- Magnetic nanoparticles grafted with β-cyclodextrin-polyurethane polymer as a novel nanomagnetic polymer brush catalyst for nucleophilic substitution reactions of benzyl halides in water
-
The polymer coated magnetic nanoparticles has gained significant attention for potential applications in biomedicine, separations, and magnetic storage. In this study, β-cyclodextrin-polyurethane polymer coated Fe 3O4 magnetic nanoparticle as a novel class of hybrid organic/inorganic molecular catalyst was successfully prepared and evaluated as solid-liquid phase-transfer catalyst and molecular host system for nucleophilic substitution reactions. The nanocomposite has demonstrated the ability to catalytic the nucleophilic substitution reaction of benzyl halides with thiocyanate, azide, cyanide and acetate anions in water. No evidence for the formation of by-products for example isothiocyanate or alcohol was observed and the products obtained in pure form without further purification. The nanomagnetic polymer brush catalyst was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. Results obtained from scanning electron microscopy (SEM) and vibrating sample magnetometery (VSM) show that the synthesized magnetic nanocomposite are superparamagnetic with a mean diameter of 59 nm. The grafting of β-cyclodextrin-polyurethane polymer to Fe3O4 magnetic nanoparticle is confirmed by Fourier transform infrared spectroscopy (FT-IR).
- Kiasat, Ali Reza,Nazari, Simin
-
-
Read Online
- Discovery of novel anti-angiogenesis agents. Part 9: Multiplex inhibitors suppressing compensatory activations of RTKs
-
Aberrant angiogenesis is a hallmark of various diseases including cancers. VEGFR-2 inhibitors have been utilized as anti-angiogenic agents for several years. However, compensatory activation of various receptor tyrosine kinases (RTK) could induce the occu
- Shan, Yuanyuan,Si, Ru,Wang, Jin,Zhang, Qingqing,Zhou, Huaxin,Song, Jie,Zhang, Jie,Chen, Qinhua
-
-
Read Online
- Synthesis and rational design of new appended 1,2,3-triazole-uracil ensembles as promising anti-tumor agents via in silico vegfr-2 transferase inhibition
-
Angiogenesis inhibition is a key step towards the designing of new chemotherapeutic agents. In a view to preparing new molecular entities for cancer treatment, eighteen 1,2,3-triazole-uracil ensembles 5a–r were designed and synthesized via the click reaction. The ligands were well characterized using1 H-,13 C-NMR, elemental analysis and ESI-mass spectrometry. The in silico binding propinquities of the ligands were studied sequentially in the active region of VEGFR-2 using the Molegro virtual docker. All the compounds produced remarkable interactions and potentially inhibitory ligands against VEGFR-2 were obtained with high negative binding energies. Drug-likeness was assessed from the ADME properties. Cytotoxicity of the test compounds was measured against HeLa and HUH-7 tumor cells and NIH/3T3 normal cells by MTT assay. Compound 5h showed higher growth inhibition activity than the positive control, 5-fluorouracil (5-FU), against both HeLa and HUH-7 cells with IC50 values of 4.5 and 7.7 μM respectively. Interestingly, the compounds 5a–r did not show any cytotoxicity towards the normal cell lines. The results advance the position of substituted triazoles in the area of drug design with no ambiguity.
- Bhaskar, Kuthati,Hu, Anren,Hung, Sung-Jen,Raju, Atcha Krishnam,Rao, Vankadari Srinivasa,Reddy, Nadipolla Naresh,Reddy, Puchakayala Muralidhar,Rohini, Rondla,Sanjeev, Ananthula,Swamy, Merugu Kumara
-
-
Read Online
- Design, synthesis, and antimycobacterial activity of novel ciprofloxacin derivatives
-
Tuberculosis is the deadliest infectious disease affecting humankind with a death toll of approximately 1.7 million people in 2016. The increasing prevalence of multidrug-resistant strains of the causative pathogen, Mycobacterium tuberculosis (Mtb) which
- Cilliers, Pieter,Seldon, Ronnett,Smit, Frans J.,Aucamp, Janine,Jordaan, Audrey,Warner, Digby F.,N'Da, David D.
-
-
Read Online
- Exploring the potential intracellular targets of vascular normalization based on active candidates
-
We previously developed two candidates with potency of inducing vascular normalization, BD7 and B14. However, the definite intracellular molecular target(s) responsible for their activity remains unknown. Herein, we report the discovery and functional assessment of several multifunctional photoaffinity probes for determining the potential biological targets of active compounds. The probes bear a photoaffinity moiety and a bioorthogonal unit attached to B7 or B14 and maintained the bioactivity of the parent active molecules. Using in vitro biological assays, we preliminarily identified VEGFR-2 as a potential intracellular target for the active candidates. Our results demonstrate the utility of these multifunctional photoaffinity probes for analyzing the biological activity and subcellular localization of the intracellular target proteins of active candidates.
- Shan, Yuanyuan,Wang, Jin,Si, Ru,Ma, Yuexiang,Li, Jing,Zhang, Qingqing,Lu, Wen,Zhang, Jie
-
-
Read Online
- Synthesis and antifungal activity of the novel triazole derivatives containing 1,2,3-triazole fragment
-
A series of fluconazole analogues containing 1,2,3-triazole fragment have been designed and synthesized on the basis of the active site of the cytochrome P450 14α-demethylase (CYP51). Their structures were characterized by 1H NMR, 13C NMR and LC-MS. The MIC80 values indicate that the target compounds 1a-r showed higher activities against nearly all the fungi tested to some extent except against Aspergillus fumigatus. Compounds 1c, e, f, l and p showed 128 times higher activity (with the MIC 80 value of 0.0039 mg/mL) than that of fluconazole against Candida albicans and also showed higher activity than that of the other positive controls.
- Yu, Shichong,Wang, Nan,Chai, Xiaoyun,Wang, Baogang,Cui, Hong,Zhao, Qingjie,Zou, Yan,Sun, Qingyan,Meng, Qingguo,Wu, Qiuye
-
-
Read Online
- Synthesis of novel 1,2,3-triazole derivatives of 2,3-dihydroquinazolin-4(1H)-one
-
Abstract: This work reports an efficient route for the synthesis of novel 1,2,3-triazole derivatives of 2,3-dihydroquinazolin-4(1H)-one starting from isatoic anhydride via a three-step reaction. The resulting 2-amino-N-substituted benzamides from the reaction of isatoic anhydride and benzylamines underwent coupling cyclization reaction with 4-(prop-2-yn-1-yloxy)benzaldehyde, and then click reaction with in situ prepared organic azides afforded the title compounds in good yields. Graphical abstract: [Figure not available: see fulltext.]
- Mahdavi, Mohammad,Saeedi, Mina,Karimi, Maryam,Foroughi, Niloufar,Hasanshahi, Fatemeh,Alinezhad, Heshmatollah,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
-
-
Read Online
- Crown ether functionalized magnetic hydroxyapatite as eco-friendly microvessel inorganic-organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives
-
In this paper, high catalytic activity of 4′,4″-diformyl dibenzo-18-crown-6 anchored onto the functionalized magnetite hydroxyapatite (γ-Fe2O3@HAp–Crown) as a new, versatile and magnetically recoverable catalyst, was prepared. It evaluated as phase-transfer catalyst and molecular host system for nucleophilic substitution reactions of benzyl halides with thiocyanate, cyanide, azide and acetate anions in water. No evidence for the formation of by-products was observed and the products obtained in pure form without further purification. The nanocomposite was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. The synthesized nanocomposite was characterized by several techniques such as FT-IR, TGA-DTG, EDX, XRD, BET, FE-SEM, TEM and VSM.
- Azaroon, Maedeh,Kiasat, Ali Reza
-
-
Read Online
- New 1,2,3-triazole–(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation
-
A new series of 1,2,3-triazole–(thio)barbituric acid hybrids 8a–n was designed and synthesized on the basis of potent pharmacophores with urease inhibitory activity. Therefore, these compounds were evaluated against Helicobacter pylori urease. The obtained result demonstrated that all the synthesized compounds, 8a–n, were more potent than the standard urease inhibitor, hydroxyurea. Moreover, among them, compounds 8a, 8c–e, 8g,h, and 8k,l exhibited higher urease inhibitory activities than the other standard inhibitor used: thiourea. Docking studies were performed with the synthesized compounds. Furthermore, molecular dynamic simulation of the most potent compounds, 8e and 8l, showed that these compounds interacted with the conserved residues Cys592 and His593, which belong to the active site flap and are essential for enzymatic activity. These interactions have two consequences: (a) blocking the movement of a flap at the entrance of the active site channel and (b) stabilizing the closed active site flap conformation, which significantly reduces the catalytic activity of urease. Calculation of the physicochemical and topological properties of the synthesized compounds 8a–n predicted that all these compounds can be orally active. The ADME prediction of compounds 8a–n was also performed.
- Asgari, Mohammad S.,Azizian, Homa,Nazari Montazer, Mohammad,Mohammadi-Khanaposhtani, Maryam,Asadi, Mehdi,Sepehri, Saghi,Ranjbar, Parviz R.,Rahimi, Rahmatollah,Biglar, Mahmood,Larijani, Bagher,Amanlou, Massoud,Mahdavi, Mohammad
-
-
Read Online
- Application of β-cyclodextrin-polyurethane as a stationary microvessel and solid-liquid phase-transfer catalyst: Preparation of benzyl cyanides and azides in water
-
Application of water tolerant heterogeneous catalyst, β-cyclodextrin- polyurethane (β-CDPU) polymer, as an efficient microvessel and polymeric host system for nucleophilic substitution reaction of benzyl halides with cyanide and azide anions in water has been described. The reactions gave only pure products, which did not require any further purification. The most important features of this method are high yields, clean reactions and that the catalyst can be recovered and recycled.
- Kiasat, Ali Reza,Nazari, Simin
-
-
Read Online
- Design, synthesis and antibacterial activity evaluation of novel 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives
-
In this paper, a novel series of 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives are synthesized in two steps. The first step involved Ugi multicomponent reaction of β-alanine, o-(propargyl)benzaldehyde and i
- Zarei, Samaneh,Komeili, Golzar,Bahadorikhalili, Saeed,Yahya-Meymandi, Azadeh,Karami-Zarandi, Morteza,Larijani, Bagher,Biglar, Mahmood,Sadat Ebrahimi, Seyed Esmaeil,Mahdavi, Mohammad
-
-
Read Online
- Synthesis and antibacterial activity of novel 4″-O-(1-aralkyl-1,2,3-triazol-4-methyl-carbamoyl) azithromycin analogs
-
Three novel structural series of 4″-O-(1-aralkyl-1,2,3-triazol-4-methyl-carbamoyl) azithromycin analogs were designed, synthesized and evaluated for their in vitro antibacterial activity. All the target compounds exhibited excellent activity against erythromycin-susceptible Streptococcus pyogenes, and significantly improved activity against three phenotypes of erythromycin-resistant Streptococcus pneumoniae compared with clarithromycin and azithromycin. Among the three series of azithromycin analogs, the novel series of 11,4″-disubstituted azithromycin analogs 9a–k exhibited the most effective and balanced activity against susceptible and resistant bacteria. Among them, compound 9j showed the most potent activity against Staphylococcus aureus ATCC25923 (0.008?μg/mL) and Streptococcus pyogenes R2 (1?μg/mL). Besides, all the 11,4″-disubstituted azithromycin analogs 9a–k except 9f shared the identical activity with the MIC value 0.002?μg/mL against Streptococcus pyogenes S2. Furthermore, compounds 9g, 9h, 9j and 9k displayed significantly improved activity compared with the references against all the three phenotypes of resistant S. pneumoniae. Particularly, compound 9k was the most effective (0.06, 0.03 and 0.125?μg/mL) against all the erythromycin-resistant S. pneumoniae expressing the erm gene, the mef gene and the erm and mef genes, exhibiting 2133, 133 and 2048-fold more potent activity than azithromycin, respectively.
- Wang, Yinhu,Cong, Chao,Chern Chai, Wern,Dong, Ruiqian,Jia, Li,Song, Di,Zhou, Ziteng,Ma, Shutao
-
-
Read Online
- Synthesis of nerol derivatives containing a 1,2,3-triazole moiety and evaluation of their activities against cancer cell lines
-
In the present investigation, a collection of twenty two nerol derivatives, containing 1,2,3-triazolic appendages, was synthesized and screened in vitro for their cytotoxic activity against HL60, Nalm6, and Jurkat human leukemia cells as well as against B16F10 (melanoma cell line). In most cases, derivatives were able to reduce cell viability. The most potent compound (Z)-4-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-1-(4-(trifluoromethoxy)benzyl)-1H-1,2,3 triazole showed antiproliferative activity against Jurkat cells and reduced B16F10 cell migration. Physicochemical properties of the compounds were calculated in order to evaluate their potential for drug development. Most of the evaluated physicochemical parameters seemed to be favorable for drug development. In addition, for a better understanding of the biological activity results, 3D quantitative structure-activity relationship (QSAR) studies were carried out. 3D-QSAR studies indicate that the anticancer activities observed for the cell lines HL60 and Jurkat may occur by a similar mechanism of action and the same was found for the Nalm6 and B16F10 cell lines.
- Teixeira, Róbson R.,Da Silva, Adalberto M.,Siqueira, Raoni P.,Gon?alves, Victor Hugo S.,Pereira, Higor S.,Ferreira, Rafaela S.,Costa, Adilson V.,de Melo, Eduardo B.,Paula, Fávero R.,Ferreira, Márcia M.C.,Bressan, Gustavo C.
-
-
Read Online
- Leishmanicidal and cytotoxic activity of hederagenin-bistriazolyl derivatives
-
Aiming to obtain new potent leishmanicidal and cytotoxic compounds from natural sources, the triterpene hederagenin was converted into several new 1,2,3-triazolyl derivatives tethered at C-23 and C-28. For this work hederagenin was isolated from fruits of
- Rodríguez-Hernández, Diego,Barbosa, Luiz C.A.,Demuner, Antonio J.,Nain-Perez, Amalyn,Ferreira, Sebasti?o R.,Fujiwara, Ricardo T.,de Almeida, Raquel M.,Heller, Lucie,Csuk, René
-
-
Read Online
- Design and synthesis of a magnetic hierarchical porous organic polymer: A new platform in heterogeneous phase-transfer catalysis
-
Recyclable phase transfer catalysts containing magnetic nanoparticles (MNPs) have been known as a major trend towards sustainable catalysts. In this study, a novel class of magnetic porous polymer on the basis of calix[4]resorcinarene was synthesized starting from silica-coated Fe3O4 core-shell nanoparticles. This compound was found as an efficient phase transfer catalyst to the conversion of benzyl halides into benzyl azides and cyanides in good yields. The catalyst could be used at least for five consecutive cycles without appreciable loss in the catalytic activity.
- Mouradzadegun, Arash,Ganjali, Mohammad Reza,Mostafavi, Mahsa Alsadat
-
-
Read Online
- Synthesis of α-santonin derived acetyl santonous acid triazole derivatives and their bioevaluation for T and B-cell proliferation
-
A new series of α-santonin derived acetyl santonous acid 1,2,3-triazole derivatives were synthesised using Huisgen 1,3-dipolar cyclo-addition reaction (click chemistry approach) and evaluated for their in vitro inhibition activity on concanavalin A (ConA) induced T cell proliferation and lipopolysaccharide (LPS) induced B cell proliferation. Among the synthesised series, compounds 2-10 and 19 exhibited significant inhibition against ConA and LPS stimulated T-cell and B-cell proliferation in a dose dependent manner. More significantly compounds 4, 9-10 and 19 exhibited potent inhibition activity with remarkably lower cytotoxicity on the mitogen-induced T cell and B cell proliferation at 1 μM concentration. The compound 6 displayed potent immunosuppressive effects with ~89% against LPS induced B-cell and ~83% against ConA stimulated T-cell proliferation at 100 μM concentration without cytotoxicity. Compound 10 was more selective against B cell proliferation and exhibited 81% and 69% suppression at 100 and 1 μM concentration respectively. The present study led to the identification of several santonin analogs with reduced cytotoxicity and strong inhibition activity against the cell proliferation induced by the mitogens.
- Dangroo, Nisar A.,Singh, Jasvinder,Dar, Alamgir A.,Gupta, Nidhi,Chinthakindi, Praveen K.,Kaul, Anpurna,Khuroo, Mohmmed A.,Sangwan, Payare L.
-
-
Read Online
- One-pot synthesis of oxoisoindoline-1,2,3-triazole hybrid by a Ugi–click reaction
-
1,2,3-Triazole-3-oxoisoindoline-1-carboxamide system was successfully synthesized by using a combination of Ugi and click reactions. This two-step, one-pot synthesis was started by the reaction of 2-formyl benzoic acid, propargyl amine, and cyclohexyl iso
- Akrami, Sara,Firoozpour, Loghman,Goli-Garmroodi, Fereshteh,Moghimi, Setareh,Mahdavi, Mohammad,Zonouzi, Afsaneh,Foroumadi, Alireza
-
-
Read Online
- Construction of sequence-defined polytriazoles by IrAAC and CuAAC reactions
-
Here we report the first synthesis of sequence-defined polytriazoles, in which different side groups are sequentially anchored to the C-5 position of 1,2,3-triazole rings. By using efficient synthetic strategies based on IrAAC and CuAAC, different monodis
- Ding, Shengtao,Ju, Changhong,Ma, Jiahao,Meng, Congcong,Zhang, Xueyan
-
-
Read Online
- Nicotinoyl azide (NCA)-mediated Mitsunobu reaction: An expedient one-pot transformation of alcohols into azides
-
A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.
- Papeo, Gianluca,Posteri, Helena,Vianello, Paola,Varasi, Mario
-
-
Read Online
- Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides
-
The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we present a stereoselective α-amination of amides employing simple azides that proceeds under mild conditions with release of nitrogen gas. The
- Tona, Veronica,De La Torre, Aurélien,Padmanaban, Mohan,Ruider, Stefan,González, Leticia,Maulide, Nuno
-
-
Read Online
- Environmentally benign nucleophilic substitution reactions
-
Herein, the development of environmentally benign conditions for heterogeneous nucleophilic addition reactions under novel high speed ball milling conditions is described.
- Vogel, Philip,Figueira, Sarah,Muthukrishnan, Sivaramakrishnan,Mack, James
-
-
Read Online
- Design, synthesis, biological evaluation, and docking study of new acridine-9-carboxamide linked to 1,2,3-triazole derivatives as antidiabetic agents targeting α-glucosidase
-
A new series of acridine-9-carboxamide-1,2,3-triazole derivatives 7a-m were designed, synthesized, and evaluated as novel α-glucosidase inhibitors. Acridine-9-carboxamide-1,2,3-triazole scaffold has been designed by combination of effective moieties from potent α-glucosidase inhibitors. Most of the synthesized compounds were more potent than standard inhibitor acarbose. Among the title compounds, the most potent compounds were compounds 7j, 7k, and 7a with IC50 values of 120.2 ± 1.0, 151.1 ± 1.4, and 157.6 ± 1.6 μM, respectively (IC50 value of acarbose = 750.0 ± 10.0 μM). Docking study of the most potent compounds demonstrated that these compounds formed stable complexes with α-glucosidase active site. Anti-α-amylase assay of compounds 7j, 7k, and 7a was performed and no activity was observed. in vitro cytotoxicity assay of the latter compounds revealed that these compounds were not cytotoxic toward human normal (HDF) and cancer (MCF-7) cell lines. ADME and toxicity prediction of compounds 7j, 7k, and 7a were also performed.
- Asgari, Mohammad S.,Tahmasebi, Behnam,Mojtabavi, Somayeh,Faramarzi, Mohammad A.,Rahimi, Rahmatollah,Ranjbar, Parviz R.,Biglar, Mahmood,Larijani, Bagher,Rastegar, Hossein,Mohammadi-Khanaposhtani, Maryam,Mahdavi, Mohammad
-
-
Read Online
- Synthesis, characterization and cytotoxic activity of some new 1,2,3-triazole, oxadiazole and Aza- β-lactam Derivatives
-
A series of 1,2,3-triazole, oxadiazole and aza-β-lactam derivatives were synthesized through consecutive reaction began from o-(N-propargyl) sulfonamido benzoic acid (1a). The reaction of (1a) with absolute ethanol in the presence of concentrated H2SO4 resulted in the formation of ester derivative (2a). The product of the previous reaction was reacted with 80% hydrazine hydrate to prepare benzohydrazide derivative (3a). 1,3,4-oxadiazole compound (4a) was obtained by condensation of compound (3a) with CS2 in presence KOH. Compound (3a) react with Phenyl isocyanates to give Carboxamide derivative (5a), that Condensation either with 2,4-dimethoxybenzaldhyde and p-hydroxybenzaldehyde to prepare the Schiff bases (6a-b). The cycloaddotion of Schiff-bases (6a-b) with phenyl isocyanate gave aza-β-lactams (7a-b). Benzamide derivatives (8a-c) were prepared via the reaction of compound (1a) with aniline derivatives, such as (p-toluidine, o-nitroaniline and m-nitroaniline). In a regioselective reaction 1,4-disubstituted-1,2,3-triazole derivative (9a-j) were synthesized via the click reaction of compounds 4a,5a and (8a-c) with benzyl azide and p-bromobenzyl azide. The compounds were identified using the spectral methods shown in the work. Cytotoxic effects of some final prepared compounds were studied in one cultured cellular models (MCF7 cell line) breast cancer (at various concentrations) by MTT assay, compound (9j) showed the better cytotoxic activity among the tested compounds.
- Qader, Kany A. Abdul,Naser, Ahmed W.,Farhan, Muthanna S.,Salih, Sabah J.
-
-
Read Online
- Synthesis of 1,2,3-triazole derivatives of 4,4'-dihydroxybenzophenone and evaluation of their elastase inhibitory activity
-
The present investigation describes the synthesis of a series of novel triazole derivatives from 4,4'-dihydroxybenzophenone along with their elastase inhibitory activity. The 1,2,3-triazoles were obtained via the copper(I)-catalyzed azide-alkyne cycloaddi
- Dias, Maria C.F.,Gularte, Thiago Q.,Teixeira, Róbson R.,Santos, Jorge A.N.,Pilau, Eduardo J.,Mendes, Tiago,Demuner, Ant?nio J.,Dos Santos, Marcelo H.
-
-
Read Online
- Design, synthesis, and evaluation of metronidazole-1,2,3-triazole derivatives as potent urease inhibitors
-
A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as Helicobacter pylori urease inhibitors. All the synthesized compounds were more potent than standard inhibitor thiourea against urease. Among the synthesized compounds, compound 6f (IC50 = 1.975 ± 0.25?μM) with inhibitory activity around 11-fols more than thiourea (IC50 = 22.00 ± 0.14?μM) was the most potent compound. Kinetic study of this compound revealed that compound 6f inhibited urease in an uncompetitive mode. Based on molecular modeling study, compound 6f pointed toward the bi-nickel center and stabilized by H-bond and T-shape π–π hydrophobic interactions with the critical residues His492 and Asp633. Moreover, it anchored to the helix-turn-helix motif in the active site cavity through interaction with His593 and Arg609. Consequently, it proposed that compound 6f through stabilization of active site flap inhibited urease activity.
- Rezaei, Elham Babazadeh,Abedinifar, Fahimeh,Azizian, Homa,Montazer, Mohammad Nazari,Asadi, Mehdi,Hosseini, Samanesadat,Sepehri, Saghi,Mohammadi-Khanaposhtani, Maryam,Biglar, Mahmood,Larijani, Bagher,Amanlou, Massoud,Mahdavi, Mohammad
-
-
Read Online
- β-Cyclodextrin conjugated magnetic nanoparticles as a novel magnetic microvessel and phase transfer catalyst: Synthesis and applications in nucleophilic substitution reaction of benzyl halides
-
This paper presents a feasible protocol for the preparation of β-cyclodextrin conjugated Fe3O4 magnetic nanoparticles as an efficient microvessel and host system for nucleophilic substitution reaction of benzyl halides in water. No evidence for the formation of by-product for example isothiocyanate or benzyl alcohol was observed and the products were obtained in pure form without further purification. The characteristics results of FT-IR, XRD, TGA and SEM shows that β-CD is grafted onto Fe3O4 nanoparticles. The nanomagnetic catalyst could be readily separated from solution via application of an external magnet, allowing straightforward recovery and reuse.
- Kiasat, Ali Reza,Nazari, Simin
-
-
Read Online
- Complexation-induced circular dichroism and circularly polarised luminescence of an aggregation-induced emission luminogen
-
We here report a molecule with chiral recognition capability by a mechanism of complexation-induced circularly polarised luminescence (CPL) in the solid thin film state. A molecule (1) containing the luminogenic unit silole and chiral phenylethanamine pen
- Ng, Jason C. Y.,Liu, Jianzhao,Su, Huimin,Hong, Yuning,Li, Hongkun,Lam, Jacky W. Y.,Wong, Kam Sing,Tang, Ben Zhong
-
-
Read Online
- Discovery of novel anti-angiogenesis agents. Part 10: Multi-target inhibitors of VEGFR-2, Tie-2 and EphB4 incorporated with 1,2,3-triazol
-
VEGFR-2, Tie-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we developed a series of pyridines incorporated with 1,2,3-triazole as multi-target inhibitors based on the crystal structure alignment of the kinase domain of angiog
- Pan, Xiaoyan,Liang, Liyuan,Si, Ru,Wang, Jin,Zhang, Qingqing,Zhou, Huaxin,Zhang, Lin,Zhang, Jie
-
-
Read Online
- Synthesis, inhibition properties against xanthine oxidase and molecular docking studies of dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives
-
This study focused on synthesis various dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives under the conditions of green chemistry without the use of solvent and catalysts. Their inhibition properties were also investigated on xanthine oxidase (XO) activity. All dimethanol and dicarboxylate derivatives exhibited significant inhibition activities with IC50 values ranging from 0.71 to 2.25 μM. Especially, (1-(3-bromobenzyl)-1H-1,2,3-triazole-4,5-diyl)dimethanol (5c) and dimethyl 1-(4-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylate (6 g) compounds were found to be the most promising derivatives on the XO enzyme inhibition with IC50 values 0.71 and 0.73 μM, respectively. Moreover, the double docking procedure was to evaluate compound modes of inhibition and their interactions with the protein (XO) at atomic level. Surprisingly, the docking results showed a good correlation with IC50 [correlation coefficient (R2 = 0.7455)]. Also, the docking results exhibited that the 5c, 6f and 6 g have lowest docking scores ?4.790, ?4.755, and ?4.730, respectively. These data were in agreement with the IC50 values. These results give promising beginning stages to assist in the improvement of novel and powerful inhibitor against XO.
- Yagiz, Güler,Noma, Samir Abbas Ali,Altundas, Aliye,Al-khafaji, Khattab,Taskin-Tok, Tugba,Ates, Burhan
-
-
- New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents
-
A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.
- Gaikwad, Nikhil B.,Bansode, Sapana,Biradar, Shankar,Ban, Mayuri,Srinivas, Nanduri,Godugu, Chandraiah,Yaddanapudi, Venkata M.
-
-
- Synthesis and comparison of in vitro dual anti-infective activities of novel naphthoquinone hybrids and atovaquone
-
A principal factor that contributes towards the failure to eradicate leishmaniasis and tuberculosis infections is the reduced efficacy of existing chemotherapies, owing to a continuous increase in multidrug-resistant strains of the causative pathogens. Th
- Erasmus, Chané,Aucamp, Janine,Smit, Frans J.,Seldon, Ronnett,Jordaan, Audrey,Warner, Digby F.,N'Da, David D.
-
supporting information
(2021/07/06)
-
- Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis
-
Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.
- Bai, Rongxian,Gao, Feng,Gu, Yanlong,Li, Minghao
-
p. 7499 - 7505
(2021/10/12)
-
- Synthesis of 1,2,3-triazole benzophenone derivatives and evaluation of in vitro sun protection, antioxidant properties, and antiproliferative activity on HT-144 melanoma cells
-
Benzophenones display several biological activities, including antioxidant, anticancer, and photoprotective. Furthermore, antioxidants can minimize both ultraviolet absorption and tumor development. In the present investigation, a series of twenty-six 1,2
- Dias, Maria C.F.,de Sousa, Bianca L.,Ionta, Marisa,Teixeira, Róbson R.,Goulart, Thiago Q.,Ferreira-Silva, Guilherme á.,Pilau, Eduardo J.,dos Santos, Marcelo H.
-
p. 572 - 587
(2021/02/12)
-
- Synthesis of new derivatives of alepterolic acid via click chemistry
-
Alepterolic acid is a natural diterpenoid isolated from Aleuritopteris argentea (S. G. Gmél.) Fée, a fern with potential medicinal activity, used in China as a folk medicine to regulate menstruation and prevent cancer. Nevertheless, there are few reports
- Aisa, Haji Akber,Cao, Jianguo,Guo, Hongmei,Huang, Guozheng,Jin, Xin,Wang, Qi,Zhao, Qingjie
-
p. 917 - 925
(2021/11/16)
-
- Synthesis of 1,2,3,triazole modified analogues of hydrochlorothiazide via click chemistry approach and in-vitro α-glucosidase enzyme inhibition studies
-
The current study was aimed to discover potent inhibitors of α-glucosidase enzyme. A 25 membered library of new 1,2,3-triazole derivatives of hydrochlorothiazide (1) (HCTZ, a diuretic drug also being used for the treatment of high blood pressure) was synt
- Baheej, M. A. A.,Choudhary, M. Iqbal,Haniffa, Haroon M.,Iqbal, Shazia,Rizvi, Fazila,Siddiqui, Hina,Ullah, Saeed,Wahab, Atia-tul
-
-
- Anti-Lung Cancer Activities of 1,2,3-Triazole Curcumin Derivatives via Regulation of the MAPK/NF-κB/STAT3 Signaling Pathways
-
In this study, a series of curcumin derivatives containing 1,2,3-triazole were designed and synthesized, and their inhibitory activities against the proliferation of lung cancer cells were studied. Compound 5 k (3,4-dichlorobenzyltriazole methyl curcumin)
- Cai, Kun Yi,He, Xin Hua,Li, Zhen Wang,Liu, Kai Qiang,Sun, Xian Yu,Wang, Xin,Zhao, Yu Chao,Zhi, Tai Xin
-
-
- Synthesis and in vitro Leishmania promastigote growth inhibition efficacy of novel 4(3H)-quinazolinone derivatives
-
Molecular hybridization is an increasingly important strategy in rational drug design and development. A series of novel quinazolinone-triazole hybrids have been synthesized and their antileishmanial activity investigated. Derivatives (E)-3-(prop-2-yn-1-yl)-2-styrylquinazolin-4(3H)-one, and (E)-3-{[1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-2-styrylquinazolin-4(3H)-one were observed to moderately inhibit the growth of promastigotes. An overall lack of significant antileishmanial activity may be attributable to the poor aqueous solubility of the derivatives. Future research endeavors will focus on potential remediation by investigating the anchoring of hydrophilic moieties to the quinazolinone scaffold.
- Ralph, Greg L.,Zuma, Nonkululeko H.,Aucamp, Janine,N'Da, David D.
-
-
- Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes
-
α-Fluoroalkynes are elusive molecules due to their instability and inaccessibility. Here, we show that α-fluoronitroalkenes can serve as synthetic surrogates of α-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid (TFA). This work provides the first regioselective method to access 4-fluoro-1,5-disubstituted-1,2,3-triazoles.
- Jana, Sampad,Adhikari, Sweta,Cox, Michael R.,Roy, Sudeshna
-
supporting information
p. 1871 - 1874
(2020/02/20)
-
- Synthesis, Characterization and Cytotoxic Activity of some New 1,2,3-Triazole, Oxadiazole and Aza- β-lactam Derivatives
-
A series of 1,2,3-triazole, oxadiazole and aza-β-lactam derivatives were synthesized through consecutive reaction began from o-(N-propargyl) sulfonamido benzoic acid (1a). The reaction of (1a) with absolute ethanol in the presence of concentrated H2SO4 resulted in the formation of ester derivative (2a). The product of the previous reaction was reacted with 80% hydrazine hydrate to prepare benzohydrazide derivative (3a). 1,3,4-oxadiazole compound (4a) was obtained by condensation of compound (3a) with CS2 in presence KOH. Compound (3a) react with Phenyl isocyanates to give Carboxamide derivative (5a), that Condensation either with 2,4-dimethoxybenzaldhyde and p-hydroxybenzaldehyde to prepare the Schiff bases (6a-b). The cycloaddotion of Schiff-bases (6a-b) with phenyl isocyanate gave aza-β-lactams (7a-b). Benzamide derivatives (8a-c) were prepared via the reaction of compound (1a) with aniline derivatives, such as (p-toluidine, o-nitroaniline and m-nitroaniline). In a regioselective reaction 1,4-disubstituted-1,2,3-triazole derivative (9a-j) were synthesized via the click reaction of compounds 4a,5a and (8a-c) with benzyl azide and p-bromobenzyl azide. The compounds were identified using the spectral methods shown in the work. Cytotoxic effects of some final prepared compounds were studied in one cultured cellular models (MCF7 cell line) breast cancer (at various concentrations) by MTT assay, compound (9j) showed the better cytotoxic activity among the tested compounds.
- Abdul Qader, Kany A.,Farhan, Muthanna S.,Naser, Ahmed W.,Salih, Sabah J.
-
p. 2350 - 2360
(2020/12/21)
-
- Visible-Light-Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron-Transfer Strategy
-
Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate a novel strategy for the azide–alkyne cycloaddition reaction that involves a photoredox electron-transfer radical mechanism instead of the traditional metal-catalyzed coordination process. This newly developed photocatalyzed azide–alkyne cycloaddition reaction can be performed under mild conditions at room temperature in the presence of air and visible light and shows good functional group tolerance, excellent atom economy, high yields of up to 99 %, and absolute regioselectivity, affording a variety of 1,4-disubstituted 1,2,3-triazole derivatives, including bioactive molecules and pharmaceuticals. The use of a recyclable photocatalyst, solar energy, and water as solvent makes this photocatalytic system sustainable and environmentally friendly. Moreover, the azide–alkyne cycloaddition reaction could be photocatalyzed in the presence of a metal-free catalyst with excellent regioselectivity, which represents an important development for click chemistry and should find versatile applications in organic synthesis, chemical biology, and materials science.
- Wu, Zheng-Guang,Liao, Xiang-Ji,Yuan, Li,Wang, Yi,Zheng, You-Xuan,Zuo, Jing-Lin,Pan, Yi
-
supporting information
p. 5694 - 5700
(2020/04/24)
-
- Furfuryl Cation Induced Three-Component Reaction to Synthesize Triazole-Substituted Thioesters
-
A furfuryl cation induced three-component thioesterification reaction between thiols, 5-bromo-2-furylcarbinols and azides is reported. This metal-free method relies on the acetyl chloride/HFIP-mediated cascade formal [3+2] cycloaddition/ring-opening/thioesterification, which allows the efficient construction of a series of complex triazole-thioesters linked with an (Z)-olefin. Selenols are also suitable for this strategy. Further derivatization of thioesters highlighted the potential utility of our method.
- Zhong, Ying,Xu, Xiaoming,Xing, Qingzhao,Yang, Song,Gou, Jing,Gao, Ziwei,Yu, Binxun
-
supporting information
p. 3251 - 3256
(2020/05/25)
-
- 1,2,3-Triazole-linked 5-benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free-radical scavengers
-
In this study, benzyl-1,2,3-triazole-linked 5-benzylidene (thio)barbiturate derivatives 7a–d and 8a–h were designed as potential tyrosinase inhibitors and free-radical scavengers. The twelve derivatives were synthesized via the [3+2] cycloaddition reactio
- Ranjbar, Sara,Shahvaran, Parisa-sadat,Edraki, Najmeh,Khoshneviszadeh, Mahsima,Darroudi, Mahdieh,Sarrafi, Yaghoub,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi
-
-
- Design, synthesis, biological evaluation and molecular docking study of novel pyridoxine-triazoles as anti-Alzheimer's agents
-
A series of multi-target natural product-pyridoxine based derivatives were designed, synthesized, characterized and evaluated as anti-Alzheimer agents. In vitro testing revealed the multi-functional properties of compounds such as inhibition of acetylcholinesterase (AChE), antioxidant and metal chelation. Among the series, 5i derivative was found most potent AChE inhibitor, possess antioxidant potential and chelating metal ions. Further binding interaction of 5i with AChE was studied using molecular docking, showed interaction with both PAS and CAS site of AChE. In silico predictions were also performed to predict toxicity and ADME properties of the molecule 5i and found within drug likeness range. Therefore, 5i could be a promising multi-functional compound that can be used for further development of novel drug for Alzheimer disease.
- Bhimaneni, Saipriyanka,Flora, S. J. S.,Pal, Tiyas,Sharma, Abha
-
p. 26006 - 26021
(2020/08/21)
-
- Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2 (TMS-EDTA)
-
In the present work, novel 5-((1-benzyl-1,2,3-triazol-4-yl)methoxybenzylidene)-2-(arylamino)thiazol-4-one thiazolone incorporated triazole derivatives have been designed as tyrosinase inhibitors. The compounds were synthesized through click reaction in good yield. Moreover, the antityrosinas activity of the synthesized derivatives was evaluated. In the search for establishing a click copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction under strict conditions, in terms of a novel air-stable, a recyclable and efficient magnetic catalyst was planned for new triazole derivatives as a well-organized copper iodide supported on the functionalized Fe3O4@SiO2 core-shell (CuI/Fe3O4@SiO2(TMS-EDTA) nanoparticles). The engineered nanocatalyst synthesized for the first time and characterized by different methods, including FT-IR spectroscopy, XRD, FESEM, EDX, TEM, TGA, and BET analysis. The excellent catalytic performance in ethanol with high surface area (351.7 m2g?1) and short reaction time for diverse functional groups (120–200 min), no use of toxic solvents, reusability of the catalyst, and using eco-friendly conditions are the advantageous of this work. Moreover,the nanocatalyst can be used at least five times without any significant decrease in the yield of the reaction. The thiazolidine-triazole derivatives 9a, 9c, 9e, and 9 g showed promising tyrosinase inhibitory activity with IC50 values in the range of 5.90–9.81 μM. The compounds were found to be considerably more potent tyrosinase inhibitors than the reference inhibitor kojic acid (IC50 = 18.36 μM).
- Darroudi, Mahdieh,Ranjbar, Sara,Esfandiar, Mohammad,Khoshneviszadeh, Mahsima,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi,Sarrafi, Yaghoub
-
-
- Synthesis of 1,2,3-triazole derivatives of hydnocarpic acid isolated from carpotroche brasiliensis seed oil and evaluation of antiproliferative activity
-
Carpotroche brasiliensis is a tree native to Brazil, belonging to the family Flacurtiaceae, whose seeds contain a group of cyclopentenyl fatty acids: Gorlic (12%), chaulmugric (27%), and hydnocarpic (48.7%). These compounds are considered the main therapeutic agents in the treatment of leprosy. In the present study, a series of novel triazole compounds were obtained by conjugation between hydnocarpic acid and functionalized azides via copper(I)-catalyzed azidealkyne cycloaddition reaction (CuAAC). Hydnocarpic acid and its derivatives were tested against estrogen-positive breast carcinoma (MCF-7), hepatocellular carcinoma (HepG2), and non-small cell lung cancer (A549) cell lines. The (R)-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl-11-(cyclopent-2-en-1-yl)undecanoate (8) displayed promising antiproliferative activity against A549 cells. We demonstrated that this compound selectively inhibited the viability of A549 cell cultures. Furthermore, compound 8 inhibited the clonogenic capacity of A549 cells, and this effect was associated to its ability to inhibit cell cycle progression at G1 phase. These findings indicate that 8 is a promising antitumor agent on A549 cells and support further studies to evaluate the molecular mechanisms underlying its antiproliferative activity. In addition, hydnocarpic acid should be considered as a promising chemical prototype to obtain novel antineoplastic agents.
- De Sousa, Bianca L.,Demuner, Antonio J.,Dos Santos, Marcelo H.,Ferraz, Guilherme O.,Ferreira-Silva, Guilherme A.,Ionta, Marisa,Osorio, Liseth S.,Pilau, Eduardo J.,Silva, Evandro,Vareja?, Eduardo V. V.
-
p. 2500 - 2510
(2020/11/18)
-
- Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction
-
The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.
- Yadav, Dolly,Singh, Nem,Kim, Tae Wu,Kim, Jae Young,Park, No-Joong,Baeg, Jin-Ook
-
supporting information
p. 2677 - 2685
(2019/06/13)
-
- Synthesis of cinnamic acid derivatives and leishmanicidal activity against Leishmania braziliensis
-
Leishmania braziliensis is one of the pathogenic agents of cutaneous and mucocutanoeous leishmaniasis. There are no validated vaccines to prevent the infection and the treatment relies on drugs that often present severe side effects, which justify the efforts to find new potential antileishmanial drugs. An alternative to promote the discovery of new drugs would be the association of different chemical groups of bioactive compounds. Here we describe the synthesis and bioactivity evaluation against L. braziliensis of cinnamic acid derivatives possessing isobenzofuranone and 1,2,3-triazole functionalities. We tested 25 compounds at 10 μM concentration against extracellular promastigotes and intracellular amastigotes during macrophage infection. Most compounds were more active against amastigotes than to promastigotes. The derivatives (E)-3-oxo-1,3-dihydroisobenzofuran-5-yl-(3,4,5-trimethoxy) cinnamate (5c), (1-(3,4-difluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl cinnamate (9g), and (1-(2-bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl cinnamate (9l) were the most effective presenting over 80% toxicity on L. braziliensis amastigotes. While compound 5c is a cinnamate with an isobenzofuranone portion, 9g and 9l are triazolic cinnamic acid derivatives. The action of these compounds was comparable to amphotericin B used as positive control. Ultrastructural analysis revealed that 5c-treated parasites showed impaired cytokinesis and apoptosis triggering. Taken together, these results highlight the potential of cinnamic acid derivatives in development of novel anti-leishmanial drugs.
- Rodrigues, Michelle Peixoto,Tomaz, Deborah Campos,?ngelo de Souza, Luciana,Onofre, Thiago Souza,Aquiles de Menezes, Wemerson,Almeida-Silva, Juliana,Suarez-Fontes, Ana Márcia,Rogéria de Almeida, Márcia,Manoel da Silva, Adalberto,Bressan, Gustavo Costa,Vannier-Santos, Marcos André,Rangel Fietto, Juliana Lopes,Teixeira, Róbson Ricardo
-
-
- Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation
-
1,2-Amino alcohols and α-aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. cis-Selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcohols or α-amino ketones using hydrogenation or hydrolysis, respectively.
- Greenwood, Phillip D. G.,Grenet, Erwann,Waser, Jerome
-
supporting information
p. 3010 - 3013
(2019/02/07)
-
- Synthesis and characterization of active cuprous oxide particles and their catalytic application in 1,2,3-triazole synthesis via alkyne-azide cycloaddition reaction in water
-
Active cuprous oxide materials are synthesized from CuSO4.5H2O using sodium stannite as reducing agent in the presence of various stabilizers, viz., cetyl trimethyl ammonium bromide, sodium dodecyl sulphate, and polyvinyl pyrrolidone
- Sawkmie, Micky Lanster,Paul, Dipankar,Kalita, Gitumoni,Agarwala, Khushboo,Maji, Pradip K.,Chatterjee, Paresh Nath
-
p. 3277 - 3288
(2019/11/11)
-
- Carcarinic acid-1, 2, 3- based triazole compound as well as preparation method and application thereof (by machine translation)
-
The method comprises the following steps: firstly 1, 2, 3 - oxidizing and opening the carbon- carbon double bond of the, carcarinic acid into methylene to, obtain carcarinic acid (not shown, in the technical field of, organic 3 - synthesis), Wolf - Kishner - 1, 2, 3 - 1, 2, 3 - 1, 2, 3 - 3 . (by machine translation)
- -
-
Paragraph 0181-0183
(2019/12/25)
-
- Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry
-
The over-expression of aminopeptidase N on diverse malignant cells is associated with the tumor angiogenesis and metastasis. In this report, one new series of leucine ureido derivatives containing the triazole moiety was designed, synthesized and evaluated as APN inhibitors. Among them, compound 13v showed the best APN inhibition with an IC50 value of 0.089 ± 0.007 μM, which was two orders of magnitude lower than that of bestatin (IC50 = 9.4 ± 0.5 μM). Compound 13v also showed dose-dependent anti-angiogenesis activities. Even at the lower concentration (10 μM), compound 13v presented similar anti-angiogenesis activity compared with bestatin at 100 μM in both the human umbilical vein endothelial cells (HUVECs) capillary tube formation assay and the rat thoracic aorta rings test. Moreover, compared with bestatin, 13v exhibited comparable, if not better in vivo anti-metastasis activity in a mouse H22 pulmonary metastasis model.
- Cao, Jiangying,Ma, Chunhua,Zang, Jie,Gao, Shuai,Gao, Qianwen,Kong, Xiujie,Yan, Yugang,Liang, Xuewu,Ding, Qin'ge,Zhao, Chunlong,Wang, Binghe,Xu, Wenfang,Zhang, Yingjie
-
p. 3145 - 3157
(2018/06/01)
-
- Synthesis and leishmanicidal activity of eugenol derivatives bearing 1,2,3-triazole functionalities
-
In this paper, it is described the synthesis and the evaluation of the leishmanicidal activity of twenty-six eugenol derivatives bearing 1,2,3-triazole functionalities. The evaluation of the compounds on promastigotes of Leishmania amazonensis (WHOM/BR/75/Josefa) showed that eugenol derivatives present leishmanicidal activities with varying degrees of effectiveness. The most active compound, namely 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(4-methylbenzyl)-1H-1,2,3-triazole (7k) (IC50 = 7.4 ± 0.8 μmol L?1), also targeted Leishmania parasites inside peritoneal macrophages (IC50 = 1.6 μmol L?1) without interfering with cell viability. The cytotoxicity of 7k against macrophage cells presented IC50 of 211.9 μmol L?1 and the selective index was equal to 132.5. Under similar conditions, compound 7k was more effective than glucantime and pentamidine, two drugs currently in the clinic. In addition, theoretical calculations showed that this compound also presents most physicochemical and pharmacokinetic properties within the ranges expected for orally available drugs. It is believed that eugenol bearing 1,2,3-triazole functionalities may represent a scaffold to be explored toward the development of new agents to treat leishmaniasis.
- Teixeira, Róbson Ricardo,Gazolla, Poliana Aparecida Rodrigues,da Silva, Adalberto Manoel,Borsodi, Maria Paula Gon?alves,Bergmann, Bartira Rossi,Ferreira, Rafaela Salgado,Vaz, Boniek Gontijo,Vasconcelos, Géssica Adriana,Lima, Wallace Pacienza
-
p. 274 - 286
(2018/02/10)
-
- Synthesis of potential anti-Trypanosoma cruzi azole-naftifine analogues by azide–alkyne click reaction
-
Twenty novel azole-naftifine analogues were obtained using azide–alkyne click reaction. Five of them were more potent than the positive control naftifine revealing an unprecedented antiproliferative effects against Trypanosoma cruzi.
- Callegario Zacchi, Carlos Henrique,Maior Federighi, Stephanie Souto,Ramos Gadelha, Fernanda,Terra Martins, Felipe,Brondi Alves, Rosemeire,de Fátima, ?ngelo
-
p. 195 - 197
(2018/04/05)
-
- Pyridine compound and application
-
The invention provides a pyridine compound and application. Based on the find of VEGFR-2 (Vascular Endothelial Growth Factor Receptor-2), EphB4 (Ephrin type-B receptor 4) and TIE-2 compensatory activation, biphenyl arylurea is used as a novel leading comp
- -
-
Paragraph 0033; 0034
(2018/11/03)
-
- Pyrazole compounds and application thereof
-
The invention provides pyrazole compounds and application thereof. Based on discovery of compensatory activation of VEGFR-2, EphB4 and TIE-2 and taking biphenyl aryl urea as a novel primer, conservative conformation of active sites of three kinds of recep
- -
-
Paragraph 0023; 0032
(2018/11/04)
-
- Pyrimidine compound and application thereof
-
The invention discloses a pyrimidine compound and an application thereof. Based on the discovery of compensatory activation of VEGFR-2, EphB4 and TIE-2, biphenylarylurea is used as a novel lead compound, the conservative conformations of three receptor ac
- -
-
Paragraph 0034; 0035
(2019/01/07)
-
- Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents
-
A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.
- Cui, Fei-Hu,Chen, Jing,Mo, Zu-Yu,Su, Shi-Xia,Chen, Yan-Yan,Ma, Xian-Li,Tang, Hai-Tao,Wang, Heng-Shan,Pan, Ying-Ming,Xu, Yan-Li
-
supporting information
p. 925 - 929
(2018/02/22)
-
- [3 + 3] Cycloaddition of azides with in situ formed azaoxyallyl cations to synthesize 1,2,3,4-Tetrazines
-
A formal [3 + 3] cycloaddition reaction between azides and in situ formed azaoxyallyl cations has been realized. This reaction provided an efficient and practical pathway to synthesize 1,2,3,4-tetrazines in good yields under mild conditions. Biologically active molecules could also be well compatible, highlighting the potential value of this reaction.
- Xu, Xiaoying,Zhang, Kaifan,Li, Panpan,Yao, Hequan,Lin, Aijun
-
supporting information
p. 1781 - 1784
(2018/04/14)
-
- A convergent formal [4 + 2] cycloaddition of 1,6-diynes and benzyl azides: Construction of spiro-polyheterocycles
-
A convergent formal [4 + 2] cycloaddition reaction for the construction of structurally appealing spiro-tetrahydroquinolines has been developed, in which, a one-pot reaction is established for the in situ generation of two reagents, a cyclic alkyne and an
- Bao, Ming,Lu, Wei,Su, Han,Qiu, Lihua,Xu, Xinfang
-
supporting information
p. 3258 - 3265
(2018/05/22)
-
- An efficient synthesis of novel triazoles incorporating barbituric motifs via [3+2] cycloaddition reactions: An experimental and theoretical study
-
In this work, the synthesis of novel triazole derivatives with barbituric motifs in good yields is described. The alkyne was prepared through the Knoevenagel reaction of barbituric derivatives with ortho and para O-propargylated hydroxybenzaldehyde. The m
- Darroudi, Mahdieh,Sarrafi, Yaghoub,Hamzehloueian, Mahshid
-
p. 821 - 835
(2018/08/21)
-
- Natural phosphate-supported Cu(ii), an efficient and recyclable catalyst for the synthesis of xanthene and 1,4-disubstituted-1,2,3-triazole derivatives
-
Cu(NO3)2 supported on natural phosphate, Cu(ii)/NP, was prepared by co-precipitation and applied as a heterogeneous catalyst for synthesizing xanthenes (2-3 h, 85-97%) through Knoevenagel-Michael cascade reaction of aromatic aldehydes with 1,3-cyclic diketones in ethanol under refluxing conditions. It was further used for regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles (1-25 min, 95-99%) via a three-component reaction between organic halides, aromatic alkynes and sodium azide in methanol at room temperature. The proposed catalyst, Cu(ii)/NP, was characterized using X-ray fluorescence, X-ray diffraction, Fourier-transform infrared spectroscopy, scanning electron microscopy, Brunauer-Emmett-Teller, Barrett-Joyner-Halenda and inductively coupled plasma analyses. Compared to other reports in literature, the reactions took place through a simple co-precipitation, having short reaction time (85%), and high recyclability of catalyst (>5 times) without significant decrease in the inherent property and selectivity of catalyst. The proposed protocols provided significant economic and environmental advantages.
- Amini, Abbas,Fallah, Azadeh,Cheng, Chun,Tajbakhsh, Mahmood
-
p. 41536 - 41547
(2019/01/03)
-
- Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study
-
A library of 1,2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Nawale, Laxman,Arkile, Manisha,Sarkar, Dhiman,Shingate, Bapurao B.
-
p. 413 - 421
(2017/02/03)
-
- CuI@UiO-67-IM: A MOF-Based Bifunctional Composite Triphase-Transfer Catalyst for Sequential One-Pot Azide-Alkyne Cycloaddition in Water
-
A CuI-loaded and n-pentadecyl-attached imidazolium salt decorated UiO-67-type metal-organic framework (CuI@UiO-67-IM, 2) based on a new premodified ligand L (n-pentadecyl-attached imidazolium (IM) decorated dicarboxylic acid) and ZrCl4 is reported. Compound 2 can be a bifunctional composite heterogeneous phase-transfer catalyst to promote the azide-alkyne cycloaddition (H2O, air, 80 °C) from corresponding halogenated compounds and sodium azide as a sequential one-pot procedure with high yields and excellent regioselectivity.
- Hu, Yu-Hong,Wang, Jian-Cheng,Yang, Song,Li, Yan-An,Dong, Yu-Bin
-
supporting information
p. 8341 - 8347
(2017/07/22)
-