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Srinu Bhoomandla Shravan Kumar Gunda Srawanthi Kotoori Phani Raja Kanuparthy 《Journal of heterocyclic chemistry》2019,56(7):1986-1998
A series of novel alkyl amide functionalized trifluoromethyl substituted furo/thieno pyridine derivatives 4a–h , 5a–d , and 6a–h were prepared starting from 2‐oxo/thioxo‐6‐phenyl/thien‐2‐yl‐4‐(trifluoromethyl)‐1,2‐dihydropyridine‐3‐carbonitrile 1 on reaction with bromoethylacetate followed by reaction with different primary aliphatic amines, cyclic secondary amines, or l ‐amino acids under different set of conditions. All the synthesized compounds 4a–h , 5a–d , and 6a–h were screened for anticancer activity against four cancer cell lines such as HeLa—cervical cancer (CCL‐2), COLO205—colon cancer (CCL‐222), HepG2—liver cancer (HB‐8065), and MCF7—breast cancer (HTB‐22). Compounds 4g and 4h are found to have promising anticancer activity at micromolar concentration. CoMFA and CoMSIA methods were applied to derive 3D‐QSAR models for alkyl amide tagged furo/thieno pyridine derivatives as potential anticancer inhibitors. 3D‐QSAR models provided a strong basis for future rational design of more active and selective HeLa, COLO205, HepG2, and MCF‐7 cell line inhibitors. 相似文献
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Senem Demir Cigdem
zen Meltem Ceylan‐Ünlüsoy Mehmet
ztürk Oya Bozda‐Dündar 《Journal of heterocyclic chemistry》2019,56(4):1341-1351
Medicinal plant extracts have been used for medical purposes throughout human history. In this study, khellin, having furochromone structure, which is obtained from a well‐known traditional medicinal plant, was selected. A series of furochromonyl compounds ( K1 – K14 ) were synthesized for their anticancer activities. Furochromonyl compounds ( K1 – K14 ) were synthesized by Knoevenagel reaction of substituted 2,4‐thiazolidinediones ( Ia – j )/rhodanines ( Ik – n ) with khellin‐2‐carboxaldehyde ( V ), and their cytotoxicity was investigated in 22 cancer cell lines, which were originated from tissues such as the liver, breast, colon, and cervix. As the first step, two hepatocellular carcinoma cell lines Huh7 and PLC/PRF/5 (Alexander cells) were treated with 10 μM of each compound for 72 h, and then sulforhodamine B assay was performed to analyze their anti‐growth activities. Ethyl 2‐(5‐((4,9‐dimethoxy‐5‐oxo‐5H‐furo[3,2‐g]chromen‐7‐yl)methylene)‐4‐oxo‐2‐thioxothiazolidin‐3‐yl)acetate ( K11 ) was found as the most cytotoxic compound of primary screening. Afterwards, 12 hepatocellular carcinoma, seven breast cancer, two colon cancer, and a cervical cancer cell lines were selected to test K11 for 72 h at multiple concentrations to determine 50% effective doses. Results showed that the 14 cell lines were affected by K11 quantities lower than 10 μM. The structure of K11 , which is particularly effective on breast cancers, can be used to slow down the progression of tumors. Furthermore, the discovery of more effective compounds can be carried out on the basis of this structure. 相似文献
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《合成化学》2015,(7)
以3-甲基-1-苯基-2-吡唑啉-5-酮为原料,经Vilsmeier-Haack反应和Biginelli反应制得4-(5-氯-3-甲基-1-苯基-唑-4-基)-5-甲酸乙酯-6-甲基-3,4-二氢嘧啶-2(1H)-硫酮(3);3与芳醛经Knoevenagel反应合成了5个新型的含吡唑的噻唑[3,2-a]并嘧啶类化合物(5a~5e),其结构经1H NMR,13C NMR,IR和ESI-MS表征。采用MTT法测定了5a~5e的抗肿瘤活性。结果表明:5a~5e对人前列腺癌PC-3细胞均具有一定的体外抗增殖活性,其中2-【4-{[6-(乙氧羰酯)-5-(5-氯-3-甲基-1-苯基-吡唑-4-基)-3-氧代-7-甲基-噻唑并[3,2-a]嘧啶-2(5H)-亚基]甲基}苯氧基】乙酸(5a)活性最强,其IC50为44.45μM。 相似文献
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以双氢青蒿素(DHA)为原料,与草酰氯和哌嗪经“一锅”法制得DHA哌嗪衍生物(2); 2与脂肪族酰氯经酰化反应合成了6个新型的双氢青蒿素哌嗪-酰胺类衍生物(4a~4f),其结构经1H NMR, 13C NMR,IR和HR-ESI-MS进行表征。以四甲基偶氮唑盐比色法(MTT法)初步研究了4a~4f对人肝癌细胞株SMMC-7721的抑制活性。结果表明,4a~4f显著抑制SMMC-7721的增殖,并诱导其凋亡。其中,双氢青蒿素哌嗪-氯乙酰胺(4c)的活性最好,IC50为0.05 μM,优于青蒿素(IC50 0.53 μM)和DHA(IC500.52 μM)。 相似文献
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Dmytro Havrylyuk Borys Zimenkovsky Roman Lesyk 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3):638-650
A series of new 2-{4-oxo-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-arylacetamides ( 4a–e ), 5-(2-oxo-2-aryl-ethyl)-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidine-4-ones ( 5a–d ), 2-(4-oxo-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidin-5-yl)-N-arylacetamides ( 7a–e ), and 5-(2-oxo-2-aryl-ethyl)-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidine-4-ones ( 8a–d ) have been synthesized starting from 2-thioxothiazolidin-4-one and 4-thioxothiazolidin-2-one through a multistep reaction sequence. 2-Thioxothiazolidin-4-one was alkylated via the intermediate formation of the triethylammonium salt 1 by ethyl chloroacetate. Compound 2 and 4-thioxothiazolidin-2-one reacted with thiosemicarbazides to give the 1-(4-thiazolidinone-2-ylidene)-4-R-thiosemicarbazones ( 3a,b ) and 1-(2-thiazolidinone-4-ylidene)thiosemicarbazones ( 6a,b ), respectively. Following [2+3]-cyclization of thiazolidinone-substituted thiosemicarbazones ( 3a,b and 6a,b) with N-arylmaleimides and aroylacrylic acids as equivalents of dielectrophilic synthon [C2]2 +, novel non-fused bicyclic thiazolidinones ( 4a–e, 5a–d, 7a–e, 8a–d ) were synthesized. The structures of the new compounds ( 4a–e, 5a–d, 7a–e, 8a–d ) were established on the basis of their elemental analysis and 1H NMR and mass spectral data. Eight of the synthesized compounds were tested, and three of them displayed different levels of antitumor activity. The most efficient antitumor agent—2-{4-oxo-3-furylmethyl-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-4-chlorophenylacetamide ( 4d ) was found to be active against leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancer cell lines with mean lgGI50 and lgTGI values of –5.35 and –4.78, respectively. 相似文献
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以糠醛为原料,依次与偏二甲基肼发生成腙反应、与马来酸酐发生D-A反应、芳环化、水解及与肼和取代苯肼反应得到呔嗪酮-5-羧酸,随后经酰胺化反应合成了17个新型的呔嗪酮-5-甲酰胺衍生物(6a~6g和9a~9j),总收率21%~27%,其结构经1H NMR, 13C NMR及HR-MS(ESI)表征。采用MTT法考察了化合物对人胰腺癌细胞(Capan 1)、人结直肠腺癌细胞(SW620)、人结肠癌细胞(HCT116)和人乳腺癌细胞(MDA-MB-231)的增殖抑制活性。结果表明:化合物9j对Capan-1细胞的增殖具有良好的抑制活性,IC50为6.65 μM。 相似文献
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水杨醛与2,4-二氯苯乙酮缩合形成α,β不饱和酮后与水合肼关环形成3-(2,4-二氯苯基)-5-(2-羟基苯基)吡唑(2),2与烷基酰氯反应合成了6个未见文献报道的3-(2,4-二氯苯基)-5-(2-酯基苯基)-4,5-二氢-N-酰基吡唑衍生物(3a~3f),其结构经1HNMR,IR和元素分析表征。对3进行了初步生物活性测试,结果表明3浓度为50mg·L-1时,3f,3d对水稻纹枯菌的抑菌率分别为77.4%,60.3%,对稻瘟病菌的抑菌率分别为66.3%,69.2%;3e对油菜菌核菌抑菌率为79.2%。 相似文献
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Ashok D. Madhuri E. V. L. Sarasija M. Sree Kanth S. Vijjulatha M. Gayatri Akkiraju Anjini Sagurthi Someswar Rao Krishna N. Sai 《Russian Journal of General Chemistry》2019,89(10):2129-2135
Russian Journal of General Chemistry - Biaryl derivatives of spirofurochromanones have been synthesised from 4-bromophenyl derivatives of spirofurochromanones upon catalysis by Pd/C in water.... 相似文献
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Yong-Feng Guan Xiu-Juan Liu Xin-Ying Yuan Wen-Bo Liu Yin-Ru Li Guang-Xi Yu Xin-Yi Tian Yan-Bing Zhang Jian Song Wen Li Sai-Yang Zhang 《Molecules (Basel, Switzerland)》2021,26(16)
The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC50 values of 1.38, 5.34, and 5.21 µM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents. 相似文献
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Lin K. Zhang X. Dai X. Ma L. Bozorov K. Guo H. Huang G. Cao J. 《Chemistry of Natural Compounds》2021,57(6):1010-1018
Chemistry of Natural Compounds - Two series of podophyllotoxin derivatives were synthesized by addition of a 4β-sulfanilamide to or substitution of a 4β-amide into podophyllotoxin. Their... 相似文献
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含氟1,3,4-噁唑啉和1,3,4-噁二唑类化合物的合成及其抗癌活性 总被引:1,自引:0,他引:1
对氟苯甲酰腙与乙酸酐或丙酸酐反应后再脱水环化制得2-苯基-3-乙酰基-5-对氟苯基-1,3,4-噁唑啉(3)或2-苯基-3-丙酰基-5-对氟苯基-1,3,4-噁唑啉(4).N-对氟苯甲酰基-N′-苯甲酰肼在POCl3存在下脱水环化制得2-苯基-5-对氟苯基-1,3,4-噁二唑(6).新化合物3,4和6的结构经1H NMR,IR,MS和元素分析表征.用MTT方法评价了其对HepG-2,A549-1和231-2癌细胞株的体外生长抑制活性.结果表明,3,4和6均具有潜在的体外抑制癌细胞生长活性,其中3的活性最强. 相似文献
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《Journal of heterocyclic chemistry》2018,55(7):1709-1719
4‐(4‐Chlorobenzylidene)‐2,5‐diphenyl‐2,3‐dihydro‐3H‐pyrazol‐3‐one 3a and 4‐(3,4‐dimethoxybenzylidene)‐5‐phenyl‐2,3‐dihydro‐3H‐pyrazol‐3‐one 3b were prepared and were reacted with phenylhydrazine, thiosemicarbazide, hydroxylamine hydrochloride, ethyl acetoacetate, diethylmalonate, malononitrile, ethyl cyanoacetate, and thiourea yielding fused pyrazole derivatives. Some of the new compounds were reacted with cyclic and acyclic sugars to produce new S‐, O‐, and N‐glycoside derivatives. The antitumor activity against the human breast cancer cells (MCF‐7) was assessed. Four of the new compounds showed IC50 values less than those of the positive control, indicating that these four compounds are better anticancer agents than doxorubicin. 相似文献
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Various new substituted and fused pyridotriazepine analogues have been synthesized via different synthetic pathways. Among which are different heterocyclic compounds consisting of the pyridotriazepine backbone fused to different heterocyclic systems comprising either substituted pyrimidine nucleus such as compounds 3 – 9 or substituted 4‐aminopyridine nucleus such as compounds 10 – 16 . Besides, the tetrahydroquinoline derivative 17 , [1,2,4]triazolopyrimidine derivative 18 , thienodiazocine derivative 19 , dihydrobenzofuropyridine derivative 20 , and the substituted pyrrole derivative 21 were synthesized. In addition, different substituted pyridotriazepine derivatives as indicated in compounds 22 – 25 were designed and synthesized. Twenty‐five of the newly synthesized compounds were subjected to in vitro anticancer screening against mammalian colon carcinoma HCT‐116 cell line using Cisplatin as a reference drug. The anticancer activity screening results revealed that among the tested compounds, the tetrahydropyrido[1,2‐b]pyrimido[4,5‐e][1,2,4]triazepine derivative 4 substituted at C2 and C4 positions with S‐methyl and amino moieties, respectively, and the 2,4‐dithioxo analogue 9 and the 2‐thioxodipyrido[1,2‐b:2′,3′‐e][1,2,4]triazepine derivative 11 substituted at C3 and C4 with a cyano and amino moieties, respectively, exhibited moderate to strong anticancer activity against mammalian colon carcinoma HCT‐116 cell line. 相似文献