Novel Dithienylethenes with Extended π‐Systems: Synthesis by Aldol Condensation and Photochromic Properties

Altenhöner, Kai; Lamm, Jan‐Hendrik; Mattay, Jochen

doi:10.1002/ejoc.201000721

Cited by 7 publications

(9 citation statements)

References 8 publications

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“…To understand the molecular basis of anticonvulsant activity of the newly designed series of pyrimidine–triazine derivatives ( 4a–t) and to explore the binding mechanisms of these molecules, we docked these molecules into the active site of GABA A receptor (PDB ID‐4COF). The active site of GABA A receptor consists of Arg142, Pro144, Leu145, Asp146, Glu147, Gln185, Ser187, Lys215, Arg216, Asn217, Ile218, Asn439, Arg142, Glu147, Asn217, Leu145, Lys215, Asp146, Trp443, Tyr446, and Val447 . Similar to carbamazepine, a marketed GABA A inhibitor, 16 of our synthesized molecules also showed the conserved H‐bond interaction with Arg216 which is a gate‐keeper residue in the GABA A active site.…”

Section: Resultsmentioning

confidence: 76%

“…). An AB two‐spin system overlapping with a typical trans coupling of 3 J AB = 12–18 Hz confirms a CC double bond with protons in trans configuration . 1 H NMR spectra of chalcone 1a showed one doublet at 7.58–7.61 ppm ( 3 J AB = 5.7) for the CHC and another doublet at 6.75–6.78 ppm ( 3 J AB = 15.7 Hz) for the COCH, indicating that the ethylene moiety in the enone linkage is in the trans conformation.…”

Section: Resultsmentioning

confidence: 78%

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Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models

Sahu

Siddiqui

Naim

et al. 2017

Archiv der Pharmazie

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A series of new pyrimidine-triazine hybrids (4a-t) was designed and synthesized, from which potent anticonvulsant agents were identified. Most of the compounds exhibited promising anticonvulsant activity against the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests, along with minimal motor impairment with higher safety compared to the standard drugs, phenytoin and carbamazepine. In the series, 5-(4-(4-fluorophenyl)-6-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4o) and 5-(6-(4-hydroxy-3-methoxyphenyl)-4-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4s) emerged as most potent anticonvulsant agents with median doses of 22.54 and 29.40 mg/kg (MES ED ), 285.02 and 293.42 mg/kg (scPTZ ED ), and 389.11 and 412.16 mg/kg (TD ), respectively. Docking studies were also performed for all synthesized compounds to get insight into the binding pattern toward the GABA receptor as a possible mechanism of their anticonvulsant action, and in silico ADME studies were carried out to predict the safety and stability of the molecules. The increased GABA level in the experimental animals in the neurochemical estimation assay confirmed their GABAergic modulating activity. The most potent compounds were also evaluated for their neurotoxic and hepatotoxic effects. Fortunately, they did not show any sign of neurotoxicity or hepatotoxicity, suggesting that they have a broad spectrum of anticonvulsant activity with a large safety margin. Together, this research suggested that 4o and 4s may serve as leads in the discovery and development of new anticonvulsant drugs.

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Section: Resultsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 78%

Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models

Sahu

Siddiqui

Naim

et al. 2017

Archiv der Pharmazie

View full text Add to dashboard Cite

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“…NMR spectra ( 1 H at 300 and 13 C at 75 MHz) were obtained on the Varian VXR-300 spectrometer and products were reported relative to tetrametylsilane (TMS, 0.00 ppm) or CDCl 3 (7.24 ppm) Thien-2-ylethanone (1a) and its C5 methyl-, chloro-, bromo-and fluorenylidene-substituted derivatives 1b-e were synthesized following the published procedures. [45][46][47] 1-{5-[(9H-Fluorene-9-ylidene)methyl]-1-methyl-1Hpyrrol-2-yl}ethanone (1f) was synthesized in two steps according to Scheme 4 following the acetylation procedure published by us previously. 48…”

Section: Methodsmentioning

confidence: 99%

Insights into the triple self-condensation reaction of thiophene-based methyl ketones and related compounds

Andicsovà‐Eckstein¹,

Végh²,

Krutošíková³

et al. 2018

Arkivoc

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The acid catalysed triple self-condensation of 1-thien-2-ylethanone (2-acetylthiophene) and five related compounds is presented. Tetrachlorosilane used as the Lewis acid produces dry hydrogen chloride which catalyzes the self-condensation process. Depending on the reaction conditions and the substitution of the carbonyl substrates, the reaction can proceed as a [2+2+2] cyclotrimerization towards C 3 -symmetric 1,3,5trisubstituted benzenes, or as the single-type aldol condensation leading to 1,3-disubstituted (E)-β-methylchalcones. This is important for the design of new aromatic/olefinic compounds beyond the model structures. Synthesis of 4'-fluoro-3,5-di-(2-thienyl)biphenyl through a mixed-type aldol reaction using erbium triflate is discussed. Mechanistic rationale is provided.

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“…Homoconjugation can be dened as the orbital overlap of two p-systems separated by a non-conjugated group such as CH 2 (IUPAC). [1][2][3][4][5] This is an interesting theoretical postulate and has been actually conrmed in some systems [6][7][8] but provokes controversy in other systems. 9 While electronic delocalization of homoconjugated alkenes is well established in cationic homoaromatic compounds, the situation in neutral molecules remains unsettled even in homoaromatic compounds.…”

Section: Introductionmentioning

confidence: 99%

Homoconjugation in diporphyrins: excitonic behaviors in singly and doubly linked Zn(ii)porphyrin dimers

et al. 2013

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We have comparatively investigated excitonic features between singly and doubly alkyl bridged Zn(II) porphyrin dimers (SLZn and DLZn, respectively) with Zn(II)tetraphenylporphyrin (ZnTPP) as a reference by using various time-resolved anisotropy measurements. Time-resolved fluorescence anisotropy decay of the B-state of ZnTPP in toluene showed ultrafast dephasing times of 83 and 185 fs with an initial anisotropy value (r 0 ) of $0.7 being consistent with the theoretically proposed one. On the other hand, the Q-state of ZnTPP exhibited a depolarization time of 120 fs with a smaller r 0 of 0.25 than that of the B-state because of probing photo-induced absorption in transient absorption anisotropy measurements. Spectroscopic features in absorption, fluorescence, and excitation anisotropy spectra of SLZn are similar to those of ZnTPP indicating a relatively weak exciton coupling in the Q-state. As a result, the observed depolarization time with a time-constant of 1.4 ps can be explained by a Förster-type incoherent energy transfer process between two constituent subunits. When compared to ZnTPP and SLZn however, DLZn exhibited very different optical characteristics such as more red-shifted absorption and emission spectra, three times larger fluorescence excitation anisotropy values, and ultrafast sign inversion in transient absorption anisotropy. According to these results, it can be inferred that the overall p-electron densities of the electronic excited states in DLZn are fully delocalized in a whole dimer and that DLZn can be regarded as a coherently coupled single quantum system not as separate individual chromophores. Frontier p-molecular orbital structures as well as electron density difference maps between occupied and unoccupied molecular orbitals involved in the electron promotions for underlying excited states clearly represent weakly and strongly exciton-coupled natures of SLZn and DLZn, respectively.Accordingly, the extended conjugation of p-electrons over the whole DLZn molecule demonstrates an example for homoconjugation between two aromatic porphyrins.

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Novel Dithienylethenes with Extended π‐Systems: Synthesis by Aldol Condensation and Photochromic Properties

Abstract: A facile and stereoselective route to symmetric π-extended dithienylethene derivatives is described. The key step of this route is an aldol condensation of 1,2-bis(5-formyl-2-methylthiophen-3-yl)cyclopentene with a large variety of acyl com-

Cited by 7 publications

References 8 publications

Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models

Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models

Insights into the triple self-condensation reaction of thiophene-based methyl ketones and related compounds

Homoconjugation in diporphyrins: excitonic behaviors in singly and doubly linked Zn(ii)porphyrin dimers

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