- Synthesis and biological evaluation of JL-A7 derivatives as potent ABCB1 inhibitors
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Cancer chemotherapy failure is often due to the overexpression of ATP-binding cassette (ABC) transporters (particularly ABCB1), resulting in a variety of structurally and pharmacologically unrelated drugs efflux. The multidrug resistance (MDR) phenomenon could be reversed by ABCB1 inhibitors. Now, JL-A7 as the lead compound based on a triazol-N-ethyl-tetrahydroisoquinoline scaffold, 18 compounds were designed and synthesized. Substitution in para positions yielded high activities toward ABCB1. Moreover, compound 5 could effectively block the drug efflux function of ABCB1 and increase the accumulation of anti-cancer drugs to achieve effective treatment concentration in MDR cells.
- Pan, Miaobo,Cui, Jian,Jiao, Lei,Ghaleb, Hesham,Liao, Chen,Zhou, Jiaqi,Kairuki, Mutta,Lin, Haiyan,Huang, Wenlong,Qian, Hai
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p. 4194 - 4202
(2017/07/05)
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- 6,7-Dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinolines as superior reversal agents for P-glycoprotein-mediated multidrug resistance
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P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major obstacle for successful cancer chemotherapy. Based on our previous study, 17 novel compounds with the 6,7-dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinoline scaffold were designed and synthesized. Among them, 2-[(1-{4-[2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]phenyl}-1H-1,2,3-triazol-4-yl)methoxy]-N-(p-tolyl)-benzamide (compound 7h) was identified as a potent modulator of P-gp-mediated MDR, with high potency (EC50 = 127.5 ± 9.1 nM), low cytotoxicity (TI > 784.3), and long duration (> 24 h) in reversing doxorubicin (DOX) resistance in K562/A02 cells. Compound 7h also enhanced the effects of other MDR-related cytotoxic agents (paclitaxel, vinblastine, and daunorubicin), increased the accumulation of DOX and blocked P-gp-mediated rhodamine 123 efflux function in K562/A02 MDR cells. Moreover, 7h did not have any effect on cytochrome (CYP3A4) activity. These results indicate that 7h is a relatively safe modulator of P-gp-mediated MDR that has good potential for further development.
- Liu, Baomin,Qiu, Qianqian,Zhao, Tianxiao,Jiao, Lei,Li, Yunman,Huang, Wenlong,Qian, Hai
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p. 336 - 344
(2015/02/05)
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- One-pot synthesis of salicylanilides by direct amide bond formation from salicyclic acid under microwave irradiation
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A highly efficient protocol for the preparation of aromatic amides is described by the direct reactions between salicyclic acid and aromatic amines in the presence of phosphorous trichloride under microwave irradiation. The method has several advantages over the conventional methods, including operational simplicity, good yield, and reduced reaction time.
- Lu, Cheng-Rong,Zhao, Bei,Jiang, Ying-Peng,Ding, Hao,Yang, Sheng
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experimental part
p. 1257 - 1266
(2011/05/07)
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- Investigating the spectrum of biological activity of ring- substituted salicylanilides and carbamoylphenylcarbamates
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In this study, a series of twelve ring-substituted salicylanilides and carbamoylphenylcarbamates were prepared and characterized. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to the inhi
- Otevrel, Jan,Mandelova, Zuzana,Pesko, Matus,Guo, Jiahui,Kralova, Katarina,Sersen, Frantisek,Vejsova, Marcela,Kalinowski, Danuta S.,Kovacevic, Zaklina,Coffey, Aidan,Csollei, Jozef,Richardson, Des R.,Jampilek, Josef
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experimental part
p. 8122 - 8142
(2011/02/27)
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- Process for preparing aldehyde compounds
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The invention relates to a process for the making organic aldehyde compounds from an unsaturated compound by hydroformylation and in the presence of a catalyst system comprising a Group VIII metal and a bidentate phosphorus ligand having two trivalent phosphorus atoms bound to salicylanilide groups.
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Page column 15
(2010/11/29)
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- PHOTOCHEMICAL AND THERMAL REACTIONS OF 2-ARYLOXYBENZOHYDROXAMIC ACIDS
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2-Aryloxybenzohydroxamic acids 1-7 were subjected to photolysis in benzene or methanol.In each case corresponding N-arylsalicylamides 8-10 were obtained in good yields.Compounds 1-7 on thermolysis in decaline also produced 8-10.
- Hosangadi, B. D.,Nimbalkar, M. M.,Patel, N. R.
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p. 5857 - 5860
(2007/10/02)
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- BORON TRICHLORIDE CATALYZED ORTHO CARBONYLATION OF PHENOLS: SYNTHESIS OF 2-HYDROXY-ARYL-CARBOXYAMIDES AND -KETONES.
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In the presence of equimolar quantity of BCl3, phenols 1 react with isocyanates and acyl chlorides to give, usually with good-excellent yields, 2-hydroxy-aryl-carboxy-amides 2 and 2-hydroxy-aryl-ketones 3 respectively.A distinctive behaviour of BCl3 in comparison with other Lewis acids is observed.
- Piccolo, Oreste,Filippini, Lucio,Tinucci, Laura,Valoti, Ermanno,Citterio, Attilio
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p. 885 - 892
(2007/10/02)
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