- Design, synthesis, antibacterial evaluation and molecular docking studies of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives
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The development of new antimicrobial drugs is most needed due to rapid growth in global antimicrobial resistance. Thus, in this context, a series of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives (7a–j) was synthesized. All the derivatives we
- Depa, Navaneetha,Erothu, Harikrishna
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- Syntheses, crystal structures, and antibacterial activities of helical M(II) phenyl substituted pyrazole carboxylate complexes
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Six new metal complexes with two kinds of phenyl substituted pyrazole carboxylic acid, [Co(L1)2(4,4′-bipy)(H 2O)2]n (1), [Ni(L1) 2(4,4′-bipy)(H2O)2]n/
- Liu, Hong,Yang, Gao-Shan,Liu, Chong-Bo,Lin, Yi,Yang, Yi,Gong, Yun-Nan
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- Electrosynthesis of 5-chloro- and 5-azido-4-pyrazole carboxylic acid at the nickel hydroxide electrode
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Pyrazole derivatives are valuable intermediates for drugs and agrochemicals. The literature seems to be almost devoid of suitable methods, from environmental point of view for the preparation of simple pyrazole carboxylic acid derivatives which could be prepared from aldehydes with oxidizing agents such as NaCIO4. These reagents are partially toxic and large scale conversions create waste disposal problems. A clean oxidation technique would be the indirect electrochemical oxidation at the nickel hydroxide anode. Until recently there have been few examples of oxidation of heterocyclic aldehydes to the corresponding acids. We represent here an electrochemical method for oxidizing 5-chloro-4-pyrazole carbaldehyde (1) and 5-azido-4-pyrazole carbaldehyde (2) to their corresponding acids (3 and 4) at a nickel hydroxide anode in good yields (80-85%) (scheme 1).
- Abdel-Azzem,Zahran
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- Design, Synthesis, DFT study and antifungal activity of pyrazolecarboxamide derivatives
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A series of novel pyrazole amide derivatives were designed and synthesized by multi-step reactions from phenylhydrazine and ethyl 3-oxobutanoate as starting materials, and their structures were characterized by NMR, MS and elemental analysis. The antifungal activity of the title compounds was determined. The results indicated that some of title compounds exhibited moderate antifungal activity. Furthermore, DFT calculations were used to study the structure-activity relationships (SAR).
- Mu, Jin-Xia,Shi, Yan-Xia,Yang, Ming-Yan,Sun, Zhao-Hui,Liu, Xing-Hai,Li, Bao-Ju,Sun, Na-Bo
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- Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
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The pyrazole core has been recognized by their biological properties and included in the synthesis of modern agrochemicals. Part of these studies consists of making structural modifications to pesticides for commercial purposes to increase efficacy. In th
- González-López, Edwin,Grande-Tovar, Carlos D.,León-Jaramillo, Jhair,Peralta-Ruiz, Yeimmy,Quiroga, Jairo,Trilleras, Jorge
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p. 1917 - 1925
(2020/10/09)
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- 1, 3, 5-substituent-4-pyrazole amide derivative and preparation method thereof
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The invention discloses a 1, 3, 5-substituent-4-pyrazole amide derivative and a preparation method of the 1, 3, 5-substituent-4-pyrazole amide derivative. The 1, 3, 5-substituent-4-pyrazole amide derivative has a general formula disclosed by the invention
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Paragraph 0045; 0064; 0082-0083
(2020/02/14)
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- Discovery of novel triazole-containing pyrazole ester derivatives as potential antibacterial agents
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To develop new antibacterial agents, a series of novel triazole-containing pyrazole ester derivatives were designed and synthesized and their biological activities were evaluated as potential topoisomerase II inhibitors. Compound 4d exhibited the most potent antibacterial activity with Minimum inhibitory concentration (MIC) alues of 4 μg/mL, 2 μg/mL, 4 μg/mL, and 0.5 μg/mL against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella gallinarum, respectively. The in vivo enzyme inhibition assay 4d displayed the most potent topoisomerase II (IC50 = 13.5 μg/mL) and topoisomerase IV (IC50 = 24.2 μg/mL) inhibitory activity. Molecular docking was performed to position compound 4d into the topoisomerase II active site to determine the probable binding conformation. In summary, compound 4d may serve as potential topoisomerase II inhibitor.
- Chu, Ming-Jie,Wang, Wei,Ren, Zi-Li,Liu, Hao,Cheng, Xiang,Mo, Kai,Wang, Li,Tang, Feng,Lv, Xian-Hai
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- Design, synthesis and biological evaluation of novel pyrazole sulfonamide derivatives as potential AHAS inhibitors
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Acetohydroxy acid synthase (AHAS; EC 2.2.1.6, also referred to as acetolactate synthase, ALS) has been considered as an attractive target for the design of herbicides. In this work, an optimized pyrazole sulfonamide base scaffold was designed and introduced to derive novel potential AHAS inhibitors by introducing a pyrazole ring in flucarbazone. The results of in vivo herbicidal activity evaluation indicates compound 3b has the most potent activity with rape root length inhibition values of 81percent at 100 mg/L, and exhibited the best inhibitory ability against Arabidopsis thaliana AHAS. With molecular docking, compound 3b insert into Arabidopsis thaliana AHAS stably by an H-bond with Arg377 and cation-p interactions with Arg377, Trp574, Tyr579. This study suggests that compound 3b may serve as a potential AHAS inhibitor which can be used as a novel herbicides and provides valuable clues for the further design and optimization of AHAS inhibitors.
- Lv, Xian-Hai,Ren, Zi-Li,Liu, Hao,Li, Hai-Dong,Li, Qing-Shan,Wang, Li,Zhang, Li-Song,Yao, Xiao-Kang,Cao, Hai-Qun
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p. 358 - 362
(2018/04/09)
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- Acylaminoimidazole derivative and use thereof
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The invention belongs to the technical field of medicines and relates to an acylaminoimidazole derivative shown in the general formula I and its stereisomer and pharmaceutical acceptable salt, hydrate, solvate or prodrug. In the formula I, substituents R, R1, Ar, M and X are defined in the specification. The invention also relates to a method for preparing the compound shown in the formula I, a medicinal composition containing the compound and a use of the compound and the medicinal composition in preparation of drugs for treating and/or preventing cancers and other skin proliferative diseases. An antifungal experiment proves that the compound has strong resistance to shallow and deep fungi and can be used for preparation of an antibacterial drug.
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Paragraph 0638; 0639
(2016/10/07)
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- Friedel-Crafts Chemistry. Part 46. Unprecedented Construction of Tricyclic Pyrazolo[3,4-b]quinolines, -[1,8]naphthyridines, -azepines, -azocines, -pyrido[3,2-g]azocines, and pyrazolo[3,4-b]azonines via Friedel-Crafts Ring Closures
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A series of keto-substituted pyrazolo[3,4-b]quinolines, pyrazolo[3,4-b][1,8]naphthyridines, benzo[e]pyrazolo[3,4-b]azepines, benzo[g]pyrazolo[3,4-b]azocines, pyrazolo[3,4-b]pyrido[3,2-g]azocines, and benzo[g]pyrazolo[3,4-b]azonines scaffolds were synthesi
- Abd El-Aal, Hassan A. K.,Khalaf, Ali A.
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p. 652 - 661
(2016/07/06)
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- Pyrazole amides compound, preparation method therefor and application thereof
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The present invention discloses a pyrazole amides compound. The structural formula of the compound is as shown in the description, wherein R is optionally substituted with one or more substituents of C1-C6 alkyl, alkoxy, halogen, nitro, and trifluoromethyl. The present invention also discloses a preparation method for the pyrazole amides compound. The pyrazole amides compound can be used for antibacterium, in particular for prevention and control of tomato late blight, tomato damping-off, corynespora cassiicola, botrytis cinerea, and cucumber sheath blight. The pyrazole amides compound can also be used for weeding, in particular for prevention and control of barnyard grass and rape.
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Paragraph 0011; 0040
(2016/10/10)
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- Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)
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All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities. All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 μM (compared to liarozole (IC50 = 2.45 μM) and S8 (IC50 = 3.21 μM)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of β-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development.
- Zhao, Dongmei,Sun, Bin,Ren, Jinhong,Li, Fengrong,Song, Shuai,Lv, Xuejiao,Hao, Chenzhou,Cheng, Maosheng
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p. 1356 - 1365
(2015/03/04)
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- Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors
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All-trans-retinoic acid (ATRA) as a physiological metabolite of vitamin A is widely applied in the treatment of cancer, skin, neurodegenerative and autoimmune diseases. CYP26A1 enzyme, induced by ATRA in liver and target tissues, metabolizes ATRA into 4-hydroxyl-RA. Inhibition of CYP26A1 metabolic enzyme represents a promising strategy for discovery of new specific anticancer agents. Herein, we describe the design, synthesis and biological evaluation of a series of new amide imidazole derivatives as retinoic acid metabolism blocking agents (RAMBAs) toward CYP26A1 enzyme. First, based on the recent theoretical models (Sun et al., J. Mol. Graph. Model., 2015, 56, 10-19) a series of RAMBAs with novel scaffolds were designed using fragment-based drug discovery approach. Subsequently, the new RAMBAs were synthesized and evaluated for their biological activities. All the compounds demonstrated appropriate enzyme activities and cell activities. The promising inhibitors 20 and 23 with IC50 value of 0.22 μM and 0.46 μM toward CYP26A1, respectively, were further evaluated for CYP selectivity and the metabolic profile of ATRA. Both compounds 20 and 23 showed higher selectivity for CYP26A1 over other CYPs (CYP2D6, CYP3A4) when compared to liarozole. They also showed better inhibitory activities for the metabolism of ATRA when also compared to liarozole. These studies further validated the pharmacophore and structure-activity relationship models obtained about CYP26A1 inhibitors and highlighted the promising activities of the new series of CYP26A1 inhibitors designed from such models. They also paved the way for future development of those candidates as potential drugs.
- Sun, Bin,Liu, Kai,Han, Jing,Zhao, Li-Yu,Su, Xiao,Lin, Bin,Zhao, Dong-Mei,Cheng, Mao-Sheng
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p. 6763 - 6773
(2015/10/20)
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- Design, synthesis and anti-tobacco mosaic virus (TMV) activity of 5-chloro-n-(4-cyano-1-aryl-1H-pyrazol-5-yl)-1-aryl-3-methyl-1H-pyrazole-4-carboxamide derivatives
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A series of novel pyrazole amide derivatives 3a-3p which take TMV PC protein as the target has been designed and synthesized by the reactions of 5-chloro-1-aryl-3-methyl-1H-pyrazole-4-carboxylic acids with 5-amino-1-aryl-1H-pyrazole-4-carbonitriles. All the compounds were characterized by 1H-NMR, mass spectroscopy and elemental analysis. Preliminary bioassays indicated that all the compounds acted against the tobacco mosaic virus (TMV) with different in vivo and in vitro modes at 500 μg/mL and were found to possess promising activity. Especially, compound 3p showed the most potent biological activity against tobacco mosaic virus (TMV) compared to ningnanmycin, and a molecular docking study was performed and the binding model revealed that the pyrazole amide moiety was tightly embedded in the binding sites of TMV PC (PDB code: 2OM3).
- Xiao, Jin-Jing,Liao, Min,Chu, Ming-Jie,Ren, Zi-Li,Zhang, Xin,Lv, Xian-Hai,Cao, Hai-Qun
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p. 807 - 821
(2015/01/30)
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- Disulfide linked pyrazole derivatives inhibit phagocytosis of opsonized blood cells
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Immune thrombocytopenia (ITP) is caused by production of an autoantibody to autologous platelets. ITP can be treated either by reducing platelet destruction or by increasing platelet production. Fcγ receptor mediated phagocytosis of the opsonized blood ce
- Purohit, Meena K.,Scovell, Iain,Neschadim, Anton,Katsman, Yulia,Branch, Donald R.,Kotra, Lakshmi P.
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supporting information
p. 2324 - 2327
(2013/05/09)
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- New pyrazole derivatives of potential biological activity
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5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde (1) was reacted with hydrazine hydrate and thiosemicarbazide to afford the corresponding hydrazones 2 and thiosemicarbazones 4. The latter compounds were used to obtain the pyrazole derivatives 3, 5-
- Farghaly, Abdel-Rahman,Esmail, Sabah,Abdel-Hafez, Ali,Vanelle, Patrice,El-Kashef, Hussein
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p. 228 - 241
(2013/01/16)
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- Efficient [5 + 1]-strategy for the assembly of 1,8-naphthyridin-4(1H)-ones by domino amination/conjugate addition reactions of 1-(2-chloropyridin-3-yl) prop-2-yn-1-ones with amines
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A facile synthetic approach for the synthesis of 1,8-naphthyridine-4(1H)- one derivatives via a catalyst free and Pd-supported tandem amination sequence is developed and described. In a case of aliphatic amines reaction proceeds in a catalyst free mode, however anilines demand Pd-supported reaction conditions. The Royal Society of Chemistry 2012.
- Iaroshenko, Viktor O.,Knepper, Ingo,Zahid, Muhammad,Kuzora, Rene,Dudkin, Sergii,Villinger, Alexander,Langer, Peter
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supporting information; scheme or table
p. 2955 - 2959
(2012/05/05)
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- Synthesis and bioactivity of pyrazole acyl thiourea derivatives
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Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3- methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3- methyl -1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, 1H-NMR, 13C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.
- Wu, Jian,Shi, Qing,Chen, Zhuo,He, Ming,Jin, Linhong,Hu, Deyu
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scheme or table
p. 5139 - 5150
(2012/07/03)
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- Heterocyclic analogues of xanthone and xanthione. 1H-pyrano[2,3-c:6,5-c] dipyrazol-4(7H)-ones and thiones: Synthesis and NMR data
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The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K 2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson's reagent. Detailed NMR spectroscopic investigations (1H, 13C, 15N) of the ring systems and their precursors are presented.
- Datterl, Barbara,Troestner, Nicole,Kucharski, Dorota,Holzer, Wolfgang
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experimental part
p. 6106 - 6126
(2010/11/04)
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- Synthesis of pyrazolotriazolopyrimidine tri-fused heterocyclic compounds
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This paper uses basic-catalysed method to convert 1H-pyrazole-4-carboxamides into tri-fused heterocyclic systems containing two kinds of pyrazolotriazolopyrimidine framework. The synthesis of compounds 5-6 and reactions of them with some electrophiles hav
- Liu, Ying,Ren, Jun,Jin, Gui-Yu
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- Synthesis of 5-chloro-3-methyl-1 phenyl-1H pyrazole-4-carboxylic acd heterocyclic-2-ylamide
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Reaction of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride 4 with substituted benzothiazol-2-ylamine and substituted [1,3,4] thiadiazol-2-ylamine yields 5-chloro-3-methyl-1-phenyl-1H pyrazole-4-carboxylic acid-substituted benzothiazol-2-ylamid
- Liming, Hu,Xueshu, Li,Zhiyuan, Chen,Xiaopeng, Liu,Zhaojie, Liu
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p. 199 - 202
(2007/10/03)
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