- Crystal structure, spectroscopic and thermal properties of the coordination compounds M(1,3-diethyl-2-thiobarbiturate) M = Rb+, Cs+, Tl+ and NH4+
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Four new compounds of 1,3-diethyl-2-thiobarbituric acid (C8H11N2O2S, Hdetba) with Rb+, Cs+, Tl+ and NH4+ ions were prepared by Hdetba neutralization with the metal carbonates or ammonium hydroxide in aqueous solution. The colorless crystals have been investigated using X-ray diffraction techniques, differential scanning calorimetry, thermogravimetry and infrared spectroscopy. The coordination compounds of MDetba with M = Rb, Cs and Tl crystallize in the orthorhombic space group P212121, but compound NH4Detba crystallizes in the triclinic space group P1ˉ. The MDetba structures were compared at the molecular and supramolecular levels. The Detba- ion in the NH4+ compound forms conformer (A) with two diethyl groups on one side of the ion ring, whereas the Detba- ion in the Rb(I), Cs(I) and Tl(I) compounds forms conformer (B) with two diethyl groups on different sides of the ring. The results of IR spectroscopy and thermal analysis are consistent with the X-ray data.
- Molokeev, Maxim S.,Golovnev, Nicolay N.,Vereshchagin, Sergey N.,Atuchin, Victor V.
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- Design and synthesis of thiobarbituric acid analogues as potent urease inhibitors
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A series of thiobarbiturates 4a–4e and bis-thiobarbiturates analogues 5a–5o has been synthesized by condensing 1,3-diethylthiobarbituric acid 3 with a variety of aromatic aldehydes with varied structural features and substitution at active methylene position of thiobarbituric acid. Afterward, chemical structures of newly synthesized analogues of thiobarbituric acid were characterized through FT-IR, NMR spectroscopy and mass spectrometry. Subsequently, the inhibitory potential of thiobarbiturates 4a–4e and bis-thiobarbiturates analogues 5a–5o against urease enzyme was evaluated. The inhibitory potential of all synthesized analogues in terms of IC50 value was observed in the range of 8.42 ± 0.32 to 79.34 ± 0.52 μM by comparing with thiourea (IC50 21.25 ± 0.15 μM) as a standard urease inhibitor. Out of these twenty analogues, most of the analogues exhibited potent inhibitory activity against urease. After interesting findings, structure activity relationship (SAR) has been established for all analogues. Docking studies revealed that synthesized analogues interacted with active site residues of bimetallic nickel center of the urease enzyme through, thiolate, π-π stacking and hydrogen bonding interactions.
- Khan, Matee Ullah,Aslam, Misbah,Shahzad, Sohail Anjum,Khan, Zulfiqar Ali,Khan, Nazeer Ahmad,Ali, Muhammad,Naz, Sadia,Rahman, Jameel,Farooq, Umar
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- A ring-locking strategy to enhance the chemical and photochemical stability of A-D-A-type non-fullerene acceptors
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Recently, the power conversion efficiencies (PCEs) of bulk-heterojunction organic solar cells (BHJ-OSCs) based on non-fullerene acceptors (NFAs) have made a very impressive progress in the research field. However, less attention has been paid to the intrinsic chemical and photochemical stability of NFAs, although they are correlated greatly with the resulting device stability. Herein, we describe a new molecular design strategy to enhance the intrinsic chemical and photochemical stability of acceptor-donor-acceptor (A-D-A)-type NFAs by introducing ring-locked carbon-carbon double bonds between D-A conjugation, attributed to increased steric hindrance of nucleophilic attack and the formation of intramolecular C-H?O interactions. Based on this strategy, two types of NFAs were successfully prepared, 2-(1,1-dicyanomethylene)rhodanine-based IDT-CR and IDTT-CR and thiobarbituric acid-based IDT-CT and IDTT-CT. When blended with a wide-bandgap polymer donor (P3HT), the IDTT-CR-based solar cells can exhibit a PCE of 2.86%. Moreover, a much enhanced PCE of 6.13% was realized by adopting a low-bandgap polymer donor PTB7-Th to pair with IDTT-CT. The fabricated PTB7-Th:IDTT-CT-based OSCs showed very encouraging photostability, the PCE of which could retain >80% of the initial values after 200 h one sun irradiation in air without a UV filter. Such photostability performance has greatly outperformed those from conventional NFAs like ITIC, IT-4F, and IT-M, suggesting the effectiveness of our ring-locking design strategy. Moreover, PTB7-Th:IDTT-CT-based OSCs could retain ~70% of its initial PCE after heating at 85 °C for 100 h. Furthermore, we reported an inferior device stability for P3HT:IDTT-CR based OSCs, which is primarily attributed to the evolution of BHJ film morphology under light illumination.
- Liu, Hongtao,Wang, Wen,Zhou, Yinhua,Li, Zhong'An
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- Compound with aggregation-induced emission property, and application thereof in field of surgical navigation
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The invention belongs to the technical field of synthesis of compounds with aggregation-induced emission properties, and relates to a compound with an aggregation-induced emission property, and application thereof. The compound has the beneficial effects that 1, a new thought of surgical navigation is provided; 2, materials are easy to obtain, cost is low, and preparation is easy; 3, the biotoxicity is low; and 4, the luminescent wavelength is long, the interference of background fluorescence is small, and the tissue penetrability is strong.
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Paragraph 0051-0053; 0058
(2021/07/14)
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- Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells
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A series of novel thio- and seleno-barbituric acid derivatives were synthesized by varying the substituents at N1 and N3 (ethyl, methyl, allyl, and phenyl), and C5 tethered with dienyl and trienyl moieties attached to substituents such as phenyl, 2-furanyl, 2-thiophenyl, 1-naphthyl, and 3-pyridyl. The cytotoxic potential of these derivatives was evaluated by using MTT assay against melanoma cell lines expressing either wild-type (CHL-1) or mutant (UACC 903) BRAF gene. Among all, 2b and 8b were identified as the most potent compounds. Both 2b and 8b inhibited viability of various melanoma cells and induced cell death as evidenced by Live and Dead assay. Western blot analysis showed that they induce PARP cleavage and inhibit anti-apoptotic Bcl-2, Bcl-xL and Survivin in a dose-dependent manner within 24 h of the treatment. Novel thiobarbituric acid analogs also inhibited viability of various other solid tumor cell lines, such as pancreatic, breast, and colon. Overall, 2b, 2d, and 8b emerged as the most effective compounds and make good leads for the development of future therapeutic agents.
- Ramisetti, Srinivasa Rao,Pandey, Manoj K.,Lee, Sang Y.,Karelia, Deepkamal,Narayan, Satya,Amin, Shantu,Sharma, Arun K.
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p. 1919 - 1930
(2017/11/17)
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- An efficient one-pot protocol for regioselective synthesis of 3-aryl-6,8-dialkyl-7-thioxo-7,8-dihydropyrimido[4,5-c ] pyridazine-5(6 H)-ones
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A series of 3-aryl-6,8-dialkyl-7-thioxo-7,8-dihydropyrimido[4,5-c] pyridazine-5(6H)-one derivatives have been regioselectively synthesized via the one-pot three-component reaction of 1,3-dimethylthiobarbituric acid and 1,3-diethylthiobarbituric acid with various arylglyoxals in the presence of hydrazinium dihydrochloride in warm ethanol. These new substituted pyrimidopyridazines may be potential monoamine oxidase inhibitors.
- Khalafy, Jabbar,Rimaz, Mehdi,Rabiei, Hossein,Panahi, Leila
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p. 395 - 406
(2013/09/23)
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- Chemical modification of plant alkaloids. 2. Reaction of cotarnine with barbituric acid derivatives and structure of 5-dihydrocotarnylbarbituric acids
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The reaction of barbituric acid and its N-substituted derivatives and 2-thio analogs with cotarnine forms 5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-1,3-methylenedioxy-[4,5-g]isoquinolinyl-1)barbituric acids, a new class of zwitter-ions, the structure of which was studied by 1H and 13C NMR spectroscopy and mass spectrometry. The prepared compounds exist in solution as stable intermolecular associates and have a complicated H-bonded structure.
- Krasnov,Kartsev,Yurova
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p. 543 - 550
(2007/10/03)
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