5798-75-4Relevant articles and documents
Combination of a new chiroptical probe and theoretical calculations for chirality detection of primary amines
Kuwahara, Shunsuke,Nakamura, Masaya,Yamaguchi, Akira,Ikeda, Mari,Habata, Yoichi
, p. 5738 - 5741 (2013)
A method to determine absolute configurations of primary amines by combined use of a chiroptical probe 1 and theoretical calculations is reported. Probe 1 is linked to chiral primary amines yielding 1-amine conjugates, which exhibited exciton coupled circular dichroism in the m-quaterphenyl chromophores. The ratios between the P and M conformers of the 1-amine conjugates, which are calculated with DFT, were correlated highly with the sign and amplitude of the observed CD spectra.
Design, synthesis and characterization of π-conjugated 2,5-diphenylsubstituted-1,3,4-oxadiazole-based D-π-A-π’-D′ form of efficient deep blue functional materials: Photophysical properties and fluorescence “Turn-off” chemsensors approach
Najare, Mahesh S.,Patil, Mallikarjun K.,Garbhagudi, Manjunatha,Yaseen, Mohammed,Inamdar, Sanjeev R.,Khazi, Imtiyaz Ahmed M.
, (2021)
This paper primarily deals with the design and synthesis of three novel conjugated organic molecules containing 1,3,4-oxadiazole unit (abbreviated as CHEM-6(a-c)) with Donor-π-Acceptor-π’-Donor’ structures by utilizing palladium catalyzed Suzuki cross coupling reaction. Molecular structures of these compounds were characterized by using various spectroscopic and analytical techniques namely 1H NMR, 13C NMR, FT-IR, GC–MS and elemental analysis. Optical properties of these compounds have been investigated by using UV–visible absorption and fluorescence spectroscopy. Also, the PL investigations on solid state samples (as thin films) were carried out. Furthermore, solvatochromism and Density Functional Theory (DFT) computations are studied in detail. The experimentally measured optical band gap (Egopt) values of compounds CHEM-6a, CHEM-6b and CHEM-6c were determined to be 3.11, 3.03 and 2.70 eV, respectively. The DSC and TGA results revealed that the compounds exhibit good thermal stabilities. Current results indicate that the compounds CHEM-6(a-c) are promising candidates and could play an important role in the field of optoelectronic devices and possibly find potential applications in development of OLEDs. In addition, the compounds CHEM-6(a-c) showed an interesting property of chemical sensing for Hg(II) ion which can be clearly observed by naked eyes from the changes in solution color and fluorescence (under UV excitation).
Novel cycloaddition of 2-alkyl-3-benzoyl-2-thianaphthalenes
Shimizu, Hiroshi,Yonezawa, Takenori,Watanabe, Tomoko,Kobayashi, Kazuhiro
, p. 1659 - 1660 (1996)
Deprotonation of 2-alkyl-3-benzoyl-2-thiochromenium salts 1 or 2 with 2 equiv. of triethylamine in ethanol affords the unexpected benzothiopyran derivatives 3 and 4; the structure of 3a is confirmed by X-ray crystallography.
Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof
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Paragraph 0055-0056; 0070; 0090; 0092; 0095; 0103, (2021/07/24)
The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.
Oxazole ring-containing honokiol thioether derivative and preparation method and application thereof
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Paragraph 0042-0044, (2021/08/11)
The invention discloses an oxazole ring-containing honokiol thioether derivative, a preparation method thereof and application of the oxazole ring-containing honokiol thioether derivative as an alpha-glucosidase inhibitor, the chemical structure of the oxazole ring-containing honokiol thioether derivative is shown as a general formula (I), and R is selected from non-substituted or substituted phenyl. Compared with the prior art, the invention provides the novel honokiol thioether derivative containing the oxazole ring, and the honokiol thioether derivative containing the oxazole ring has good inhibitory activity on alpha-glucosidase, provides more possibilities for treating diabetes, and is expected to be used for preparing novel candidate drug molecules for treating diabetes. In addition, the preparation process is simple, the cost is low, and the yield is high.
Using m icrowave and ultrasound to synthesis of substituted bis-acyl hydrazone derivatives
Mohammed, Salim J.,Sheat, Attallah M.,A.abood, Salih,Yahya, Omar M.
, p. 6423 - 6427 (2021/11/01)
In this paper, some new bis-acyl hydrazone derivatives (4a-f) were prepared through the reaction of carboxylic acid hydrazides with 1,4-diacetylbenzene using classical methods, microwave and ultrasound irradiation methods. These compounds are obtained through a series of reactions where some carboxylic acids react with ethanol first in the presence of concentrated sulfuric acid to give the corresponding esters (2a-f), which when treatment with aqueous hydrazine give carboxylic acid hydrazides (3a-f).thus, The results proved that the use of microwave and ultrasound techniques is much better than the classical methods, as it gave a higher yield, shorter reaction time, and the absence of the use of solvents. All newly synthesized compounds were confirmed by IR, (1H & 13C) NMR spectral analysis and the corresponding reactions were monitored by TLC using the reported eluent.
Schiff Base Functionalized 1,2,4-Triazole and Pyrene Derivative for Selective and Sensitive Detection of Cu2+?ion?in the Mixed Organic- Aqueous Media
Choi, Nam Gyu,Vanjare, Balasaheb D.,Mahajan, Prasad G.,Nagarajan, Rajendran,Ryoo, Hyang Im,Lee, Ki Hwan
, p. 1739 - 1749 (2021/09/03)
We have prepared Schiff base functionalized 1,2,4-triazole and pyrene derivative for selective, sensitive, and naked eye colorimetric detection of Cu2+ in the mixed organic- aqueous media. Amongst the 18 different metal ions studied for absorption and fluorescence titration, only Cu2+ ion encourages the modification in spectral properties of Schiff base functionalized 1,2,4-Triazole and Pyrene Probe. The stoichiometric ratio of the TP-Cu2+ complex was determined to be 2:1 according to Job’s plot. The lower detection limit estimated for Cu2+ is 0.234?nM which shows excellent sensitivity and selectivity of the present analytical method towards detection of Cu2+ ion in the mixed organic-aqueous media. The present approach has been successfully utilized for the quantitative determination of Cu2+ ion from environmental aqueous solution.
Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker
Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi
, (2021/05/17)
A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.
Synthesis and biological evaluation of honokiol derivatives bearing 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3h)-ones as potential viral entry inhibitors against sars-cov-2
Bai, Li-Ping,Guo, Yong,Jiang, Zhi-Hong,Liu, Jia-Zheng,Meng, Jie-Ru,Xu, Ting,Zheng, Zhi-Yuan
, (2021/09/08)
The 2019 coronavirus disease (COVID-19) caused by SARS-CoV-2 virus infection has posed a serious danger to global health and the economy. However, SARS-CoV-2 medications that are specific and effective are still being developed. Honokiol is a bioactive component from Magnoliae officinalis Cortex with damp-drying effect. To develop new potent antiviral molecules, a series of novel honokiol analogues were synthesized by introducing various 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones to its molecule. In a SARS-CoV-2 pseudovirus model, all honokiol derivatives were examined for their antiviral entry activities. As a result, 6a and 6p demonstrated antiviral entry effect with IC50 values of 29.23 and 9.82 μM, respectively. However, the parental honokiol had a very weak antiviral activity with an IC50 value more than 50 μM. A biolayer interfero-metry (BLI) binding assay and molecular docking study revealed that 6p binds to human ACE2 protein with higher binding affinity and lower binding energy than the parental honokiol. A competitive ELISA assay confirmed the inhibitory effect of 6p on SARS-CoV-2 spike RBD’s binding with ACE2. Importantly, 6a and 6p (TC50 > 100 μM) also had higher biological safety for host cells than honokiol (TC50 of 48.23 μM). This research may contribute to the discovery of potential viral entrance inhibitors for the SARS-CoV-2 virus, although 6p’s antiviral efficacy needs to be validated on SARS-CoV-2 viral strains in a biosafety level 3 facility.
Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests
Cheng, Wanqing,Fan, Jiangping,Guo, Yong,Han, Meiyue,Ma, Nannan,Yan, Xiaoting,Yang, Ruige
, p. 15544 - 15553 (2022/01/03)
To improve the insecticidal activity of (+)-nootkatone, a series of 42 (+)-nootkatone thioethers containing 1,3,4-oxadiazole/thiadiazole moieties were prepared to evaluate their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal evaluation revealed that most of the title derivatives exhibited more potent insecticidal activities than the precursor (+)-nootkatone after the introduction of 1,3,4-oxadiazole/thiadiazole on (+)-nootkatone. Among all of the (+)-nootkatone derivatives, compound 8c (1 mg/mL) exhibited the best growth inhibitory (GI) activity against M. separata with a final corrected mortality rate (CMR) of 71.4%, which was 1.54- and 1.43-fold that of (+)-nootkatone and toosendanin, respectively; 8c also displayed the most potent aphicidal activity against M. persicae with an LD50 value of 0.030 μg/larvae, which was closer to that of the commercial insecticidal etoxazole (0.026 μg/larvae); and 8s showed the best larvicidal activity against P. xylostella with an LC50 value of 0.27 mg/mL, which was 3.37-fold that of toosendanin and slightly higher than that of etoxazole (0.28 mg/mL). Furthermore, the control efficacy of 8s against P. xylostella in the pot experiments under greenhouse conditions was better than that of etoxazole. Structure-activity relationships (SARs) revealed that in most cases, the introduction of 1,3,4-oxadiazole/thiadiazole containing halophenyl groups at the C-13 position of (+)-nootkatone could obtain more active derivatives against M. separata, M. persicae, and P. xylostella than those containing other groups. In addition, toxicity assays indicated that these (+)-nootkatone derivatives had good selectivity to insects over nontarget organisms (normal mammalian NRK-52E cells and C. idella and N. denticulata fries) with relatively low toxicity. Therefore, the above results indicate that these (+)-nootkatone derivatives could be further explored as new lead compounds for the development of potential eco-friendly pesticides.
