4472-44-0Relevant articles and documents
Solvatochromic behavior of a pyrene-pyrimidine-based Schiff base and detection of heavy metal ions in aqueous media
Ghosh, Swadesh,Singharoy, Dipti,Konar, Saugata,Naskar, Jnan Prakash,Bhattacharya, Subhash Chandra
, p. 1272 - 1283 (2021/03/26)
The synthesis and solvatochromic behavior of pyrimidine based Schiff-base (PYPH) were studied to develop a fluorescent chemo sensor for the detection of Hg2+ in aqueous solution. The characterization of PYPH was investigated on the basis of UV–vis, FTIR, 1H-NMR and mass spectral data. PYPH displays selective fluorescent turn-off response to Hg2+ in aqueous solution. The sensitivity and selectivity of PYPH toward Hg2+ among different metal ions was examined by absorption, fluorescence, 1H-NMR and mass spectral studies. Binding stoichiometry (2:1) has been confirmed by a Job’s plot, HRMS spectral studies and 1H-NMR analysis. A low detection limit was 4.2 × 10?6 M for Hg2+. Ground state geometry of PYPH has been optimized using density functional theory (DFT). These results demonstrate that PYPH has promise to detect Hg2+ ion in environmental analysis systems.
NLRX1 ligands
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Page/Page column 17, (2019/12/09)
Provided are compounds that target the nucleotide-binding oligomerization domain, leucine rich repeat containing X1 (NLRX1) pathway. The compounds can be used to treat multiple conditions, including chronic and/or inflammatory gastrointestinal diseases, cancers, and infectious diseases.
Nonionic Surfactants as Potential Carriers of a Synthesized Pyrimidine Derivative: Spectroscopic and Quantum Chemical Investigations
Ghosh, Swadesh,Singharoy, Dipti,Dhara, Anamika,Naskar, Jnan Prakash,Bhattacharya, Subhash Chandra
, p. 2695 - 2701 (2018/06/27)
Currently, a major problem is the poor water solubility and bioavailability of many pharmaceuticals. Using different types of surfactants is an effective strategy to overcome this problem. Herein a pyrimidine-based Schiff base, 2-[2-(anthracen-9-ylmethylene) hydrazinyl]-4,6-dimethyl pyrimidine (ANHP), has been synthesized and characterized by different spectroscopic methods. A comparative study of drug carrier properties of cationic, anionic, and the nonionic surfactants with this pyrimidine derivative (ANHP) in aqueous solution is the key research interest of this work. From fluorescence studies, the interaction of ANHP with the different types of surfactants were compared and binding constants of ANHP in vesicles were determined. The drug carrier properties of different surfactants were investigated by using different spectroscopic techniques. DLS, zeta potential, and AFM studies have shown that in the presence of ANHP, nonionic surfactants take a vesicular shape. Several experimental results clearly indicate that Ig-720 is the better choice as ANHP carrier among all the surfactants investigated. In addition, the structure of ANHP has been optimized by density functional theory (DFT). The theoretical and experimental results have been compared.
Discovery of indolylpiperazinylpyrimidines with dual-target profiles at adenosine A2A and dopamine D2 receptors for Parkinson’s disease treatment
Shao, Yi-Ming,Ma, Xiaohua,Paira, Priyankar,Tan, Aaron,Herr, Deron Raymond,Lim, Kah Leong,Ng, Chee Hoe,Venkatesan, Gopalakrishnan,Klotz, Karl-Norbert,Federico, Stephanie,Spalluto, Giampiero,Cheong, Siew Lee,Chen, Yu Zong,Pastorin, Giorgia
, (2018/01/12)
Parkinson’s disease (PD) is a neurodegenerative disorder characterized by progressive loss of dopaminergic neurons in the substantia nigra of the human brain, leading to depletion of dopamine production. Dopamine replacement therapy remains the mainstay for attenuation of PD symptoms. Nonetheless, the potential benefit of current pharmacotherapies is mostly limited by adverse side effects, such as drug-induced dyskinesia, motor fluctuations and psychosis. Non-dopaminergic receptors, such as human A2A adenosine receptors, have emerged as important therapeutic targets in potentiating therapeutic effects and reducing the unwanted side effects. In this study, new chemical entities targeting both human A2A adenosine receptor and dopamine D2 receptor were designed and evaluated. Two computational methods, namely support vector machine (SVM) models and Tanimoto similarity-based clustering analysis, were integrated for the identification of compounds containing indole-piperazine-pyrimidine (IPP) scaffold. Subsequent synthesis and testing resulted in compounds 5 and 6, which acted as human A2A adenosine receptor binders in the radioligand competition assay (Ki = 8.7–11.2 μM) as well as human dopamine D2 receptor binders in the artificial cell membrane assay (EC50 = 22.5–40.2 μM). Moreover, compound 5 showed improvement in movement and mitigation of the loss of dopaminergic neurons in Drosophila models of PD. Furthermore, in vitro toxicity studies on compounds 5 and 6 did not reveal any mutagenicity (up to 100 μM), hepatotoxicity (up to 30 μM) or cardiotoxicity (up to 30 μM).
Synthesis and biological activity of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives
Wang, Bao-Lei,Zhang, Yan,Liu, Xing-Hai,Zhang, Li-Yuan,Zhan, Yi-Zhou,Zhang, Xiao,Wang, Li-Zhong,Li, Yong-Hong,Li, Zheng-Ming
, p. 34 - 41 (2016/12/24)
A series of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives have been conveniently synthesized via Mannich reaction in good yields. Their structures were identified by IR,1H NMR,13C NMR, and elemental analysis. The preliminary bioassays showed that among 14 new compounds, the trifluoromethyl-containing compounds exhibited superior activity than the methyl-containing ones; some of the compounds displayed significant in vitro and in vivo fungicidal activity against several plant fungi and were comparable with the control Triadimefon; several compounds exhibited certain herbicidal activity against Brassica campestris; several compounds possessed favorable KARI inhibitory activity, especially 8D could be a promising KARI inhibitor for further study. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic Mannich base structures containing piperazine moiety.
Synthesis and Fungicidal Activities of Novel 1,2,4-Triazole Thione Derivatives Containing 1,2,3-Triazole and Substituted Piperazine Moieties
Wang, Bao-Lei,Zhan, Yi-Zhou,Zhang, Li-Yuan,Zhang, Yan,Zhang, Xiao,Li, Zheng-Ming
, p. 48 - 54 (2016/01/25)
A series of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties were synthesized via the Mannich reaction of 1,2,3-triazole-containing 1,2,4-triazole thiol intermediates with various substituted piperazines and formaldehyde in high yields. The structures of 14 title compounds were confirmed by melting points, IR, 1H NMR, 13C NMR, and elemental analysis. The bioassay results showed that some of the title compounds exhibit significant fungicidal activities against several plant fungi at 50 μg/mL, especially trifluoromethyl-containing triazole thione derivative 9g showed broad activities and could be made further structural optimization for novel fungicides innovation research.
Synthesis and biological activity of novel N-glucosides containing substituted piperazine moiety
Zhang, Li-Yuan,Wang, Bao-Lei,Zhan, Yi-Zhou,Hua, Xue-Wen,Liu, Ming,Zhang, Xiao,Song, Hai-Bin,Li, Zheng-Ming
, p. 343 - 351 (2016/04/04)
A series of novel acetylated piperazine-containing N-glucosides and bis(N-glucoside) 8a-i were synthesized by the nucleophilic addition of acetylated glucopyranosyl isothiocyanate with various substituted piperazines in THF with high yields. Their novel deacetylated products 9a-i were also synthesized after Me-ONa/MeOH treatment. The preliminary bioassays for 18 novel title compounds showed that several compounds have significant fungicidal activity against Fusarium omysporum, Cercospora arachidicola and Phytophthora capsici at 50 μg/mL.
Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties
Wang, Bao-Lei,Shi, Yan-Xia,Zhang, Shu-Jun,Ma, Yi,Wang, Hong-Xue,Zhang, Li-Yuan,Wei, Wei,Liu, Xing-Hai,Li, Yong-Hong,Li, Zheng-Ming,Li, Bao-Ju
, p. 167 - 178 (2016/04/26)
A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.
Synthesis and biological activities of novel 1,2,4-triazole thiones and bis(1,2,4-triazole thiones) containing phenylpyrazole and piperazine moieties
Wang, Bao-Lei,Zhang, Li-Yuan,Zhan, Yi-Zhou,Zhang, Yan,Zhang, Xiao,Wang, Li-Zhong,Li, Zheng-Ming
, p. 36 - 44 (2018/03/27)
A series of novel 1,2,4-triazole thione and bis(1,2,4-triazole thione) derivatives containing phenylpyrazole and substituted piperazine moieties have been conveniently synthesized via Mannich reaction using various 1,2,4-triazole thiols, substituted piperazines, and formaldehyde at room temperature in short time. Their structures were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. The preliminary bioassays for 27 new title compounds have shown that some of them possess certain herbicidal activities against Echinochloa crusgalli at 100 μg/mL concentration. Some of the compounds exhibited significant in vitro fungicidal activities, especially against Cercospora arachidicola and Rhizoctonia cerealis at the concentration of 50 μg/mL, and were comparable with that of control Triadimefon. Meanwhile, IXp held the control efficacy of 60% against Puccinia sorghi Schw. at 200 μg/mL concentration in the in vivo test. The SAR analysis has indicated that compounds with two CF3 groups both on triazole and pyrazole rings are more effective than compounds with one CF3 group or two CH3 groups according to their fungicidal activity data. On the whole, compounds VIIIg, IXi, IXo and IXp could be used as novel lead structures for the design and discovery of new fungicides.
2-Amino-1,3,5-triazine chemistry: hydrogen-bond networks, Takemoto thiourea catalyst analogs, and olfactory mapping of a sweet-smelling triazine
Hintermann, Lukas,P?thig, Alexander,Xiao, Li
supporting information, p. 1529 - 1539 (2015/08/18)
Abstract The chemistry of 4,6-dialkyl-2-amino-1,3,5-triazines with bulky alkyl substituents was investigated and their use as building blocks for preparing chiral thiourea organocatalysts explored. Reaction of ammonia with 4,6-di-tert-butyl-2-chloro-1,3,5-triazine gave 4,6-di-tert-butyl-1,3,5-triazin-2-amine which formed extended hydrogen-bond networks in the solid state according to X-ray crystallography. Selected heterocyclic amines were converted to isothiocyanates, and the latter reacted with (S,S)-2-(dimethylamino)cyclohexylamine to give enantiopure 1-hetaryl-3-[2-(dimethylamino)cyclohexyl]thioureas, with hetaryl representing either 4,6-dimethyl-1,3-diazin-2-yl, 4,6-diisopropyl-1,3,5-triazin-2-yl, or 4,6-di-tert-butyl-1,3,5-triazin-2-yl groups. These compounds are structural analogs of Takemotos's chiral thiourea organocatalysts (1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea) with an aza-aryl instead of the 3,5-bis(trifluoromethyl)phenyl group. They feature a strong intramolecular N-H to N-1 hydrogen bond, as shown by X-ray crystallography of 1-(4,6-di-tert-butyl-1,3,5-triazin-2-yl)-3-[2-(dimethylamino)cyclohexyl]thiourea in the solid state and by 1H NMR spectroscopy of all derivatives in CDCl3 solution, which prevents them from acting as bifunctional organocatalyst. In the reaction of 4,6-di-tert-butyl-2-chloro-1,3,5-triazine with ammonia, 4,6-di-tert-butyl-2-ethoxy-1,3,5-triazine was identified as side-product displaying a mildly sweet, floral odor that is unusual for a 1,3,5-triazine. Analogs (>35) of 4,6-di-tert-butyl-2-ethoxy-1,3,5-triazine were prepared to define the important structural factors of the olfactophore.
