Synthesis of bis[N-(p-aryl)-carbamoyloxy]alkanes as new low-molecular weight organogelators

Demir-Ordu, Öznur; Şimşir, Hamza; Alper, Koray

doi:10.1016/j.tet.2015.01.042

Cited by 10 publications

(10 citation statements)

References 87 publications

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“…When commercial isocyanates were employed, the reaction was performed at 110 °C in toluene. 54 In the case of compounds 42 and 47, the corresponding isocyanate was previously prepared from otoluidine by the reaction with triphosgene in basic conditions (Na 2 CO 3 ). 55 In a second step, dicarbamate was generated in milder conditions, using DMAP in dichloromethane at rt (Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Serinol-Based Benzoic Acid Esters as New Scaffolds for the Development of Adenovirus Infection Inhibitors: Design, Synthesis, and In Vitro Biological Evaluation

et al. 2020

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Over the years, human adenovirus (HAdV) has progressively been recognized as a significant viral pathogen. Traditionally associated with self-limited respiratory, gastrointestinal, and conjunctival infections, mainly in immunocompromised patients, HAdV is currently considered to be a pathogen presenting significant morbidity and mortality in both immunosuppressed and otherwise healthy individuals. Currently available therapeutic options are limited because of their lack of effectivity and related side effects. In this context, there is an urgent need to develop effective anti-HAdV drugs with suitable therapeutic indexes. In this work, we identified new serinol-derived benzoic acid esters as novel scaffolds for the inhibition of HAdV infections. A set of 38 compounds were designed and synthesized, and their antiviral activity and cytotoxicity were evaluated. Four compounds (13, 14, 27, and 32) inhibited HAdV infection at low micromolar concentrations (2.82–5.35 μM). Their half maximal inhibitory concentration (IC50) values were lower compared to that of cidofovir, the current drug of choice. All compounds significantly reduced the HAdV DNA replication process, while they did not block any step of the viral entry. Our results showed that compounds 13, 14, and 32 seem to be targeting the expression of the E1A early gene. Moreover, all four derivatives demonstrated a significant inhibition of human cytomegalovirus (HCMV) DNA replication. This new scaffold may represent a potential tool useful for the development of effective anti-HAdV drugs.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…Method A. 54 Urea derivatives (9−11) (0.64 mmol) and isocyanate (1.47 mmol) were mixed in toluene (10 mL). The resulting suspension was refluxed (110 °C) for 24 h; then, the reaction mixture was filtered and washed with fresh toluene.…”

Section: ■ Methodsmentioning

confidence: 99%

Serinol-Based Benzoic Acid Esters as New Scaffolds for the Development of Adenovirus Infection Inhibitors: Design, Synthesis, and In Vitro Biological Evaluation

et al. 2020

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“…The same situation was observed for T 2 . The absence of a free N–H stretching vibration (around 3400 cm −1 ) and a free C=O stretching vibration (around 1720 cm −1 ) suggested that strong hydrogen bonds between urethane groups were formed [ 25 – 26 ]. These results indicated that π–π interactions and hydrogen bonding were the main driving forces behind the self-assembly.…”

Section: Resultsmentioning

confidence: 99%

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Sun

Lai

et al. 2015

Beilstein J. Org. Chem.

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SummaryThis paper reports the self-assembly of two new tetrathiafulvalene (TTF) derivatives that contain one or two urethane groups. The formation of nanoribbons was evidenced by scanning electron microscopy (SEM) and X-ray diffraction (XRD), which showed that the self-assembly ability of T 1 was better than that of T 2. The results revealed that more urethane groups in a molecule did not necessarily instigate self-assembly. UV–vis and FTIR spectra were measured to explore noncovalent interactions. The driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and π–π stacking interactions. The electronic conductivity of the T 1 and T 2 films was tested by a four-probe method.

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“… 21 In another study, p -alkoxyphenyl substituted biscarbamate derivatives having odd numbered methylene units in their bridging alkyl spacer were shown to increase the ability of gelation. 3 Interestingly, increasing the chain length in odd and even numbered units may influence the gelation in a completely different manner. 3,11,12,22 For example, Sumiyoshi et al claim that as the central spacer length increases, the odd numbered systems lead to an improved gelation.…”

Section: Introductionmentioning

confidence: 99%

“… 3 Interestingly, increasing the chain length in odd and even numbered units may influence the gelation in a completely different manner. 3,11,12,22 For example, Sumiyoshi et al claim that as the central spacer length increases, the odd numbered systems lead to an improved gelation. In contrast, for even numbered systems longer central spacer lengths result in the loss of gelation ability.…”

Section: Introductionmentioning

confidence: 99%

Influence of odd–even effect and intermolecular interactions in 2D molecular layers of bisamide organogelators

et al. 2018

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Synthesis of bis[N-(p-aryl)-carbamoyloxy]alkanes as new low-molecular weight organogelators

Cited by 10 publications

References 87 publications

Serinol-Based Benzoic Acid Esters as New Scaffolds for the Development of Adenovirus Infection Inhibitors: Design, Synthesis, and In Vitro Biological Evaluation

Serinol-Based Benzoic Acid Esters as New Scaffolds for the Development of Adenovirus Infection Inhibitors: Design, Synthesis, and In Vitro Biological Evaluation

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Influence of odd–even effect and intermolecular interactions in 2D molecular layers of bisamide organogelators

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