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A novel 2-(2-formyl-4-methyl-phenoxy)-N-phenyl-acetamide-based fluorescence turn-on chemosensor for selenium determination with high selectivity and sensitivity
(Graph Presented) A novel turn-on fluorescent chemosensor, 2-(2-Formyl-4-methyl-phenoxy)-N-phenyl-acetamide (FMPPA) was designed and synthesized, and its photophysical properties were characterized. Upon coordination with Se (IV), the chemosensor showed i
Song, Cairui,Fei, Qiang,Shan, Hongyan,Feng, Guodong,Cui, Minghui,Liu, Yameng,Huan, Yanfu
p. 497 - 500
(2013)
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Design, synthesis and biological evaluation studies of novel small molecule ENPP1 inhibitors for cancer immunotherapy
Ecto-nucleotide pyrophosphatase/phosphodiesterases 1 (ENPP1 or NPP1), is an attractive therapeutic target for various diseases, primarily cancer and mineralization disorders. The ecto-enzyme is located on the cell surface and has been implicated in the control of extracellular levels of nucleotide, nucleoside and (di) phosphate. Recently, it has emerged as a critical phosphodiesterase that hydrolyzes cyclic 2′3′- cGAMP, the endogenous ligand for STING (STimulator of INterferon Genes). STING plays an important role in innate immunity by activating type I interferon in response to cytosolic 2′3′-cGAMP. ENPP1 negatively regulates the STING pathway and hence its inhibition makes it an attractive therapeutic target for cancer immunotherapy. Herein, we describe the design, optimization and biological evaluation studies of a series of novel non-nucleotidic thioguanine based small molecule inhibitors of ENPP1. The lead compound 43 has shown good in vitro potency, stability in SGF/SIF/PBS, selectivity, ADME properties and pharmacokinetic profile and finally potent anti-tumor response in vivo. These compounds are a good starting point for the development of potentially effective cancer immunotherapy agents.
Gangar, Mukesh,Goyal, Sandeep,Raykar, Digambar,Khurana, Princy,Martis, Ashwita M.,Goswami, Avijit,Ghoshal, Ishani,Patel, Ketul V.,Nagare, Yadav,Raikar, Santosh,Mukherjee, Apurba,Cyriac, Rajath,Paquin, Jean-Fran?ois,Kulkarni, Aditya
supporting information

(2021/12/20)

Anti-melanogenesis and anti-tyrosinase properties of aryl-substituted acetamides of phenoxy methyl triazole conjugated with thiosemicarbazide: Design, synthesis and biological evaluations
A series of aryl phenoxy methyl triazole conjugated with thiosemicarbazides were designed, synthesized, and evaluated for their tyrosinase inhibitory activities in the presence of L-dopa and L-tyrosine as substrates. All the compounds showed tyrosinase inhibition in the sub-micromolar concentration. Among the derivatives, compound 9j bearing benzyl displayed exceptionally high potency against tyrosinase with IC50 value of 0.11 μM and 0.17 μM in the presence of L-tyrosine and L-dopa as substrates which is significantly lower than that of kojic acid as the positive control with an IC50 value of 9.28 μM for L-tyrosine and 9.30 μM for L-dopa. According to Lineweaver–Burk plot, 9j demonstrated an uncompetitive type of inhibition in the kinetic assay. Also, in vitro antioxidant activities determined by DPPH assay recorded an IC50 value of 68.43 μM for 9i. The melanin content of 9j was determined on B16F10 melanoma human cells which demonstrated a significant reduction of the melanin content. Moreover, the binding energies corresponding to the same ligand as well as computer-aided drug-likeness and pharmacokinetic studies were also carried out. Compound 9j also possessed metal chelation potential correlated to its high anti-TYR activity.
Hosseinpoor, Hona,Moghadam Farid, Sara,Iraji, Aida,Askari, Sadegh,Edraki, Najmeh,Hosseini, Samanesadat,Jamshidzadeh, Akram,Larijani, Bagher,Attarroshan, Mahshid,Pirhadi, Somayeh,Mahdavi, Mohammad,Khoshneviszadeh, Mehdi
(2021/06/21)

Synthesis, pharmacological evaluation, and in-silico studies of thiophene derivatives
The relevance of Retinoic acid receptor-related orphan receptors in cancer progression has sparked interest in developing multifunctional therapeutics. In the search for potentially active novel compounds with anticancer characteristics, the Gewald reaction was employed to develop different thiophene derivatives (8a–8i). Physicochemical and spectroanalytical investigations verified the molecular structures of the synthesized derivatives. Using an in vitro primary anticancer assay, NCI chose all of the synthesized molecules as prototypes and assessed their anticancer efficacy against a panel of various cancer cell lines representing nine distinct neoplasms. The compounds were found to have a wide range of anticancer activity. Following significant anticancer efficacy against all cell lines in the initial screening, compound 8e was chosen for a five-dose test. Compound 8e inhibited growth at concentrations ranging from 0.411 to 2.8 μM. The antioxidant activity of the compounds was further evaluated using the radical scavenging action of the stable DPPH free radical. In comparison to Ascorbic Acid, compounds 8e and 8i showed outstanding antioxidant activity, while the remaining compounds in the series demonstrated acceptable antioxidant activity. In a molecular docking investigation, 8e demonstrated excellent docking scores inside the binding pocket of the specified pdb-id (6q7a), complementing the results of anticancer screening. Based on our results, novel ethyl 5-acetyl-2-amino-4-methylthiophene-3-carboxylate derivatives could be useful in the development of potential anticancer treatments.
Mishra, Raghav,Kumar, Nitin,Sachan, Neetu
(2021/12/23)

Synthesis, Characterization and Thermal Study of some new Organochalcogenide compounds containing arylamide group
Two Series of organochalcogen compounds were prepared. The first series was prepared by the reaction of 2-chloro-N-arylacetamide (where aryl is benzyl, phenyl, o-toluene, or p-toluene) with sodium hydrogen selenide (prepared in situ) to give diorganyl selenide compounds (R2Se). The second series was prepared by reaction of N-benzyl-2-chloro-N-(2-chloroacetyl) acetamide with sodium chalcogenate, Na2E (where E= S, Se, and Te) to give the corresponding cyclic chalcogenide compounds. Diiodo derivatives of cyclic selenide and telluride were also prepared. The thermal stability of the new selenium compounds (R2Se) were decomposed at 300°C. Thermogram showed a phase transfer point between 120-150°C indicating that these compounds may act as liquid crystal compounds. All new compounds were characterized by CHN elemental analysis, UV-Visible, FT-IR and 1H NMR spectroscopic data.
Hassan,Abdulwahid,Al-Luaibi,Al-Jadaan
p. 5009 - 5015
(2021/08/31)

N-Aryl mercaptoacetamides as potential multi-target inhibitors of metallo-β-lactamases (MBLs) and the virulence factor LasB fromPseudomonas aeruginosa
Increasing antimicrobial resistance is evolving to be one of the major threats to public health. To reduce the selection pressure and thus to avoid a fast development of resistance, novel approaches aim to target bacterial virulence instead of growth. Another strategy is to restore the activity of antibiotics already in clinical use. This can be achieved by the inhibition of resistance factors such as metallo-β-lactamases (MBLs). Since MBLs can cleave almost all β-lactam antibiotics, including the “last resort” carbapenems, their inhibition is of utmost importance. Here, we report on the synthesis andin vitroevaluation ofN-aryl mercaptoacetamides as inhibitors of both clinically relevant MBLs and the virulence factor LasB fromPseudomonas aeruginosa. All testedN-aryl mercaptoacetamides showed low micromolar to submicromolar activities on the tested enzymes IMP-7, NDM-1 and VIM-1. The two most promising compounds were further examined in NDM-1 expressingKlebsiella pneumoniaeisolates, where they restored the full activity of imipenem. Together with their LasB-inhibitory activity in the micromolar range, this class of compounds can now serve as a starting point for a multi-target inhibitor approach against both bacterial resistance and virulence, which is unprecedented in antibacterial drug discovery.
Brunst, Steffen,Ducho, Christian,Frank, Denia,Hirsch, Anna K. H.,Kramer, Jan S.,Proschak, Ewgenij,Rotter, Marco,Voos, Katrin,Weizel, Lilia,Wichelhaus, Thomas A.,Yahiaoui, Samir,Haupenthal, J?rg
supporting information
p. 1698 - 1708
(2021/11/23)

ANTHRAQUINONIC DERIVATIVES AND THEIR USE AS COLOURING AGENTS
The present invention relates to a compound of formula (I-0) or a salt thereof. The invention further relates to the use of such compound as a colouring agent. The invention also relates to a colouring composition comprising such compound.
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(2020/02/14)

Highly Efficient and Selective Visible-Light Driven CO2Reduction by Two Co-Based Catalysts in Aqueous Solution
Photocatalytic CO2 reduction has been considered as a promising approach to solve energy and environmental problems. Nevertheless, developing inexpensive photocatalysts with high efficiency and selectivity remains a big challenge. In this study, two Co-ba
Zhang, Liyan,Li, Shiwei,Liu, Huiping,Cheng, Yuan-Sheng,Wei, Xian-Wen,Chai, Xiaomin,Yuan, Guozan
p. 17464 - 17472
(2020/11/30)

Design, synthesis and biological evaluation of novel naturally-inspired multifunctional molecules for the management of Alzheimer's disease
In our overall goal to overcome the limitations associated with natural products for the management of Alzheimer's disease and to develop in-vivo active multifunctional cholinergic inhibitors, we embarked on the development of ferulic acid analogs. A systematic SAR study to improve upon the cholinesterase inhibition of ferulic acid with analogs that also had lower logP was carried out. Enzyme inhibition and kinetic studies identified compound 7a as a lead molecule with preferential acetylcholinesterase inhibition (AChE IC50 = 5.74 ± 0.13 μM; BChE IC50 = 14.05 ± 0.10 μM) compared to the parent molecule ferulic acid (% inhibition of AChE and BChE at 20 μM, 15.19 ± 0.59 and 19.73 ± 0.91, respectively). Molecular docking and dynamics studies revealed that 7a fits well into the active sites of AChE and BChE, forming stable and strong interactions with key residues Asp74, Trp286, and Tyr337 in AChE and with Tyr128, Trp231, Leu286, Ala328, Phe329, and Tyr341 in BChE. Compound 7a was found to be an efficacious antioxidant in a DPPH assay (IC50 = 57.35 ± 0.27 μM), and it also was able to chelate iron. Data from atomic force microscopy images demonstrated that 7a was able to modulate aggregation of amyloid β1-42. Upon oral administration, 7a exhibited promising in-vivo activity in the scopolamine-induced AD animal model and was able to improve spatial memory in cognitive deficit mice in the Y-maze model. Analog 7a could effectively reverse the increased levels of AChE and BChE in scopolamine-treated animals and exhibited potent ex-vivo antioxidant properties. These findings suggest that 7a can act as a lead molecule for the development of naturally-inspired multifunctional molecules for the management of Alzheimer's and other neurodegenerative disorders.
Chittiboyina, Amar G.,Doerksen, Robert J.,Modi, Gyan,Nayak, Prasanta Kumar,Pandey, Amruta,Pandey, Pankaj,Priya, Khushbu,Rai, Geeta,Shankar, Gauri,Singh, Yash Pal,Tej, Gullanki Naga Venkata Charan,Vishwakarma, Swati
(2020/05/05)

Synthesis, in silico Study and Antimicrobial Evaluation of New Selenoglycolicamides
Nine new compounds derived from selenoglycolic acid were synthesized, and their structures were fully characterized by elemental analysis, infrared (IR),1H and13C nuclear magnetic resonance (NMR). The compounds were evaluated in an i
Souza, Helivaldo D.S.,De Sousa, Roxana P.F.,Lira, Bruno F.,Vilela, Raquel F.,Borges, Nathalie H.P.B.,De Siqueira?Junior, José P.,Lima, Edeltrudes O.,Jardim, Jeane U.G.,Da Silva, Gracielle A.T.,Barbosa?Filho, José M.,De Athayde?Filho, Petr?nio F.
p. 188 - 197
(2018/12/13)

Combined structure- and ligand-based virtual screening aiding discovery of selenoglycolicamides as potential multitarget agents against Leishmania species
Leishmaniasis is a neglected disease that does not have adequate treatment. We created a database with 30 selenoglycolicamides and evaluated their potential anti-Leishmanial activity (L. amazonensis and L. donovani) through ligand- and structure-based vir
de Sousa Luis, José Alixandre,da Silva Souza, Helivaldo Diógenes,Lira, Bruno Freitas,da Silva Alves, Francinara,de Athayde-Filho, Petr?nio Filgueiras,de Souza Lima, Tatjana Keesen,Rocha, Juliana Camara,Mendon?a Junior, Francisco Jaime Bezerra,Scotti, Luciana,Scotti, Marcus Tullius
(2019/08/12)

Stereochemistry of Hexacoordinated Zn(II), Cu(II), Ni(II), and Co(II) Complexes with Iminodiacetamide Ligands
Metal complexes of iminodiacetamide (imda) ligands and metal ions Zn(II), Cu(II), Ni(II), and Co(II) were prepared using eight imda ligands (L1-L8) substituted with groups of different steric and electronic properties on the central amine N atom (H atom,
Pantalon Juraj, Natalija,Mileti?, Goran I.,Peri?, Berislav,Popovi?, Zora,Smre?ki, Neven,Vianello, Robert,Kirin, Sre?ko I.
supporting information
p. 16445 - 16457
(2019/12/11)

Rad51/BRCA2 disruptors inhibit homologous recombination and synergize with olaparib in pancreatic cancer cells
Olaparib is a PARP inhibitor (PARPi). For patients bearing BRCA1 or BRCA2 mutations, olaparib is approved to treat ovarian cancer and in clinical trials to treat breast and pancreatic cancers. In BRCA2-defective patients, PARPi inhibits DNA single-strand break repair, while BRCA2 mutations hamper double-strand break repair. Recently, we identified a series of triazole derivatives that mimic BRCA2 mutations by disrupting the Rad51-BRCA2 interaction and thus double-strand break repair. Here, we have computationally designed, synthesized, and tested over 40 novel derivatives. Additionally, we designed and conducted novel biological assays to characterize how they disrupt the Rad51-BRCA2 interaction and inhibit double-strand break repair. These compounds synergized with olaparib to target pancreatic cancer cells with functional BRCA2. This supports the idea that small organic molecules can mimic genetic mutations to improve the profile of anticancer drugs for precision medicine. Moreover, this paradigm could be exploited in other genetic pathways to discover innovative anticancer targets and drug candidates.
Roberti, Marinella,Schipani, Fabrizio,Bagnolini, Greta,Milano, Domenico,Giacomini, Elisa,Falchi, Federico,Balboni, Andrea,Manerba, Marcella,Farabegoli, Fulvia,De Franco, Francesca,Robertson, Janet,Minucci, Saverio,Pallavicini, Isabella,Di Stefano, Giuseppina,Girotto, Stefania,Pellicciari, Roberto,Cavalli, Andrea
p. 80 - 92
(2019/01/23)

Pharmacological and physicochemical profile of arylacetamides as tools against human cancers
Arylacetamides are widely used as synthetic intermediates to obtain medicinal substances. This work evaluated in vitro antiproliferative activity of ten 2-Chloro-N-arylacetamides on human normal and cancer cells and detailed in vivo toxicological and anticancer investigations. Initially, cytotoxic colorimetric assays were performed using tumor lines, peripheral blood mononuclear cells (PBMC) and erythrocytes. Compounds 2, 3 and 4 were tested for acute toxicity (50, 150 and 300 mg/kg) and for subacute antitumoral capacity in HCT-116 colon carcinoma-bearing xenograft mice for 15 days at 25 mg/kg/day. Most compounds revealed cytotoxic action on tumor lines and PBMC, but activity on human erythrocytes were not detected. Molecular dipole moment, lipophilicity and electronic constant of aryl substituents had effects upon in vitro antiproliferative capacity. More common in vivo acute behavioral signals with compounds 2, 3 and 4 were muscle relaxation, reduction of spontaneous locomotor activity and number of entries in closed arms and increased number of falls andtime spent in open arms, suggesting diazepam-like anxiolytic properties. Decrease of grabbing strength and overall activity were common, but palpebral ptosis and deaths occurred at 300 mg/kg only. Compounds 2 and 3 reduced colon carcinoma growth (21.2 and 27.5%, respectively, p 0.05) without causing apparent signals of organ-specific toxicity after subacute exposure. The structural chemical simplicity of arylacetamides make them cost-effective alternatives and justifies further improvements to enhance activity, selectivity and the development of pharmaceutical formulations.
Ferreira, Paulo Michel Pinheiro,Machado, Kátia da Concei??o,Lavorato, Stefania Neiva,de Oliveira, Fátima de Cássia Evangelista,Silva, Jurandy do Nascimento,de Almeida, Antonia Amanda Cardoso,Santos, Luciano de Souza,Silva, Valdenizia Rodrigues,Bezerra, Daniel Pereira,Soares, Milena Botelho Pereira,Pessoa, Cláudia,de Moraes Filho, Manoel Odorico,Ferreira, José Roberto de Oliveira,Sousa, Jo?o Marcelo de Castro e,Maltarollo, Vinícius Gon?alves,Alves, Ricardo José
(2019/08/02)

An unsymmetrical covalent organic polymer for catalytic amide synthesis
Herein, we present the first report on the Covalent Organic Polymer (COP) directed non-classical synthesis of an amide bond. An economical route has been chosen for the synthesis of APC-COP using p-aminophenol and cyanuric chloride. APC-COP acts as a smart, valuable and sustainable catalyst for efficient access to the amide bond under mild conditions at room temperature in 30 min. APC-COP exhibits selectivity towards carboxylic acids over esters. The key features of this protocol involve the variety of parameters, viz. wider substrate scope, no use of additive and recyclability, which makes this approach highly desirable in gramscale synthesis. Moreover, we have shown the practical utility of the present method in the catalytic synthesis of paracetamol.
Yadav, Deepika,Awasthi, Satish Kumar
supporting information
p. 179 - 186
(2019/12/28)

5-aminothiazole derivative, preparation method thereof and application of derivative
The invention provides a preparation method and an application of an amicarthiazol analogue, and relates to a 5-aminothiazole derivative which has a general formula as shown in the specification. R isselected from hydrogen, 4-methoxyl, 4-nitryl, 3-nitro,
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(2019/01/14)

Fragment-Based Approach to Targeting Inosine-5′-monophosphate Dehydrogenase (IMPDH) from Mycobacterium tuberculosis
Tuberculosis (TB) remains a major cause of mortality worldwide, and improved treatments are needed to combat emergence of drug resistance. Inosine 5′-monophosphate dehydrogenase (IMPDH), a crucial enzyme required for de novo synthesis of guanine nucleotid
Trapero, Ana,Pacitto, Angela,Singh, Vinayak,Sabbah, Mohamad,Coyne, Anthony G.,Mizrahi, Valerie,Blundell, Tom L.,Ascher, David B.,Abell, Chris
p. 2806 - 2822
(2018/04/23)

Synthesis and biological evaluation of novel N-aryl-ω-(benzoazol-2-yl)-sulfanylalkanamides as dual inhibitors of α-glucosidase and protein tyrosine phosphatase 1B
α-Glucosidase is known to catalyze the digestion of carbohydrates and release free glucose into the digestive tract. Protein tyrosine phosphatase 1B (PTP1B) is engaged in the dephosphorylation of the insulin receptor and regulation of insulin sensitivity.
Wang, Mei-Yan,Cheng, Xian-Chao,Chen, Xiu-Bo,Li, Yu,Zang, Lan-Lan,Duan, Yu-Qing,Chen, Ming-Zhu,Yu, Peng,Sun, Hua,Wang, Run-Ling
p. 1647 - 1656
(2018/09/10)

Synthesis method and application of 2-oxo-2-(aryl phenylamine)ethyl substituted moxifloxacin series compound
The invention discloses a synthesis method and application of a 2-oxo-2-(aryl phenylamine) ethyl substituted moxifloxacin series compound. The compound has a structural formula I, wherein R1 is hydrogen, or halogen, or nitryl, or methyl or methoxyl; R2 is
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(2018/04/26)

With anti-prostate cancer activity of 2 - oxo - 2 - (aryl aniline) ethyl substituted star seriation of the medicinal composition (by machine translation)
The invention discloses a with anti-prostate cancer activity of 2 - oxo - 2 - (aryl aniline) ethyl substituted star seriation of the medicinal composition, its structure is of formula I, R1 Represents hydrogen or halogen or nitro or methyl or m
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(2018/04/26)

Design, synthesis, bioactivity, and computational studies of some morpholine-clubbed coumarinyl acetamide and cinnamide derivatives
Abstract: The novel derivatives of morpholine-clubbed 3-substituted coumarinyl acetamide and cinnamide derivatives 5a–5j and 6a–6j have been synthesized via various 2-chloro-N-phenyl acetamide and cinnamoyl chloride derivatives, respectively. The required motif has been generated through Vilsmeier–Haack reaction on 4-hydroxycoumarin annelation of morpholine followed by imine formation and subsequently condensation with various 2-chloro-N-phenylacetamide and cinnamoyl chloride to furnish the desired molecule. The synthesized molecules were characterized by various spectroscopic methods viz IR, 1H NMR, 13C NMR. Their antimicrobial activities against various strains of bacteria and fungi have been evaluated, and computational studies have also been performed for all the newly synthesized analogs. Graphical Abstract: [Figure not available: see fulltext.].
Chauhan, Prakashsingh M.,Thummar, Sandeep N.,Chikhalia, Kishor H.
p. 1261 - 1277
(2018/05/22)

In silico identification, synthesis and biological evaluation of novel tetrazole inhibitors of MurB
In the context of antibacterial drug discovery resurgence, novel therapeutic targets and new compounds with alternative mechanisms of action are of paramount importance. We focused on UDP-N-acetylenolpyruvylglucosamine reductase (i.e. MurB), an underexplo
Hrast, Martina,Juki?, Marko,Patin, Delphine,Tod, Julie,Dowson, Christopher G.,Roper, David I.,Barreteau, Hélène,Gobec, Stanislav
p. 1101 - 1112
(2018/02/19)

Discovery of benzimidazole-based Leishmania mexicana cysteine protease CPB2.8ΔCTE inhibitors as potential therapeutics for leishmaniasis
Chemotherapy is currently the only effective approach to treat all forms of leishmaniasis. However, its effectiveness is severely limited due to high toxicity, long treatment length, drug resistance, or inadequate mode of administration. As a consequence,
De Luca, Laura,Ferro, Stefania,Buemi, Maria Rosa,Monforte, Anna-Maria,Gitto, Rosaria,Schirmeister, Tanja,Maes, Louis,Rescifina, Antonio,Micale, Nicola
p. 1585 - 1596
(2018/06/06)

Amide compound, pharmaceutical composition, preparation method and application thereof
The invention provides an amide compound, a pharmaceutical composition, a preparation method and application thereof and belongs to the field of medicine. Structure of the amide compound is shown as aformula I. The preparation method includes: in an alkaline condition and in an organic solvent, allowing a compound I and a compound II to be in condensation reaction. The amide compound or pharmaceutically acceptable salt thereof have long-acting sensory and/or motion blocking activity, can be used for preparing long-acting local anesthetic or analgesic and is long in efficacy lasting time, little side effect and high in medication safety.
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(2018/09/11)

Potent, Selective, and Cell Active Protein Arginine Methyltransferase 5 (PRMT5) Inhibitor Developed by Structure-Based Virtual Screening and Hit Optimization
PRMT5 plays important roles in diverse cellular processes and is upregulated in several human malignancies. Besides, PRMT5 has been validated as an anticancer target in mantle cell lymphoma. In this study, we found a potent and selective PRMT5 inhibitor by performing structure-based virtual screening and hit optimization. The identified compound 17 (IC50 = 0.33 μM) exhibited a broad selectivity against a panel of other methyltransferases. The direct binding of 17 to PRMT5 was validated by surface plasmon resonance experiments, with a Kd of 0.987 μM. Kinetic experiments indicated that 17 was a SAM competitive inhibitor other than the substrate. In addition, 17 showed selective antiproliferative effects against MV4-11 cells, and further studies indicated that the mechanism of cellular antitumor activity was due to the inhibition of PRMT5 mediated SmD3 methylation. 17 may represent a promising lead compound to understand more about PRMT5 and potentially assist the development of treatments for leukemia indications.
Mao, Ruifeng,Shao, Jingwei,Zhu, Kongkai,Zhang, Yuanyuan,Ding, Hong,Zhang, Chenhua,Shi, Zhe,Jiang, Hualiang,Sun, Dequn,Duan, Wenhu,Luo, Cheng
p. 6289 - 6304
(2017/08/02)

A study of diketopiperazines as electron-donor initiators in transition metal-free haloarene-arene coupling
Several diketopiperazines have been shown to promote carbon-carbon coupling between benzene and aryl halides in the presence of potassium tert-butoxide and without the assistance of a transition metal catalyst. The structure of the diketopiperazine has an influence on its reductive potential and can help to promote the coupling of the more challenging aryl bromides with benzene.
Cumine, Florimond,Zhou, Shengze,Tuttle, Tell,Murphy, John A.
p. 3324 - 3336
(2017/04/21)

Synthesis and antibacterial activity of 3-benzylamide derivatives as FtsZ inhibitors
The emergence and spread of multidrug-resistant strains of the human pathological bacteria are generating a threat to public health worldwide. In the current study, a series of PC190723 derivatives was synthesized and investigated for their antimicrobial activity. The compounds exhibited good activity against several Gram-positive bacteria as determined by comparison of diameters of the zone of inhibition of test compounds and standard antibiotics. Compound 9 with a fluorine substitution on the phenyl ring showed the best antibacterial activity in the series against M. smegmatis with the zone ratio of 0.62, and against S. aureus with the zone ratio of 0.44. The results from this study indicate that based on the unique 3-methoxybenzamide pharmacophore, compound 9 may represent a promising lead candidate against Gram-positive bacteria that are worthy of further investigation
Hu, Zhongping,Zhang, Shasha,Zhou, Weicheng,Ma, Xiang,Xiang, Guangya
supporting information
p. 1854 - 1858
(2017/04/04)

Improved Potency of Indole-Based NorA Efflux Pump Inhibitors: From Serendipity toward Rational Design and Development
The NorA efflux pump is a potential drug target for reversal of resistance to selected antibacterial agents, and recently we described indole-based inhibitor candidates. Herein we report a second class of inhibitors derived from them but with significant differences in shape and size. In particular, compounds 13 and 14 are very potent inhibitors in that they demonstrated the lowest IC50 values (2 μM) ever observed among all indole-based compounds we have evaluated.
Buonerba, Federica,Lepri, Susan,Goracci, Laura,Schindler, Bryan D.,Seo, Susan M.,Kaatz, Glenn W.,Cruciani, Gabriele
supporting information
p. 517 - 523
(2017/04/26)

1,3-dimethyl-7-substituted-quinazolinyl-2,4-diones, and synthesis method and application thereof
The invention discloses 1,3-dimethyl-7-substituted-quinazolinyl-2,4-diones. The structural general formula of the compounds is disclosed in the specification, wherein R1 is hydrogen or ethyl; and R2 is a benzene ring, benzene ring derivative, heterocyclic ring or aliphatic hydrocarbon. Part of compounds have favorable inhibiting activities for Candida albicans, Aspergillus flavus, Torula histolytica and Aspergillus fumigatus. The compounds have obvious inhibiting activities for chitin synthetase, have favorable antibacterial effects, and can be used for preparing drugs for anti-pathogenic microorganisms.
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(2017/07/31)

A case study of supramolecular organization: One ferrocene substituted iminodiacetamide and its chloroform solvate
This paper describes the synthesis of an amide based conjugate of ferrocene (Fc), ethylenediamine (eda) and iminodiacetamide (imda), Fc-eda-imda (2). The compound (2) is characterized by various spectroscopic, crystallographic and thermoanalytical techniq
Juraj, Natalija P.,Le Pennec, Jeremy,Peri?, Berislav,Kirin, Sre?ko I.
p. 613 - 623
(2018/05/07)

Molecular docking, synthesis and CNS activity of some novel 1, 4-Benzodiazepine derivatives
Background: A series of new class of twenty four 1, 4-benzodizepines were designed and by using molecular docking study with GABAA receptor, high scoring fourteen molecules were synthesized from this library. Binding affinity of ligands towards GABAA was evaluated on the basis of dock score and bonding interactions like hydrogen bonds, hydrophobic bonds and pi-stacking. Methods: All compounds were found to possess a good dock score, but varied in the formation of bonding interactions. Methoxy group substituted ligands showed particularly very important role in these interactions. All the synthesized molecules were characterized by IR, 1H-NMR and Mass spectrometric data and investigated for their antianxiety and antiepileptic actions. Conclusion: Compound 3-(3-ethoxy-4-hydroxybenzylidene)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one was found to possess very effective in both the activities. All results, docking as well as pharmacological evaluations were compared to diazepam.
Menghani, Sunil S.,Chikhale, Rupesh,Pant, Amit,Mathew, Bijo,Khedekar, Pramod
p. 690 - 698
(2017/07/15)

A process for preparing N - aryl amide compound
The method discloses a method used for preparing an N-aryl amide compound from amides and aniline compounds. According to the method, a palladium salt and a ligand are taken as catalysts; an N,N-dimethyl formamide compound, an aniline compound, a protonic acid, a Lewis acid, and an organic solvent are mixed; and an obtained mixture is subjected to heating reaction so as to obtain the N-aryl amide compound. Advantages of the method are that: preparation route is short, substrate universality is excellent, reaction conditions are mild, synthesis yield is high, and used raw materials and catalysts are simple and easily available.
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(2017/08/02)

Synthesis and cytotoxic evaluation of some 2-{4-[(2-oxo-1,2-dihydro-3h-indol-3-ylidene)methyl] phenoxy}-n-phenylacetamide
A series of 2-oxindole derivatives were synthesized and evaluated for cytotoxic activity against different human and murine cancer cell lines and cancer chemopreventive activity. Among the tested compounds VS-06, 08, 12 and 17 displayed cytotoxic activity in the range of 5.0 to 8.5 μM against human T-lymphocyte cells (CEM). Results showed that molecules with electron withdrawing substituent at 4 position of N-phenylacetamide group exhibited an increase in activity against the human tumor cell line CEM. The cancer chemopreventive effect of VS-01 (IC50 = 451 nM) displayed equipotent activity in comparison to standard oleanolic acid (IC50 = 449 nM).
Bhadauria, Vivek Singh,Sravanthi, Vishnu,Kumar, Sujeet,Das, Debajyoti,De Clercq, Erik,Schols, Dominique,Tokuda, Harukuni,Karki, Subhas S.
p. 137 - 145
(2017/01/17)

Synthesis and biological evaluation of potential inhibitors of the cysteine proteases cruzain and rhodesain designed by molecular simplification
Analogues of 8-chloro-N-(3-morpholinopropyl)-5H-pyrimido[5,4-b]indol-4-amine 1, a known cruzain inhibitor, were synthesized using a molecular simplification strategy. Five series of analogues were obtained: indole, pyrimidine, quinoline, aniline and pyrrole derivatives. The activity of the compounds was evaluated against the enzymes cruzain and rhodesain as well as against Trypanosoma cruzi amastigote and trypomastigote forms. The 4-aminoquinoline derivatives showed promising activity against both enzymes, with IC50values ranging from 15 to 125?μM. These derivatives were selective inhibitors for the parasitic proteases, being unable to inhibit mammalian cathepsins B and S. The most active compound against cruzain (compound 5a; IC50?=?15?μM) is considerably more synthetically accessible than 1, while retaining its ligand efficiency. As observed for the original lead, compound 5a was shown to be a competitive enzyme inhibitor. In addition, it was also active against T. cruzi (IC50?=?67.7?μM). Interestingly, the pyrimidine derivative 4b, although inactive in enzymatic assays, was highly active against T. cruzi (IC50?=?3.1?μM) with remarkable selectivity index (SI?=?128) compared to uninfected fibroblasts. Both 5a and 4b exhibit drug-like physicochemical properties and are predicted to have a favorable ADME profile, therefore having great potential as candidates for lead optimization in the search for new drugs to treat Chagas disease.
Braga, Saulo Fehelberg Pinto,Martins, Luan Carvalho,da Silva, Elany Barbosa,Sales Júnior, Policarpo Ademar,Murta, Silvane Maria Fonseca,Romanha, Alvaro José,Soh, Wai Tuck,Brandstetter, Hans,Ferreira, Rafaela Salgado,de Oliveira, Renata Barbosa
supporting information
p. 1889 - 1900
(2017/03/08)

2,4,5-triarylimidazole compounds as well as preparation methods and application thereof
The invention discloses 2,4,5-triarylimidazole compounds as well as preparation methods and an application thereof. The compounds have a structure shown as a formula (I). According to the preparation methods, substituted aniline and chloroacetyl chloride
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Paragraph 0009

(2016/10/17)

Synthesis and trypanocidal activity of novel benzimidazole derivatives
The present work reports the synthesis and biological activity of a series of 14 benzimidazole derivatives designed to act on the enzyme triosephosphate isomerase of Trypanosoma cruzi (TcTIM). This enzyme is involved in the metabolism of glucose, the only source of energy for the parasite. In this study, we found four compounds that inhibit TcTIM moderately and lack inhibitory activity against human TIM (HsTIM). In vitro studies against T. cruzi epimastigotes showed two compounds that were more active than the reference drug nifurtimox, and these presented a low cytotoxic effect in mouse macrophages (J744 cell line).
Velázquez-López, José Miguel,Hernández-Campos, Alicia,Yépez-Mulia, Lilián,Téllez-Valencia, Alfredo,Flores-Carrillo, Paulina,Nieto-Meneses, Rocío,Castillo, Rafael
supporting information
p. 4377 - 4381
(2016/08/18)

Synthesis and Fluorescence Properties of Eu3+, Tb3+ Complexes with Schiff Base Derivatives
Novel Schiff base ligands derived from N′-benzylidene-benzohydrazide (substituted by-H,-CH3,-OCH3,-Cl) and 2-chloro-N-phenylacetamide were synthesized. The solid complexes of rare earth (Eu, Tb) nitrate with these Schiff base ligands
Liu, Yanhong,Kong, Weihua,Yang, Zehui,Dai, Ming,Shi, Ling,Guo, Dongcai
p. 567 - 576
(2016/03/12)

Triazolylthioacetamide: A Valid Scaffold for the Development of New Delhi Metallo-β-Lactmase-1 (NDM-1) Inhibitors
The metallo-β-lactamases (MβLs) cleave the β-lactam ring of β-lactam antibiotics, conferring resistance against these drugs to bacteria. Twenty-four triazolylthioacetamides were prepared and evaluated as inhibitors of representatives of the three subclasses of MβLs. All these compounds exhibited specific inhibitory activity against NDM-1 with an IC50 value range of 0.15-1.90 μM, but no activity against CcrA, ImiS, and L1 at inhibitor concentrations of up to 10 μM. Compounds 4d and 6c are partially mixed inhibitors with Ki values of 0.49 and 0.63 μM using cefazolin as the substrate. Structure-activity relationship studies reveal that replacement of hydrogen on the aromatic ring by chlorine, heteroatoms, or alkyl groups can affect bioactivity, while leaving the aromatic ring of the triazolylthiols unmodified maintains the inhibitory potency. Docking studies reveal that the typical potent inhibitors of NDM-1, 4d and 6c, form stable interactions in the active site of NDM-1, with the triazole bridging Zn1 and Zn2, and the amide interacting with Lys 211 (Lys224).
Zhai, Le,Zhang, Yi-Lin,Kang, Joon S.,Oelschlaeger, Peter,Xiao, Lin,Nie, Sha-Sha,Yang, Ke-Wu
supporting information
p. 413 - 417
(2016/05/19)

Rational design and synthesis of dihydropyrimidine based dual binding site acetylcholinesterase inhibitors
Based on the pharmacological importance of dihydropyrimidine (DHPM) scaffold, substituted DHPMs linked with acetamide linker to substituted aromatic anilines were synthesized and evaluated for their potency as acetylcholinesterase (AChE) and butyrylcholin
Ahmad, Sufyan,Iftikhar, Fatima,Ullah, Farhat,Sadiq, Abdul,Rashid, Umer
p. 91 - 101
(2016/10/25)

Design and synthesis of novel 4'-demethyl-4-deoxypodophyllotoxin derivatives as potential anticancer agents
A group of podophyllotoxin (PPT) derivatives (7a-j) were synthesized by conjugating aryloxyacetanilide moieties to the 4'-hydroxyl of 4'-demethyl-4-deoxypodophyllotoxin (DDPT), and their anticancer activity was evaluated. It was found that the most potent compound 7d inhibited the proliferation of three cancer cell lines with sub to low micromolar IC50 values. Furthermore, it was demonstrated that 7d induced cell cycle arrest in G2/M phase in MGC-803 cells, and regulated the expression of cell cycle check point proteins, such as cyclin A, cyclin B, CDK1, cdc25c, and p21. Finally, 4 mg/kg of 7d reduced the weights and volumes of HepG2 xenografts in mice. Our findings suggest that 7d might be a potential anticancer agent.
Zhu, Xiong,Fu, Junjie,Tang, Yan,Gao, Yuan,Zhang, Shijin,Guo, Qinglong
supporting information
p. 1360 - 1364
(2016/02/23)

Synthesis, characterization and properties of salicylhydrazide-salicylacylhydrazone derivatives and their terbium complexes
A series of terbium complexes with salicylhydrazide-salicylacylhydrazone derivatives were synthesized and characterized by elemental analysis, IR spectra, UV/vis spectra and thermal analysis. The luminescence and electrochemical properties of the terbium complexes were investigated. The results show that all the target complexes exhibited characteristic emissions of terbium ions and the complex substituted by the chlorine has the strongest luminescence intensity with the highest quantum yield at 0.609. The introduction of donating electron groups could increase the oxidation potential and the highest occupied molecular orbital energy level of the terbium complex; however, the introduction of accepting electron groups gave the opposite result.
Meng, Defen,Liu, Fen,Li, Yingying,Yang, Zehui,Li, Guizhi,Guo, Dongcai
p. 507 - 514
(2016/03/05)

5-Benzylidene-2,4-thiazolidenedione derivatives: Design, synthesis and evaluation as inhibitors of angiogenesis targeting VEGR-2
A series of novel 5-benzylidene-2,4-thiazolidinediones were designed as inhibitors of angiogenesis targeting VEGFR-2. In docking study, molecules showed similar way of binding with VEGFR-2 as that of the co-crystallized ligand. Compounds were then synthes
Bhanushali, Umesh,Rajendran, Saranya,Sarma, Keerthana,Kulkarni, Pushkar,Chatti, Kiranam,Chatterjee, Suvro,Ramaa
p. 139 - 147
(2016/07/12)

Templated C-C and C-N Bond Formation Facilitated by a Molybdenum(VI) Metal Center
Preparation of molybdenum dioxido complexes with novel iminophenolate ligands bearing pendant secondary amide functionalities led to unprecedented C-C and C-N coupling reactions of two α-iminoamides upon coordination. The diastereoselective cyclization to asymmetric imidazolidines occurs at the metal center in two consecutive steps via a monocoupled intermediate. A meaningful mechanism is proposed on the basis of full characterization of intermediate and final molybdenum-containing products by spectroscopic means and by single-crystal X-ray diffraction analyses. This process constitutes the first example of a diastereoselective self-cyclization of two α-iminoamides.
Zwettler, Niklas,Dupé, Antoine,Schachner, J?rg A.,Belaj, Ferdinand,M?sch-Zanetti, Nadia C.
p. 11969 - 11976
(2015/12/30)

Thioimidazoline based compounds reverse glucocorticoid resistance in human acute lymphoblastic leukemia xenografts
Glucocorticoids form a critical component of chemotherapy regimens for pediatric acute lymphoblastic leukemia (ALL) and the initial response to glucocorticoid therapy is a major prognostic factor, where resistance is predictive of poor outcome. A high-throughput screen identified four thioimidazoline-containing compounds that reversed dexamethasone resistance in an ALL xenograft derived from a chemoresistant pediatric ALL. The lead compound (1) was synergistic when used in combination with the glucocorticoids, dexamethasone or prednisolone. Synergy was observed in a range of dexamethasone-resistant xenografts representative of B-cell precursor ALL (BCP-ALL) and T-cell ALL. We describe here the synthesis of twenty compounds and biological evaluation of thirty two molecules that explore the structure-activity relationships (SAR) of this novel class of glucocorticoid sensitizing compounds. SAR analysis has identified that the most effective dexamethasone sensitizers contain a thioimidazoline acetamide substructure with a large hydrophobic moiety on the acetamide. This journal is
Toscan, Cara E.,Rahimi, Marwa,Bhadbhade, Mohan,Pickford, Russell,McAlpine, Shelli R.,Lock, Richard B.
p. 6299 - 6312
(2015/06/08)

Synthesis and luminescence properties of 1,3,4-oxadiazole acetamide derivatives and their rare earth complexes
A series of 1,3,4-oxadiazole acetamide derivatives have been designed and synthesized, and their complexes with Eu(III) and Tb(III) were also prepared. The luminescence properties of the target complexes were investigated, and the results indicated that a
Zhang, Wu,He, Wei,Guo, Xiaorui,Chen, Yanwen,Wu, Limin,Guo, Dongcai
p. 383 - 389
(2015/02/02)

Azolylthioacetamide: A highly promising scaffold for the development of metallo-β-lactamase inhibitors
A new scaffold, azolylthioacetamide, was constructed and assayed against metallo-β-lactamases (MβLs). The obtained molecules specifically inhibited MβL ImiS, and 1c was found to be the most potent inhibitor, with a Ki = 1.2 μM using imipenem as substrate. Structure-activity relationships reveal that the aromatic carboxyl improves inhibitory activity of the inhibitors, but the aliphatic carboxyl does not. Compounds 1c-d and 1h-i showed the best antibacterial activities against E. coli BL21(DE3) cells producing CcrA or ImiS, resulting in 32- and 8-fold reduction in MIC values, respectively; 1c and 1f-j resulted in a reduction in MIC against P. aeruginosa. Docking studies revealed that 1a, 1c, and 1d fit tightly into the substrate binding site of CphA as a proxy for ImiS with the aromatic carboxylate forming interactions with Lys224, the Zn(II) ion, the backbone of Asn233, and hydrophobic portions of the inhibitors aligning with hydrophobic patches of the protein surface.
Yang, Shao-Kang,Kang, Joon S.,Oelschlaeger, Peter,Yang, Ke-Wu
supporting information
p. 455 - 460
(2015/04/27)

Synthesis and luminescence properties of salicylaldehyde isonicotinoyl hydrazone derivatives and their europium complexes
Four novel salicylaldehyde isonicotinoyl hydrazone derivatives and their corresponding europium ion complexes were synthesized and characterized, while the luminescence properties and the fluorescence quantum yields of the target complexes were investigated. The results indicated that the ligands favored energy transfers to the emitting energy level of europium ion, and four target europium complexes showed the characteristic luminescence of central europium ion. Besides the luminescence intensity of the complex with methoxy group, which possessed the highest fluorescence quantum yield (0.522), was stronger than that of other complexes. Furthermore, the electrochemical properties of the target complexes were further investigated by cyclic voltammetry, the results indicated that the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) energy levels and the oxidation potential of the complexes with electron donating group increased, however, that of the complexes with accepting electron group decreased.
Shan, Wenfei,Liu, Fen,Liu, Jiang,Chen, Yanwen,Yang, Zehui,Guo, Dongcai
p. 100 - 107
(2015/12/08)

Synthesis of N-arylcarboxamides by the efficient transamidation of DMF and derivatives with anilines
A novel protocol for the transamidation of DMF and derivatives with weakly nucleophilic anilines has been developed, utilizing a catalytic amount of Pd(OAc)2 and 2,2′-bipyridine, and with PivOH and BF3·Et2O as additives. This methodology has a broad substrate scope, and various corresponding transamidation products were prepared in good to excellent yields from commercially available DMF derivatives and anilines. The synthetic utility of the reported protocol was further demonstrated with a gram-scale experiment. Control experiments suggested the efficient transformation of DMF and derivatives with anilines might owe to the synergistic effect of palladium complex, PivOH, and BF3·Et2O.
Gu, Da-Wei,Guo, Xun-Xiang
p. 9117 - 9122
(2015/11/09)

METAL COMPLEXES AND FLUORINATION THEREOF
The present invention relates to a method of labelling biological molecules with 18F, via attachment of fluorine to a metal complex, where the metal complex is conjugated to the biological molecule. The invention highlights the incorporation of hydrogen bonding (H-bonding) into the metal complex scaffold, and how this can be utilised to improve the kinetics of fluoride incorporation. Also provided are pharmaceutical compositions, kits and methods of in vivo imaging.
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(2014/11/13)

Synthesis, cytotoxic study and docking based multidrug resistance modulator potential analysis of 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamides
The present study describes the synthesis of fifteen 2-(9-oxoacridin-10(9H) -yl)-N-phenyl acetamide derivatives (13a-o) through condensation of 2-chloro-N-phenyl acetamides (12a-o) with acridone molecule (10). All the synthesized compounds were screened f
Kumar, Rajesh,Kaur, Maninder,Bahia, Malkeet Singh,Silakari, Om
p. 83 - 91
(2014/05/06)

Synthesis, characterization and antimicrobial activity of 2-(11-oxodibenzo [b,f][1,4]thiazepin-10(11H)-yl)-N (substituted phenyl) acetamide derivatives
Substituted dibenzo [b,f][1,4]thiazepines analogues carrying 2-chloro N-phenylacetamide moiety attached to 11-C position have been synthesized and evaluated using IR, 1H NMR and mass spectra. Antibacterial properties have been examined for the synthesized derivatives against gram positive and gram negative bacteria. 2-(11-Oxodibenzo [b,f][1,4]thiazepin-10(11H)-yl)-N phenylacetamide derivatives show good significant antimicrobial activity.
Tailor, Jitesh H.,Patel, Priti C.,Malik
p. 1263 - 1268
(2014/12/10)