A series of novel 2-(2-cyanophenyl)-N-phenylacetamide derivatives 3(a-u) were designed and synthesized via selective amidation of methyl-2-(2-cyanophenyl)acetates over amidine formation by using AlMe3 as catalyst in good yields. All the newly synthesized derivatives were well characterized by 1H NMR, 13C NMR, FTIR and HRMS spectral techniques. All the synthesized title compounds were evaluated for their in vitro anticancer activity against three cancer cell lines. Among all compounds, 3i (IC50?=?1.20 μM, IC50?=?1.10 μM), 3j (IC50?=?0.11 μM, IC50?=?0.18 μM), 3o (IC50?=?0.98 μM, IC50?=?2.76 μM) showed excellent inhibitory activity than the standard Etoposide (IC50?=?2.11 μM, IC50?=?3.08 μM) against MCF-7 and A-549 cell lines, respectively. Docking analysis of all the compounds with the human topoisomerase II revealed that the compound 3j fitted well in the active site pocket, showing the best docking score of 158.072 kcal/mol.
A novel series of bis-1,2,4-oxadiazole fused benzothiazole derivatives 9a–9j are synthesized, and their structures are confirmed by 1H and 13C NMR, and mass spectral data. All products are evaluated in vitro for their anticancer potential against a panel of four human cancer cell lines such as lung cancer (A549), breast carcinoma (MCF-7), melanoma (A375), and colon cancer (HT-29). The combretastatin-A4 is used as standard drug. All compounds 9a–9j exhibit significant anticancer activity with IC50 values ranging from 0.11±0.01 to 14.6±3.89 μM. Among these, compounds 9a–9d, 9h, 9i demonstrate more potent activity than the control.
Abstract A series of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-thiones were synthesized by the reaction of substituted 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones with Lawesson's Reagent in toluene under standard reaction conditions. All synthesized compounds were characterized by IR, NMR (1H and 13C), and mass spectra. Moreover, 2D-NMR (HOMOCOSY, HSQC, and HMBC) studies were also performed for compound 10b. The synthesized compounds were also screened for their antibacterial activities. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures.]相似文献
AbstractTwo new eremophilane sesquiterpenoides, 6α,9α-dihydroxyeremophilenolide (1), and 1β,10β-dihydroxyeremophilenolide (2), along with ten known eremophilane sesquiterpenoides (3–12) were isolated from the aerial parts of Ligularia dictyoneura (Franch.) Hand.-Mazz. Their structures were elucidated by means of extensive spectroscopic analysis. Compounds 3–6 were assessed for their cytotoxicity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that they had no activity. 相似文献
AbstractA novel series pyrrolo[3,2-b]pyridine-3-carboxamide linked 2-methoxypyridine derivatives have been designed, synthesized and confirmed by FT-IR, 1H NMR, 13C NMR, 19F NMR, MS, and elemental analysis. The synthesized compounds were screened for their antitubercular activity using microplate alamar blue assay method and antibacterial activity. Among the tested compounds, 4- fluorophenyl (8m), 4- chlorophenyl (8n) and 4-methoxyphenyl (8i) showed potent anti-TB activity (3.12?µg/mL) in comparison with reference drug, Pyrazinamide ((3.12?µg/mL). In addition, all compounds were docked into DprE1 (PDB code: 4KW5) to explore their binding interactions at the active site. The compounds exhibited essential key interactions as that of reported DprE1 inhibitors and hence, the synthesized compounds may be considered as molecular scaffolds for antitubercular activity. Compounds, 4-chlorophenyl (8n) and 4-flurophenyl (8m) showed significant antibacterial activity against Escherichia coli and Staphylococcus aureus strains. In silico prediction of toxicities, druglikeness and drug score profiles of the tested compounds are promising. 相似文献
AbstractA series of amide derivatives of azaindole-oxazoles (11a-n) were designed and synthesized and their structures were confirmed by 1HNMR, 13CNMR and mass spectral analysis. Further, these derivatives were screened for their anticancer activity against human cancer cell lines viz; MCF7 (breast), A549 (lung) and A375 (melanoma). In vitro anticancer activity screening indicated that most of the hybrids exhibited potent inhibitory activities in a variety of cancer cell lines. Among the compounds 11d, 11e, 11f, 11j, 11k, 11l, 11m, and 11n were exhibited more potent activity than standard, in those mainly two compounds 11m and 11j were exhibited excellent activity in MCF-7 cell line with IC50 values 0.034 and 0.036?µM. Moreover, all these compounds were carried out their molecular docking studies on EGFR receptor results indicated that two potent compounds 11m and 11j were strongly binds to protein EGFR (PDB ID: 4hjo). It was found that the energy calculations were in good agreement with the observed IC50 values. 相似文献
Abstract 9-Oxo-10-acridineacetic acid, CMA, has been found to be an interferon inducer.1-5 Moreover, it has been shown that some analogues of CMA may significantly enhance the titres of serum interferon in mice. Among them, the sodium salt CMANa, (I), was synthesized and its biological activity was recently analysed.6 This work presents the results of a study on the interaction of CMA- with Co(II), Ni(II), Cu(II), and Zn(II). 相似文献
Abstract Chloranil (2,3,5,6-teterachloro-p-benzoquinone) reacts with certain aminoglycosoide antibiotics in borate buffer at pH 9.0 to give charge-transfer complexes. The complexes possese an absorption maxmum at about 350 nm with molar absorptivities of 3.78 × 105, 4.69 × 105, 5.0 × 105 and 7.08 × 105 for kanamycin, neomycin B, amikacin and tobramycin reepectively, These high intensity of the chargetransfor band and confirmity to beer's law enabled assay of these antibiotics with appreciable sensitivity and good precision. Aminoglycosoide antibiotics have a broad spectrum of activity against both gram-negative and gram-positive bacteria. The official compendia1,2 recommend the microbiological assay for their evalution. The high experimental errors in microbiological estimation heae been reported3. Numerous spectrophotometric, fluorometric and chromatographic techniques for their quantitation have been thoroughly reviewed4,5. Substituted quinones such as 2,5 dichloroquinone6, 7,7,8,8-tetracyanoqulnone dimethane7, flouranil8 are used as TT- acceptors with various electron donors to form charge-transfer(CT) complexes and radical ions9,10. Some aromatic amines11,12 and aminoacids have been determined with chloranil13–15. The present work describes the utility of chloranil for the spectrophotometric determination of kanamycin sulphate, amikacin sulphate tobramycin aulphate, and neorycin B sulphate (framycetine sulphate) either in bulk or in their reepective doaage forms. 相似文献
Twelve coordinate lanthanide (III) complexes with the general composition [Ln L3Xn(H2O)n] where Ln = Pr(III), Sm(III), Eu (III), Gd (III), Tb (III), Dy (III), X = Cl?1, NO3?2, n = 2–7, and L is 1-(4-chlorophenyl)-3-(4-fluoro/hydroxyphenyl)prop-2-en-1- thiosemicarbazone have been prepared. The lanthanide complexes (5) were derived from the reaction between 1-(4-chlorophenyl)-3-(4-fluoro/hydroxyphenyl)prop-2-en-1-thiosemicarbazone (4) with an aqueous solution of lanthanide salt. Chalcone thiosemicarbazone ligand (4) was prepared by the reaction of [1-(4-chlorophenyl)-3-(4-fluoro/hydroxyphenyl)]prop-2-enone (chalcone) (3) with thiosemicarbazide in the presence of hot ethanol. All the lanthanide-ligand 1:3 complexes have been isolated in the solid state, are stable in air, and characterized on the basis of their elemental and spectral data. Thiosemicarbazone ligands behave as bidentate ligands by coordinating through the sulfur of the isocyanide group and nitrogen of the cyanide residue. The probable structure for all the lanthanide complexes is also proposed. The chalcone thiosemicarbazone ligands and their lanthanide complexes have been screened for their antifungal and antibacterial studies. Some of the synthesized lanthanide complexes have shown enhanced activity compared with that of the free ligand. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. 相似文献
Abstract A series of fluorophenylpyrazole-picolinamide derivatives were synthesized in high yields using a cross-coupling reaction catalyzed by in situ formed palladium-N-heterocyclic carbenes (Pd-NHCs). The synthesized novel derivatives were evaluated for in vitro anticancer activity against a panel of four human tumor cell lines, HeLa (cervical), A-549 (lung), MCF-7 (breast), and IMR-32 (neuroblastoma). Four compounds, 11c, 11e, 11j, and 11k, showed growth inhibition (low µM) comparable with the standard drug cisplatin, providing a preliminary structure–activity relationship for the series. The present procedure is operationally simple and works with a wide range of substrates and may thus be useful in further compound optimization. 相似文献
1,4-Naphthoquinones (1,4-NQ) have been reported to possess a variety of pharma-cological properties including antibacterial, antifungal, antiviral, anti-inflammatory, anti-artherosclerotic, and anticancer effects. In this study, new N- and S,S-substituted-1,4-NQ derivatives were synthesized in excellent yields and were completely characterized by spectroscopic analysis IR, NMR (1H and 13C), MS and microanalysis. The cytotoxic activities of 1,4-NQ derivatives were examined against to A-549, DU145, HCT-116 and MDA-MB-231 cancer cells. Among these compounds, 2-[4-(2-furoyl)piperazine-1-yl]-3-chloro-1,4-NQ 5 and 2,3-bis(cyclobuthylsulfanyl)-1,4-NQ 17 were identified as the most potent anticancer agents with cytotoxic activity against three cell lines (breast (MDA-MB-231), prostate (DU145), colorectal (HCT-116). 相似文献
Co(II), Ni(II), Cu(II) and Zn(II) complexes have been synthesized from hydrazone ligands (HL1–HL4) obtained by condensation reaction of 6-chlorothiochroman-4-one with benz hydrazide/nicotinic hydrazide/isonicotinic hydrazide/p-toluic hydrazide. The synthesized compounds (1–20) were characterized by physicochemical procedures, i.e. (FTIR, 1H NMR, 13C NMR, mass, ESR, UV–Vis), TGA/DTA, powder XRD, elemental analysis (CHN), magnetic susceptibility and molar conductance measurements. The various data suggested bidentate nature (NO) of hydrazones, which coordinate with central metal ions via nitrogen of azomethine (–C=N–) group and deprotonated carbonyl oxygen in the enolized form, resulting in octahedral complexes. Low values of molar conductance suggested their non-electrolytic nature. Thermal decomposition pattern of complexes confirms the metal oxides as end product. In vitro antimicrobial activity of hydrazones and their metal complexes were evaluated against two gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus); two gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli); and two fungal strains (Candida albicans and Aspergillus niger) by serial dilution method, and it was found that the metal complexes were highly active as compared to hydrazones. Among all the compounds, complexes 11, 13, 14 and 19 were found most efficient antimicrobial agent. The anticancer activity of (1–20) compounds was performed on human cancer cell lines A549 (lung), DU145 (prostate) and SW620 (colorectal) by MTT assay using paclitaxel as reference drug. The cytotoxicity results suggested compounds [Cu(L2)2(H2O)2] 11 as most potent against A549, DU145 and SW620 cancer cell lines with IC50 values of 3.46, 18.21 and 7.61 µM. Furthermore, compounds (9, 10, 11, 12) were also investigated on A549 cell line for their ROS generation and mitochondrial membrane potential loss and suggested that complex [Cu(L2)2(H2O)2] 11 has highest ROS production and induction of apoptosis by mitochondrial depolarization in cancer cells.
Graphic abstract
The synthesized compounds (1–20) were screened for in vitro cytotoxicity against A549 (lung), DU145 (prostate), SW620 (colorectal) human cancer cell lines. Copper complex (11) was found to be the most active antitumor agent which enhance ROS production and MMP loss on A549 cells.
Abstract Compounds of the following structure (R1O)2(X)P[sbnd]Y–P(X)(OR2)2 (X = O, Y = Sn (n = 1–4), R1 = R2 = Me, iPr; X = S, Y = Sn (n = 1–4), R1, R2 = Me, Et, iPr, iBu; X = S, Y = S-Se-S, S-Te-S, R1 = R2 = Me were prepared and their NMR spectra were analysed. Depending on the number of sulfur atoms, bonded between the phosphorus atoms, typical ranges of the P-P coupling constants were found for the different sulfanes investigated: 2JPP from-10 to-20 Hz, 3JPP less than 3 Hz, 4JPP from +10 to +13 Hz and 5JPP less than 1 Hz. For the small vicinal coupling constants and the relatively large values of 4JPP different possibilities of their interpretation are given. 相似文献
Abstract A series of novel acyclic and cyclic diaryl sulphides was synthesized from 2,2′-dithiobenzoic acid. The various diaryl sulphides were characterized by use of spectral (IR, 1H and 13C NMR, ESI/MS) and elemental analyses. The antimicrobial activities of the compounds were evaluated in terms of their minimum inhibition concentration (MIC) against a panel of clinical isolates bacteria and were found to possess only moderate antimicrobial activities. N,N′-Bis(2-hydroxyphenyl)-2,2′-thiodibenzamide (13), exhibiting a hydroxy group at the phenyl ring, was the most active antimicrobial agent within the series, with MIC values of 0.05 mg mL–1 and 10 mg mL–1 against Staphylococcus aureus and Bacillus cereus, respectively. The antioxidant efficiency of the diaryl sulphides was determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity with 13 being the most active compound. The interaction of 2,2′-thiodibenzanilide, N,N′-bis(2-methylphenyl)-2,2′-thiodibenzamide, and N,N′-bis(2-hydroxyphenyl)-2,2′-thiobenzamide with guanine, glutamic acid, and urea were studied quantitatively with binding constants ranging from 1 × 103 M?1 to 2.7 × 104 M?1. 相似文献
AbstractA new 22,26-seco physalin, physalin XI (1) together with 5 known compounds, were isolated from the dichloromethane extract of Physalis angulata L. The structure of isolated compounds was elucidated by spectroscopic analysis. The effects of isolated compounds on in vitro cytotoxicity were investigated. Compound 1 was assessed for its cytotoxicity against cancer cell lines (HepG2, HeLa, HuCCA-1, T47-D and A-549) and a normal cell line (MRC-5), and the result showed that it has no activity. Compounds 2 and 4 are highly toxic to H69AR and MDA-MB-23 cell lines. This property appears to be related to the presence of their conjugated double bond or epoxy groups and is a more reliable indication of toxicity than substitution on C(5)–C(6). 相似文献
Two cobalt(II) complexes [Co(QCT)2]·Cl·1.5H2O (1) (QCT = quinoline-2-carboxaldehyde thiosemicarbazone) and [Co(QCMT)(CH3OH)Cl2] (2) (QCMT = quinoline-2-carboxaldehyde N4-methyl-thiosemicarbazone) have been synthesized and structurally characterized. Complex 1 crystallizes in a triclinic system with space group P–1 and complex 2 crystallizes in a monoclinic system with space group P2(1)/n. In both complexes the cobalt(II) center is six coordinated with distorted octahedral geometry. The interactions of two complexes with CT-DNA were investigated by electronic absorption spectra, circular dichroism (CD) spectra and fluorescence spectra. Results suggest that the complexes bind to DNA via groove binding mode, and complex 2 has stronger binding ability than complex 1. The in vitro cytotoxicity has been tested against the human lung adenocarcinoma cell line A-549, cisplatin-resistant cell line A-549/CDDP, and human breast adenocarcinoma cell line MCF-7. Complex 2 is more cytotoxic than complex 1, and both of them show higher cytotoxicity than the parent ligands alone. Compared with cisplatin, the two cobalt(II) complexes are more active against A-549/CDDP and MCF-7 cell lines at most experimental concentrations. Notably, although complex 2 is found to be less effective than cisplatin against the parent cell line A-549, it is much more effective than cisplatin against the resistant cell A-549/CDDP. 相似文献
Two new heteroleptic Pd(II) dithiocarbamates (1 and 2) have been synthesized by reaction of equimolar quantities of palladium(II) chloride, sodium 4-(3-methoxyphenyl)piperazine-1-carbodithioate, and appropriate substituted triphenylphosphines. The synthesized complexes have been characterized by their physical, spectral (IR, 1H, 13C, and 31P NMR), and X-ray crystallographic data. Complexes 1 and 2 showed square-planar geometry both in solution and solid states. The crystal packing of both complexes revealed similar 3-D-supramolecular networks comprised of 1-D chains. However, the nature and strength of various non-covalent interactions of these networks were slightly different. The DNA interaction studies of the complexes have been carried out by UV–visible spectroscopy to evaluate their anticancer potential. The study suggested intercalative interaction with 2.402 × 104 and 2.713 × 103 M?1 binding constants, respectively. The complexes have also been evaluated for their anticancer activity against HeLa cell line. Both complexes showed higher activity with IC50 values much lower (22.176 and 26.166 μM for 1 and 2, respectively) than the standard cisplatin (78.075 μM). Furthermore, the complexes induced stronger DNA fragmentation as investigated by DNA ladder assay for apoptosis. Our findings suggested that the anticancer action of these compounds stems from their interaction with DNA leading to DNA damage and apoptosis. The excellent activity of 1 and 2 deserves to be a focus for further research and in vivo studies. 相似文献
Abstract The synthesis of transition metal complexes which can serve as catalysts for the oxidation of organic molecules involves the search for both more efficient and more selective catalysts.1 The design of complexes in which structural and electronic features are selectively varied allows the analysis of structure/activity relationships in the study of their oxídation chemistry. Successful probing of these features would therefore allow a more fundamental understanding of the catalysts' properties. We are particularly interested in the air oxidation of catechol to quinone (shown below), since this is one of the reactions catalyzed by the copper-containing enzyme tyrosinase.2相似文献