- Bonding in Phenylhydrazones: X-Ray Crystal Structure and Theoretical Calculations Involving (E)-Acetophenone Phenylhydrazone
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Semiempirical (PM3 type) calculations have been carried out on the E isomer of acetophenone phenylhydrazone and extended to include acetophenoneimine and phenylhydrazone.The optimized structure of acetophenone phenylhydrazone ha also been compared with th
- Porter, L. C.,Ming-Li,Cervantes-Lee, F.,Murray III, H. H.
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- Antispasmodic and antimicrobial activities of pyrazole-containing ferrocenyl alkanols versus their phenyl analogs, and the entry point to potential multitarget treatment for inflammatory bowel diseases
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Inflammatory bowel diseases (IBM), such as Crohn's disease, and their common complications represent a global health challenge. Many pyrazole derivatives, such as the spasmolytic drug metamizole, have already found their place among the frequently used th
- Radulovi?, Niko S.,Nikoli?, Milica G.,Mladenovi?, Marko Z.,Ran?elovi?, Pavle,Stojanovi?, Nikola M.,Stojanovi?-Radi?, Zorica,Jovanovi?, Ljiljana
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- Silver-Free Au(I) Catalysis Enabled by Bifunctional Urea- and Squaramide-Phosphine Ligands via H-Bonding
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A library of gold(I) chloride complexes with phosphine ligands incorporating pendant (thio)urea and squaramide H-bond donors was prepared with the aim of promoting chloride abstraction from Au(I) via H-bonding. In the absence of silver additives, complexes bearing squaramides and trifluoromethylated aromatic ureas displayed good catalytic activity in the cyclization of N-propargyl benzamides, as well as in a 1,6-enyne cycloisomerization, a tandem cyclization-indole addition reaction and the hydrohydrazination of phenylacetylene. Kinetic studies and DFT calculations indicate that the energetic span of the reaction is accounted by both the chloride abstraction step, facilitated by the bidentate H-bond donor via an associative mechanism, and the subsequent cyclization step.
- Echavarren, Antonio M.,Franchino, Allegra,Martí, àlex,Nejrotti, Stefano
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supporting information
p. 11989 - 11996
(2021/07/06)
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- Synthesis, Characterization, and Biological Evolution of New Pyrazole Derivatives of 4-(4-Aminophenyl)morpholin-3-one through Ugi Reaction
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A new heterocyclic library was synthesized using multicomponent reactions (MCRs). A green strategy during which a set of molecules with an excellent diversity is generated with a minimum of synthetic effort, time, and by-products formation. This new series prepared using the Ugi MCRs in which aldehyde, amine, acid, and isocyanide reacts to make α-bisamide. During this work, we practice the Ugi reaction to synthesize an extremely functionalized heterocyclic library which was characterized and tested for biological evaluation. This innovative synthetic route involves for pyrazole derivatives of 4-(4-aminophenyl)morpholin-3-one by Ugi four component reaction and methanol as a solvent in good yield and high purity. All the produced compounds of library were characterized using 1H-NMR, IR, and mass spectroscopic methods.
- Joshi, Harsh H.,Parsania, M. V.
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p. 247 - 253
(2021/08/03)
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- Pd-catalyzed post-Ugi intramolecular cyclization to the synthesis of isoquinolone-pyrazole hybrid pharmacophores & discover their antimicrobial and DFT studies
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A novel microwave assisted ligand-free palladium-catalyzed post Ugi reaction for the synthesis of isoquinolone and pyrazole mixed pharmacophore derivatives was achieved from isocyanide and pyrazole substituted amide molecules (synthesized by using Ugi rea
- Pandya, Keyur M.,Battula, Satyanarayana,Naik, Parth J.
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supporting information
(2021/09/13)
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- Substituted imidazole-pyrazole clubbed scaffolds: Microwave assisted synthesis and examined their in-vitro antimicrobial and antituberculosis effects
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A series of substituted imidazole-pyrazole fused compounds were designed & fused synthesized by employing Debus-Radziszewski one-pot synthesis reaction. Azoles are an extensive and comparatively new class of synthetic compounds including imidazoles and pyrazoles. The current clinical treatment uses compounds of azole framework. Azoles act by inhibiting ergosterol synthesis pathway (a principal component of the fungal cell wall). In addition, a literature review shows that the compounds that include imidazoles and pyrazoles have significant anti-bacterial and anti-mycobacterial effects. In light of the above findings, a series of compounds with imidazole and pyrazole scaffolds were sketched and developed to examine anti-bacterial, antifungal and anti-mycobacterial activities. The structures of the synthesized compounds were characterized using1HNMR,13CNMR, elemental analysis, and MS spectral data. The target compounds were screened for their in-vitro antimicrobial activity against gram-positive and gram-negative bacterial species by disc diffusion method according to the NCCLS (National Committee for Clinical Laboratory Standards) and anti-mycobacterial activity against the Mycobacterium tuberculosis H37Rv strain. The results revealed that imidazole-pyrazole fused scaffold compounds have potential anti-bacterial, antifungal and anti-mycobacterial activities which can be further optimized to get a lead compound.
- Desai, Piyush. S.,Pandya, Keyur M.,Patel, Arpan H.,Patel, Janki J.,Patel, Navin B.
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p. 574 - 582
(2021/07/25)
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- Novel carboxamide compound and compositions for preventing or treating metabolic diseases comprising the same
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The present invention relates to a novel carboxamide compound and a composition for preventing or treating metabolic diseases comprising the same, wherein the composition is potent and selective estrogen related receptor (Estrogen-related receptor). ERR)
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Paragraph 0095-0099; 0108-0109
(2021/09/14)
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- Broad-Spectrum Antifungal Agents: Fluorinated Aryl- and Heteroaryl-Substituted Hydrazones
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Fluorinated aryl- and heteroaryl-substituted monohydrazones displayed excellent broad-spectrum activity against various fungal strains, including a panel of clinically relevant Candida auris strains relative to a control antifungal agent, voriconazole (VRC). These monohydrazones displayed less hemolysis of murine red blood cells than that of VRC at the same concentrations, possessed fungicidal activity in a time-kill study, and exhibited no mammalian cell cytotoxicity. In addition, these monohydrazones prevented the formation of biofilms that otherwise block antibiotic effectiveness and did not trigger the development of resistance when exposed to C. auris AR Bank # 0390 over 15 passages.
- Thamban Chandrika, Nishad,Dennis, Emily K.,Brubaker, Katelyn R.,Kwiatkowski, Stefan,Watt, David S.,Garneau-Tsodikova, Sylvie
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supporting information
p. 124 - 133
(2020/10/20)
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- Design, synthesis, biological evaluation, and molecular docking studies of some novel N,N-dimethylaminopropoxy-substituted aurones
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In continuation of our ongoing research on the discovery of novel and potentially bioactive aurones, we have designed and synthesized some novel N,N-dimethylaminopropoxy-substituted pyrazole-based aurones 10(a-l). These pyrazole-benzofuranone hybrid compounds were characterized by using their IR, 1H-NMR, 13C-NMR, and mass spectrometry data. Compound 10c was used as a model to further explicate the structure of tilted compounds by means of 1H-1H COSY, 1H-13C HMQC, 1H-13C HMBC, 1H-1H TOCSY, 1H-1H NOSEY, DEPT-45°, DEPT-90°, and DEPT-135° NMR spectra. The comparative molecular docking study of N,N-dimethylaminopropoxy-substituted pyrazole-based aurones and standard drugs (Ampicillin and Chloramphenicol) against Bacillus subtilis (PDB: 6tzp) active site was performed to determine the binding interactions, binding energy, and orientation of the molecules at the active site of the target protein. Out of these synthesized compounds, five best analogs (10b, 10f, 10h, 10k, and 10l) of docking results were also evaluated for their in vitro antibacterial potential against Bacillus subtilis to validate the docking results.
- Dalal, Sunita,Kumar, Gourav,Kumar, Ramesh,Kumar, Suresh,Kumari, Meena,Saroha, Bhavna
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- New library of pyrazole–imidazo[1,2-α]pyridine molecular conjugates: Synthesis, antibacterial activity and molecular docking studies
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A library of novel pyrazole–imidazo[1,2-α]pyridine scaffolds was designed and synthesized through a one-pot three-component tandem reaction. The structures of synthesized conjugates were confirmed by spectroscopic techniques (NMR, IR and HRMS). In vitro antibacterial evaluation of the twelve synthesized molecules (7a, 8a–k) against methicillin-resistant Staphylococcus aureus and normal strains of Escherichia coli, Salmonella typhimurium, Klebsiella pneumonia and Pseudomonas aeruginosa established 8b, 8d, 8e, 8h and 8i as potent antibacterial agents with superior minimum bactericidal concentration, compared with standard drug ciprofloxacin. Molecular docking studies of all active compounds into the binding site of glucosamine-6-phosphate synthase were further performed in order to have a comprehensive understanding of putative binding modes within the active sites of the receptor.
- Ebenezer, Oluwakemi,Awolade, Paul,Koorbanally, Neil,Singh, Parvesh
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p. 162 - 173
(2019/11/03)
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- Microwave-assisted synthesis and biological evaluation of pyrazole-4-carbonitriles as antimicrobial agents
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An efficient microwave-assisted method of synthesis of pyrazole-4-carbonitriles has been developed. Condensation of pyrazole-4-carbaldehydes with hydroxylamine hydrochloride followed by reaction of the resulting oximes with the Vilsmeier-Haack reagent pre-formed from phthaloyl dichloride and dimethylformamide under microwave irradiation afforded the corresponding pyrazole-4-carbonitriles in 73percent to 91percent yield. The operational simplicity, avoidance of toxic reagents such as POCl3, shorter reaction time, higher yield compared to the classical version, easy work up, and the use of the by-product in the regeneration of phthaloyl dichloride are the advantages of this methodology. All the target compounds were tested for antimicrobial activity against Gram-positive bacteria Bacillus cereus and Staphylococcus aureus; Gram-negative bacteria Escherichia coli and Yersinia enterocolitica, and the fungal species Candida albicans.
- Kumar, Anil,Kumari, Poonam,Singh, Karan,Sood, Sumit,Yadav, Ajar Nath
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- Microwave-assisted Vilsmeier-Haack synthesis of Pyrazole-4-carbaldehydes
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The synthesis of 4-formylpyrazoles using Vilsmeier-Haack reagent is a common protocol in pyrazole chemistry. An efficient microwave-assisted synthesis of 4-formylpyrazoles by employing Vilsmeier-Haack reagent (OPC-VH) derived from phthaloyl dichloride/dimethylformamide has been described. This method offers the advantages of operational simplicity, avoiding the use of POCl3 as toxic reagents and reuse of the by-product in the preparation of phthaloyl dichloride.
- Kumari, Poonam,Sood, Sumit,Kumar, Anil,Singh, Karan
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p. 796 - 804
(2019/11/28)
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- Pyrazole–coumarin and pyrazole–quinoline chalcones as potential antitubercular agents
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Pyrazole, coumarin, and quinoline are medicinally important moieties. In this study, two series of novel pyrazole–coumarin chalcones and pyrazole–quinoline chalcones were synthesized using multiple-step reactions. All the synthesized compounds were well c
- Kumar, Gautam,Siva Krishna, Vagolu,Sriram, Dharmarajan,Jachak, Sanjay M.
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- Solution equilibrium, structural and cytotoxicity studies on Ru(η6-p-cymene) and copper complexes of pyrazolyl thiosemicarbazones
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Solution chemical properties of two bidentate pyrazolyl thiosemicarbazones 2-((3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinecarbothioamide (Me-pyrTSC), 2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)hydrazinecarbothioamide (Ph-pyrTSC), stability of their Cu(II) and Ru(η6-p-cymene) complexes were characterized in aqueous solution (with 30% DMSO) by the combined use of UV–visible spectrophotometry, 1H NMR spectroscopy and electrospray ionization mass spectrometry in addition to their solid phase isolation. The solid phase structures of Me-pyrTSC?H2O, [Ru(η6-p-cymene)(Me-pyrTSC)Cl]Cl and [Cu(Ph-pyrTSCH?1)2] were determined by single crystal X-ray diffraction. High stability mononuclear Ru(η6-p-cymene) complexes with (N,S) coordination mode are formed in the acidic pH range, and increasing the pH the predominating dinuclear [(Ru(η6-p-cymene))2(L)2]2+ complex with μ2-bridging sulphur donor atoms is formed (where L? is the deprotonated thiosemicarbazone). [CuL]+ and [CuL2] complexes show much higher stability compared to that of complexes of the reference compound benzaldehyde thiosemicarbazone. [CuL2] complexes predominate at neutral pH. Me-pyrTSC and Ph-pyrTSC exhibited moderate cytotoxicity against human colonic adenocarcinoma cell lines (IC50 = 33–76 μM), while their complexation with Ru(η6-p-cymene) (IC50 = 11–24 μM) and especially Cu(II) (IC50 = 3–6 μM) resulted in higher cytotoxicity. Cu(II) complexes of the tested thiosemicarbazones were also cytotoxic in three breast cancer and in a hepatocellular carcinoma cell line. No reactive oxygen species production was detected and the relatively high catalase activity of SUM159 breast cancer cells was decreased upon addition of the ligands and the complexes. In the latter cell line the tested compounds interfered with the glutathione synthesis as they decreased the concentration of this cellular reductant.
- D?m?t?r, Orsolya,Kiss, Márton A.,Gál, G. Tamás,May, Nóra V.,Spengler, Gabriella,Nové, Márta,Ga?parovi?, Ana ?ipak,Frank, éva,Enyedy, éva A.
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- Discovery of pyrazole derivatives as cellular active inhibitors of histone lysine specific demethylase 5B (KDM5B/JARID1B)
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KDM5B (also known as PLU-1 and JARID1B) is 2-oxoglutarate and Fe2+ dependent oxygenase that acts as a histone H3K4 demethylase, which is a key participant in inhibiting the expression of tumor suppressors as a drug target. Here, we present the discovery of pyrazole derivatives compound 5 by structure-based virtual screening and biochemical screening with IC50 of 9.320 μM against KDM5B, and its subsequent optimization to give 1-(4-methoxyphenyl)-N-(2-methyl-2-morpholinopropyl)-3-phenyl-1H-pyrazole-4-carboxamide (27 ab), a potent KDM5B inhibitor with IC50 of 0.0244 μM. In MKN45 cells, compound 27 ab can bind and stabilize KDM5B and induce the accumulation of H3K4me2/3, bona fide substrates of KDM5B, while keep the amount of H3K4me1, H3K9me2/3 and H3K27me2 without change. Further biological study also indicated that compound 27 ab is a potent cellular active KDM5B inhibitor that can inhibit MKN45 cell proliferation, wound healing and migration. In sum, our finding gives a novel structure for the discovery of KDM5B inhibitor and targeting KDM5B may be a new therapeutic strategy for gastric cancer treatment.
- Liang, Qianqian,Liu, Hong-Min,Ma, Li-Ying,Ren, Hongmei,Wu, Yang,Zhang, Kun,Zhang, Xinhui,Zhao, Bing,Zheng, Yi-Chao
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- Synthesis and SAR studies of novel 1,2,4-oxadiazole-sulfonamide based compounds as potential anticancer agents for colorectal cancer therapy
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A diverse series of 1,2,4-oxadiazoles based substituted compounds were designed, synthesized and evaluated as anticancer agents targeting carbonic anhydrase IX (CAIX). Initial structure-activity analysis suggested that the thiazole/thiophene-sulfonamide conjugates of 1,2,4-oxadiazoles exhibited potent anticancer activities with low μM potencies. Compound OX12 exhibited antiproliferative activity (IC50 = 11.1 μM) along with appreciable inhibition potential for tumor-associated CAIX (IC50 = 4.23 μM) isoform. Therefore, OX12 was structurally optimized and its SAR oriented derivatives (OX17-27) were synthesized and evaluated. This iteration resulted in compound OX27 with an almost two-fold increase in antiproliferative effect (IC50 = 6.0 μM) comparable to the clinical drug doxorubicin and significantly higher potency against CAIX (IC50 = 0.74 μM). Additionally, OX27 treatment decreases the expression of CAIX, induces apoptosis and ROS production, inhibited colony formation and migration of colon cancer cells. Our studies provide preclinical rational for the further optimization of identified OX27 as a suitable lead for the possible treatment of CRC.
- Abid, Mohammad,Alajmi, Mohamed F.,Garrison, Jered,Hasan, Phool,Hussain, Afzal,Imtaiyaz Hassan, Md,Khan, Parvez,King, Hannah M.,Queen, Aarfa,Rana, Sandeep,Rizvi, M. Moshahid Alam,Shamsi, Farheen,Zahid, Muhammad,Zeya, Bushra
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- Synthesis and computational studies of highly selective inhibitors of human recombinant tissue non-specific alkaline phosphatase (h-TNAP): A therapeutic target against vascular calcification
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In this study, we have discovered small druglike molecules as selective inhibitors of human tissue-nonspecific alkaline phosphatase (h-TNAP), an enzyme critical for the regulation of extracellular matrix calcification. The upregulation of h-TNAP is associated with various pathologies particularly the vascular calcification (VC). Selective inhibition of h-TNAP over h-NPP1 may serve as a useful therapeutic strategy against vascular calcification. A series of novel triazolyl pyrazole derivatives (10a-y) in which thiol bearing triazole moiety as the zinc binding functional group was introduced to a pyrazole based pharmacophore was synthesized and evaluated as potent and selective inhibitors of h-TNAP over h-NPP1. The biological screening against h-TNAP, h-IAP, h-NPP1 and h-NPP3 showed that many of the synthesized compounds are selective inhibitors of TNAP. Particularly, the compounds 10a-h, 10j, 10m-q, 10u, 10w and 10x displayed high potency and complete selectivity towards h-TNAP over h-NPP1. Compound 10q emerged as a highly potent inhibitor (IC50 = 0.16 μM or 160 nM) against h-TNAP with 127-fold increased inhibition compared to levamisole. On the other hand, compound 10e was found to be most selective inhibitor against the tested APs and NPPs (IC50 = 1.59 ± 0.36 μM). Binding sites architecture analysis, molecular-docking and molecular dynamics simulations (MDS), revealed the basis for h-TNAP and h-IAP ligand selectivity as well as selectivity towards h-TNAP over h-NPP1. These newly discovered inhibitors are believed to represent valuable lead structures to further streamline the generation of candidate compounds to target VC.
- Abida Ejaz, Syeda,Andleeb, Hina,Farman, Muhammad,Hameed, Shahid,Hussain, Muzammal,Iqbal, Jamshed,Sevigny, Jean,Yasinzai, Masoom,Zhang, Jiancun
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- Shaken, not stirred: a schools test for aldehydes and ketones
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A schools test for aldehydes and ketones in water at room temperature using test tubes has been developed in this laboratory using either phenylhydrazine hydrochloride or phenylhydrazine hydrochloride with NaOAc . 3H2O. The role of one equivalent of a strong or weak acid which catalyses the reaction is discussed.
- Plater, M John
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p. 104 - 107
(2019/11/22)
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- In vitro studies of potent aldose reductase inhibitors: Synthesis, characterization, biological evaluation and docking analysis of rhodanine-3-hippuric acid derivatives
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Inhibitors of aldose reductase are rate-limiting enzymes and could play a key role to prevent the complications of diabetes. In our attempt to develop novel inhibitors of aldose reductase, the derivatives of rhodanine-3-hippuric acid-pyrazole hybrid were synthesized and characterised by spectral data. The biological studies reveal that all the compounds show an excellent activity against ALR2 with IC50 values ranging from 0.04 to 1.36 μM. Among these the synthesised compounds 6a-m, 6g and 6e showed specific inhibitory activity with IC50 values of 0.04 and 0.06 μM respectively against ALR2 and found to be more potent than epalrestat (IC50 = 0.87 μM), the only aldose reductase inhibitor currently used in the therapy. Molecular docking analysis using the AR-NADP+ complex as a receptor was performed with all the synthesized compounds. All the compounds exhibit a well-defined binding mode within the AR active site, similarly to previous described AR inhibitors, with the anion head group bound to the catalytic center, blocking thus its activity. By forming hydrogen bonds with Tyr48 and His110 of the protein from ALR2 (PDB ID: 2FZD), the compounds 6g and 6e interrupt the proton donation mechanism, which is necessary for the catalytic activity of ALR2.
- Celestina, Stephen Kumar,Ravi, Subban,Sundaram, Kaveri
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- Design, synthesis, modeling studies and biological screening of novel pyrazole derivatives as potential analgesic and anti-inflammatory agents
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Reported herein are the design, synthesis, and pharmacologic evaluation of novel pyrazole and pyrazoline derivatives. The study presents the effect of lengthening of carbon chain in different pyrazole derivatives bearing various amine moieties. Combinatio
- Taher, Azza T.,Mostafa Sarg, Marwa T.,El-Sayed Ali, Nermeen R.,Hilmy Elnagdi, Noha
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- Copper catalysed cross-dehydrogenative coupling (CDC) reaction of 4-thiazolidinone with terminal alkyne
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Cross dehydrogenative coupling (CDC) strategy has been employed for C-alkynylation of 4-thiazolidinone with terminal alkyne under copper catalysis. Present reaction involves coupling of C(sp3) adjacent to sulfur of 4-thiazolidinone with C(sp) of terminal alkyne under CDC strategy is unprecedented to the best of our knowledge. Significant functional group tolerance, considerable yield and DFT study for mechanism make this synthetic task more interesting and compatible.
- Shaikh, Mohammedumar M.,Patel, Anuj P.,Chikhalia, Kishor H.
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p. 475 - 485
(2019/01/04)
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- Synthesis and biological evaluation of pyrazole linked benzothiazole-β-naphthol derivatives as topoisomerase I inhibitors with DNA binding ability
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A series of new pyrazole linked benzothiazole-β-naphthol derivatives were designed and synthesized using a simple, efficient and ecofriendly route under catalyst-free conditions in good to excellent yields. These derivatives were evaluated for their cytotoxicity on selected human cancer cell lines. Among those, the derivatives 4j, 4k and 4l exhibited considerable cytotoxicity with IC50 values ranging between 4.63 and 5.54 μM against human cervical cancer cells (HeLa). Structure activity relationship was elucidated by varying different substituents on benzothiazoles and pyrazoles. Further, flow cytometric analysis revealed that these derivatives induced cell cycle arrest in G2/M phase and spectroscopic studies such as UV–visible, fluorescence and circular dichroism studies showed that these derivatives exhibited good DNA binding affinity. Additionally, these derivatives can effectively inhibit the topoisomerase I activity. Viscosity studies and molecular docking studies demonstrated that the derivatives bind with the minor groove of the DNA.
- Nagaraju, Burri,Kovvuri, Jeshma,Kumar, C. Ganesh,Routhu, Sunitha Rani,Shareef, Md. Adil,Kadagathur, Manasa,Adiyala, Praveen Reddy,Alavala, Sateesh,Nagesh, Narayana,Kamal, Ahmed
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p. 708 - 720
(2019/01/25)
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- Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors
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Two series of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, IIIv was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.67 ± 0.09 μM) and the best selectivity (9-fold) between PTP1B and T-cell protein tyrosine phosphatase (TCPTP). Molecular docking studies demonstrated that compounds IIIm, IIIv and IVg could occupy simultaneously at both the catalytic site and the adjacent pTyr binding site. These results provide novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.
- Sun, Liangpeng,Wang, Peipei,Xu, Lili,Gao, Lixin,Li, Jia,Piao, Huri
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p. 1187 - 1193
(2019/03/26)
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- Synthesis and evaluation of pyrazole-incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents
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A series of pyrazole-incorporated monocarbonyl analogues of curcumin were synthesized via Clasien–Schimidt-type condensation and subsequently screened for in vitro antiproliferative and antioxidant activity. The analogues 4c, 5d, 5e, 5g, 6e, and 6f showed
- Nagargoje, Amol A.,Akolkar, Satish V.,Siddiqui, Madiha M.,Bagade, Aditi V.,Kodam, Kisan M.,Sangshetti, Jaiprakash N.,Damale, Manoj G.,Shingate, Bapurao B.
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p. 1658 - 1665
(2019/03/29)
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- Synthesis of some hippuric acid substrate linked novel pyrazoles as antimicrobial agents
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Escalating resistance of microorganisms to the currently accessible antimicrobial drugs has forced to synthesize some novel biologically active compounds as efficient alternates via economical substrates. Hence, hippuric acid was used as one of the starting materials to synthesize pyrazole derivatives. All the synthesized compounds were characterized by IR, NMR (1H & 13C) and mass spectral data. The antimicrobial potential of synthesized compounds has been explored against four bacterial and two fungal strains. Among the 12 compounds, 3 compounds 8j, 8k and 8l were found to exhibit prominent antimicrobial potential as compared with the standards ciprofloxacin and amphotericin-B.
- Verma, Anil,Kumar, Vinod,Khare, Rajshree,Singh, Joginder
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p. 522 - 526
(2019/02/06)
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- Unveiling novel diphenyl-1H-pyrazole based acrylates tethered to 1,2,3-triazole as promising apoptosis inducing cytotoxic and anti-inflammatory agents
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Meagre and suboptimal therapeutic response along with the side effect profile associated with the existing anticancer therapy have necessitated the development of new therapeutic modalities to curb this disease. Bearing in mind the current scenario, a series of 1,2,3-triazole linked 3-(1,3-diphenyl-1H-pyrazol-4-yl)acrylates was synthesized following a multi-step reaction scheme. Initial screening for anticancer potential was done by in vitro sulforhodamine B assay against four human cancer cell lines- MCF-7 (breast), A549 (Lung) and HCT-116 and HT-29 (Colon). On evaluation, several compounds showed promising growth inhibition against all the cell lines, particularly compounds 6e, 6f and 6n. Among them, compound 6f displayed IC50 values of 1.962, 3.597, 1.764 and 4.496 μM against A549, HCT-116, MCF-7 and HT-29 cell lines respectively. Furthermore, the apoptosis inducing potential of the compounds was determined by Hoechst staining and DNA fragmentation assay. Colony formation inhibition assay was also carried out to determine the long term cytotoxic potential of the molecules. Moreover, compounds 6e, 6f and 6n were also evaluated for anti-inflammatory activity by protein albumin denaturation assay and red blood cell membrane stabilizing assay.
- Khan, Mohemmed Faraz,Anwer, Tarique,Bakht, Afroz,Verma, Garima,Akhtar, Wasim,Alam, M. Mumtaz,Rizvi, Moshahid Alam,Akhter, Mymoona,Shaquiquzzaman, Mohammad
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p. 667 - 678
(2019/04/05)
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- Pyrazole-4-carboxylic Acids from Vanadium-catalyzed Chemical Transformation of Pyrazole-4-carbaldehydes
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The conversion of aldehydes into carboxylic acids using oxidizing agents is a common protocol in transformation chemistry. An efficient oxidation strategy of transformation of pyrazole-4-aldehydes to the corresponding acids using vanadium catalysts in the presence of 30% H2O2 as an oxidant is described. The catalytic technology was successfully applied to a range of various 4-formylpyrazoles, and plausible mechanism is also discussed.
- Bala, Renu,Kumari, Poonam,Sood, Sumit,Phougat, Harshita,Kumar, Anil,Singh, Karan
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p. 1787 - 1793
(2019/04/30)
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- Synthesis of Spiro[indole-3,5′-isoxazoles] with Anticancer Activity via a Formal [4 + 1]-Spirocyclization of Nitroalkenes to Indoles
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An acid-assisted [4 + 1]-cycloaddition of indoles with nitrostyrenes affords 4′H-spiro[indole-3,5′-isoxazoles] in a diastereomerically pure form. Several of these spirocyclic molecules exhibit promising anticancer activity by reducing viability and inducing differentiation of neuroblastoma cells.
- Aksenov, Alexander V.,Aksenov, Dmitrii A.,Arutiunov, Nikolai A.,Aksenov, Nicolai A.,Aleksandrova, Elena V.,Zhao, Zhenze,Du, Liqin,Kornienko, Alexander,Rubin, Michael
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p. 7123 - 7137
(2019/06/18)
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- Substituted 2-phenylpyrazole derivatives and preparation method and application thereof
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The invention provides substituted 2-phenylpyrazole derivatives and a preparation method and application thereof, and belongs to the technical field of medicinal chemistry. The substituted 2-phenylpyrazole derivatives having structures shown as the formul
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Paragraph 0079-0082
(2019/07/29)
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- Probing the high potency of pyrazolyl pyrimidinetriones and thioxopyrimidinediones as selective and efficient non-nucleotide inhibitors of recombinant human ectonucleotidases
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With the aim to discover novel, efficient and selective inhibitors of human alkaline phosphatase and nucleotide pyrophosphatase enzymes, two new series of pyrazolyl pyrimidinetriones (PPTs) (6a–g) and thioxopyrimidinediones (PTPs) (6h–n) were synthesized in good chemical yields using Knoevenagel condensation reaction between pyrazole carbaldehydes (4a–g) and pharmacologically active N-alkylated pyrimidinetrione (5a) and thioxopyrimidinedione (5b). The inhibition potential of the synthesized hybrid compounds was evaluated against human alkaline phosphatase (h-TNAP and h-IAP) and ectonucleotidase (h-NPP1 and h-NPP3) enzymes. Most of the tested analogs were highly potent with a variable degree of inhibition depending on the functionalized hybrid structure. The detailed structure-activity relationship (SAR) of PPT and PTP derivatives suggested that the compound with unsubstituted phenyl ring from PPT series led to selective and potent inhibition (6a; IC50 = 0.33 ± 0.02 μM) of h-TNAP, whereas compound 6c selectively inhibited h-IAP isozyme with IC50 value of 0.86 ± 0.04 μM. Similarly, compounds 6b and 6h were identified as the lead scaffolds against h-NPP1 and h-NPP3, respectively. The probable binding modes for the most potent inhibitors were elucidated through molecular docking analysis. Structure-activity relationships, mechanism of action, cytotoxic effects and druglikeness properties are also discussed.
- Andleeb, Hina,Hameed, Shahid,Ejaz, Syeda Abida,Khan, Imtiaz,Zaib, Sumera,Lecka, Joanna,Sévigny, Jean,Iqbal, Jamshed
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- Targeting malaria and leishmaniasis: Synthesis and pharmacological evaluation of novel pyrazole-1,3,4-oxadiazole hybrids. Part II
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In continuance with earlier reported work, an extension has been carried out by the same research group. Mulling over the ongoing condition of resistance to existing antimalarial agents, we had reported synthesis and antimalarial activity of certain pyrazole-1,3,4-oxadiazole hybrid compounds. Bearing previous results in mind, our research group ideated to design and synthesize some more derivatives with varied substitutions of acetophenone and hydrazide. Following this, derivatives 5a–r were synthesized and tested for antimalarial efficacy by schizont maturation inhibition assay. Further, depending on the literature support and results of our previous series, certain potent compounds (5f, 5n and 5r) were subjected to Falcipain-2 inhibitory assay. Results obtained for these particular compounds further strengthened our hypothesis. Here, in this series, compound 5f having unsubstituted acetophenone part and a furan moiety linked to oxadiazole ring emerged as the most potent compound and results were found to be comparable to that of the most potent compound (indole bearing) of previous series. Additionally, depending on the available literature, compounds (5a–r) were tested for their antileishmanial potential. Compounds 5a, 5c and 5r demonstrated dose-dependent killing of the promastigotes. Their IC50 values were found to be 33.3 ± 1.68, 40.1 ± 1.0 and 19.0 ± 1.47 μg/mL respectively. These compounds (5a, 5c and 5r) also had effects on amastigote infectivity with IC50 of 44.2 ± 2.72, 66.8 ± 2.05 and 73.1 ± 1.69 μg/mL respectively. Further target validation was done using molecular docking studies. Acute oral toxicity studies for most active compounds were also performed.
- Verma, Garima,Khan, Mohemmed Faraz,Mohan Nainwal, Lalit,Ishaq, Mohd,Akhter, Mymoona,Bakht, Afroz,Anwer, Tariq,Afrin, Farhat,Islamuddin, Mohammad,Husain, Ibraheem,Alam, Mohammad Mumtaz,Shaquiquzzaman, Mohammad
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- Pyrazolo-benzothiazole hybrids: Synthesis, anticancer properties and evaluation of antiangiogenic activity using in vitro VEGFR-2 kinase and in vivo transgenic zebrafish model
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A series of new pyrazolo-benzothiazole hybrids (7–26) were synthesised and screened for their cytotoxic activity towards several cancer cell lines [colon (HT-29), prostate (PC-3), lung (A549), glioblastoma (U87MG)] and normal human embryonic kidney cell line (Hek-293T). Compounds 8, 9, 13, 14, 18, 19, 23, and 24 displayed significant activity, with compound 14 being particularly potent towards all the tested cancer cell lines with IC50 values in the range 3.17–6.77 μM, even better than reference drug axitinib (4.88–21.7 μM). Compound 14 also showed the strongest growth inhibition in 3D multicellular spheroids of PC-3 and U87MG cells. The mechanism of cellular toxicity in PC-3 cells was found to be cell cycle arrest and apoptosis induction through depolarisation of mitochondrial membrane potential, increased ROS production and subsequent DNA damage. Further, compound 14 displayed significant in vitro (VEGFR-2 inhibition) and in vivo [transgenic zebrafish Tg(flila:EGFP) model] antiangiogenic properties. Overall, these results provide strong evidence that compound 14 could be considered for a lead candidate in anticancer and antiangiogenic drug discovery.
- Reddy, Velma Ganga,Reddy, T. Srinivasa,Jadala, Chetna,Reddy, M. Soumya,Sultana, Faria,Akunuri, Ravikumar,Bhargava, Suresh K.,Wlodkowic, Donald,Srihari,Kamal, Ahmed
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- Synthesis and biological evaluation of thiazolidine-2,4-dione-pyrazole conjugates as antidiabetic, anti-inflammatory and antioxidant agents
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A series of fourteen novel thiazolidine-2,4-dione derivatives clubbed with pyrazole moiety were synthesized via four step reaction procedure. Reactions were monitored by thin layer chromatography and were characterized by physicochemical and spectrophotometric (IR, Mass, 1HNMR and 13CNMR) analysis. The spectral data were in good agreement with their structures. The title compounds were docked against peroxisome proliferated activated receptors (PPAR-γ) and alpha-amylase and further evaluated for in vivo and in vitro antidiabetic, in vitro anti-inflammatory and antioxidant activities. Compound GB14 exhibited significant blood glucose lowering activity and was also found to be active inhibitor of alpha-amylase. Compound GB7 was found to be potent anti-inflammatory agent in terms of reducing inflammatory markers (TNF-α, IL-β, MDA) and also showed antioxidant activity to good extent. Therefore, these compounds may be considered as promising candidates for the development of new antidiabetic agents.
- Bansal, Garima,Singh, Shamsher,Monga, Vikramdeep,Thanikachalam, Punniyakoti Veeraveedu,Chawla, Pooja
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- Novel acetohydrazide pyrazole derivatives: Design, synthesis, characterization and antimicrobial activity
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Eleven acetohydrazide linked pyrazole derivatives were designed and synthesized via condensation of acetohyadrazide with different substituted formyl pyrazole derivatives under mild reaction conditions. Synthesized compounds were characterized on the basis of IR, NMR (1H & 13C) and mass spectrometry. The antimicrobial activities of all the compounds were screened against four bacterial and two fungal strains. Among the synthesized compounds, three compounds viz. 6b, 6c and 6d were found as efficient antimicrobial agents in reference to the standard drugs viz. ciprofloxacin and amphotericin-B. Further, structure-activity relationship (SAR) study revealed that electron-withdrawing group enhances the antimicrobial potential of synthesized derivatives as compared to other groups present in the ring. Hence, among compounds 6b-c, compound 6d could be explored further against other microbes to prove its vitality.
- Verma, Anil,Kumar, Vinod,Kataria, Ramesh,Singh, Joginder
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p. 2740 - 2744
(2019/11/21)
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- Synthesis of novel dihydrotriazine derivatives bearing 1,3-diaryl pyrazole moieties as potential antibacterial agents
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Three novel series of dihydrotriazine derivatives bearing 1,3-diaryl pyrazole moieties were designed, synthesized and evaluated in terms of their antibacterial and antifungal activities. Most of the synthesized compounds showed potent inhibition of several Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains with minimum inhibitory concentration values in the range of 1–64 μg/mL. Compounds 4b and 4c presented the most potent inhibitory activity against Gram-positive bacteria (S. aureus 4220, MRSA 3167, QRSA 3519) and Gram-negative bacteria (E. coli 1924), with minimum inhibitory concentration values of 1 or 2 μg/mL. Compared with previous studies, these compounds exhibited a broad spectrum of inhibitory activity. The cytotoxic activity of the compounds 4a, 4b, 4c and 11n were assessed in L02 cells. In vitro enzyme study implied that compound 4c exerted its antibacterial activity through DHFR inhibition.
- Zhang, Tian-Yi,Zheng, Chang-Ji,Wu, Jie,Sun, Liang-Peng,Piao, Hu-Ri
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supporting information
p. 1079 - 1084
(2019/03/06)
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- Design, synthesis and cytotoxicity evaluation of pyrazolyl pyrazoline and pyrazolyl aminopyrimidine derivatives as potential anticancer agents
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In an attempt to find bio-active heterocyclic analogues, a series of novel 1-(5-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-3-(pyridin-3-yl)-4,5-dihydropyrazol-1-yl)ethanones 5a–i and 4-(3-(aryl)-1-phenyl-1H-pyrazol-4-yl)-6-(pyridine-3-yl)pyrimidin-2-amines 6a–i were designed, synthesized, and evaluated for their in vitro cytotoxicity against a panel of human cancer cell lines namely, HeLa (human cervix), NCI-H460 (human lung), PC-3 (human prostate), and NIH-3T3 (mouse embryo fibroblasts) cell lines. Most of these compounds exhibited moderate to good cytotoxicity against the tested cancer cell lines and weak toxicity against normal cell line. Analogs 5f, 5g, 5i, 6b–g showed significant cytotoxicity as compared to the standard drug etoposide. The compound 6g exhibited superior activity with IC50 value of 5.47 ± 0.44 μM against Hela cancer cell line.
- Alam, Raquib,Alam, Aftab,Panda, Amulya K.,Rahisuddin
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p. 560 - 570
(2017/10/13)
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- An ionic receptor for Zn2+ metal ion using synthesised bis-formylpyrazole calix[4]arene and its computational study
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Newly synthesised receptor Bis-(1,3-diphenyl-pyrazolyl methylene acetohydrazide)Calix[4]arene (DPPMACA) was evaluated for cation binding ability. The receptor DPPMACA selectively interact with Zn2+ metal ion as assessed through UV-visible spect
- Mohan, Brij,Modi, Krunal,Bhatia, Pankaj,Sharma,Mishra, Divya,Jain, Vinod K.,Arora, Lakhbeer Singh
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p. 589 - 599
(2017/12/26)
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- Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
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A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
- Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
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supporting information
p. 3527 - 3530
(2018/06/26)
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- Palladium-catalyzed [5+2] oxidative annulation of N-Arylhydrazones with alkynes through C–H activation to synthesize Benzo[d][1,2]diazepines
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An efficient and novel method using palladium catalyst for the synthesis of benzo[d][1,2]diazepines by [5 + 2] annulation of N-arylhydrazones with alkynes has been developed. This methodology undergoes through eight membered palladacycle serving as a back
- Asamdi, Manjoorahmed,Shaikh, Mohammedumar M.,Chauhan, Prakashsingh M.,Chikhalia, Kishor H.
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supporting information
p. 3719 - 3727
(2018/05/29)
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- Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity
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Hydrazone and oxime bond formation between α-nucleophiles (e.g. hydrazines, alkoxy-amines) and carbonyl compounds (aldehydes and ketones) is convenient and is widely applied in multiple fields of research. While the reactants are simple, a substantial drawback is the relatively slow reaction at neutral pH. Here we describe a novel molecular strategy for accelerating these reactions, using bifunctional buffer compounds that not only control pH but also catalyze the reaction. The buffers can be employed at pH 5-9 (5-50 mM) and accelerate reactions by several orders of magnitude, yielding second-order rate constants of >10 M-1 s-1. Effective bifunctional amines include 2-(aminomethyl)imidazoles and N,N-dimethylethylenediamine. Unlike previous diaminobenzene catalysts, the new buffer amines are found to have low toxicity to human cells, and can be used to promote reactions in cellular applications.
- Larsen, Dennis,Kietrys, Anna M.,Clark, Spencer A.,Park, Hyun Shin,Ekebergh, Andreas,Kool, Eric T.
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p. 5252 - 5259
(2018/06/21)
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- Synthesis, Characterization, Molecular Docking Studies and Anticancer Activity of Schiff Bases Derived from 3-(Substituted phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde and 2-Aminophenol
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Abstract: A series of new Schiff bases were synthesized by microwave assisted reactions of substituted 1-phenyl-1H-pyrazole-4-carbaldehyde and 2-aminophenol in ethanol and characterized by elemental analysis and spectroscopic (IR, 1H NMR and MS) data. The crystal structures of four compounds were studied using single-crystal XRD data. Molecular docking studies of all synthesized compounds were performed into the binding site of a protein 3GCW to gain comprehensive understanding into possible binding modes. These compounds were also screened for anticancer activity against the liver (HEP-G2) cell line using the sulphorhodamine-B assay method. Adriamycin i.e. doxorubicin was used as reference standard. One of the compounds shows anticancer activity close to the famous anticancer agent doxorubicin, which was used as control in this study. It is observed that all molecules show activity close to the standard in high concentrations only. Graphical Abstract: Present study describes the anticancer activity and crystal structure study of Schiff bases of substituted pyrazole-4-carbaldehyde with 2-aminophenol. Docking study of all compounds against human hepatoma cell line, HEP-G2 correlates with in vitro activity. [Figure not available: see fulltext.].
- Wazalwar, Sachin S.,Banpurkar, Anita R.,Perdih, Franc
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p. 185 - 199
(2018/08/27)
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- Thiazolo[3,2-a] Pyrimidones as a Novel Anti-TB Agents
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A series of novel thiazolo pyrimidine derivatives were designed, synthesized, and assessed for their in vitro anti-mycobacterial activities. All hybrids displayed considerable antitubercular activities against primary Mycobacterium smegmatis mc2 155 screening and successive Mycobacterium tuberculosis H37Rv. In particular, the hybrid entities 13 and 14 (minimum inhibitory concentration: 47 and 39?μg/mL) were found to be equipotent candidates with first-line antitubercular agent rifampicin, which could act as a lead for further optimization.
- Jadhav, Sunil B.,Fatema, Samreen,Bhagat, Sunil S.,Farooqui, Mazahar
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p. 2893 - 2900
(2018/10/24)
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- Synthesis, Reactions and Antitumor Activity of Certain 1,3-diphenylpyrazole-4-carboxaldehyde Derivatives
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IN activity continuation especially of our the interest antitumor in synthesis activity.In of novel this paper heterocycles we have with discussed anticipat
- Amer, Atef M.,Ramses, Neveen,Mahgoub, Sebaey
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- Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives
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N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a-c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d-f were observed as a result. Reactions between the aldehydes 3a-f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a-c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d-f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, 1H, 13C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, 4a-c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus Niger at the concentration of 25 μg/mL and 50 μg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus Niger at the concentration of 25 μg/mL.
- Le, Trong Duc,Pham, Ngoc Nam,Nguyen, Tien Cong
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- Synthesis, pharmacological activities and molecular docking studies of pyrazolyltriazoles as anti-bacterial and anti-inflammatory agents
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A series of novel pyrazolyl alcohols (5a-h), pyrazolyl azides (6a-h), and pyrazolyltriazoles (8a-h, 10a-p and 12a-l) were prepared and evaluated for their bioactivity (anti-bacterial and anti-inflammatory) profile. The compound 5c displayed the potent anti-bacterial activity against Micrococcus luteus (MIC 3.9 and MBC 7.81 μg/mL). In vitro anti-inflammatory activity data denoted that compound 8b is effective among the tested compounds against IL-6 (IC50 6.23 μM). Docking analysis of compounds 5f, 8a-b, 8e-f and 8h displayed high binding energies for the compounds 8a-b and 8h towards TNF-α dimer (2AZ5 protein) and IL-6 (1ALU protein). In vivo anti-inflammatory activity of compounds 8b and 8h with respect to LPS induced mice model indicated that compound 8h showed significant reduction in TNF-α.
- Dayakar, Cherupally,Kumar, Buddana Sudheer,Sneha, Galande,Sagarika, Gudem,Meghana, Koneru,Ramakrishna, Sistla,Prakasham, Reddy Shetty,China Raju, Bhimapaka
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p. 5678 - 5691
(2017/10/09)
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- T-Shaped Gold→Stiborane Complexes as Carbophilic Catalysts: Influence of the Peripheral Substituents
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As part of our efforts toward the discovery of new late transition metal catalysts, we synthesized [(o-(Ph2P)C6H4)2(o-C6Cl4O2)SbPh)Au]+ (3+) and [(o-(iPrsu
- Sen, Srobona,Ke, Iou-Sheng,Gabba?, Fran?ois P.
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p. 4224 - 4230
(2017/11/21)
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- Simple and efficient approach for synthesis of hydrazones from carbonyl compounds and hydrazides catalyzed by meglumine
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A simple, environmentally benign protocol for synthesis of hydrazones from carbonyl compounds and hydrazides has been developed in the presence of meglumine in aqueous-ethanol media at room temperature. The salient features of the present protocol are mild reaction conditions, short reaction time, high yields, operational simplicity, metal-free, applicability toward large-scale synthesis, and biodegradable and inexpensive catalyst.
- Zhang, Mo,Shang, Ze-Ren,Li, Xiao-Tang,Zhang, Jia-Nan,Wang, Yong,Li, Kang,Li, Yang-Yang,Zhang, Zhan-Hui
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p. 178 - 187
(2017/01/10)
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- Design, synthesis and biological evaluation of hydrazone derivatives as anti-proliferative agents
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A series of triaryl-substituted hydrazones as structural acyclic prototypes were synthesized and screened for anti-proliferative activity against breast (Michigan cancer foundation-7 and MD Anderson metastatic breast-231) and uterine cancer (Ishikawa) cel
- Shankar, Ravi,Rawal, Ravindra K.,Singh, Uma S.,Chaudhary, Preeti,Konwar, Rituraj,Hajela, Kanchan
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p. 1459 - 1468
(2017/06/05)
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- Sulfamic acid as a green, reusable catalyst for stepwise, tandem & one-pot solvent-free synthesis of pyrazole derivatives
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Sulfamic acid (SA) is a bi-functional, cost-effective and reusable green catalyst for the synthesis of 4-(pyrazol-4-yl)methylenepyrazol-5(4H)-one derivatives by one-pot, three-component condensation of pyrazol-4-carbaxaldehydes, β-ketoesters and phenyl hydrazine (Route-I). In addition to this method, another simple condensation of pyrazol-4-carbaxaldehydes with pyrazolone in the presence of SA under the solvent-free condition in good yield is reported. The merits of these protocols are mild conditions, non-aqueous workup, high yields, easy availability of the catalyst, no chromatographic separation and inexpensive solid acid catalyst. Furthermore, SA could be recycled and reused for five times without losing its catalytic activity.
- Konkala, Veera Swamy,Dubey, Pramod Kumar
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p. 1571 - 1576
(2017/07/17)
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- One-pot Synthesis of 3-phenyl-4-pyrazolylmethylene-isoxazol-(5H)-ones Catalyzed by Sodium Benzoate in Aqueous Media under the Influence of Ultrasound Waves: A Green Chemistry Approach
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A series of 4-pyrazolylmethylene-3-phenylisoxazol-5(4H)-ones have been prepared from Knoevenagel condensation of pyrazole-4-carbaxaldehyde with isoxazolone precursors or via one-pot three-component cyclocondensation of pyrazole-4-carbaxaldehyde with β-ketoesters and hydroxylamine hydrochloride in the presence of sodium benzoate in water under the influence of ultrasonic waves. The merits of this method are efficient, clean, green, easy work-up, high yields, and shorter reaction time, and the catalyst could be recycled easily without affecting the catalytic activity.
- Konkala, Veera Swamy,Dubey, Pramod Kumar
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p. 2483 - 2492
(2017/07/25)
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- Synthesis of novel α,α-difluoro-β-hydroxycarbonyl pyrazole derivatives as antioxidant, anti-inflammatory and anticancer agents
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A series of novel α,α-difluoro-β-hydroxyl pyrazole esters was prepared by Reformatsky reaction. Subsequently, these esters were converted to acids and hydrazides. All the synthesized compounds were evaluated for their in vitro antioxidant, anti-inflammatory and anticancer potential at various concentrations (50, 100 μM). Compounds 4d and 6e were found to be potent (93.19 and 90.91 %) and compounds 5d, 6c and 5f were good OH radical scavengers (79.55–72.73 %) as compared to the standard drug ascorbic acid (88.63 %). Compounds 6a, 5c, 6f, 4d and 5a showed significant 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity (75.95–70.89 %). All the compounds have shown higher cyclooxygenase-1 (COX-1) inhibition over cyclooxygenase-2 (COX-2) at concentrations 100 and 50 μM. Compounds 5f, 6b, 4a, 5c, 4f, 5 and 6d showed significant COX-2 inhibition (38.56–28.30 %) at a concentration of 100 μM compared to standard drug aspirin (11.11 %). Compounds 6f, 6e and 5f have shown significant cytotoxicity against MCF-7 (51.03–40.59 %), whereas 6d, 5f and 5a showed moderate cytotoxicity against HL-60 (26.98–20.21 %) cancer cell lines compared to the methotrexate as reference standard (68.42 and 54.29 % respectively). All compounds have shown almost neglisible cytotoxicity against normal cell line 293.
- Mukarram, Salman,Bandgar, Babasaheb P.,Shaikh, Rafik U.,Ganapure, Shriram D.,Chavan, Hemant V.
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p. 262 - 273
(2017/01/12)
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