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Keywords = arylsulfonylindole

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32 pages, 2748 KiB  
Article
Novel N-Arylsulfonylindoles Targeted as Ligands of the 5-HT6 Receptor. Insights on the Influence of C-5 Substitution on Ligand Affinity
by Loreto Arrieta-Rodríguez, Daniela Espinoza-Rosales, Gonzalo Vera, Young Hwa Cho, David Cabezas, David Vásquez-Velásquez, Jaime Mella-Raipán, Carlos F. Lagos and Gonzalo Recabarren-Gajardo
Pharmaceuticals 2021, 14(6), 528; https://doi.org/10.3390/ph14060528 - 1 Jun 2021
Cited by 2 | Viewed by 3367
Abstract
A new series of twenty-two C-5 substituted N-arylsulfonylindoles was prepared with the aim of exploring the influence of C-5 substitution on 5-HT6 receptor affinity. Eleven compounds showed moderate to high affinity at the receptor (Ki = 58–403 nM), with [...] Read more.
A new series of twenty-two C-5 substituted N-arylsulfonylindoles was prepared with the aim of exploring the influence of C-5 substitution on 5-HT6 receptor affinity. Eleven compounds showed moderate to high affinity at the receptor (Ki = 58–403 nM), with compound 4d being identified as the most potent ligand. However, regarding C-5 substitution, both methoxy and fluorine were detrimental for receptor affinity compared to our previously published unsubstituted compounds. In order to shed light on these observations, we performed docking and molecular dynamics simulations with the most potent compounds of each series (4d and 4l) and PUC-10, a highly active ligand previously reported by our group. The comparison brings about deeper insight about the influence of the C-5 substitution on the binding mode of the ligands, suggesting that these replacements are detrimental to the affinity due to precluding a ligand from reaching deeper inside the binding site. Additionally, CoMFA/CoMSIA studies were performed to systematize the information of the main structural and physicochemical characteristics of the ligands, which are responsible for their biological activity. The CoMFA and CoMSIA models presented high values of q2 (0.653; 0.692) and r2 (0.879; 0.970), respectively. Although the biological activity of the ligands can be explained in terms of the steric and electronic properties, it depends mainly on the electronic nature. Full article
(This article belongs to the Special Issue Molecular Pharmacology of 5-HT Receptors)
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10 pages, 2122 KiB  
Article
Microwave-Assisted Expeditious Synthesis of 2-Alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines Catalyzed by HgCl2 under Solvent-Free Conditions as Potential Anti-HIV-1 Agents
by Zhiping Che, Yuee Tian, Shengming Liu, Jia Jiang, Mei Hu and Genqiang Chen
Molecules 2018, 23(11), 2936; https://doi.org/10.3390/molecules23112936 - 10 Nov 2018
Cited by 6 | Viewed by 2679
Abstract
A series of 2-alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines were expeditious prepared under microwave-assisted, catalyzed by HgCl2 and solvent-free conditions. This method has the advantage of low catalyst loading and recovering catalyst, ease reaction and repaid reaction times, easy separation products and excellent [...] Read more.
A series of 2-alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines were expeditious prepared under microwave-assisted, catalyzed by HgCl2 and solvent-free conditions. This method has the advantage of low catalyst loading and recovering catalyst, ease reaction and repaid reaction times, easy separation products and excellent yields, and more conducive to the large-scale synthesis products. Furthermore, compounds 3s, 3y, 3a′, 3b′, 3f′, 3i′, 3q′, and 3r′ exhibited more potent anti-HIV-1 activity with EC50 values of 3.35, 6.12, 3.63, 9.54, 1.79, 0.51, 3.00, and 4.01 μg/mL, and TI values of 32.66, >32.68, 31.22, 13.94, 24.27, 39.59, 26.01, and 24.51, respectively. Especially compound 3i′ displayed the highest anti-HIV-1 activity with TI values of 39.59. Full article
(This article belongs to the Special Issue Microwave-Mediated Chemistry)
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7 pages, 2198 KiB  
Communication
1-[1-(4-Chlorobenzenesulfonyl)-1H-indole-3-yl]-3-[4-(pyridin-2-yl)piperazin-1-yl]propan-1-one
by Benjamín Diethelm, Sebastián Almendras and Gonzalo Recabarren-Gajardo
Molbank 2018, 2018(2), M991; https://doi.org/10.3390/M991 - 18 Apr 2018
Cited by 1 | Viewed by 10937
Abstract
The title compound was prepared by an aza-Michael addition reaction between 1-[1-(4-chlorobenzenesulfonyl)-1H-indole-3-yl]prop-2-en-1-one and 2-piridylpiperazine catalyzed by SiO2. The structural identity of the title compound was proven by elemental analysis and spectroscopic methods (IR, NMR). The compound was assayed in [...] Read more.
The title compound was prepared by an aza-Michael addition reaction between 1-[1-(4-chlorobenzenesulfonyl)-1H-indole-3-yl]prop-2-en-1-one and 2-piridylpiperazine catalyzed by SiO2. The structural identity of the title compound was proven by elemental analysis and spectroscopic methods (IR, NMR). The compound was assayed in a binding assay at the 5-HT6 receptor, showing poor affinity. Full article
(This article belongs to the Special Issue Heterocycles)
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13 pages, 3603 KiB  
Article
Synthesis and Bioactivity Evaluation of N-Arylsulfonylindole Analogs Bearing a Rhodanine Moiety as Antibacterial Agents
by Ming-Xia Song, Song-Hui Li, Jiao-Yang Peng, Ting-Ting Guo, Wen-Hui Xu, Shao-Feng Xiong and Xian-Qing Deng
Molecules 2017, 22(6), 970; https://doi.org/10.3390/molecules22060970 - 14 Jun 2017
Cited by 14 | Viewed by 4095
Abstract
Due to the rapidly growing bacterial resistance to antibiotics and the scarcity of novel agents under development, bacterial infections are still a pressing global problem, making new types of antibacterial agents, which are effective both alone and in combination with traditional antibiotics, urgently [...] Read more.
Due to the rapidly growing bacterial resistance to antibiotics and the scarcity of novel agents under development, bacterial infections are still a pressing global problem, making new types of antibacterial agents, which are effective both alone and in combination with traditional antibiotics, urgently needed. In this paper, seven series of N-arylsulfonylindole analogs 5–11 bearing rhodanine moieties were synthesized, characterized, and evaluated for antibacterial activity. According to the in vitro antimicrobial results, half of the synthesized compounds showed potent inhibition against four Gram-positive bacteria, with MIC values in the range of 0.5–8 µg/mL. For multidrug-resistant strains, compounds 6a and 6c were the most potent, with MIC values of 0.5 µg/mL, having comparable activity to gatifloxacin, moxiflocaxin and norfloxacin and being 128-fold more potent than oxacillin (MIC = 64 µg/mL) and 64-fold more active than penicillin (MIC = 32 µg/mL) against Staphylococcus aureus ATCC 43300. Full article
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35 pages, 11017 KiB  
Article
Extended N-Arylsulfonylindoles as 5-HT6 Receptor Antagonists: Design, Synthesis & Biological Evaluation
by Gonzalo Vera, Carlos F. Lagos, Sebastián Almendras, Dan Hebel, Francisco Flores, Gissella Valle-Corvalán, C. David Pessoa-Mahana, Jaime Mella-Raipán, Rodrigo Montecinos and Gonzalo Recabarren-Gajardo
Molecules 2016, 21(8), 1070; https://doi.org/10.3390/molecules21081070 - 16 Aug 2016
Cited by 14 | Viewed by 6653
Abstract
Based on a known pharmacophore model for 5-HT6 receptor antagonists, a series of novel extended derivatives of the N-arylsulfonyindole scaffold were designed and identified as a new class of 5-HT6 receptor modulators. Eight of the compounds exhibited moderate to high [...] Read more.
Based on a known pharmacophore model for 5-HT6 receptor antagonists, a series of novel extended derivatives of the N-arylsulfonyindole scaffold were designed and identified as a new class of 5-HT6 receptor modulators. Eight of the compounds exhibited moderate to high binding affinities and displayed antagonist profile in 5-HT6 receptor functional assays. Compounds 2-(4-(2-methoxyphenyl)piperazin-1-yl)-1-(1-tosyl-1H-indol-3-yl)ethanol (4b), 1-(1-(4-iodophenylsulfonyl)-1H-indol-3-yl)-2-(4-(2-methoxyphenyl)piperazin-1-yl)ethanol (4g) and 2-(4-(2-methoxyphenyl)piperazin-1-yl)-1-(1-(naphthalen-1-ylsulfonyl)-1H-indol-3-yl)ethanol (4j) showed the best binding affinity (4b pKi = 7.87; 4g pKi = 7.73; 4j pKi = 7.83). Additionally, compound 4j was identified as a highly potent antagonist (IC50 = 32 nM) in calcium mobilisation functional assay. Full article
(This article belongs to the Section Medicinal Chemistry)
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14 pages, 825 KiB  
Article
Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers
by Julio Zukerman-Schpector, Lucas Sousa Madureira, Glaudeston Dutra Wulf, Hélio A. Stefani, Stanley N. S. Vasconcelos, Seik Weng Ng and Edward R. T. Tiekink
Molecules 2014, 19(2), 1990-2003; https://doi.org/10.3390/molecules19021990 - 13 Feb 2014
Viewed by 7192
Abstract
Two independent molecules that differ in terms of rotation about the central S-N bond comprise the asymmetric unit of the title compound 1. The molecules have a V-shape with the dihedral angles between the fused ring system and benzene ring being 79.08(6)° [...] Read more.
Two independent molecules that differ in terms of rotation about the central S-N bond comprise the asymmetric unit of the title compound 1. The molecules have a V-shape with the dihedral angles between the fused ring system and benzene ring being 79.08(6)° and 72.83(5)°, respectively. The packing is mostly driven by p···p interactions occurring between the tolyl ring of one molecule and the C6 ring of the indole fused ring system of the other. DFT and IRC calculations for these and related 1-(arylsulfonyl)indole molecules showed that the rotational barrier about the S-N bond between conformers is within the 2.5–5.5 kcal/mol range. Crystal data for C16H13NO3S (1): Mr = 299.33, space group Pna21, a = 19.6152(4) Å, b = 11.2736(4) Å, c = 12.6334(3) Å, V = 2793.67(13) Å3, Z = 8, Z' = 2, R = 0.034. Full article
(This article belongs to the Section Organic Chemistry)
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