4282-77-3Relevant articles and documents
Identification of HDAC6-Selective Inhibitors of Low Cancer Cell Cytotoxicity
Gaisina, Irina N.,Tueckmantel, Werner,Ugolkov, Andrey,Shen, Sida,Hoffen, Jessica,Dubrovskyi, Oleksii,Mazar, Andrew,Schoon, Renee A.,Billadeau, Daniel,Kozikowski, Alan P.
, p. 81 - 92 (2016)
The histone deacetylases (HDACs) occur in 11 different isoforms, and these enzymes regulate the activity of a large number of proteins involved in cancer initiation and progression. The discovery of isoform-selective HDAC inhibitors (HDACIs) is desirable, as it is likely that such compounds would avoid some of the undesirable side effects found with the first-generation inhibitors. A series of HDACIs previously reported by us were found to display some selectivity for HDAC6 and to induce cell-cycle arrest and apoptosis in pancreatic cancer cells. In the present work, we show that structural modification of these isoxazole-based inhibitors leads to high potency and selectivity for HDAC6 over HDAC1-3 and HDAC10, while unexpectedly abolishing their ability to block cell growth. Three inhibitors with lower HDAC6 selectivity inhibit the growth of cell lines BxPC3 and L3.6pl, and they only induce apoptosis in L3.6pl cells. We conclude that HDAC6 inhibition alone is insufficient for disruption of cell growth, and that some degree of class 1 HDAC inhibition is required. Moreover, the highly selective HDAC6Is reported herein that are weakly cytotoxic may find use in cancer immune system reactivation. High or low selectivity: A new class of HDAC inhibitors bearing an isoxazole ring show high potency and selectivity for HDAC6 over HDAC1-3 and HDAC10, while unexpectedly showing little potency in blocking cell growth. These results suggest that HDAC6 inhibition alone is insufficient for disruption of cell growth, and that some degree of class 1 HDAC inhibition is required. The highly selective HDAC6 inhibitors reported herein that are weakly cytotoxic may find use in cancer immune system reactivation.
‘Quick CuAAC’ Chemistry for Hg(II) and Mn(II) ion sensing via 9H-carbazole derivatives
Kaur, Gurpreet,Rani, Alisha,Saini, Parveen,Singh, Gurjaspreet,Singh, Harminder,Singh, Jandeep,Sushma
, (2021)
The synthesis of 1,2,3-triazole merged 9H–carbazole derivative is being reported with excellent yield but drastic reduction in the reaction time. The 1,2,3-triazole linker has been synthesized under thermal conditions within 20 min and yield of more than 90%, using Cu(I) as catalyst. Using UV–Vis spectral technique, the alkyne product displayed excellent detection capability towards Hg(II) and Mn(II) ions in methanol with the detection limit as low as 20 μM and 10 μM, respectively, whereas the triazolyl product can efficiently sense Cu(II) ions.
σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals
Demangeat, Catherine,Dou, Yixuan,Hu, Bin,Bretonnière, Yann,Andraud, Chantal,D'Aléo, Anthony,Wu, Jeong Weon,Kim, Eunkyoung,Le Bahers, Tangui,Attias, André-Jean
, p. 2446 - 2454 (2021)
Long-lived room temperature phosphorescence from organic molecular crystals attracts great attention. Persistent luminescence depends on the electronic properties of the molecular components, mainly π-conjugated donor–acceptor (D-A) chromophores, and their molecular packing. Here, a strategy is developed by designing two isomeric molecular phosphors incorporating and combining a bridge for σ-conjugation between the D and A units and a structure-directing unit for H-bond-directed supramolecular self-assembly. Calculations highlight the critical role played by the two degrees of freedom of the σ-conjugated bridge on the chromophore optical properties. The molecular crystals exhibit RTP quantum yields up to 20 % and lifetimes up to 520 ms. The crystal structures of the efficient phosphorescent materials establish the existence of an unprecedented well-organization of the emitters into 2D rectangular columnar-like supramolecular structure stabilized by intermolecular H-bonding.
ELECTROPHILIC REACTIONS OF GROUP SIX ELEMENT HALIDES. 11. SYNTHESIS OF THE CONDENSED SYSTEM SELEN (TELLUR) AZINOCARBAZOLE
Lendel, V. G.,Pak, B. I.,Balog, I. M.,Kiyak, M. V.,Migalina, Yu. V.
, p. 108 - 110 (1990)
2-Halomethylidene-1,4-selen(tellur)azinocarbazoles are prepared by the seleno(telluro)halogenation of N-propargylcarbazole under heterogeneous reaction conditions.
Synthesis and photo-electro-thermal characterization of non-symmetrical 4,7-dibromobenzo[c][1,2,5]thiadiazole derivatives
Brondani, Daniela,Cercená, Rodrigo,Dal-Bó, Alexandre Gon?alves,Rodembusch, Fabiano Severo,Teixeira Alves Duarte, Luís Gustavo,Zambon Atvars, Teresa Dib,Zapp, Eduardo,da Costa Duarte, Rodrigo,da Silveira Santos, Fabiano
, (2020)
This work describes the synthesis of new fluorophores based on non-symmetric 4,7-dibromobenzo[c][1,2,5]thiadiazole derivatives with benzene ethynyl tetrazole and propargyl carbazole as terminal groups. The new compounds were obtained using the Sonogashira
9H-Carbazole Derivatives Containing the N-Benzyl-1,2,3-triazole Moiety as New Acetylcholinesterase Inhibitors
Akrami, Hamidreza,Mirjalili, Bibi F.,Khoobi, Mehdi,Moradi, Alireza,Nadri, Hamid,Emami, Saeed,Foroumadi, Alireza,Vosooghi, Mohsen,Shafiee, Abbas
, p. 366 - 374 (2015)
A series of triazole-containing carbazole derivatives were designed as new anti-acetylcholinesterase (AChE) agents. The target compounds 6a-q were simply prepared via a one-pot three-component click reaction of N-propargyl-9H-carbazole, sodium azide, and
Concerning the product of [2 + 2] cyclodimerization of 9-allenylcarbazole
Kharaneko,Shishkina,Shishkin,Kibalnyi,Dulenko
, p. 1427 - 1434 (2004)
The isomerization of 9-propargylcarbazole in alcoholic alkali leads to the product of dimerization of 9-allenylcarbazole, 1,2-bis(9-carbazolylmethylene) cyclobutane, the structure of which was established by X-ray diffraction analysis.
Synthesis and thermal, electrochemical, and photophysical investigation of carbazole/diphenyl benzothiadiazole-based fluorophores
Cercená, Rodrigo,Dal-Bó, Alexandre Gon?alves,Rodembusch, Fabiano Severo,Silva Wakabayashi, Priscila Sayoko,Teixeira Alves Duarte, Luís Gustavo,Zapp, Eduardo,da Costa Duarte, Rodrigo,da Silveira Santos, Fabiano
, (2020)
Herein, we describe the syntheses of symmetric and asymmetric benzothiadiazole (BTD)-based fluorophores via the Sonogashira coupling reaction, using 4,7-dibromobenzothiadiazole as the central core and propargyl carbazole and/or propargyl diphenylamine as the side groups. The synthesized fluorophores exhibited absorption bands in the ultraviolet region, with a maxima between 372 and 380 nm due to the π→π* electronic transitions. Although they presented very low fluorescence quantum yields in solution, they demonstrated typical aggregation-induced emission phenomenon. Their oxidation potentials ranged from 0.91 to 1.18 V vs. NHE and reduction potentials from ?1.20 to 1.26 V vs. NHE. Their HOMO energies ranged from ?5.35 to 5.62 eV electron affinity from ?3.18 to 3.24 eV. Thus, the electrochemical bandgap of the BTD-based fluorophores was in the range of 2.16–2.38 eV. The symmetric BTD derivatives 3 and 5 exhibited good thermal stability, with decomposition temperatures at ~330 °C and 200 °C, respectively. BTD 7 showed lower thermal stability with a decomposition temperature of ~110 °C. BTD 3 and 5 showed glass transition temperature (Tg) values of ~75 °C (first heating) and 60 °C (first and second heating), respectively. BTD 7 did not show any Tg. The density functional theory (DFT) and time-dependent DFT calculations were performed at the CAM-B3LYP/6-31G** level of theory, which corroborated with the charge transfer characteristics of these compounds.
Optoelectronic properties of poly(2,5-dithienylpyrrole)s with fluorophore groups
Guven, Nese,Camurluz, Pinar
, p. H867 - H876 (2015)
In this study two new, fluorophore anchored 2,5-dithienylpyrrole derivatives (SNS-Carb, SNS-Flo) were successfully synthesized via click chemistry. Both monomers were subjected to electrochemical polymerization and the corresponding polymers (PSNS-Carb and PSNS-Flo) were thoroughly characterized for their electrochromic properties. PSNS-Carb displayed yellow to blue coloration in 1.31 s with a coloration efficiency of 120 cm2 C-1 whereas PSNS-Flo revealed longer switching time (2.67 s) and lower coloration efficiency (78 cm2 C-1). Coexistence of 3,4-ethylenedioxythiophene (EDOT) with SNS-Carb or SNS-Flo in polymerization media resulted in the formation of novel copolymer films (P1 and P2, respectively) having entirely diverged multichromic, superior optoelectronic properties. P1 revealed a switching time of 1.33 s, with a coloration efficiency of 164 cm2 C-1, whereas P2 exhibited a slower response time (1.87 s) with a lower coloration efficiency (155 cm2 C-1), as in the case of their respective homopolymers. In general, P1 was shown to reveal higher ΔE values which indicate it's more noticeable and vivid color changing nature compared to P2. When the optoelectronic properties of homopolymers were compared with that of their respective copolymers, there was an explicit enhancement of the color pallet, switching time, optical contrast and coloration efficiency.
TiO2/Cu2O nanoparticle-catalyzed direct C(sp)-P bond formation: Via aerobic oxidative coupling in air and visible light
Hosseini-Sarvari, Mona,Jafari, Fattaneh
supporting information, p. 3001 - 3006 (2020/03/13)
The synthesis of organophosphorus compounds is one of the important goals in organic chemistry. Among these compounds, alkynylphosphonates are significantly utilized as the main precursors for the synthesis of biologically active molecules in medicinal chemistry and have attracted extensive interest in the past few decades. Although few efforts have been made towards the direct and atom-economical synthesis of alkynylphosphonates, efforts towards the utilization of visible light as a green and renewable energy source have not been made to date. Here, we have promoted a strategy to construct a type of nano metal oxide composite photocatalyst (Cu2O decorated on TiO2) for the synthesis of alkynylphosphonates via direct C-P bond formation between terminal alkyne and H-phosphonate under visible light irradiation. In this p-n heterojunction photocatalyst, Cu2O acted as a visible-light absorber; moreover, the CB (conduction band) of TiO2 was favorable for accepting a photogenerated electron, and the generated electron hole (e-/h+) pair could initiate the reaction. The present study can provide a new way for the synthesis of this important class of phosphorus organic compounds.
