Synthesis, spectral- and theoretical study, x-ray analysis, and antiproliferative activity of 4,5-dihydrobenzoferroceno[1,2-d][1,2,3]selenadiazole and its benzo-fused analogue

Pasinszki, Tibor; Dzsotján, Dániel; Lajgut, Győző György; Harmat, V.; Bor, Andrea; Zupkó, István; Csámpai, Antal

doi:10.1016/j.jorganchem.2018.03.031

Cited by 11 publications

(9 citation statements)

References 18 publications

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“…Two of these associate via a single interaction as shown in Fig. 3f, whereas the two-molecule aggregate in 45 [68] is disposed about a centre of inversion like most aggregates in this section; the fourth independent molecule does not form equivalent Se … N interactions.…”

Section: Two-molecule Aggregates Featuring Two Se … N Interactions: Selenadiazole Ringsmentioning

confidence: 88%

“…In seven crystals of mononuclear selenium(II) compounds zero-dimensional assemblies are formed mediated by a single Se … N secondary-bonding interaction. The chemical diagrams for the interacting species in 1-7 [63][64][65][66][67][68] are given in Fig. 2.…”

Section: Two-molecule Aggregates Featuring One Se … N Interactionmentioning

confidence: 99%

“…The selenium atoms in 5 and 6, being sp 2 hybridised adopt a more side-on approach to the nitrogen atoms. The final structure in this section, that is 7 [68], provides a convenient segue to the next section. There are four independent molecules in the asymmetric-unit and as for 1, each participates in a Se … N interaction.…”

Section: Two-molecule Aggregates Featuring One Se … N Interactionmentioning

confidence: 99%

“…The next five crystals, that is, 42 [86], 43 [87], 44 [88], Fig. 7c, 45 [68] and 46 [89] feature 1,2,3selenadiazole rings and form centrosymmetric dimers via {SeN … }2 synthons. In 47 [90], two 1,2,3-thiaselenaazole rings associate about a centre of inversion to form the {SeN … }2 synthon, as illustrated in Fig.…”

Section: Two-molecule Aggregates Featuring Two Se … N Interactions: Selenadiazole Ringsmentioning

confidence: 99%

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Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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An evaluation of the Cambridge Structural Database for crystals containing Se … N secondary--bonding interactions was conducted. The presence of Se … N secondary-bonding interactions has been established in nearly 9% of crystals of mono-nuclear selenium compounds where such interactions can potentially form, that is, having at least one nitrogen atom. The Se … N interactions feature in 71 zero-dimensional, usually di-nuclear aggregates, 63 one-dimensional chains and tapes, and smaller numbers of two-and three-dimensional arrays, that is seven and one, respectively. Selenium(II) compounds form the majority of the dataset with only eight selenium(IV) compounds included in the survey. In most cases (112 out of 142), the selenium centre forms a single Se … N contact with 26 aggregates having a selenium atom forming two contacts and four examples where three Se … N contacts are evident. The great propensity of selenadiazole rings (75%) and selenocyanates (50%) to form Se … N secondary-bonding interactions in their crystals is particularly noteworthy.

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Section: Two-molecule Aggregates Featuring Two Se … N Interactions: Selenadiazole Ringsmentioning

confidence: 88%

Section: Two-molecule Aggregates Featuring One Se … N Interactionmentioning

confidence: 99%

Section: Two-molecule Aggregates Featuring One Se … N Interactionmentioning

confidence: 99%

Section: Two-molecule Aggregates Featuring Two Se … N Interactions: Selenadiazole Ringsmentioning

confidence: 99%

See 2 more Smart Citations

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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“…Another efficient route to produce molecules incorporating the thiadiazole unit could be the replacement of substituent atoms or groups at the 3-and 5-positions of the 1,2,4-thiadiazole moiety. This is especially important for the covalent amalgamation of 1,2,4-thiadiazole with reasonably selected fragments of different biologically active agents, which could lead to compounds with improved activity and selectivity due to synergistic effects [9,10]. Therefore, the development of synthetic protocols to this end is of crucial importance.…”

Section: Introductionmentioning

confidence: 99%

Toward the synthesis of thiadiazole-based therapeutic agents: synthesis, spectroscopic study, X-ray analysis, and cross-coupling reactions of the key intermediate 3,5-diiodo-1,2,4-thiadiazole

2019

Self Cite

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The 1,2,4-thiadiazole moiety is an important component of several biologically active compounds, and varying substituents on this aromatic ring is one of the possible methods to develop novel thiadiazole-based drugs for medicine. A key building block to this end, namely 3,5-diiodo-1,2,4-thiadiazole (1), has been synthesized and characterized in this work for the first time. 1 has exhibited high selectivity for the replacement of iodine atom at position C5 (carbon next to sulfur) in Sonogashira-type cross-coupling reactions with phenylacetylene. Therefore, 3-iodo-5-(phenylethynyl)-1,2,4-thiadiazole (4) or 3,5-bis(phenylethynyl)-1,2,4-thiadiazole (5) could be synthesized selectively depending on reaction conditions. All three novel molecules have been characterized by NMR, IR, Raman, mass, and UV spectroscopies, and their solid phase structures have been determined by single-crystal X-ray diffraction. 1 is expected to be a key starting material for producing thiadiazole-based therapeutic agents using cross-coupling reactions.

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Three or Four Heteroatoms Including at Least One Selenium or Tellurium

Yamazaki

2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis, spectral- and theoretical study, x-ray analysis, and antiproliferative activity of 4,5-dihydrobenzoferroceno[1,2-d][1,2,3]selenadiazole and its benzo-fused analogue

Cited by 11 publications

References 18 publications

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Toward the synthesis of thiadiazole-based therapeutic agents: synthesis, spectroscopic study, X-ray analysis, and cross-coupling reactions of the key intermediate 3,5-diiodo-1,2,4-thiadiazole

Three or Four Heteroatoms Including at Least One Selenium or Tellurium

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