- Reversible switching of arylazopyrazole within a metal-organic cage
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Arylazopyrazoles represent a new family of molecular photoswitches characterized by a near-quantitative conversion between two states and long thermal half-lives of the metastable state. Here, we investigated the behavior of a model arylazopyrazole in the
- Hanopolskyi, Anton I.,De, Soumen,Bia?ek, Micha? J.,Diskin-Posner, Yael,Avram, Liat,Feller, Moran,Klajn, Rafal
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- Photoresponsive host-guest chemistry and relaxation time of fluorinated cyclodextrin and T1=T* 2 arylazopyrazole-functionalized DOTA metal complexes
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Light-responsive modulation of the longitudinal (T1) and transversal T *2) relaxation times of a fluorinated cyclodextrin has been achieved by host-guest complexation with arylazopyrazole-modified metal complexes in aqueous solution. This supramolecular concept can potentially be applied to the development of contrast agents for19F magnetic resonance imaging (MRI).
- Simke, Julian,B?ckermann, Till,Bergander, Klaus,Klabunde, Sina,Hansen, Michael Ryan,Ravoo, Bart Jan
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supporting information
p. 2186 - 2191
(2021/03/24)
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- Chemoproteomics-Enabled De Novo Discovery of Photoswitchable Carboxylesterase Inhibitors for Optically Controlled Drug Metabolism
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Herein, we report arylazopyrazole ureas and sulfones as a novel class of photoswitchable serine hydrolase inhibitors and present a chemoproteomic platform for rapid discovery of optically controlled serine hydrolase targets in complex proteomes. Specifica
- Dwyer, Brendan G.,Wang, Chao,Abegg, Daniel,Racioppo, Brittney,Qiu, Nan,Zhao, Zhensheng,Pechalrieu, Dany,Shuster, Anton,Hoch, Dominic G.,Adibekian, Alexander
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supporting information
p. 3071 - 3079
(2020/12/09)
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- ARYLAZO-HETEROARYL COMPOUNDS AND THEIR USE FOR LONG-TERM THERMAL ENERGY STORAGE
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The present invention relates to a compound of Formula (I): wherein R1, R2, m, n, p, Q, X, Y, W, and "A" are as described herein. The present invention also relates to a process for preparation of a compound of Formula (I). Also disclosed is a thermal-storage device comprising one or more compounds of Formula (I) and a method of storing energy.
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Paragraph 0140; 0143-0144
(2021/08/13)
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- Mixed isatin with 3-(2-(aryl)hydrazono)acetylacetone mn(ii), co(ii) and ni(ii) complexes: Antibacterial evaluation and molecular properties prediction
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The metal complexes {Ni (II), Co (II) and Mn (II)} of 3-(2-(aryl)hydrazono)acetylacetone with isatin were synthesized and screened for their in vitro antibacterial activity against four pathogenic microorganisms {two Gram-positive and two Gram negative}.
- Hassan, Ashraf S.
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p. 533 - 541
(2021/02/03)
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- Photoresponsive Zn2+-specific metallohydrogels coassembled from imidazole containing phenylalanine and arylazopyrazole derivatives
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Stimuli-responsive supramolecular gels and metallogels have been widely explored in the past decade, but the fabrication of metallogels with reversible photoresponsive properties remains largely unexplored. In this study, we report the construction of pho
- Ghebreyessus, Kesete,Sallee, Ashanti
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supporting information
p. 10441 - 10451
(2020/09/18)
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- Arylazopyrazoles for Long-Term Thermal Energy Storage and Optically Triggered Heat Release below 0 °c
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Arylazopyrazole derivatives based on four core structures (4pzMe, 3pzH, 4pzH, and 4pzH-F2) and functionalized with a dodecanoate group were demonstrated to store thermal energy in their metastable Z isomer liquid phase and release the energy by optically triggered crystallization at -30 °C for the first time. Three heat storage-release schemes were discovered involving different activation methods (optical, thermal, or combined) for generating liquid-state Z isomers capable of storing thermal energy. Visible light irradiation induced the selective crystallization of the liquid phase via Z-to-E isomerization, and the latent heat stored in the liquid Z isomers was preserved for longer than 2 weeks unless optically triggered. Up to 92 kJ/mol of thermal energy was stored in the compounds, demonstrating remarkable thermal stability of Z isomers at high temperatures and liquid-phase stability at temperatures below 0 °C.
- Gerkman, Mihael A.,Gibson, Rosina S. L.,Calbo, Joaquín,Shi, Yuran,Fuchter, Matthew J.,Han, Grace G. D.
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supporting information
p. 8688 - 8695
(2020/12/23)
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- Arylazo-3,5-dimethylisoxazoles: Azoheteroarene Photoswitches Exhibiting High Z-Isomer Stability, Solid-State Photochromism, and Reversible Light-Induced Phase Transition
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Reversibly photoswitchable phenylazo-3,5-dimethylisoxazole and 37 aryl-substituted derivatives were synthesized. Excellent photoswitching ability of these compounds in solution and the solid state was demonstrated. Through kinetics studies by means of NMR spectroscopy, high Z-isomer stability was demonstrated. Interestingly, the majority of the derivatives showed light-induced contrasting color changes in solution and the solid state. Besides, many of the derivatives exhibit partial phase transition upon UV irradiation. The highlight of this class of photoswitches is the reversible light-induced phase transition between solid and liquid phases in the parent compound, which can be used in patterned crystallization. These results show that this new class of azoheteroarene based photoswitches has opportunities to be useful in various domains.
- Devi, Sudha,Kumar, Pravesh,Sah, Chitranjan,Srivastava, Anjali,Venkataramani, Sugumar
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supporting information
(2019/08/21)
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- Hierarchical supramolecular hydrogels: Self-assembly by peptides and photo-controlled release: Via host-guest interaction
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A hierarchical supramolecular hydrogel was self-assembled from a Fmoc-RGDS tetrapeptide and showed photo-controlled release directed by host-guest interaction. Multiple payloads, including vesicles, were successively released from a single peptide hydrogel.
- Chu, Chih-Wei,Ravoo, Bart Jan
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supporting information
p. 12450 - 12453
(2017/11/22)
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- Structure-Based Rational Design of Novel Inhibitors Against Fructose-1,6-Bisphosphate Aldolase from Candida albicans
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Class II fructose-1,6-bisphosphate aldolases (FBA-II) are attractive new targets for the discovery of drugs to combat invasive fungal infection, because they are absent in animals and higher plants. Although several FBA-II inhibitors have been reported, none of these inhibitors exhibit antifungal effect so far. In this study, several novel inhibitors of FBA-II from C. albicans (Ca-FBA-II) with potent antifungal effects were rationally designed by jointly using a specific protocols of molecular docking-based virtual screening, accurate binding-conformation evaluation strategy, synthesis and enzymatic assays. The enzymatic assays reveal that the compounds 3c, 3e-g, 3j and 3k exhibit high inhibitory activity against Ca-FBA-II (IC50 50 value of 2.7 μM. Importantly, the compounds 3f, 3g, and 3l possess not only high inhibitions against Ca-FBA-II, but also moderate antifungal activities against C. glabrata (MIC80 = 4-64 μg/mL). The compounds 3g, 3l, and 3k in combination with fluconazole (8 μg/mL) displayed significantly synergistic antifungal activities (MIC80 0.0625 μg/mL) against resistant Candida strains, which are resistant to azoles drugs. The probable binding modes between 3g and the active site of Ca-FBA-II have been proposed by using the DOX (docking, ONIOM, and XO) strategy. To our knowledge, no FBA-II inhibitors with antifungal activities against wild type and resistant strains from Candida were reported previously. The positive results suggest that the strategy adopted in this study are a promising method for the discovery of novel drugs against azole-resistant fungal pathogens in the future.
- Han, Xinya,Zhu, Xiuyun,Hong, Zongqin,Wei, Lin,Ren, Yanliang,Wan, Fen,Zhu, Shuaihua,Peng, Hao,Guo, Li,Rao, Li,Feng, Lingling,Wan, Jian
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p. 1426 - 1438
(2017/07/03)
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- Arylazopyrazoles as Light-Responsive Molecular Switches in Cyclodextrin-Based Supramolecular Systems
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A simple and high yield synthesis of water-soluble arylazopyrazoles (AAPs) featuring superior photophysical properties is reported. The introduction of a carboxylic acid allows the diverse functionalization of AAPs. Based on structural modifications of th
- Stricker, Lucas,Fritz, Eva-Corinna,Peterlechner, Martin,Doltsinis, Nikos L.,Ravoo, Bart Jan
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supporting information
p. 4547 - 4554
(2016/05/09)
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- Arylazopyrazoles: Azoheteroarene photoswitches offering quantitative isomerization and long thermal half-lives
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Arylazopyrazoles, a novel class of five-membered azo photoswitches, offer quantitative photoswitching and high thermal stability of the Z isomer (half-lives of 10 and ～1000 days). The conformation of the Z isomers of these compounds, and also the arylazop
- Weston, Claire E.,Richardson, Robert D.,Haycock, Peter R.,White, Andrew J. P.,Fuchter, Matthew J.
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supporting information
p. 11878 - 11881
(2014/11/08)
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- Discovery of 1-[2-Fluoro-4-(1 H -pyrazol-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1 H -pyrazol-5-yl)pyridazin-4(1 H)-one (TAK-063), a highly potent, selective, and orally active phosphodiesterase 10A (PDE10A) inhibitor
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A novel series of pyridazinone-based phosphodiesterase 10A (PDE10A) inhibitors were synthesized. Our optimization efforts using structure-based drug design (SBDD) techniques on the basis of the X-ray crystal structure of PDE10A in complex with hit compound 1 (IC50 = 23 nM; 110-fold selectivity over other PDEs) led to the identification of 1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (27h). Compound 27h has potent inhibitory activity (IC50 = 0.30 nM), excellent selectivity (>15000-fold selectivity over other PDEs), and favorable pharmacokinetics, including high brain penetration, in mice. Oral administration of compound 27h to mice elevated striatal 3,5-cyclic adenosine monophosphate (cAMP) and 3,5-cyclic guanosine monophosphate (cGMP) levels at 0.3 mg/kg and showed potent suppression of phencyclidine (PCP)-induced hyperlocomotion at a minimum effective dose (MED) of 0.3 mg/kg. Compound 27h (TAK-063) is currently being evaluated in clinical trials for the treatment of schizophrenia.
- Kunitomo, Jun,Yoshikawa, Masato,Fushimi, Makoto,Kawada, Akira,Quinn, John F.,Oki, Hideyuki,Kokubo, Hironori,Kondo, Mitsuyo,Nakashima, Kosuke,Kamiguchi, Naomi,Suzuki, Kazunori,Kimura, Haruhide,Taniguchi, Takahiko
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p. 9627 - 9643
(2015/01/09)
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- Synthesis, characterization and cytotoxicity of mixed ligand Mn(II), Co(II) and Ni(II) complexes
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Complexes of the type [ML'L(OH)(H2O)], where M = Ni(II), Co(II) or Mn(II), L' = isatin and HL = 3-(2-phenylhydrazono)acetylacetone, 3-(2-(4- -chlorophenyl)hydrazono)acetylacetone or 3-(2-(4-bromophenyl)hydrazono)- acetylacetone, were synthesize
- Osman, Souad A.,Mousa, Hanan A.,Yosef, Hisham Abdallah A.,Hafez, Taghrid S.,El-Sawy, Abdallah A.,Abdallah, Mohamed M.,Hassan, Ashraf S.
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p. 953 - 964
(2014/11/07)
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- Synthesis, characterization and antibacterial screening of new pyrazole and pyrazoline-5-one derivatives
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A series of N′-(p-toluene sulphonyl)-3-methyl-4-(substituted arylhydrazono)-2-pyrazoline-5-ones and N′-(2-hydroxybenzoyl)-3,5-dimethyl- 4-(substituted arylazo)pyrazoles have been synthesized and characterized by chemical analysis, IR and 1H NMR spectral data. The compounds have been screened for antibacterial activity against Staphylococcus aureus and Escherichia coli.
- Nagaraju,Srinivasulu,Doraswamy,Venkata Ramana
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experimental part
p. 293 - 298
(2012/03/11)
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- Pyridazinone compounds
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The present invention provides a compound which has the effect of PDE inhibition, and which is useful as a medicament for preventing or treating schizophrenia or so on. A compound of formula (I0): wherein R1 represents a substituent, R2 represents a hydrogen atom, or a substituent, R3 represents a hydrogen atom, or a substituent, Ring A represents an aromatic ring which can be substituted, and Ring B represents a 5-membered heteroaromatic ring which can be substituted, or a salt thereof.
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Page/Page column 46
(2010/08/08)
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- Synthesis and structural study of 2′- and 2′,6′- positioned methyl- and nitro-substituted 3-(arylhydrazono)pentane-2,4-diones
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A systematic series of ortho-methyl- and nitro-substituted arylhydrazones 2-6 formed by Japp-Klingemann reaction between pentane-2,4-dione and the respective aryldiazonium salts have been synthesized and studied by X-ray crystal structure analysis, with a
- Marten, Jan,Seichter, Wilhelm,Weber, Edwin,Boehme, Uwe
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p. 716 - 731
(2008/03/13)
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- Synthesis and biological evaluation of new N-substituted-N′-(3,5-di/ 1,3,5-trimethylpyrazole-4-yl)thiourea/urea derivatives
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Several thiourea and urea derivatives were prepared by the reaction of 4-aminopyrazoles with substituted isothiocyanates or isocyanates. The novel compounds were tested anticonvulsant activity using by pentylenetetrazole- induced seizure (PTZ) and maximal electroshock seizure (MES) tests. Among the tested compounds, thiourea derivatives of 4b were afforded 90 and 100% protection in PTZ and MES tests at 50 mg/kg, respectively. Urea derivatives of 5a and 5b were afforded 82 and 100% protection both at 25 and 50 mg/kg. Also synthesized compounds were screened for antituberculosis activity against Mycobacterium tuberculosis H37Rv at 6.25 μg/mL concentration but they were not found active at these concentration. In addition, some selected compounds were evaluated for in vitro anti-HIV activity and they were all negative.
- Kaymakcioglu, Bedia Kocyigit,Rollas, Sevim,Koercegez, Eylem,Aricioglu, Feyza
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- Arylamidrazones as novel corticotropin releasing factor receptor antagonists
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The arylamidrazones have been found to be potent corticotropin releasing factor (CRF) receptor antagonists structurally distinct from previously reported CRF1 antagonists. Attempts to modify the arylamidrazone core suggested an important role f
- Wilson, Dean M.,Termin, Andreas P.,Mao, Long,Ramirez-Weinhouse, Michele M.,Molteni, Valentina,Grootenhuis, Peter D. J.,Miller, Keith,Keim, Susan,Wise, Gwendolyn
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p. 2123 - 2126
(2007/10/03)
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- Gas-Phase Kinetics of Elimination Reactions of Pentane-2,4-Dione Derivatives
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Gas-phase elimination reactions of pentane-2,4-dione, methyl acetoacetate, ethyl acetoacetate, 3-phenylhydroazopentane-2,4-dione, and ethyl 3-oxo-2-phenylhydrazonobutyrate have been measured in the temperature ranges of 744-783, 662-695, 614-663, 604-664, and 503-555 K, respectively, using a flow-thermolysis technique.These compounds undergo unimolecular first-order elimination reactions, for which log A = 11.9, 11.2, 11.7, 11.5, and 11.7 s-1 and Ea = 198.3, 167.1, 141.7, 165.6, and 141.7 kJ mol-1, respectively.The kinetic data and product analysis shows that the reactions are highly affected by the electronic nature of the substituents at the carbonyl and methylene carbon atoms of the substrates investigated.
- Al-Awadi, Nouria A.,El-Nagdi, Mohamed H.,Mathew, Tommy
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p. 517 - 524
(2007/10/02)
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- Reaction of (cyano)thioacetamide with arylhydrazones of β-diketones: Novel synthesis of 2(1H)-pyridinethiones, thieno[2,3-b]pyridines, and pyrazolo[3,4-b]pyridines
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A novel synthesis of 2(1H)-pyridinethiones, thieno[2,3-b]pyridines and pyrazolo[3,4-b]pyridines utilizing (cy-ano)thioacetamide and arylhydrazones of 1,3-diketones as starting components is described.
- Elgemeie, Galal Eldin Hamza,El-Zanate, Ali Mahmoud,Mansour, Abdel-Kader E.
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p. 555 - 561
(2017/03/31)
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