994;Ferlin, Gatto, Chiarelotto, & Palumbo, 2001;Gamal, Khan, Maksoud, El-Din, & Oh, 2014;Heiniger, Gakhar, Prasain, Hua, & Nguyen, 2010;Kim et al, 2001;Martirosyan, Rahim-Bata, Freeman, Clarke, & Howard, 2004;Perzyna et al, 2002;Tseng, Chen, Lu, Yang, & Tzeng, 2008;Tseng et al, 2009Tseng et al, , 2010Utsugi et al, 1997). In particular, compounds based on 4-aminoquinolines have received largely attention by its significant anticancer activity (Chen, Chen, Wang, Han, & Tzeng, 2005;Chen, Chung, Chen, Chen, & Jeng, 2002;Chen et al, 2006Chen et al, , 2011Kakadiya et al, 2010;Lee et al, 2004;Lu et al, 2010;Mejía et al, 2009;Sanchez et al, 2011;Su et al, 1995;Via, Gia, Gasparotto, & Ferlin, 2008).…”

Section: Introductionmentioning

confidence: 99%

“…Specifically, antimalarial drugs such as chloroquine, hidroxychloroquine, mefloquine, quinine, and quinacrine have demonstrated an appreciable antiproliferative effect against different cancer cells, exhibiting sub-micromolar IC 50 values (Choi, Kim, Woo, Kim, & Yoon, 2016;Grimaldi et al, 2015;Maes, Kuchnio, Carmeliet, & Agostinis, 2016;Preet et al, 2012;Salentin et al, 2017;Verbaanderd et al, 2017;Yan et al, 2013). In general, most of the anticancer quinolines are targeted to tyrosine kinase enzymes, proteasome, tubuline polymerization, topoisomerase, or DNA repair (Beauchard et al, 2009;Czoch et al, 1994;Ferlin et al, 2001;Gamal et al, 2014;Heiniger et al, 2010;Kim et al, 2001;Martirosyan et al, 2004;Perzyna et al, 2002;Tseng et al, 2008Tseng et al, , 2009Tseng et al, , 2010Utsugi et al, 1997). Modulation of the large-conductance calcium-activated potassium (BK) channels also has been identified as target for 4-substituted quinolines and 4-substituted quinolin-2-ones, representing an attractive target for the 4-aminoquinolines tested in this investigation (Dinsmore & Bergman, 2003;Hewawasam, Sit, & Starrett, 2003;Hewawasam, Starrett, & Swartz, 1997;Kang et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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Identification of dehydroxy isoquine and isotebuquine as promising anticancer agents targeting K+ channel

et al. 2019

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Traditional antimalarial drugs based on 4‐aminoquinolines have exhibited good antiproliferative activities against human tumor cells; however, their low relative efficacy has limited their corresponding clinical uses. In order to identify new potent anticancer agents based on 4‐aminoquinoline, we evaluated the antiproliferative activity of a series of dehydroxy isoquines and isotebuquines against five human cancer lines. HeLa and SKBr3 were significantly more sensitive to the action of tested quinolines than the A549, MCF‐7, and PC‐3 cancer lines. Compound 2h was by far the most potent derivative against four of the tested lines (except to PC3 line), exhibiting low micromolar or nanomolar IC50 values superior to adriamycin reference, low toxicities on dermis human fibroblasts (LD50 > 250 μM), and excellent selectivity indexes against the mentioned cancer cells. A structure–activity relationship analysis put in evidence that a pyrrolidine or morpholine moiety as N‐alkyl terminal substitution and the incorporation of the extra phenyl attached to aniline ring are pharmacophore essentials for improvement the anticancer activity of the studied dehydroxy isoquines and isotebuquines. From the results, compound 2h emerged as a promising anticancer candidate for further in vitro assays against resistant‐strain and in vivo studies as well as pharmacokinetic and genotoxicity studies. Mechanistic assays suggested that the most active quinoline 2h act as calcium‐activated potassium channel activator.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Identification of dehydroxy isoquine and isotebuquine as promising anticancer agents targeting K+ channel

et al. 2019

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“…According to the report by WHO it is expected to increase by 15 million new cancer patients every year by 2020. The treatment regimes in chemotherapy have fall short either in terms of toxicity or efficiency problems ,. Targeting DNA is highly crucial during development of new therapeutic modalities, since it restores its function and leads apoptotic cell death thus controlling the proliferation .…”

Section: Introductionmentioning

confidence: 99%

Design, Docking, and Synthesis of Quinoline‐2H‐1,2,4‐triazol‐3(4H)‐ones as Potent Anticancer and Antitubercular Agents

et al. 2018

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A new series quinoline‐2H‐1,2,4‐triazol‐3(4H)‐ones 7 g‐n and 11 g‐n were designed and synthesized. Docking studies of title compounds with DNA (PDB: 1AU5) and with long‐chain enoyl‐acyl carrier protein reductase (InhA) enzyme (PDB ID: 4TZK) as anticancer and antitubercular targets showed good insights on the possible interactions. Further, the compounds were tested for in vitro anticancer activity against HeLa human cervix tumor cell line and also in vitro antitubercular activity against M. tuberculosis H37Rv [MTB] (ATCC‐27294). Some of the compounds exhibited promising activities in both the protocols. Hence, these compounds may be considered as pharmacological lead molecules of interest.

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“…Several quinoline analogues were reported as anticancer agents [6][7][8][9][10][11][12][13]. The structure of some of the quinoline anticancer drug is shown in Figure 1 [6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of Some Quinoline and Oxadiazole Derivatives

Ahsan¹,

Shastri²,

Yadav³

et al. 2016

Organic Chemistry International

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In continuance of our search for newer antiproliferative agents we report herein the synthesis and antiproliferative studies of two series (5a-j and 10a-c) of heterocyclic compounds. All the new compounds were characterized by IR, NMR, and mass spectral data. The antiproliferative activity of 10 compounds (5a-j) was carried out on HeLa (cervix cancer cell line) and MDA-MB-435 (melanoma) and LC 50 , TGI, and GI 50 were calculated, while the antiproliferative activity of 3 compounds (10a-c) was carried out against nine different panels of nearly 60 cell lines (NCI-60) according to the National Cancer Institute (NCI US) Protocol at 10 M. 1-(7-Hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)-3-(4-methoxylphenyl)urea (5j) was found to have antiproliferative activity with GI 50 of 35.1 M against HeLa (cervix cancer cell line) and 60.4 M against MDA-MB-435 (melanoma), respectively. The compounds 10a, 10b, and 10c showed antiproliferative activity with comparatively higher selectivity towards HOP-92 (Non-Small Cell Lung Cancer) with percent growth inhibitions (GIs) of 34.14, 35.29, and 31.59, respectively.

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A new series of diarylamides possessing quinoline nucleus: Synthesis, in vitro anticancer activities, and kinase inhibitory effect

Cited by 30 publications

References 42 publications

Identification of dehydroxy isoquine and isotebuquine as promising anticancer agents targeting K+ channel

Identification of dehydroxy isoquine and isotebuquine as promising anticancer agents targeting K+ channel

Design, Docking, and Synthesis of Quinoline‐2H‐1,2,4‐triazol‐3(4H)‐ones as Potent Anticancer and Antitubercular Agents

Synthesis and Antiproliferative Activity of Some Quinoline and Oxadiazole Derivatives

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