99532-45-3Relevant academic research and scientific papers
Design, synthesis, and bioevaluation of pyrazolo[1,5-a]pyrimidine derivatives as tubulin polymerization inhibitors targeting the colchicine binding site with potent anticancer activities
Chen, Jianjun,Deng, Xin,Li, Gang,Li, Ling,Liu, Jin,Liu, Shuwen,Luo, Meihua,Ren, Yichang,Wang, Wei,Wang, Yuxi
, (2020/07/08)
A series of Pyrazolo[1,5-a]Pyrimidine analogs were designed and synthesized as novel tubulin inhibitors. Among them, compounds 1a and 1b showed the highest antiproliferative activity against a panel of cancer cell lines with average IC50 values
Synthesis, antimicrobial and cytotoxic activities, and molecular docking studies of N-arylsulfonylindoles containing an aminoguanidine, a semicarbazide, and a thiosemicarbazide moiety
Song, Mingxia,Wang, Shiben,Wang, Zengtao,Fu, Zhiyang,Zhou, Shengchao,Cheng, Huabin,Liang, Zhuo,Deng, Xianqing
, p. 108 - 118 (2019/01/28)
Thirty-six N-arylsulfonyl-3-substituted indoles were designed and synthesized by combining the N-arylsulfonylindoles with aminoguanidine, semicarbazide, and thiosemicarbazide, respectively. Their antibacterial activities were screened, and cytotoxic activities were evaluated. The results showed that aminoguanidines (6) exhibited much better antibacterial activity than semicarbazides (7) and thiosemicarbazides (8). Most compounds in series 6 showed potent inhibitory activity against the tested bacterial strains, including multidrug-resistant strains, with MIC values in the range of 1.08–23.46 μM. The cytotoxic activity of the compounds 6c, 6d, 6h, 6j, 6k and 6l was assessed in two human cancer cell lines A590 and SGC7901, and one human normal cell line HEK 293T. The results indicated that compounds selected exhibited excellent activity against the tested cancer cells with IC50 values in the range of 1.51–15.12 μM suggesting the potential of them as new antibacterial and anticancer agents. What's more, the results of resistance study revealed that resistance of the tested bacteria toward 6d is not easily developed. Molecular docking studies revealed that the aminoguanidine and arylsulfonylindole moieties played a significant role in binding the target site of E. coli FabH-CoA receptor.
N - benzenesulfonyl -3 - acetyl indole naked eye compound, preparation method and application
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Paragraph 0046; 0047; 0048, (2019/03/10)
The invention discloses an N-benzenesulfonyl-3-acetyl indole acyl hydrazone compound, a preparation method and application and belongs to the technical field of organic synthesis. An N-benzenesulfonyl-3-acetyl indole acyl hydrazone derivative uses benzpyr
Indole compound and applications thereof, and pharmaceutical composition and applications thereof
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Paragraph 0100; 0101; 0102; 0103, (2019/01/09)
The present invention provides an indole compound and applications thereof, wherein the compound can effectively inhibit a CBP/EP300 Bromodomain receptor, and can be used as a drug for cancers, inflammatory diseases, autoimmune diseases, septicemia and viral infections.
2-Aminoimidazole-based antagonists of the 5-HT6 receptor – A new concept in aminergic GPCR ligand design
Hogendorf, Adam S.,Hogendorf, Agata,Kurczab, Rafa?,Kalinowska-T?u?cik, Justyna,Popik, Piotr,Nikiforuk, Agnieszka,Krawczyk, Martyna,Sata?a, Grzegorz,Lenda, Tomasz,Knutelska, Joanna,Bugno, Ryszard,Staroń, Jakub,Pietru?, Wojciech,Mat?oka, Miko?aj,Dubiel, Krzysztof,Moszczyński-P?tkowski, Rafa?,Pieczykolan, Jerzy,Wieczorek, Maciej,Pilarski, Bogus?aw,Zajdel, Pawe?,Bojarski, Andrzej J.
supporting information, p. 1 - 15 (2019/06/24)
A new strategy in the design of aminergic GPCR ligands is proposed – the use of aromatic, heterocyclic basic moieties in place of the evergreen piperazine or alicyclic and aliphatic amines. This hypothesis has been tested using a benchmark series of 5-HT6R antagonists obtained by coupling variously substituted 2-aminoimidazole moieties to the well established 1-benzenesulfonyl-1H-indoles, which served as the ligands cores. The crystallographic studies revealed that upon protonation, the 2-aminoimidazole fragment triggers a resonance driven conformational change leading to a form of higher affinity. This molecular switch may be responsible for the observed differences in 5-HT6R activity of the studied chemotypes with different amine-like fragments. Considering the multiple functionalization sites of the embedded guanidine fragment, diverse libraries were constructed, and the relationships between the structure and activity, metabolic stability, and solubility were established. Compounds from the N-(1H-imidazol-2-yl)acylamide chemotype (10a–z) exhibited high affinity for 5-HT6R and very high selectivity over 5-HT1A, 5-HT2A, 5-HT7 and D2 receptors (negligible binding), which was attributed to their very weak basicity. The lead compound in the series 4-methyl-5-[1-(naphthalene-1-sulfonyl)-1H-indol-3-yl]-1H-imidazol-2-amine (9i) was shown to reverse the cognitive impairment caused by the administration of scopolamine in rats indicating procognitive potential.
Oxidative coupling of enolates using memory of chirality: An original enantioselective synthesis of quaternary α-amino acid derivatives
Mambrini, Antonin,Gori, Didier,Guillot, Régis,Kouklovsky, Cyrille,Alezra, Valérie
supporting information, p. 12742 - 12745 (2018/12/01)
We describe here the first enantioselective oxidative heterocoupling of enolates. Our strategy relies on the memory of chirality concept and allows the stereocontrolled formation of quaternary centres on α-amino acid derivatives with an enantiomeric excess of up to 94%.
Synthesis and antitumor activity of new thiazole nortopsentin analogs
Attanzio, Alessandro,Barraja, Paola,Carbone, Anna,Cascioferro, Stella,Cirrincione, Girolamo,Diana, Patrizia,Montalbano, Alessandra,Parrino, Barbara,Spanò, Virginia,Tesoriere, Luisa
, (2017/01/04)
New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode of action. Results showed that the three compounds act as pro-apoptotic agents inducing a clear shift of viable cells towards early apoptosis, while not exerting necrotic effects. They also caused cell cycle perturbation with significant decrease in the percentage of cells in the G0/G1 and S phases, accompanied by a concomitant percentage increase of cells in the G2/M phase, and appearance of a subG1-cell population.
Targeting the Gatekeeper MET146 of C-Jun N-Terminal Kinase 3 Induces a Bivalent Halogen/Chalcogen Bond
Lange, Andreas,Günther, Marcel,Büttner, Felix Michael,Zimmermann, Markus O.,Heidrich, Johannes,Hennig, Susanne,Zahn, Stefan,Schall, Christoph,Sievers-Engler, Adrian,Ansideri, Francesco,Koch, Pierre,Laemmerhofer, Michael,Stehle, Thilo,Laufer, Stefan A.,Boeckler, Frank M.
supporting information, p. 14640 - 14652 (2015/12/09)
We target the gatekeeper MET146 of c-Jun N-terminal kinase 3 (JNK3) to exemplify the applicability of X···S halogen bonds in molecular design using computational, synthetic, structural and biophysical techniques. In a designed series of aminopyrimidine-ba
Access to biaryl sulfonamides by palladium-catalyzed intramolecular oxidative coupling and subsequent nucleophilic ring opening of heterobiaryl sultams with amines
Laha, Joydev K.,Dayal, Neetu,Jethava, Krupal P.,Prajapati, Dilip V.
supporting information, p. 1296 - 1299 (2015/03/14)
The installation of sulfonamide pharmacophores on heterobiaryls has successfully been executed by a previously unknown palladium-catalyzed intramolecular oxidative coupling in N-arylsulfonyl heterocycles followed by novel ring opening of heterobiaryl sultams with amine nucleophiles. The protocol has a wide scope of substrates warranting broad applications in the synthesis of heterobiaryls containing an o-sulfonyl or carboxyl functional group.
Synthesis and quantitative structure-activity relationship (QSAR) study of novel N-arylsulfonyl-3-acylindole arylcarbonyl hydrazone derivatives as nematicidal agents
Che, Zhiping,Zhang, Shaoyong,Shao, Yonghua,Fan, Lingling,Xu, Hui,Yu, Xiang,Zhi, Xiaoyan,Yao, Xiaojun,Zhang, Rui
, p. 5696 - 5705 (2013/07/26)
In continuation of our program aimed at the discovery and development of natural-product-based pesticidal agents, 54 novel N-arylsulfonyl-3-acylindole arylcarbonyl hydrazone derivatives were prepared, and their structures were well characterized by 1
