- Solvatochromic and solid-state emissive azlactone-based AIEE-active organic dye: Synthesis, photophysical properties and color-conversion LED application
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Here, we report one-pot synthesis of a new azlactone-based dye bearing isoxazole moiety as a donor group (i.e., Dye-Iso), which displays fluorescence emission both in solution and solid-state, and a systematic study of its photophysical properties. The an
- Olutas, Murat,Sag?rl?, Ak?n
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- Synthesis, cytotoxic activity and binding model analysis of novel isoxazole-docetaxel analogues with C3′-N modification
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Structure–activity relationship (SAR) studies confirm that modifications at C-3′ position can lead to the development of highly potent novel taxoids. We designed and synthesized a series of novel isoxazole-docetaxel analogues A1–A5 by introducing isoxazol
- Chen, Ming,Liu, Jiyuan,Tian, Zhen,Liu, Xueying,Zhang, Shengyong
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p. 1355 - 1365
(2018/04/10)
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- Synthesis and SAR of new isoxazole-triazole bis-heterocyclic compounds as analogues of natural lignans with antiparasitic activity
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Despite the impressive scientific and technological advances of recent decades, no effective treatment is currently available for Chagas disease. Our research group has been studying the design and synthesis of analogues of natural lignans aiming to identify compounds with antiparasitic activity. This article reports the synthesis of 42 novel bis-heterocyclic derivatives and the structure-activity relationship study conducted based on results of biological assays against Trypanosoma cruzi amastigotes. Thirty-seven compounds were active, and eight of them had GI50 values lower than 100 μM (GI50 88.4–12.2 μM). A qualitative structure activity relationship study using three dimensional descriptors was carried out and showed a correlation between growth inhibitory potency and the presence of bulky hydrophobic groups located at rings A and D of the compounds. Compound 3-(3,4-dimethoxyphenyl)-5-((4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl)methyl)isoxazole (31) was the most active in the series (GI50 12.2 μM), showing, in vitro, low toxicity and potency similar to benznidazole (GI50 10.2 μM). These results suggest that this compound can be a promising scaffold for the design of new trypanocidal compounds.
- Zimmermann, Lara A.,de Moraes, Milene H.,da Rosa, Rafael,de Melo, Eduardo B.,Paula, Fávero R.,Schenkel, Eloir P.,Steindel, Mario,Bernardes, Lílian S.C.
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p. 4850 - 4862
(2018/09/11)
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- Synthesis and in vitro biological evaluation of novel coumarin derivatives containing isoxazole moieties on melanin synthesis in B16 cells and inhibition on bacteria
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A novel series of coumarin derivatives 6a–o, bearing isoxazole moieties were designed and synthesized. After that, they were evaluated for melanin synthesis in murine B16 cells and inhibitory effect on the growth of CA (Candida albicans), EC (Escherichia coli), SA (Staphylococcus aureus). It was found that eleven compounds (6b–f, 6j–o) showed a better activity on melanin synthesis than positive control (8-MOP). Among them, compounds 6d (242%) and 6f (390%), with nearly 1.6 and 2.6-fold potency compared with 8-MOP (149%) respectively, were recognized as the most promising candidate hits for further pharmacological study of anti-vitiligo. Seven halogen substituted compounds exhibited moderate antimicrobial activity against CA. It is interesting that 6e–f and 6l–m, which had two halogens on the benzene showed a comparable activity with Amphotericin B against CA. The evaluation of melanin synthesis in B16 cells and inhibitory effect on bacteria of above structurally diverse derivatives had also led to an outline of structure-activity relationship.
- Pang, Guang Xian,Niu, Chao,Mamat, Nuramina,Aisa, Haji Akber
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supporting information
p. 2674 - 2677
(2017/05/29)
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- Synthesis of new arylisoxazole–oxindole conjugates as potent antiproliferative agents
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A new series of arylisoxazole–oxindole derivatives (6a–r) were synthesized and evaluated for their antiproliferative activity against human cancer cell lines including non-small cell lung (A549), cervical (HeLa), breast (MCF-7), and prostate (DU-145) cancer cell lines. The synthesized compounds (6a–r) demonstrated excellent to moderate cytotoxicity with IC50 values ranging from 0.82 to 3.69?μm. Some new compounds (6m–r) exhibited profound cytotoxicity better or similar to positive control. More particularly, the compound 6q possesses donating substituent like methoxy group presented at 5-position on D ring exhibited remarkable antiproliferative activity against A-549 (lung cancer) with an IC50 value 0.82?μm. Further studies to determine the mechanistic aspects of these conjugates are under progress.
- Kumar, Gajjela Bharath,Bukhari, Syed Nasir Abbas,Qin, Hua-Li
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p. 634 - 638
(2017/04/06)
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- Ultrasonic-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles via various terminal acetylenes and azide and their quorum sensing inhibition
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An efficient synthesis of 1,4-disubstituted 1,2,3-triazole derivatives was studied. 1,4-Disubstituted 1,2,3-triazoles containing isoxazole and thymidine structures were synthesized in 84–96% yields starting from various terminal isoxazole ether alkynes and β-thymidine azide derivatives via a 1,3-dispolar cycloaddition using copper acetate, sodium ascorbate as the catalyst under ultrasonic assisted condition. All the target compounds were characterized by HRMS, FT-IR, 1H NMR and 13C NMR spectroscopy. Furthermore, the quorum sensing inhibitory activities of synthesized compounds were evaluated with Chromobacterium violaceum (C. Violaceum CV026) based on their inhibition of violacein production, with compound C10-HSL as a positive control. The compounds 8a, 8c and 8f exhibited considerable levels of inhibitory activity against violacein production, and IC50 values were 217?±?19, 223?±?20 and 42.8?±?4.5?μM, respectively, which highlighted the potential of these compounds as lead structures for further research towards the development of novel QS inhibitors.
- Zhang, Da-wei,Zhang, Yu-min,Li, Jing,Zhao, Tian-qi,Gu, Qiang,Lin, Feng
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p. 343 - 353
(2016/12/23)
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- Design and synthesis of a new series of 3,5-disubstituted isoxazoles active against Trypanosoma cruzi and Leishmania amazonensis
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Chagas disease and leishmaniasis are neglected tropical diseases (NTDs) endemic in developing countries. Although there are drugs available for their treatment, efforts on finding new efficacious therapies are continuous. The natural lignans grandisin (1)
- da Rosa, Rafael,de Moraes, Milene H?ehr,Zimmermann, Lara Almida,Schenkel, Eloir Paulo,Steindel, Mario,Bernardes, Lílian Sibelle Campos
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- A rapid and efficient solvent-free microwave-assisted synthesis of pyrazolone derivatives containing substituted isoxazole ring
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An efficient synthesis of 4-substituted pyrazolone derivatives was developed. 4-Substituted pyrazolone derivatives were synthesized in 78-97% yields starting from various 3-substituted isoxazole-5-carbaldehydes, ethyl acetoacetate and hydrazine under micr
- Zhang, Dawei,Zhang, Yumin,Zhao, Tianqi,Li, Jing,Hou, Yaya,Gu, Qiang
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p. 2979 - 2987
(2016/05/19)
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- Synthesis and bioactivity of novel isoxazole chalcone derivatives on tyrosinase and melanin synthesis in murine B16 cells for the treatment of vitiligo
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A new series of chalcone derivatives 1–18, bearing isoxazole moieties were designed and synthesized, and biologically evaluated for their activity on mushroom tyrosinase and melanin synthesis in murine B16 cells. The result indicated that most of prepared compounds 1–18 showed potent activating effect on tyrosinase, especially for 1–2, 4, 6–7, 9 and 15. Among them, compounds 2, 4 and 9 demonstrated the best activity with EC50?=?1.3, 2.5 and 3.0?μmol·L?1respectively, much better than the positive control 8-methoxypsoralan (8-MOP, EC50?=?14.8?μmol·L?1); In B16 cells, all the tested compounds exhibited a stronger activity on melanogenesis than 8-MOP (with the value of 115%). It was interesting that derivatives substituted with halogen (1, 2, 4, 5, 7, 9) were generally more potent. Compounds 2 (463%) and 18 (438%) with 3 and 4-fold potency compared with 8-MOP respectively, were recognized as the most promising candidate hits for further pharmacological study of anti-vitiligo.
- Niu, Chao,Yin, Li,Nie, Li Fei,Dou, Jun,Zhao, Jiang Yu,Li, Gen,Aisa, Haji Akber
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p. 5440 - 5448
(2016/10/24)
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- Synthesis of (Z)-(arylamino)-pyrazolyl/isoxazolyl-2-propenones as tubulin targeting anticancer agents and apoptotic inducers
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A new class of pyrazole and isoxazole conjugates were synthesized and evaluated for their cytotoxic activity against various human cancer cell lines. These compounds have shown significant cytotoxicity with lower IC50 values. FACS results revealed that A549 cells treated with these compounds arrested cells at the G2/M phase of the cell cycle apart from activating cyclin B1 protein levels. Particularly, compounds 9a and 9b demonstrated a remarkable inhibitory effect on tubulin polymerization and showed a pronounced inhibitory effect on tubulin polymerization with IC50 values of 1.28 μM and 0.28 μM respectively, whereas nocodazole, a positive control, has shown lower antitubulin activity with an IC50 value of 2.64 μM. Furthermore, these compounds induced apoptosis by loss of mitochondrial membrane potential, propidium iodide (PI) staining and the activation of caspase-3. Results of a fluorescence based competitive colchicine binding assay suggest that these conjugates bind successfully at the colchicine binding site of tubulin. These investigations reveal that such conjugates containing pyrazole with a trimethoxy phenyl ring and indole moieties have potential for the development of newer chemotherapeutic agents. This journal is
- Kamal, Ahmed,Reddy, Vangala Santhosh,Shaik, Anver Basha,Kumar, G. Bharath,Vishnuvardhan,Polepalli, Sowjanya,Jain, Nishant
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p. 3416 - 3431
(2015/03/18)
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- Design and synthesis of pyrazole/isoxazole linked arylcinnamides as tubulin polymerization inhibitors and potential antiproliferative agents
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As pyrazole and isoxazole based derivatives are well-known for displaying a considerable biological profile, an attempt has been made to unravel their cytotoxic potential. In this context, a number of pyrazole/isoxazole linked arylcinnamide conjugates (15
- Kamal, Ahmed,Shaik, Anver Basha,Rao, Bala Bhaskara,Khan, Irfan,Bharath Kumar,Jain, Nishant
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p. 10162 - 10178
(2015/10/28)
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- Efficient solvent-free synthesis of bis(indolyl)methanes on SiO2 solid support under microwave irradiation
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An efficient synthesis of bis(indolyl)methanes was developed. Bis(indolyl)methanes were synthesized starting from various aromatic aldehydes with indole under microwave irradiation and solvent-free conditions (85-98 %). Solid support SiO2 was found to possess favorable catalytic and dispersancy parameters for the condensation reaction. Moreover, novel bis(indolyl)methanes containing an isoxazole ring were synthesized via this method in excellent yields (> 94 %) using 3-substituted isoxazole-5-carbaldehydes and indole.
- Zhang, Da-Wei,Zhang, Yu-Min,Zhang, Yi-Liang,Zhao, Tian-Qi,Liu, Hong-Wei,Gan, Yuan-Ming,Gu, Qiang
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p. 470 - 478
(2015/01/30)
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- Efficient synthesis of bis-isoxazole ethers via 1,3-dipolar cycloaddition catalysed by Zn/Zn2+ and their antifungal activities
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An efficient method was developed for synthesising isoxazoles. A series of novel bis-isoxazole ether compounds VI, VII and VIII were synthesised starting from different substituted aldehydes (I) via a 1,3-dispolar cycloaddition using Zn/Zn2+ as a catalyst; these were characterised by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. In addition, the antimicrobial properties of the synthesised products were investigated. The synthesised compounds exhibited significant antifungal activities in comparison with the standard drugs, fluconazole and itraconazole. It was found that Candida albicans was sensitive to 2-substituted phenyl bis-isoxazole ethers bearing pyridyl.
- Zhang, Da-Wei,Lin, Feng,Li, Bo-Chao,Liu, Hong-Wei,Zhao, Tian-Qi,Zhang, Yu-Min,Gu, Qiang
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p. 1500 - 1511
(2015/09/15)
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- Copper-doped silica cuprous sulfate (CDSCS) as a highly efficient heterogeneous nano catalyst for synthesis of 3,5-disubstituted isoxazoles
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A facile and highly efficient protocol for 1,3-dipolar cycloaddition of in situ generated nitrile oxides with terminal alkynes catalyzed by copper-doped silica cuprous sulfate (CDSCS) as a new and convenient heterogeneous nano catalyst is described. In th
- Soltani Rad,Behrouz,Faghihi
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p. 361 - 367
(2014/04/03)
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- NITROGEN-CONTAINING AROMATIC HETEROCYCLYL COMPOUND
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The present invention provides a compound having excellent regulating action on blood lipid level. The present invention provides a compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof, etc., wherein A represents a 5-membered nitrogen-containing aromatic heterocyclyl group; R1 represents COOH or the like; each R2 represents an alkyl or the like; each R3 represents an optionally substituted phenyl, an optionally substituted phenylalkyl, or the like; m represents 0, 1, 2, or 3; n represents 0 or 1; each of R4, R5, R6, and R7 represents H, an alkyl, or the like; and B represents an optionally substituted naphthyl, an optionally substituted aromatic heterocyclyl, or a group represented by the following formula (II) wherein each of B1 and B2 represents an optionally substituted phenyl or an optionally substituted aromatic heterocyclyl.
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Page/Page column 78
(2011/04/25)
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- Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry
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Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.
- Yermolina, Maria V.,Wang, Jizhen,Caffrey, Michael,Rong, Lijun L.,Wardrop, Duncan J.
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p. 765 - 781
(2011/04/15)
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- Design, synthesis and antibacterial activity of novel N-formylhydroxylamine derivatives as PDF inhibitors
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A new series of N-formylhydroxylamines 11a-i have been synthesized through a multi-step protocol starting from diethyl malonate. These compounds have been structurally characterized by IR, 1H NMR and HRMS. All the synthesized compounds 11a-i have been screened for antibacterial activities. All the compounds are found to exhibit potent in vitro inhibitory activity against Staphylococcus aureus and relatively weak antibacterial activity against Klebsiella pneumoniae.
- Yin,Jia,Zhao,Xu,Tang,Wang
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p. 695 - 703
(2011/07/29)
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- One-pot synthesis of (3-phenylisoxazol-5-yl) methanol derivatives under ultrasound
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An ultrasonic-assisted, one-pot, efficient, convenient procedure for the synthesis of (3-phenylisoxazol-5-yl)methanol derivatives has been developed. (3-Phenylisoxazol-5-yl)-methanol derivatives with biological and pharmaceutical property have been synthe
- Shen, Chuansheng,Zhang, Yumin,Gan, Yuanming,Zhao, Tianqi,Gu, Qiang
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experimental part
p. 278 - 281
(2012/04/18)
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- Concise synthesis and antimicrobial activities of new substituted 5-isoxazolpenicillins
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The synthesis of a series of new 5-isoxazolpenicillins is described, which were obtained by coupling substituted isoxazoles with 6-APA. Concise large-scale synthesis of 3,5-disubstituted isoxazoles by 1,3-dipolar cycloaddition using copper(I) as catalyst was also investigated. Representative compounds were assayed for antimicrobial activities, showing satisfactory antimicrobial activities against Gram-negative bacteria.
- Wang, Xi-Zhao,Jia, Jiong,Zhang, Yan,Xu, Wei-Ren,Liu, Wei,Shi, Fang-Niu,Wang, Jian-Wu
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p. 643 - 652
(2008/03/11)
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- One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles
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3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional
- Hansen, Trond V.,Wu, Peng,Fokin, Valery V.
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p. 7761 - 7764
(2007/10/03)
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- Synthesis of isoxazolines and isoxazoles using poly(ethylene glycol) as support
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A general method for the liquid-phase syntheses of isoxazoles and isoxazolines through a 1,3-dipolar cycloaddition is described. The poly(ethylene glycol) (PEG)-supported alkyne 2 or alkene 6 reacted with nitrile oxides generated in situ from aldoximes 3, followed by cleavage from the PEG, to give isoxazoles or isoxazolines in good yield and purity.
- Shang, Yong-Jia,Wang, Yan-Guang
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p. 1663 - 1668
(2007/10/03)
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