<i>S</i>,<i>N</i>‐Chelated organotin(IV) compounds containing 6‐phenylpyridazine‐3‐thiolate ligand—structural, antibacterial and antifungal study

Ozerianskyi, Andrii; Vaňkátová, Hana; Vejsová, Marcela; Česlová, Lenka; Padělková, Zdeňka; Růžička, Aleš; Holeček, Jaroslav

doi:10.1002/aoc.1823

Cited by 9 publications

(5 citation statements)

References 63 publications

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“…ethanol and refluxed for 4 h. After completion of the reaction, 50 mL of water was added to obtain a precipitate that was filtered, washed with warm water, and dried under a vacuum. 61 5.1.4. General Procedure for the Preparation of 6a−b.…”

Section: Experimental Protocolsmentioning

confidence: 99%

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Ligand-Based Design on the Dog-Bone-Shaped BIBR1532 Pharmacophoric Features and Synthesis of Novel Analogues as Promising Telomerase Inhibitors with In Vitro and In Vivo Evaluations

et al. 2022

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Telomerase is an outstanding biological target for cancer treatment. BIBR1532 is a non-nucleoside selective telomerase inhibitor; however, it experiences ineligible pharmacokinetics. Herein, we aimed to design new BIBR1532-based analogues as promising telomerase inhibitors. Therefore, two novel series of pyridazine-linked to cyclopenta[b]thiophene (8a−f) and tetrahydro-1-benzothiophene (9a−f) were synthesized. A quantitative real-time polymerase chain reaction was utilized to investigate the telomerase inhibitory activity of candidates. Notably, 8e and 9e exhibited the best inhibition profiles. Moreover, 8e showed strong antitumor effects against both MCF-7 and A549 cancer cell lines. The effects of 8e on the cell cycle and apoptosis were measured. Besides, 8e was evaluated for its in vivo antitumor activity using solid Ehrlich carcinoma. The reduction in both the tumor weight and volume was greater than doxorubicin. Also, molecular docking and ADME studies were performed. Finally, a SAR study was conducted to gain further insights into the different telomerase inhibition potentials upon variable structural modifications.

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Section: Experimental Protocolsmentioning

confidence: 99%

“…3-Chloropyridazine derivatives 3a–f (4 mmol, 1 equiv) and thiourea (6 mmol, 1.5 equiv) were dissolved in 20 mL of abs. ethanol and refluxed for 4 h. After completion of the reaction, 50 mL of water was added to obtain a precipitate that was filtered, washed with warm water, and dried under a vacuum …”

Section: Experimental Protocolsmentioning

confidence: 99%

Ligand-Based Design on the Dog-Bone-Shaped BIBR1532 Pharmacophoric Features and Synthesis of Novel Analogues as Promising Telomerase Inhibitors with In Vitro and In Vivo Evaluations

et al. 2022

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“…Compound 9.17 was found to be potential in this respect [ 76 ]. (9.6) Ozerianskyi et al [ 77 ] reported on antibacterial and antifungal activities in medical studies on main group metal cyclometalation compounds, e.g., organotin compounds, 9.22 , 9.23 , and 9.24 , as shown in Eqs. ( 9.7 , 9.8 , and 9.9 ).…”

Section: Pharmaceuticalsmentioning

confidence: 99%

Applications of Five-Membered Ring Products in Cyclometalation Reactions for Other Purposes

Omae¹

2013

Cyclometalation Reactions

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Applications of fi ve-membered ring products in cyclometalation reactions for other purposes include organic electronic devices, pharmaceuticals, dyesensitized solar cells, carbon dioxide utilizations, sensors, dendrimers, liquid crystals, resolving agents, and photosensitizers for hydrogen production. Keywords IntroductionThis monograph has already been reported in Chaps. 7 and 8 on the synthetic and catalytic applications of cyclometalation reactions and their fi ve-membered ring products, respectively. This chapter reports on other applications, such as organic electronic devices, especially organic light-emitting devices (OLEDs), pharmaceuticals, dye-sensitized solar cells, carbon dioxide utilizations, sensors, and photosensitizers for hydrogen production. Organic Electric DevicesMany compounds with luminescent properties have been found among organometallic intramolecular-coordination fi ve-membered ring compounds. An enormous number of articles have been published on organic light-emitting devices (OLEDs), in particular. Many reviews [ 1 -11 ] and a few books [ 12 -14 ] [ 14 ]. Iridium compounds, especially, are already used as representative iridium OLED materials for the three primary colors, green, Ir(ppy) 3 , red, (btp) 2 Ir(acac), and blue, Flrpic, for use in TV screens and mobile phone displays, as shown in Fig. 9.1 [ 12 ].These compounds have the representative substrates shown in Fig. 9.2 and the ancillary ligands shown in Fig. 9.3 [ 1 ].Some other representative compounds exhibiting luminescent properties are shown in Fig. 9.4 . These compounds exhibiting luminescent properties for organic light-emitting devices (OLEDs) not only have 2-phenylpyridine and 2-thiophenylpyridine as substrates but also benzoates, acetylacetonate, and bis-pyridine-, phenanthroline-, imidazole-, and triazole-based ancillary ligands as shown in Figs. 9.2 and 9.3 , respectively [ 1 ].Sony exhibited an experimental super high-resolution television (4 K TV) with this type of organic electroluminescent display at an international consumer electronic product trade show (CES) held in the United States from January 8 to 10, 2013.

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“…There are two common modes for installing chelating ligands at tinorganyl moieties: A reaction of free ligands with the tin moiety,1e,1f,3 or the pre‐connection of the ligand with the tin atoms by a Sn–C bond away from the chelating unit. In this case, the chelating ligand may then coordinate to the tin atom,1e,4 or, keep away from the tin atom to produce a vacant chelating pocket to the tin atom, which bears the additional opportunity to trap further metal atoms (Scheme ) 4a,5…”

Section: Introductionmentioning

confidence: 99%

Attachment of Chelating Ligand Pockets to Tinorganyl Moieties

2014

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Several approaches have been undertaken to realize the synthesis of a new tinorganyl compound with a 2,2Ј,6Ј,2ЈЈ-terpyridine moiety. A synthesis pathway consisting of five steps with an overall yield of 51 % was successful in producing Ph 3 Sn(CH 2 ) 3 OPhttpy [HOttpy = 2,6-bis(2Ј-pyridyl)-4Ј-(phydroxyphenyl)pyridine], and insight has been gained into (partial) halogenation reactions with this unprecedented tinorganyl compound. Halogenation with hydroiodic acid2406 produced a new dinuclear complex cation that resulted from head-to-tail coordination of two monocations. Furthermore, synthesis and yields of already known intermediates have been optimized. The products were analyzed and identified by 119 Sn NMR, 1 H NMR, and 13 C NMR spectroscopy and ESI mass spectrometry, as well as by means of single-crystal Xray diffraction.Supporting Information (see footnote on the first page of this article): Further details on single-crystal X-ray crystallography, electrospray ionization (ESI), mass spectrometry, nuclear magnetic reso-Eur.2410 nance (NMR) spectroscopy, energy dispersive X-ray (EDX) spectroscopy, and on the synthesis of 3.

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S,N‐Chelated organotin(IV) compounds containing 6‐phenylpyridazine‐3‐thiolate ligand—structural, antibacterial and antifungal study

Cited by 9 publications

References 63 publications

Ligand-Based Design on the Dog-Bone-Shaped BIBR1532 Pharmacophoric Features and Synthesis of Novel Analogues as Promising Telomerase Inhibitors with In Vitro and In Vivo Evaluations

Ligand-Based Design on the Dog-Bone-Shaped BIBR1532 Pharmacophoric Features and Synthesis of Novel Analogues as Promising Telomerase Inhibitors with In Vitro and In Vivo Evaluations

Applications of Five-Membered Ring Products in Cyclometalation Reactions for Other Purposes

Attachment of Chelating Ligand Pockets to Tinorganyl Moieties

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