Synthesis of novel 3-allylseleno-6-alkylthiopyridazines: their anticancer activity against MCF-7 cells

Kim, Chaewon; Kim, Saet-Byeul; Park, Myung‐Sook

doi:10.1007/s12272-013-0244-x

Cited by 13 publications

(11 citation statements)

References 18 publications

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“…Table lists the IC 50 values of four synthetic allylselenopyridazine derivatives of 8e , A , B , and C . The synthetic compounds of 3‐allylseleno‐6‐pentyloxypyridazine ( A ), 3‐allylseleno‐6‐pentylthiopyridazine ( B ), and 3‐allylseleno‐6‐pentylaminopyridazine ( C ) were recently reported . In vitro assays revealed the IC 50 of these compounds ( 8e = 292.61 μM, A = 218.55 μM, B = 207.00 μM, and C = 861.01 μM).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Evaluation of Novel 3‐Allylseleno‐6‐Alkylsulfonylpyridazine Derivatives with Potential Anticancer Properties

Kim

Park

2017

Bulletin Korean Chem Soc

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A new series of 3‐allylseleno‐6‐alkylsulfonylpyridazines and 3‐allylseleno‐6‐alkylsulfinylpyridazines were synthesized from 3,6‐dichloropyridazine for anticancer agent development. The inhibitory effects of 3‐allylseleno‐6‐alkylsulfonylpyridazines on human cancer cell lines were investigated. The synthesis involved thiolation, oxidation, selenylation, and Se‐allylation of alkylthiols. That is, sodium methanethiolate, ethanethiol, propanethiol, butanethiol, pentanethiol, and hexanethiol were inserted into the 6‐position of the pyridazine nucleus. These new synthetic compounds exhibited antiproliferative activity against human breast cancer (MCF‐7), hepatocarcinoma (Hep3B), and human colon carcinoma (RKO) cells in CCK‐8 assays, and are potential candidates for cancer chemotherapy.

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Section: Resultsmentioning

confidence: 99%

“…Several modifications of the alkylselenopyridazine pharmacophore have been reported. Allylselenoalkoxypyridazines, allylselenoalkylthiopyridazines, alkylselenoalkylamino‐pyridazines, and bis(alkylselanyl)pyridazines have been shown to have good antiproliferative effects on breast cancer MCF‐7 cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Novel 3‐Allylseleno‐6‐Alkylsulfonylpyridazine Derivatives with Potential Anticancer Properties

Kim

Park

2017

Bulletin Korean Chem Soc

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“…In Table , the antiproliferative activity for three synthetic allylselenopyridazine compounds of 4d , A , and B is shown. We recently reported the synthesis of 3‐allylseleno‐6‐pentyloxypyridazine ( A ) and 3‐allylseleno‐6‐pentylthiopyridazine ( B ) .…”

Section: Resultsmentioning

confidence: 99%

“…The pyridazine moiety has been combined with an allylseleno group. Allylselenoalkoxypyridazines and allylselenoalkylthiopyridazines show especially good antitumor activities against breast cancer MCF‐7 cells (Figure ). The isosteric replacement of the oxygen (or sulfur) by a nitrogen atom yields the amino compounds (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Selenium‐incorporated Aminopyridazines as Anticancer Agents

Kim

Jung

et al. 2015

Bulletin Korean Chem Soc

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A new series of 3-alkylseleno-6-alkylaminopyridazines, 3-alkylseleno-6-alkyliminopyridazines, and 3-alkylseleno-6-dialkylaminopyridazines was synthesized from 3,6-dichloropyridazine for development of new anticancer agents. The process involves the selenylation, Se-alkylation, and aralkylamination (or imination). The alkylamines such as ethylamine and the dialkylamines such as dipropylamine were introduced into the 3-position of the pyridazine ring. These new compounds showed antiproliferative activities against breast cancer (MCF-7) and hepatocellular carcinoma (Hep3B) cells in CCK-8 assays and could be promising candidates for chemotherapy of carcinomas.

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“…While several studies and research work have explored different anticancer activities for diverse fused pyridazine derivatives, little attention has been paid to investigate the anticancer activity for the non-fused 3,6-disubstituted pyridazine derivatives over the last two decades [21][22][23][24][25][26][27][28][29][30] . For example; compound I ( Figure 2) displayed potent in vitro and in vivo antitumor and anti-angiogenesis activities 21 , compound II ( Figure 2) efficiently inhibited the cell proliferation in a panel of breast, colon, prostate and liver human tumours 28 .…”

Section: Introductionmentioning

confidence: 99%

Discovery of 3,6-disubstituted pyridazines as a novel class of anticancer agents targeting cyclin-dependent kinase 2: synthesis, biological evaluation and in silico insights

Sabt

Eldehna

Al‐Warhi

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Human health in the current medical era is facing numerous challenges, especially cancer. So, the therapeutic arsenal for cancer should be unremittingly enriched with novel small molecules that selectively target tumour cells with minimal toxicity towards normal cells. In this context, herein a new series of 3,6disubstituted pyridazines 11a-r has been synthesised and evaluated for in vitro anticancer activity. They possessed good anti-proliferative action towards human breast cancer T-47D (IC 50 range: 0.43 ± 0.01 À 35.9 ± 1.18 mM) and MDA-MB-231 (IC 50 range: 0.99 ± 0.03 À 34.59 ± 1.13 mM) cell lines, whereas they displayed weak activity against the tested ovarian cancer cell line SKOV-3. Among the studied compounds, the methyltetrahydropyran-bearing pyridazine 11m emerged as the unique submicromolar growth inhibitor herein reported towards both T-47D (IC 50 ¼ 0.43 ± 0.01 mM) and MDA-MB-231 (IC 50 ¼ 0.99 ± 0.03 mM) cell lines. In addition, the biological results indicated that pyridazines 11l and 11m exerted an efficient alteration within the cell cycle progression as well as induction of apoptosis in both T-47D and MDA-MB-231 cells. Moreover, pyridazines 11l and 11m displayed good mean tumour S. I. values of 13.7 and 16.1 upon assessment of their cytotoxicity towards non-tumorigenic breast MCF-10A cells. Furthermore, an in silico study proposed CDK2 as a probable enzymatic target for pyridazines 11, and explored their binding interactions within the vicinity of CDK2 binding site. Subsequently, pyridazines 11e, 11h, 11l, and 11m were selected to be evaluated for their ability to inhibit CDK2, where they exerted good inhibitory activity (IC 50 ¼ 151, 43.8, 55.6 and 20.1 nM, respectively). Finally, the in silico study implied that target pyridazines 11 exhibited not only an efficient anticancer activity but also an acceptable ADME, physicochemical and druglikeness properties, specifically pyridazines 11l and 11m. Overall the obtained results from this study quite sustained our strategy and gave us a robust opportunity for further development and optimisation of 3,6-disubstituted pyridazine scaffold to enrich therapeutic arsenal with efficient and safe anticancer CDK inhibitors.

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Synthesis of novel 3-allylseleno-6-alkylthiopyridazines: their anticancer activity against MCF-7 cells

Cited by 13 publications

References 18 publications

Synthesis and Evaluation of Novel 3‐Allylseleno‐6‐Alkylsulfonylpyridazine Derivatives with Potential Anticancer Properties

Synthesis and Evaluation of Novel 3‐Allylseleno‐6‐Alkylsulfonylpyridazine Derivatives with Potential Anticancer Properties

Design, Synthesis, and Biological Evaluation of Selenium‐incorporated Aminopyridazines as Anticancer Agents

Discovery of 3,6-disubstituted pyridazines as a novel class of anticancer agents targeting cyclin-dependent kinase 2: synthesis, biological evaluation and in silico insights

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