93598-06-2Relevant articles and documents
Harmine-based dual inhibitors targeting histone deacetylase (HDAC) and DNA as a promising strategy for cancer therapy
Lu, Dehua,Qu, Lailiang,Wang, Cheng,Luo, Heng,Li, Shang,Yin, Fucheng,Liu, Xingchen,Chen, Xinye,Luo, Zhongwen,Cui, Ningjie,Peng, Wan,Ji, Limei,Kong, Lingyi,Wang, Xiaobing
, (2022/01/20)
Overexpression of histone deacetylases (HDACs) are observed in different types of cancers, but histone deacetylase inhibitors (HDACIs) have not shown significant efficacy as monotherapy against solid tumors. Recently, studies demonstrated that it is promi
Novel β-carboline-based indole-4,7-quinone derivatives as NAD(P)H: Quinone-oxidoreductase-1 inhibitor with potent antitumor activities by inducing reactive oxygen species, apoptosis, and DNA damage
Guo, Yibing,Xu, Liancheng,Ling, Changchun,Yang, Tao,Zheng, Wenjie,Lv, Jin,Guo, Qingsong,Chen, Bohua
, p. 1433 - 1446 (2020/07/13)
Eighteen new β-carboline-based indole-4,7-quinone derivatives (12a–i and 13a–i) were designed and synthesized, and their in vitro and in vivo antiproliferative activities were studied. Most of target compounds showed strong inhibition on three human tumor cells' proliferation. In particular, the most active compound 13g not only displayed more prominent antiproliferative activities than β-lapachone, a clinical antitumor candidate, but also exerted significant NAD(P)H: quinone-oxidoreductase-1 (NQO1) inhibitory activity and NQO1-dependent cytotoxicity in HT29 cells. Furthermore, 13g dose-dependently induced high ROS levels in HT29 cells, and selectively inhibited cancer cell but not non-tumor colon cell proliferation in vitro. Importantly, 13g promoted HT29 cell apoptosis and DNA damage by regulating relative apoptotic proteins and H2AX expression. Finally, 13g displayed significant growth inhibition of HT29 human colorectal adenocarcinoma xenograft in mice without overt toxicity.
Tetrahydro-beta-carboline dimer as well as preparation method and application thereof
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Paragraph 0067; 0072-0074, (2020/09/30)
The invention discloses an application of a tetrahydro-beta-carboline dimer derivative in the preparation of a medicine for preventing or treating Alzheimer's disease. The tetrahydro-beta-carboline dimer derivative is as shown in a structural formula I, which is described in the specification, L-tryptophan and tryptamine are used as raw materials; a tetrahydro-beta-carboline monomer is generated through a Picet-Spengler reaction and aldehyde cyclization, then a tetrahydro-beta-carboline dimer is generated through acyl chloride connection and a click chemical reaction, the synthesis steps are simple, the raw materials are easy to obtain, the yield is high, and the tetrahydro-beta-carboline dimer has remarkable inhibitory activity on butyrylcholine esterase and A[beta]1-42 aggregation. According to the neural protective effect under three AD models on cells, after the cells are independently treated by A[beta]1-42, H2O2 and OA, the survival rate of the cells is low, and apoptosis or necrosis of the cells occurs. The compounds 11, 12, 13, 17 and 19 are used for co-treatment, the compounds 11, 12, 13, 17 and 19 successfully block A[beta]1-42, H2O2 and OA induced cell death, and it is proved that the compounds 11, 12, 13, 17 and 19 have a remarkable neural protective effect.
β-Carboline and N-hydroxycinnamamide hybrids as anticancer agents for drug-resistant hepatocellular carcinoma
Ling, Yong,Gao, Wei-Jie,Ling, Changchun,Liu, Ji,Meng, Chi,Qian, Jianqiang,Liu, Siqun,Gan, Huiling,Wu, Hongmei,Tao, Jinhua,Dai, Hong,Zhang, Yanan
, p. 515 - 526 (2019/03/08)
In an effort to develop anticancer agents that may overcome drug resistance, the number one reason in caner death, we have developed a series of novel hybrids of β-carboline and N-hydroxycinnamamide as histone deacetylase (HDAC) inhibitors. Most of the hybrids 13a-p showed strong antiproliferative effects with low-micromolar IC50 values against four human cancer cells. The most potent compound of series 13p exhibited high HDAC1/6 inhibitory effects, and also increased the acetylation levels of histone H3, H4 and α-tubulin. Importantly, 13p demonstrated high anticancer potency against drug-sensitive HepG2 and Bel7402 cells and drug-resistant Bel7402/5FU cells. Hybrid 13p triggered significant apoptosis by regulating apoptotic relative proteins expression in these Bel7402/5FU cells. Finally, 13p induced a substantial amount of autophagic flux activity by the accretion of the expression of LC3-II and the degeneration of expression of p62 and LC3-I in Bel7402/5FU cells. Overall, 13p is a novel β-carboline/N-hydroxycinnamamide hybrid with significant anticancer potency that warrants further evaluation for the treatment of drug-resistant hepatocellular carcinoma.
Pd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes
Wang, Hai-Jun,Guo, Lei,Zhu, Cheng-Feng,Luo, Yun-Fei,Li, You-Gui,Wu, Xiang
, p. 5456 - 5459 (2018/10/20)
A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition. It allows the generation of structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asymmetric version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.
Design, synthesis and biological evaluation of 1,3,6-trisubstituted β-carboline derivatives for cytotoxic and anti-leishmanial potential
Lunagariya, Nitin A.,Gohil, Vikrantsinh M.,Kushwah, Varun,Neelagiri, Soumya,Jain, Sanyog,Singh, Sushma,Bhutani, Kamlesh K.
supporting information, p. 789 - 794 (2016/05/24)
In the present study, 23 derivatives of 1,3,6-trisubstituted β-carboline were synthesized and evaluated for cytotoxic potential against four human cancer cells, namely A-549, HeLa, Hep G2 and MCF-7 as well as anti-leishmanial activity against Leishmania d
A seed of common peganum alkali nenzoyl urea compound, and its preparation method and application
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Paragraph 0052; 0053, (2016/10/09)
The invention discloses banisterine benzoyl urea compounds and a preparation method and application thereof. The banisterine benzoyl urea compounds have a structural formula I shown in the specification; in the formula I, R1 can be methyl, phenyl, 3,4,5- triethoxy phenyl, p-methoxyphenyl or p-chlorphenyl, R2 can be H or Br, and X can be O or S. The banisterine benzoyl urea compounds have an outstanding insecticidal activity for Culex fatigans, prodenia litura and Chilo suppressalis; a part of the compounds are identical to a control insecticide Dibenzoyl-1-tert-butylhydrazine in term of activity; the banisterine benzoyl urea compounds have good inhibitory activity for rice sheath blight disease, alternaria solani, Collectotrichum musae, grey mould fruit rot of strawberry and sour rot pathogenic bacteria of citrus; a part of the compounds have better inhibitory activity for the above five phytopathogens than validamycin. The banisterine derivatives are simple in structure and easy to synthesize; the synthesis process is simple, the product purity is high; the banisterine benzoyl urea compounds and the preparation method thereof are suitable for large-scale industrial popularization and application.
Synthesis and herbicidal activity evaluation of novel β-carboline derivatives
Weng, Qunfang,Huang, Jingfei,Zeng, Yong,Deng, Yueye,Hu, Meiying
experimental part, p. 3969 - 3980 (2012/09/10)
Based on the original structure of harmine, several novel 1,2,3,4-tetrahydro-β- carboline, β-carboline and 1-substituted-β- carboline derivatives bearing a substituted carbohydrazide group at C-3 were designed and synthesized to investigate the structureactivity relationship of their analogues. All of the compounds were characterized by infrared (IR), proton and carbon nuclear magnetic resonance (1H-NMR, 13C-NMR), and mass spectroscopy (MS). The bioassay tests showed that N'-benzylidene-1-phenyl-β- carboline-3-carbohydrazide (C25H 18N4O, m.w. 390.4) (c2) and N'-(4- trifluoromethylbenzylidene)- 1-phenyl-β-carboline-3-carbohydrazide (C26H17N4OF3, m.w. 458) (d2) exhibited good inhibitory activity against dicotyledonous and monocotyledonous weeds, with EC50 values of 4.83 μM and 14.25 μM, respectively.
Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 2. Tadalafil analogs
Ochiana, Stefan O.,Gustafson, Alden,Bland, Nicholas D.,Wang, Cuihua,Russo, Michael J.,Campbell, Robert K.,Pollastri, Michael P.
scheme or table, p. 2582 - 2584 (2012/05/05)
In this Letter we describe our ongoing target repurposing efforts focused on discovery of inhibitors of the essential trypanosomal phosphodiesterase TbrPDEB1. This enzyme has been implicated in virulence of Trypanosoma brucei, the causative agent of human African trypanosomiasis (HAT). We outline the synthesis and biological evaluation of analogs of tadalafil, a human PDE5 inhibitor currently utilized for treatment of erectile dysfunction, and report that these analogs are weak inhibitors of TbrPDEB1.
Efficient and practical one-pot conversions of n- tosyltetrahydroisoquinolines into isoquinolines and of N-tosyltetrahydro-β- carbolines into β-carbolines through tandem β-elimination and aromatization
Dong, Jing,Shi, Xiao-Xin,Yan, Jing-Jing,Xing, Jing,Zhang, Qiang,Xiao, Sen
experimental part, p. 6987 - 6992 (2011/02/24)
An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines in good to high yields. Both one-pot conversions occurred through tandem β-elimination and aromatization. An efficient method for conversions ofN-tosyltetrahydroisoquinolines (N-tosyl-THIQs) and N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into isoquinolines and β-carbolines is described. Treatment ofN-tosyl-THIQs or N-tosyl-THBCs with base affords dihydroisoquinolines or dihydro-β- carbolines. These can be oxidized in situ by molecular oxygen to furnish isoquinolines or β-carbolines. Copyright
