Synthesis of 3-alkylthio-6-allylthiopyridazine derivatives and their antihepatocarcinoma activity

Kwon, Soon-Kyoung; Moon, Aree

doi:10.1007/bf02977666

Cited by 24 publications

(9 citation statements)

References 14 publications

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“…As shown in Scheme , condensation of dichloropyridazine 1 with various thioles, such as ethanethiol, propanethiol, butanethiol, pentanethiol, and hexanethiol, at room temperature in methanol gave alkylthiopyridazines 2a–2f . 3c and 4a–4f were also prepared by oxidation with 35% hydrogen peroxide or m ‐CPBA .…”

Section: Resultsmentioning

confidence: 99%

“…1 temperature in methanol gave alkylthiopyridazines 2a-2f. 11,12 3c and 4a-4f were also prepared by oxidation with 35% hydrogen peroxide or m-CPBA. 13 The intermediates in these synthetic routes were diselenide 5c and 6a-6f, which could be obtained from the corresponding alkylsulfonylchloropyridazines 3c and 4a-4f via a diselenylation reaction with disodium diselenide.…”

Section: Methodsmentioning

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%

Section: Methodsmentioning

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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“…We previously reported the synthesis of 3‐allylthio‐6‐chloropyridazine in 95% yield through allylthiolation . All 3‐alkoxy‐6‐chloropyridazines 3b–3d and 3‐alkylthio‐6‐chloropyridazines 4b–4e were prepared following the synthetic methods of existing literature . The intermediate dichloropyridazinyl diselenide 2 was obtainable from the corresponding 3,6‐dichloropyridazine 1 by reaction with sodium diselenide .…”

Section: Methodsmentioning

confidence: 99%

“…The alkoxypyridazines 3b–3d and alkylthiopyridazines 4b–4d were synthesized from 1 through alkoxylation (or alkylthiolation) using a modification on previously reported methods …”

Section: Methodsmentioning

confidence: 99%

Synthesis and Antiproliferative Activities of Chloropyridazine Derivatives Retain Alkylsulfonyl Moiety

Kim

Park

2016

Bulletin Korean Chem Soc

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Some chloropyridazine derivatives have shown interesting pharmacodynamics properties in terms of antioxidant 1 and anti-human rotavirus (HRV) activities ( Figure 1). 2,3 To date, however, no study has evaluated the antiproliferative effects of chloropyridazines in other types of human cancer cells.Therefore, the replacement of the heterocycle of chloropyridazines by heteroatoms (or moieties) such as oxygen (O), sulfur (S), selenium (Se), sulfinyl (SO), and sulfonyl (SO 2 ) yields the target compounds ( Figure 1). We designed substituted 3-chloropyridazine derivatives as possible antitumor candidates. These derivatives have three basic structures, namely chloropyridazine region, heteroatoms, and alkyl chain. We made an examination of antiproliferative activities for target chloropyridazines of five groups against breast cancer (MCF-7) and hepatocellular carcinoma (Hep3B) cells in Cell Counting Kit-8 (CCK-8) assays. As a result, we describe herein the preparation of some chloropyridazine derivatives and the refinement of potential proliferative inhibitors on human cancer cell lines.The chloropyridazines were obtained mostly through the substitution reaction. Scheme 1 depicts the preparation of desired substituted chloropyridazine derivatives. We previously reported the synthesis of 3-allylthio-6chloropyridazine in 95% yield through allylthiolation. 4 All 3-alkoxy-6-chloropyridazines 3b-3d and 3-alkylthio-6-chloropyridazines 4b-4e were prepared following the synthetic methods of existing literature. 5,6 The intermediate dichloropyridazinyl diselenide 2 was obtainable from the corresponding 3,6-dichloropyridazine 1 by reaction with sodium diselenide. 7 A synthetic pathway for dipyridyl diselenide has been developed 7,8 and the synthesis of substituted dipyridazinyl diselenide has been reported. 9 We applied a general method of preparing diaryl (or dialkyl) diselenide from diaryl (or dialkyl) halides and sodium diselenide. 10-12 A series of alkylselenylpyridazines 5b-5f was prepared by Se-Se bond cleavage and Se-alkylation.Treatment of alkylthiopyridazines 4a-4e with 35% hydrogen peroxide afforded corresponding alkylsulfinylchloropyridazine 6a-6e and alkylsulfonylchloropyridazine 7a-7e. Target 6a-6e and 7a-7e were synthesized as illustrated in Scheme 1. Figure 1. Bioactive chloropyridazines and target chloropyridazines. Scheme 1. Synthetic routes for target chloropyridazine analogues.

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“…Once the cytotoxic action of the compounds had been tested, we wanted to discern whether this effect was due (12), 103 (29). Table 3.…”

Section: Apoptosis and Caspase-3mentioning

confidence: 99%

Synthesis and Biological Evaluation of 2,4,6‐Functionalized Derivatives of Pyrido[2,3‐d]pyrimidines as Cytotoxic Agents and Apoptosis Inducers

Sanmartín

Dominguez

Cordeu

et al. 2007

Archiv der Pharmazie

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In the search for new derivatives with anticancer activity that are able to induce a selective pro-apoptotic mechanism in cancer cells, we have designed, synthesized, and evaluated a series of new 2-(alkylsulfanyl)-N-alkylpyrido[2,3-d]pyrimidine-4-amine derivatives as cytotoxic and apoptosis inducers. The potential antitumor activity of the compounds was evaluated in vitro by examining their cytotoxic effects against human breast, colon, and bladder cancer-cell lines. The IC(50)values of the compounds that showed cytotoxic activity were calculated. The cytotoxic compounds were then tested for their ability to induce caspase-3 activation and nuclear-chromatin degradation. Some compounds, such as 6c, 6d, 6e, 6j, 6o, and 6p, show significant in-vitro cytotoxicity in at least two of the three tested cell lines, induced apoptosis, and also produced a rapid dose-dependent increase in the caspase-3 level in some of the cell lines tested. In order to test the selectivity of the compounds, two non-tumoral human cell lines were used. Several compounds of the did not show cytotoxicity in these cell lines.

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Synthesis of 3-alkylthio-6-allylthiopyridazine derivatives and their antihepatocarcinoma activity

Cited by 24 publications

References 14 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

Synthesis and Antiproliferative Activities of Chloropyridazine Derivatives Retain Alkylsulfonyl Moiety

Synthesis and Biological Evaluation of 2,4,6‐Functionalized Derivatives of Pyrido[2,3‐d]pyrimidines as Cytotoxic Agents and Apoptosis Inducers

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