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1.
Chau VM Phan VK Nguyen X Nguyen XC Nguyen PT Nguyen HN Hoang le TA Do CT Thuy DT Kang HK Jang HD Kim YH 《Bioorganic & medicinal chemistry letters》2011,21(7):2155-2159
Two new diterpenes, lobocompactols A (1) and B (2), and five known compounds (3-7) were isolated from the methanol extract of the soft coral Lobophytum compactum using combined chromatographic methods and identified based on NMR and MS data. Each compound was evaluated for cytotoxic activity against A549 (lung) and HL-60 (acute promyelocytic leukemia) human cancer cell lines. Among them, compound 5 exhibited strong cytotoxic activity against the A549 cell line with an IC50 of 4.97 ± 0.06 μM. Compounds 3, 4, and 7 showed moderate activity with IC50 values of 23.03 ± 0.76, 31.13 ± 0.08, and 36.45 ± 0.01 μM, respectively. The cytotoxicity of 5 on the A549 cells was comparable to that of the positive control, mitoxantrone (MX). All compounds exhibited moderate cytotoxicity against the HL-60 cell line, with IC50 values ranging from 17.80 ± 1.43 to 59.06 ± 2.31 μM. Their antioxidant activity was also measured using oxygen radical absorbance capacity method, compounds 1 and 2 exhibiting moderate peroxyl radical scavenging activity of 1.4 and 1.3 μM Trolox equivalents, respectively, at a concentration of 5 μM. 相似文献
2.
Iqbal Choudhary M Shahab Alam M Atta-Ur-Rahman Yousuf S Wu YC Lin AS Shaheen F 《Steroids》2011,76(14):1554-1559
Pregnenolone (1) was used as a template to develop new anticancer compounds. Ring-D modification of 1 resulted in the synthesis of benzylidenes 2-17, pyrazolines 18-76, pyrazoles 85-91, hydrazones 77-84, and oximes 92-107 derivatives. The structure of compound 107 was also deduced through single crystal X-ray diffraction studies. The inclusion of furanyl and pyridyl rings to pregnenolone skeleton increases the cytotoxicity of all compounds significantly. Among benzylidene derivatives, only heterocyclic enone 8 (IC50 = 0.74 μM/mL against HepG2), and 17 (IC50 = 4.49 μM/mL against HepG2, IC50 = 5.01 μM/mL against MDA-MB-230 cancer cell line) exhibited a significant activity. The cytotoxicity data of pyrazoline derivatives 18-76 revealed that only furanyl bearing pyrazolines 40, 42-44, 48, and 49 exhibited significant activities. While all (O-carboxymethyl) oximes, hydazones, and pyrazoles derivatives of pregnenolone did not show any significant activity against both the cell lines. Thus the furanyl bearing enone 8 (IC50 = 0.74 μM/mL against HepG2), and its pyrazoline derivative 48 (IC50 = 0.91 μM/mL against MDA-MB-230 cancer cell lines) were identified as the most active compounds in all derivatives of pregnenolone. 相似文献
3.
Bashir R Ovais S Yaseen S Hamid H Alam MS Samim M Singh S Javed K 《Bioorganic & medicinal chemistry letters》2011,21(14):4301-4305
Thirteen new 2-pyrazoline derivatives bearing benzenesulfonamide moiety (2a-m) were synthesized by condensing appropriate chalcones with 4-hydrazinonbenzenesulfonamide hydrochloride and tested for anticancer and anti-inflammatory actions. According to the protocol of the National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay compounds 2b, 2c, 2e, 2f and 2g exhibited considerable antitumor activities against the entire tested tumor cell lines and showed effective growth inhibition GI50 (MG-MID) values of 2.63, 2.57, 6.61, 3.31 and 2.57 μM, respectively, beside a cyclostatic activity TGI (MG-MID) 9.54, 8.51, 24.0, 19.9 and 8.71 μM, respectively. Two compounds 2g and 2k showed more potent anti-inflammatory activity than celecoxib at 5 h in carrageenan-induced rat paw edema bioassay. These compounds (2g and 2k) proved to have superior gastrointestinal safety profiles as compared to celecoxib, when tested for their ulcerogenic effects. Compounds 2g and 2k showed no inhibition against the enzymatic activity of bovine COX-2 (in vitro). 相似文献
4.
Lv K Wang LL Liu ML Zhou XB Fan SY Liu HY Zheng ZB Li S 《Bioorganic & medicinal chemistry letters》2011,21(10):3062-3065
We report herein the design and synthesis of novel 1-[3-(dimethylamino)propyl]indolin-2-one derivatives based on the structural features of Sunitinib, a known multitargeted receptor tyrosine kinase inhibitor, and TMP-20, a previously discovered compound with good antitumor activity in our lab. These newly synthesized derivatives were evaluated for in vitro activity against five human cancer cell lines and VEGF/bFGF-stimulated HUVECs. Results revealed that all of the target compounds 1a-p show potent antitumor activity, compounds 1e-h (IC50’s: 0.45-5.08 μM) are more active than Sunitinib (IC50’s: 1.35-6.61 μM), and the most active compound 1h (IC50: 0.47-3.11 μM) is 2.1-4.6-fold more potent than Sunitinib against all five cancer cell lines. In addition, like Sunitinib, 1a-p have higher selectivity on VEGF-stimulated HUVEC other than bFGF-stimulated HUVEC. 相似文献
5.
6.
Tale RH Rodge AH Hatnapure GD Keche AP 《Bioorganic & medicinal chemistry letters》2011,21(15):4648-4651
A series of novel 3,4-dihydropyrimidin-2(1H)-one urea derivatives of biological interest were prepared by sequential Bigineli’s reaction, reduction followed by reaction of resulting amines with different arylisocynates. All the synthesized (1-23) compounds were screened against the pro-inflammatory cytokines (TNF-α and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological activity evaluation study reveled that among all the compounds screened, compounds 12 and 17 found to have promising anti-inflammatory activity (68-62% TNF-α and 92-86% IL-6 inhibitory activity at 10 μM). Interestingly compounds 3, 4, 5, 6, 15, 22 and 23 revealed promising antimicrobial activity at MIC of 10-30 μg/mL against selected pathogenic bacteria and fungi. 相似文献
7.
Six aporphine alkaloids, (+)-(S)-N-butyrylcaaverine (1), (+)-(S)-N-propionylcaaverine (2), (+)-(S)-N-acetylcaaverine (3), (+)-(6aR,7R)-N-butyrylnorushinsunine (4), (+)-(6aR,7R,E)-N-(but-2-enoyl)norushinsunine (5), and N-formyldehydrocaaverine (6) were isolated from the roots of Illigera luzonensis, together with 16 known compounds. Their structures were determined through spectroscopic and MS analyses. Among the isolates, (−)-deoxypodophyllotoxin (13) was the most cytotoxic, with IC50 values of 0.0057, 0.0067, 0.00004, and 0.0035 μg/mL, respectively, against DLD-1, CCRF-CEM, HL-60, and IMR-32 cell lines. In addition, (−)-yatein (12) exhibited cytotoxic effects, with IC50 values of 0.81, 0.20, and 0.59 μg/mL, respectively, against DLD-1, CCRF-CEM, and HL-60 cell lines. 相似文献
8.
Dong Y Nakagawa-Goto K Lai CY Kim Y Morris-Natschke SL Lee EY Bastow KF Lee KH 《Bioorganic & medicinal chemistry letters》2011,21(1):52-57
In our ongoing modification study of neo-tanshinlactone (1), we discovered 2-(furan-2-yl)naphthalen-1-ol (FNO) derivatives 3 and 4 as a new class of anti-tumor agents. To explore structure-activity relationships (SAR) of this scaffold, 18 new analogs, 6-12 and 14-24, were designed and synthesized. The C11-esters 7 and 12 displayed broad anti-tumor activity (ED50 1.1-4.3 μg/mL against seven cancer cell lines), while C11-hydroxymethyl 14 showed unique selectivity against the SKBR-3 breast cancer cell line (ED50 0.73 μg/mL). Compounds 15 and 22 displayed potent and selective anti-breast tumor activity (ED50 1.7 and 0.85 μg/mL, respectively, against MDA-MB-231). The SAR results demonstrated that the substitutions from the ring-opened lactone ring C of 1 are critical to the anti-tumor potency as well as the apparent tumor-tissue type selectivity. Treatment with 3 in Brca1f11/f11p53f5&6/f5&6Crec mice models significantly inhibited the proliferation of mammary epithelial cells and branching of mammary glands. 相似文献
9.
Ma SG Tang WZ Liu YX Hu YC Yu SS Zhang Y Chen XG Qu J Ren JH Liu YB Xu S Liu J Liu YY Li Y Lü HN Wu XF 《Phytochemistry》2011,72(1):115-2445
Eleven prenylated C6-C3 compounds, illioliganpyranone A (1), illioliganfunone A-D (2-5), and illioliganone D-I (6-11), together with five known prenylated C6-C3 compounds (12-16), were isolated from roots of Illicium oligandrum. The structures of 1-11 were elucidated by spectroscopic methods including 1D and 2D NMR, HRESIMS, and CD experiments. Possible biosynthetic pathways to compounds 1-16 derived from a common precursor of 5-allylbenzene-1,2,4-triol were postulated. All compounds were evaluated for cytotoxic activities against five human cancer cell lines (HCT-8, Bel-7402, BGC-823, A549 and A2780). Compound 15 exhibited significant cytotoxicity against HCT-8, BGC-823, A549, and A2780 cell lines with IC50 values of 0.30-2.57 μM. Compound 16 showed moderate selective cytotoxicity against sensitive A2780 cells with IC50 value of 1.38 μM. 相似文献
10.
Evgenija A. Djurendi? Marija N. Saka? Janoš J. ?anadi Gordana M. Bogdanovi? 《Steroids》2009,74(12):983-1081
Starting from 3β-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 4-9 were synthesized. On the other hand, 3β-hydroxy-17-oxa-d-homoandrost-5-ene-16-one (10) yielded the new d-homo derivatives 12, 13 and 15. In vitro antiproliferative activity of selected compounds against three tumor cell lines (human breast adenocarcinoma ER+, MCF-7, human breast adenocarcinoma ER−, MDA-MB-231, prostate cancer AR−, PC-3, and normal fetal lung fibroblasts, MRC-5) was evaluated. Compounds 3 and 12 showed strong antiproliferative activity against PC-3 cells, the IC50 values being 2 μM and 0.55 μM, respectively. Compounds 6 (10 μM) and 14 (9 μM) showed moderate activity against MDA-MB-231 cells. The synthesized compounds 1-3, 5-8, 10 and 12-15 were not toxic to normal fetal lung fibroblasts cells, MRC-5. 相似文献
11.
Marta Sobiesiak Agnieszka Mrozek Ingo-Peter Lorenz Urszula Krajewska 《Inorganica chimica acta》2010,363(10):2171-3244
1-Benzothiazol-2-yl-3,5-dimethyl-1H-pyrazole (1a) and 1-benzothiazol-2-yl-5-(2-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carboxylic acid methyl ester (1b) were reacted with the hexahydrates of cobalt(II) chloride, cobalt(II) nitrate and cobalt(II) perchlorate to give the corresponding complexes 2a-4a and 2b-5b, respectively. Obtained compounds differ in coordination spheres of central atoms. The complex 2a includes a fivefold coordinated cobalt(II) ion, whereas 3a shows a distorted octahedral configuration around the cobalt(II) ion. All complexes were characterised by FTIR spectroscopy, MS and elemental analysis. The X-ray structures of 2a, 3a and 5b complexes were also solved. The cytotoxic properties of the ligand 1a and both series of Co(II) complexes were examined on human leukemia NALM-6 and HL-60 cells and melanoma WM-115 cells. The ligands, were found to have very low cytotoxicity. Complex 3b exhibited the highest cytotoxic activity with IC50 values in the range of 6.9-17.1 μM for three examined cell lines. 相似文献
12.
Spychała J 《Bioorganic chemistry》2008,36(4):183-189
A series of related polycationic compounds has been screened for potential antitumor activity by the NCI’s in vitro testing (one dose primary anticancer assay and the NCI-60 full panel screening). The GI50 values of triazines 3 and 4 are on average 1.9 μM and 2.4 μM, respectively. Furan 8 deserves mention too (1.9 μM). The biological test results showed that carbazole 10 possessed cytotoxic activity in the nanomolar range, much better than the other compounds tested, only against several cancer cell lines: CCRF-CEM, HL-60(TB), MOLT-4, NCI-H522, COLO 205, SF-268, but the average GI50 value was higher (15 μM). The activity appears closely dependent on the core-shape and length of the bisimidazoline molecules (important for both high cytotoxicity and DNA binding). The mechanism of DNA minor-groove binding of diamidines 1-12, based on the anticancer parameters, is highly probable. 相似文献
13.
Mandal M Kumar D Roy R Sen R Das P Chatterjee M Jaisankar P 《Bioorganic & medicinal chemistry letters》2011,21(10):3084-3087
2,2′-Diphenyl-3,3′-diindolylethylene (DPDIE) derivatives 3a-g were regioselectively prepared in one pot from indoles 1a-g in the presence of Lewis acids and were subsequently evaluated for cytotoxic activity against human leukemic cell lines, U937 and K562. The most potent compound 3g exhibited IC50 of 13.0-17.0 μM. 相似文献
14.
Sangthong S Krusong K Ngamrojanavanich N Vilaivan T Puthong S Chandchawan S Muangsin N 《Bioorganic & medicinal chemistry letters》2011,21(16):4813-4818
6-Deoxyclitoriacetal (1) and a series of 11 further derivatives of it (2-12) were synthesized and evaluated for their cytotoxic and topoisomerase IIα inhibitory activities. Compounds bearing epoxide (2), morpholine (6) and benzylamine (10) moieties showed promising in vitro cytotoxic activities against four cancer cell lines, with IC50 values ranging from 0.38 to 0.73 μM. These three compounds also strongly inhibited topoisomerase II activity at 68.3-93.5% and showed a moderately high DNA intercalating property. 相似文献
15.
Extraction of the leaves of Zanthoxylum ailanthoides Sieb. & Zucc. affords extracts and four isolated compounds which exhibit activities against leukemia cells. The chloroform-soluble fraction (ZAC) of the crude extract of this plant showed cytotoxic activity against human promyelocytic leukemia (HL-60) and myelomonocytic leukemia (WEHI-3) cells with IC50 values of 73.06 and 42.22 μg/mL, respectively. The active ZAC was further separated to yield pheophorbide-a methyl ester (1), pheophorbide-b methyl ester (2), 132-hydroxyl (132-S) pheophorbide-a methyl ester (3) and 132-hydroxyl (132-R) pheophorbide-b methyl ester (4) whose structures were confirmed by spectroscopic methods. Compounds 2-4 showed cytotoxic activities against both leukemia cells with IC50 value in the range of 46.76-79.43 nM, whereas compound 1 exhibited only weak cytotoxic activity. The extracts and compounds 1-4 also induced apoptosis and DNA damage in leukemia cells after treatment. The results suggested that the Z. ailanthoides is biologically active against leukemia cells. 相似文献
16.
Jana M. Sandes Cláudio G.L. Junior Gabriel A.U. Carvalho Mário L.A.A. Vasconcellos Regina C.B.Q. Figueiredo 《Bioorganic chemistry》2010,38(5):190-195
We have synthesized the Morita-Baylis-Hillman adduct (MBHA) 3-hydroxy-2-methylene-3-(4-nitrophenyl)-propanenitrile (3) in quantitative yield and evaluated on Trypanosoma cruzi epimastigote and bloodstream trypomastigote forms. Compound 3 strongly inhibited epimastigote growth, with IC50/72 h of 28.5 μM and also caused intense trypomastigotes lysis, with an IC50/24 h of 25.5 μM. Ultrastructural analysis showed significant morphological changes on both parasite forms treated with 3, including increase of cell volume and rounding of cell body as well as intense intracellular disorganization. Morphological changes indicative of apoptosis, autophagy or necrosis were observed in most affected cells. Docking calculations of 1, 2 and 3 pointed out the possibility of T. cruzi Farnesyl Pyrophosphate Synthase (TcFPPS) enzyme inhibition in 3 mechanism of action. 相似文献
17.
Dong Y Nakagawa-Goto K Lai CY Morris-Natschke SL Bastow KF Lee KH 《Bioorganic & medicinal chemistry letters》2011,21(8):2341-2344
4-Amino-2H-benzo[h]chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 μM. 相似文献
18.
Gülcemal D Alankuş-Çalışkan O Perrone A Ozgökçe F Piacente S Bedir E 《Phytochemistry》2011,72(8):761-768
Eight cycloartane-type triterpene glycosides (1-8) were isolated from Astragalus aureus Willd along with ten known cycloartane-type glycosides (9-18). Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analyses. Compounds 1-5 are cyclocanthogenin glycosides, whereas compounds 6-8 are based on cyclocephalogenin as aglycon, more unusual in the plant kingdom, so far reported only from Astragalus spp. Moreover, for the first time monoglycosides of cyclocanthogenin (5) and cyclocephalogenin (7, 8) are reported. All of the compounds tested for their cytotoxic activities against a number of cancer cell lines. Among the compounds, only 8 exhibited activity versus human breast cancer (MCF7) at 45 μM concentration. 相似文献
19.
Vijaya Kumar T Tiwari AK Robinson A Suresh Babu K Sateesh Chandra Kumar R Anand Kumar D Zehra A Madhusudna Rao J 《Bioorganic & medicinal chemistry letters》2011,21(16):4928-4931
Bergenin (1), major bioactive compound isolated from methanolic extract of Mallotus philippinensis, displayed moderate AGE inhibition activity (IC50 = 186.73 μM). A series of derivatives of bergenin (3a-k) containing variety of aromatic acids were synthesized under mild conditions by modification of sugar part. Selective esterification of hydroxyl groups on the sugar part enhanced antiglycation potential of bergenin. Compounds 3j and 3k exhibited potent antiglycation activity with the IC50 values of 60.75 and 12.28 μM, respectively. 相似文献
20.
The nuclearity, bonding and H-bonded networks of copper(I) halide complexes with thiophene-2-carbaldehyde thiosemicarbazones {(C4H3S)HC2N3-N(H)-C1(S)N1HR} are influenced by R substituents at N1 atom. Thiophene-2-carbaldehyde-N1-methyl thiosemicarbazone (HttscMe) or thiophene-2-carbaldehyde-N1-ethyl thiosemicarbazone (HttscEt) have yielded halogen-bridged dinuclear complexes, [Cu2(μ-X)2(η1-S-Htsc)2(Ph3P)2] (Htsc, X: HttscMe, I, 1; Br, 2; Cl, 3; HttscEt, I, 4; Br, 5; Cl, 6), while thiophene-2-carbaldehyde-N1-phenyl thiosemicarbazone (HttscPh) has yielded mononuclear complexes, [CuX(η1-S-HttscPh)2] (X, I, 7a; Br 8; Cl, 9) and a sulfur bridged dinuclear complex, [Cu2(μ-S-HttscPh)2(η1-S-HttscPh)2I2] 7b co-existing with 7a in the same unit cell. These results are in contrast to S-bridged dimers [Cu2(μ-S-Httsc)2(η1-Br)2(Ph3P)2] · 2H2O and [Cu2(μ-S-Httsc)2(η1-Cl)2(Ph3P)2] · 2CH3CN obtained for R = H and X = Cl, Br (Httsc = thiophene-2-carbaldehyde thiosemicarbazone) as reported earlier. The intermolecular CHPh?π interaction in 1-3 (2.797 Å, 1; 3.264 Å, 2; 3.257 Å, 3) have formed linear polymers, whereas the CHPh?X and N3?HCH interactions in 4-6 (2.791, 2.69 Å, 5; 2.776, 2.745 Å, 6, respectively) have led to the formation of H-bonded 2D polymer. The PhN1H?π, interactions (2.547 Å, 8, 2.599 Å, 9) have formed H-bonded dimers only. The Cu?Cu separations are 3.221-3.404 Å (1-6). 相似文献