- Synthesis of bivalent ligands of β-carboline-3-carboxylates via a palladium-catalyzed homocoupling process
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The first synthesis of bivalent ligands of β-carboline-3-carboxylates has been achieved from β-carboline-3-carboxylate tert-butyl ester (βCCt) via Sonogashira and palladium-catalyzed homocoupling processes. The Boc protected intermediate, an iodo-β-carboline-3-carboxylate, was employed to provide a general entry into a series of bivalent ligands structurally similar to βCCt.
- Yin, Wenyuan,Sarma, P. V. V. Srirama,Ma, Jun,Han, Dongmei,Chen, Jessica L.,Cook, James M.
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- Synthesis, characterization, DNA binding ability and cytotoxicity of the novel platinum(II), copper(II), cobalt(II) and nickel(II) complexes with 3-(1H-benzo[d]imidazol-2-yl)-β-carboline
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3-(1H-benzo[d]imidazol-2-yl)-β-carbolin (Y-5) and its Pt(II), Cu(II), Co(II) and Ni(II) complexes 1-4 were synthesized and characterized by 1H NMR, MS, IR, elemental analyses and TG. Crystal structure of Y-5 and its Pt(II) complex were reported. The DNA binding and DNA cleavage ability of complexes with Cu(II) ion and Pt(II) ion as the metal center showed enhanced activities than that of the other two, which were evaluated by absorption spectra, EB displacement experiments and agarose gel electrophoresis. Assay on the cytotoxicity of the above complexes against A549 and Hela tumor cells and Helf normal cells revealed that the complexes 1 and 2 are toxic against tumor cells but relatively safe to normal cell.
- Jin, Qiao-Mei,Lu, Yi,Jin, Jian-Lin,Guo, Hao,Lin, Guo-Wu,Wang, Yue,Lu, Tao
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- β-Carbolines as benzodiazepine receptor ligands. 1. Synthesis and benzodiazepine receptor interaction of esters of β-carboline-3-carboxylic acid
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Several esters of β-carboline-3-carboxylic acid were synthesized and tested in respect to their affinity for the benzodiazepine receptor in bovine cortex membranes. Out of these derivatives, the methyl, ethyl, and n-propyl ester were clearly the most pote
- Lippke,Schunack,Wenning,Muller
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- Synthesis and biological evaluation of novel 3,9-substituted β-carboline derivatives as anticancer agents
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Abstract In our previous studies on 1-benzyl-3-(5-hydroxymethyl-2-furyl)indazole (YC-1) analogs, we synthesised numerous substituted carbazole and α-carboline derivatives, which exhibited anticancer activity. In this study, we designed and synthesised a series of 3,9-substituted β-carbolines, by replacing the tricyclic rings of carbazole and α-carboline derivatives with isosteric β-carboline, and evaluated anticancer activity. We observed that 9-(2-methoxybenzyl)-β-carboline-3-carboxylic acid (11a) inhibited the growth of HL-60 cells by inducing apoptosis, with a half maximal inhibitory concentration of 4.0 μM. Our findings indicate that β-carboline derivatives can be used as lead compounds for developing novel antitumor agents.
- Chen, Yi-Fong,Lin, Yi-Chien,Chen, Jeng-Pang,Chan, Hsu-Chin,Hsu, Mei-Hua,Lin, Hui-Yi,Kuo, Sheng-Chu,Huang, Li-Jiau
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- Molecular hybrid design, synthesis, in vitro and in vivo anticancer evaluation, and mechanism of action of N-acylhydrazone linked, heterobivalent β-carbolines
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A series of N-acylhydrazone-linked, heterobivalent β-carboline derivatives was designed and synthesized from L-tryptophan in a nine-step reaction sequence. The effort resulted in the heterobivalent β-carbolines 10a–t in good yields. The target compounds were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The in vitro cytotoxic activity of the synthesized compounds was evaluated against normal EA.HY926 cells and five cancer cell lines: LLC (Lewis lung carcinoma), BGC-823 (gastric carcinoma), CT-26 (murine colon carcinoma), Bel-7402 (liver carcinoma), and MCF-7 (breast carcinoma). Compound 10e, with an IC50 value of 2.41 μM against EA.HY926 cells, was the most potent inhibitor. It showed cytotoxicity against all five cancer cell lines of different origin – murine and human, with IC50 values ranging from 4.2 ± 0.7 to 18.5 ± 3.1 μM. A study of structure-activity relationships indicated that the influence on cytotoxic activities of the substituent in the R9′-position followed the tendency, 2,3,4,5,6-perfluorophenylmethyl > 4-fluorobenzyl > 3-phenylpropyl group. The antitumor efficacies of the selected compounds were also evaluated in mice. Compound 10e exhibited potent antitumor activity, with tumor inhibition of more than 40% for Sarcoma 180 and 36.7% for Lewis lung cancer. Furthermore, the pharmacological mechanisms showed that compound 10e has a certain impairment in the motility of LLC cells, which suggests the anti-metastatic potential. And compound 10e inhibited angiogenesis in chicken chorioallantoic membrane assay, and the anti-angiogenetic potency was more potent than the reference drug combretastatin A4-phosphate (CA4P) at a concentration 50 μM.
- Chen, Wei,Chen, Xiaofei,Dai, Bin,Fan, Wenxi,Guo, Liang,Ma, Qin,Zhang, Jie
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- 3-di-amine β- carboline base compound, preparation method and pharmaceutical composition and application thereof
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The invention discloses a 3-position diamine connected beta-carboline alkali compound, and a preparation method, a medicinal composition and a use thereof. The above di-beta-carboline alkali compound and its medicinal salt are represented by general formu
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- Design, synthesis, and anti-proliferative evaluation of 1: H -1,2,3-triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates in estrogen responsive and triple negative breast cancer cells
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A series of 1H-1,2,3 triazole grafted tetrahydro-β-carboline-chalcone/ferrocenylchalcone conjugates were synthesized and in vitro evaluated against estrogen responsive (MCF-7) and triple negative (MDA-MB-231) breast cancer cells. Comparative analysis reve
- Awolade, Paul,Cele, Nosipho,Gu, Liang,Kaur, Mandeep,Kumar, Vipan,Pillay, Ruvesh Pascal,Sharma, Bharvi,Singh, Parvesh
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p. 11137 - 11147
(2020/07/15)
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- Design, synthesis, and biological evaluation of novel N-acylhydrazone bond linked heterobivalent β-carbolines as potential anticancer agents
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Utilizing a pharmacophore hybridization approach, we have designed and synthesized a novel series of 28 new heterobivalent β-carbolines. The in vitro cytotoxic potential of each compound was evaluated against the five cancer cell lines (LLC, BGC-823, CT-26, Bel-7402, and MCF-7) of different origin—murine and human, with the aim of determining the potency and selectivity of the compounds. Compound 8z showed antitumor activities with half-maximal inhibitory concentration (IC50) values of 9.9 ± 0.9, 8.6 ± 1.4, 6.2 ± 2.5, 9.9 ± 0.5, and 5.7 ± 1.2 μM against the tested five cancer cell lines. Moreover, the effect of compound 8z on the angiogenesis process was investigated using a chicken chorioallantoic membrane (CAM) in vivo model. At a concentration of 5 μM, compound 8z showed a positive effect on angiogenesis. The results of this study contribute to the further elucidation of the biological regulatory role of heterobivalent β-carbolines and provide helpful information on the development of vascular targeting antitumor drugs.
- Chen, Xiaofei,Guo, Liang,Ma, Qin,Chen, Wei,Fan, Wenxi,Zhang, Jie
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- Pd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes
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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.
- Wang, Hai-Jun,Guo, Lei,Zhu, Cheng-Feng,Luo, Yun-Fei,Li, You-Gui,Wu, Xiang
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supporting information
p. 5456 - 5459
(2018/10/20)
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- ?-CARBOLINE, DIHYDRO-?-CARBOLINE AND TETRAHYDRO-?-CARBOLINE ALKALOID DERIVATIVES AND PREPARATION METHODS SAME AND USE IN ASPECTS OF PREVENTING AND TREATING PLANT VIRUSES, FUNGICIDES AND INSECTICIDES
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The present invention relates to β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives (I) and a method for preparing same and the use in the aspects of preventing and treating plant viruses, fungicides and insecticides. For the meaning of each group in formula (I) see the description. The β-carboline, dihydro-β-carboline and tetrahydro-β-carboline alkaloid derivatives of the present invention show a particularly ourstanding anti-plant virus activity, and also have fungicidal and insecticidal activities.
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Paragraph 0165-0166
(2016/11/28)
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- Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents
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A series of novel bivalent β-carbolines with a piperazine group spacer between 3-methylene units were synthesized and evaluated as antitumor agents. The results demonstrated that compounds 7e and 7g exhibited the most potent cytotoxic activities against ten tumor cell lines. Structure-activity relationships analysis indicated that (1) the substituents in positions 1 and 9 of the β-carboline ring played a significant role in modulating the antitumor activity; (2) the introduction of alkyl groups into position-9 of the β-carboline nucleus enhanced their cytotoxic potencies and the butyl substituent was the optimal group. Investigation of the preliminary mechanism of action demonstrated that compound 7g showed obvious anti-angiogenic activity in the in vivo CAM assay, and the potency was similar to that of CA4P (200 μM).
- Sun, Rongqin,Liu, Rui,Zhou, Chi,Ren, Zhenghua,Guo, Liang,Ma, Qin,Fan, Wenxi,Qiu, Liqin,Yu, Huijuan,Shao, Guang,Cao, Rihui
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p. 2170 - 2174
(2015/12/11)
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- Design, synthesis, anti-TMV, fungicidal, and insecticidal activity evaluation of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid derivatives based on virus inhibitors of plant sources
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By drawing the creation ideas of botanical pesticides, a series of tetrahydro-β-carboline-3-carboxylic acid derivatives were designed and synthesized, and first evaluated for their anti-TMV, fungicidal and insecticidal activities. Most of these derivatives exhibited good antiviral activity against TMV both in vitro and in vivo. Especially, the activities of compounds 8 and 15 in vivo were higher than that of ribavirin. The compound 8 exhibited more than 70% fungicidal activities against Cercospora arachidicola Hori, Alternaria solani, Bipolaris maydis, and Rhizoctonia solani at 50 mg/kg, compounds 16 and 20 exhibited more than 60% insecticidal activities against Mythimna separate and Ostrinia nubilalis.
- Song, Hong-Jian,Liu, Yong-Xian,Liu, Yu-Xiu,Huang, Yuan-Qiong,Li, Yong-Qiang,Wang, Qing-Min
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p. 5228 - 5233
(2015/01/08)
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- Synthesis and biological evaluation of novel β-carboline derivatives as antiproliferative agents
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A series of novel β-carboline derivatives was synthesized and evaluated for their cytotoxic activities in vitro against two human tumor cell lines. Most of the compounds showed moderate to potent cytotoxic activities against the tested cell lines, in whic
- Chen, Jing,Du, Wenting,Tao, Xuefen,Huang, Jiawei,Song, Yuliang,Ying, Huazhou
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p. 879 - 885
(2013/12/04)
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- Synthesis and structure of the β-carboline derivatives and their binding intensity with cyclin-dependent kinase 2
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Series of 3-substituted of 6-aminosulfonyl-β-carbolines were designed and synthesized. In addition, the binding mode of these β-carboline derivatives with cyclin-dependent kinase 2 (CDK2) was studied by means of fluorescence measurements and molecular doc
- Wang, Yue,Jin, Qiaomei,Lin, Guowu,Yang, Taotao,Wang, Zhanwei,Lu, Yi,Tang, Yimin,Liu, Lifang,Lu, Tao
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p. 435 - 441
(2012/05/04)
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- Synthesis of a novel series of 1,6-disubstituted-3-(cyclohexylmethoxy)- β-carboline derivatives via Minisci reaction
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A facile and efficient route for the synthesis of 1,6-disubstituted-3- cyclohexylmethoxy-β-carboline derivatives via the Minisci reaction has been described with good yields and selectivity. A novel series of β-carboline derivatives with various substitue
- Lin, Guowu,Wang, Yue,Zhou, Qingfa,Wang, Jian,Yang, Taotao,Wang, Zhanwei,Lu, Tao
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p. 1895 - 1910
(2012/06/18)
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- Design, synthesis, and subtype selectivity of 3,6-disubstituted β-carbolines at Bz/GABA(A)ergic receptors. SAR and studies directed toward agents for treatment of alcohol abuse
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A series of 3,6-disubstituted β-carbolines was synthesized and evaluated for their in vitro affinities at αxβ 3γ2 GABAA/benzodiazepine receptor subtypes by radioligand binding assays in search of α1 s
- Yin, Wenyuan,Majumder, Samarpan,Clayton, Terry,Petrou, Steven,Vanlinn, Michael L.,Namjoshi, Ojas A.,Ma, Chunrong,Cromer, Brett A.,Roth, Bryan L.,Platt, Donna M.,Cook, James M.
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experimental part
p. 7548 - 7564
(2011/01/04)
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- A facile synthesis of 3-substituted 9H-pyrido[3,4-b]indol- 1(2H)-one derivatives from 3-substituted β-carbolines
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A mild and efficient two-step synthesis of 3-substituted β-carbolinone derivatives from 3-substituted β-carboline in good yields is described. A possible reaction mechanism for the formation of the skeleton of β-carbolin-1-one is proposed. The structures of these compounds were established by IR, 1H-NMR, 13C-NMR, mass spectrometry and elemental analysis, as well as X-ray crystallographic analysis of 4-2 and 6-2.
- Lin, Guowu,Wang, Yue,Zhou, Qingfa,Tang, Weifang,Wang, Jian,Lu, Tao
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scheme or table
p. 5680 - 5691
(2010/12/19)
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- OXADIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
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Oxadiazole derivatives of formula (I) where ring A is a bicyclic or tricyclic system. Claimed compounds are active on nicotinic acetylcholine receptors (nAChRs), and are useful to treat neurological, psychiatric, and gastrointestinal disorders, as well as sepsis and obesity.
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Page/Page column 56
(2009/07/17)
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- HARMINE DERIVATIVES, INTERMEDIATES USED IN THEIR PREPARATION, PREPARATION PROCESSES AND USE THEREOF
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This invention relates to compounds of general formula (I), wherein R1, R2, R3, R4 and R5 are as defined specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produce harmine derivatives with enhanced antihumour activity and lower nervous system toxicity by structurally modification parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9, The compounds of the present invention can be pre easily with high yield. They can be used in manufacture of a variety of antitumour medicines and medicines used in treatm tumour diseases in combination of light or radiation therapy.
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Page/Page column 14; 15; 47; 95
(2008/06/13)
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- Esters of 6-(4'-Fluorobenzylamino)-β-carboline-3-carboxylic acid as potential benzodiazepine imaging agents for P.E.T.
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As potential P.E.T. imaging agents for the benzodiazepine receptor, two fluorine-18 labeled analogues of the β-carbolines were prepared via N-alkylation of the corresponding desbenzyl amine precursors with [18F]fluorobenzyl iodide.
- Elder,Mach,Nowak,Moroney,Rao,Ehrenkaufer
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p. 205 - 211
(2007/10/02)
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- SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF C(1)- AND N(2)-SUBSTITUTED &β-CARBOLINE DERIVATIVES
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A series of C(1) as well as N(2)-hetero-substituted β-carbolines has been synthesized from indoles via N-hydroxytryptophan derivatives (Schemes I and II).Preliminary pharmacodynamical data are provided (Tabel I).Of the β-carbolines 4,5,14-16 prepared, the
- Plate, Ralf,Nivard, Rutger J. F.,Ottenheijm, Harry C. J.,Kardos, Julianna,Simonyi, Miklos
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p. 3105 - 3114
(2007/10/02)
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- Tetrahydro-β-carboline derivatives and treatment of liver diseases
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Novel tetrahydro-β-carboline derivatives of the formula: STR1 wherein R1 is carboxyl, a lower alkoxycarbonyl, carbamoyl, an N,N-di-lower alkylcarbamoyl, an N-(phenyl-substituted lower alkylidenamino)carbamoyl, a [N,N-di(lower alkyl)amino]-lower alkyl, or a nitrogen-containing monocyclic heterocyclic group; R2 is hydrogen atom, a lower alkyl, or a hydroxy-lower alkyl group, or R2 is combined with R1 to form a group: --CO--O--CH2 --; R3 is hydrogen atom, a lower alkyl, a phenyl-lower alkyl, or a group: --CSS--R4 ; R4 is hydrogen atom, an alkyl, or a group: --(CH2)n Y1 ; n is 0, 1 or 2, Y1 is a lower alkenyl, a phenyl-substituted lower alkenyl, an N,N-di(lower alkyl)amino, a lower alkylmercapto, a lower alkoxycarbonyl, benzoyl, naphthyl, a cycloalkyl, a monocyclic heterocyclic group, or a substituted or unsubstituted phenyl, which have excellent activities for alleviating, curing and preventing hepatic damages and are useful as a therapeutic or prophylactic agent for hepatic diseases, and processes for the preparation thereof, and a pharmaceutical composition containing the above compound as an active ingredient.
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- SYNTHESIS OF 3,6-DISUBSTITUTED &β-CARBOLINES WHICH POSSESS EITHER BENZODIAZEPINE ANTAGONIST OR AGONIST ACTIVITY
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A series of 3-substituted and 3,6-disubstituted β-carbolines have been synthesized.These compounds have been screened in vitro in order to determine the size of substituents which benzodiazepine receptors will tolerate at positions -3 and -6 of the β-carboline nucleus.It has been found that the receptor will tolerate ester alkyl groups at position-3 as large as cyclohexyl 1g but not as large as adamantyl 5d.Moreover, N-aryl substituents as large as naphthobenzylamino 8b can be introduced at position-6 without significant loss of receptor binding affinity.
- Hagen, Timothy J.,Guzman, Filadelfo,Schultz, Christopher,Cook, James M.,Skolnick, Phil,Shannon, Harlan E.
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p. 2845 - 2855
(2007/10/02)
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- AROMATIZATION OF 3,4-DIHYDRO-β-CARBOLINE-3-CARBOXYLIC ACID AND ITS DERIVATIVES THROUGH A CARBANION INTERMEDIATE : MECHANISTIC STUDY AND USE IN CHEMICAL SYNTHESIS
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3,4-dihydro-β-carboline-3-carboxylic acid, its esters and amide derivatives (AH2) undergo complete aromatization into corresponding β-carboline derivatives (A) by basic treatment under mild conditions.This, together with the easy obtention of 3,4-dihydro-
- Previero, A.,Barry, L-G.,Torreilles, J.,Fleury, B.,Letellier, S.,Maupas, B.
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p. 221 - 234
(2007/10/02)
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- β-Carbolin-3-carboxylic acid derivatives
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A β-carbolin-3-carboxylic acid derivative of the formula STR1 has valuable pharmacological properties when administered to patients, e.g. humans as a drug, have been shown to possess interesting tranquilizing activity.
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- 3,4-b.
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The compounds, 3-amino-9H-pyrido left bracket 3,4-b right bracket indole and 3-amino-1-methyl-9H-pyrido left bracket 3,4-b right bracket indole, which are effectors in induction of sister chromatid exchangers in human cells, were isolated from pyrolysis products of L-tryptophan and characterized by HPLC and UV techniques.
- Tada,Saeki,Oikawa
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p. 1450 - 1454
(2007/10/02)
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