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      저자 : Ratchanok Pingaew (검색결과 2 건)
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        Synthesis, cytotoxicity and QSAR study of N-tosyl-1,2,3,4- tetrahydroisoquinoline derivatives

        Ratchanok Pingaew,Apilak Worachartcheewan,Chanin Nantasenamat,Supaluk Prachayasittikul,Somsak Ruchirawat,Virapong Prachayasittikul 대한약학회 2013 Archives of Pharmacal Research Vol.36 No.9

        1-Substituted-N-tosyl-1,2,3,4-tetrahydroisoquinolineanalogs (4a–4l) were synthesized using the modifiedPictet–Spengler reaction and evaluated for cytotoxicity. Alltetrahydroisoquinolines displayed cytotoxicity againstMOLT-3 cell lines, except for p-methoxy analog 4d. Interestingly,the o-hydroxy derivative 4k was shown to be themost potent cytotoxic againstHuCCA-1, A-549 andMOLT-3cell lines. The lowest IC50 value of 1.23 lMwas observed forMOLT-3 cells. Trimethoxy analog 4f exerted the most potentactivity against HepG2 with an IC50 of 22.70 lM, which islower than the reference drug, etoposide. QSAR studiesshowed that total symmetry index (Gu), 3D-MoRSE (Mor31vand Mor32u) and 3D Petitjean index (PJI3) were the mostimportant descriptors accounting for the observed cytotoxicities. The most potent cytotoxic compound (4k) againstMOLT-3 had the highest Gu value, correspondingly theinactive p-methoxy analog (4d) had the lowest Gu value. Onthe other hand, the highest molecular mass compound (4f)was shown to be the most potent cytotoxic against HepG2cells. The studies disclose that tetrahydroisoquinolines 4f and4k are potentially interesting lead pharmacophores thatshould be further explored. The QSAR models providedinsights into the physicochemical properties of the investigatedcompounds.

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        Synthesis and Cytotoxicity of Novel 2,2'-Bis- and 2,2',2''-Tris-indolylmethanes-Based Bengacarboline Analogs

        Ratchanok Pingaew,Supaluk Prachayasittikul,Somsak Ruchirawat,Virapong Prachayasittikul 대한약학회 2012 Archives of Pharmacal Research Vol.35 No.6

        Tungstosilicic acid hydrate was employed as an efficient catalyst for the synthesis of bisindolylmethanes 4 using the Friedel-Crafts reaction of N-sulfonyl tryptamine 5 with various aromatic aldehydes, except 3-formylindole. In the excluding case, tris-indolylmethane 7 was formed via a sequential addition-elimination-addition process. The bioactivity test revealed that the phenolic hydroxyl group plays an important role in cytotoxicity; it demonstrated that ortho- and para-hydroxy bis-indolylmethane (BIM) analogs (4b and 4d) displayed cytotoxic potency toward HepG2 (human hepatocellular liver carcinoma cell line) and MOLT-3 (human lymphoblastic leukemia cell line) cancer cell lines. Significantly, both analogs showed slightly higher inhibitory efficacy than the control drug, etoposide, in HepG2 cells, and the analog 4d exhibited the most potent activity against MOLT-3 cell lines, with an IC50 value of 1.62 μg/mL.

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