52131-82-5Relevant articles and documents
Rational Optimization of 1,2,3-Triazole-Tailored Carbazoles As Prospective Antibacterial Alternatives with Significant in Vivo Control Efficiency and Unique Mode of Action
Huang, Xing,Liu, Hong-Wu,Long, Zhou-Qing,Li, Zhen-Xing,Zhu, Jian-Jun,Wang, Pei-Yi,Qi, Pu-Ying,Liu, Li-Wei,Yang, Song
, p. 4615 - 4627 (2021/05/06)
Plant bacterial diseases can potentially damage agricultural products around the world, and few effective bactericides can manage these infections. Herein, to sequentially explore highly effective antibacterial alternatives, 1,2,3-triazole-tailored carbazoles were rationally fabricated. These compounds could suppress the growth of three main intractable pathogens including Xanthomonas oryzae pv oryzae (Xoo), X. axonopodis pv citri (Xac), and Pseudomonas syringae pv actinidiae (Psa) with lower EC50 values of 3.36 (3p), 2.87 (3p), and 4.57 μg/mL (3r), respectively. Pot experiments revealed that compound 3p could control the rice bacterial blight with protective and curative efficiencies of 53.23% and 50.78% at 200 μg/mL, respectively. Interestingly, the addition of 0.1% auxiliaries such as organic silicon and orange oil could significantly enhance the surface wettability of compound 3p toward rice leaves, resulting in improved control effectiveness of 65.50% and 61.38%, respectively. Meanwhile, compound 3r could clearly reduce the white pyogenic exudates triggered by Psa infection and afforded excellent control efficiencies of 79.42% (protective activity) and 78.74% (curative activity) at 200 μg/mL, which were quite better than those of commercial pesticide thiodiazole copper. Additionally, a plausible apoptosis mechanism for the antibacterial behavior of target compounds was proposed by flow cytometry, reactive oxygen species detection, and defensive enzyme (e.g., catalase and superoxide dismutase) activity assays. The current work can promote the development of 1,2,3-triazole-tailored carbazoles as prospective antibacterial alternatives bearing an intriguing mode of action.
Carbazole isopropanol diamine compound containing 1, 2, 3-triazole as well as preparation method and application of carbazole isopropanol diamine compound
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Paragraph 0047; 0048; 0051, (2021/04/03)
The invention relates to a carbazole isopropanol diamine compound containing 1, 2, 3-triazole as well as a preparation method and application of the carbazole isopropanol diamine compound. The compound has a structure as shown in a general formula (I) which is described in the specification. Carbazole is used as a basis, and a nitrogen-containing fragment is introduced into the system to synthesize a series of isopropanolamine-containing substructures and 1, 2, 3-triazole carbazole compounds; the compound has an excellent inhibition effect on plant pathogenic bacteria such as xanthomonas oryzae pv. Oryzae, xanthomonas axonopodis pv. Citri and Pseudomonas syringae pv.
Design, synthesis and biological activity evaluation of novel carbazole-benzylpiperidine hybrids as potential anti Alzheimer agents
Edraki, Najmeh,Faghih, Zeinab,Iraji, Aida,Nadri, Hamid,Rezaei, Zahra,Sadeghian, Batool,Sadeghian, Issa,Sakhteman, Amirhossein
, (2020/07/21)
Alzheimer's disease (AD) as the most common form of dementia in aged people, is an intricate neurodegenerative disease. Therefore, a novel strategy so-called multi-target-directed ligand has received much attention for the effective treatment of AD. In this study a series of novel carbazole-benzylpiperidine hybrids 9a-m was designed, synthesized and evaluated as acetylcholinesterase and butyrylcholinesterase inhibitors. Moreover, some of these compounds were evaluated for anti β-secretase (BACE1) activity and metal chelation properties. Among the synthesized compounds, compounds 9b (IC50 = 16.5 μM for AChE and IC50 = 0.59 μM for BuChE) and 9c (IC50 = 26.5 μM for AChE and IC50 = 0.18 μM for BuChE) showed the highest inhibitory activity against acetylcholinesterase and butyrylcholinesterase. Furthermore, these compounds (9b and 9c) displayed interaction with Zn2+ ion and compound 9c showed moderate inhibitory activity against BACE1 (24.5% at 50 μM). Kinetic and docking studies exhibited that these compounds likely act as a non-competitive inhibitor able to interact with the catalytic active site (CAS) and peripheral anionic site (PAS) of acetylcholinesterase simultaneously.
Identification of racemic and chiral carbazole derivatives containing an isopropanolamine linker as prospective surrogates against plant pathogenic bacteria: In vitro and in vivo assays and quantitative proteomics
Zhao, Yong-Liang,Huang, Xing,Liu, Li-Wei,Wang, Pei-Yi,Long, Qing-Su,Tao, Qing-Qing,Li, Zhong,Yang, Song
, p. 7512 - 7525 (2019/08/21)
Recent observations on the emergence of drug-resistant plant pathogenic bacteria have highlighted and elicited an acute campaign to develop novel, highly efficient antibiotic surrogates for managing bacterial diseases in agriculture. Thus, a type of racemic and chiral carbazole derivative containing an isopropanolamine pattern was systematically synthesized to discover low-cost and efficient antibacterial candidates. Screening results showed that compounds 2f, 6c, and 2j could significantly suppress the growth of tested plant pathogens, namely Xanthomonas oryzae pv oryzae, X. axonopodis pv citri, and Pseudomonas syringae pv actinidiae, and provided the corresponding EC50 values of 1.27, 0.993, and 0.603 μg/mL, which were significantly better than those of existing commercial drugs. In vivo studies confirmed their prospective applications for controlling plant bacterial diseases. Label-free quantitative proteomics analysis indicated that compound 2f could dramatically induce the up- and down-regulation of a total of 247 differentially expressed proteins, which was further validated by the parallel reaction monitoring technique. Moreover, fluorescence spectra and SEM images were obtained to further explore the antibacterial mechanism.
Design, Synthesis, and Biological Evaluation of a New Series of Carvedilol Derivatives That Protect Sensory Hair Cells from Aminoglycoside-Induced Damage by Blocking the Mechanoelectrical Transducer Channel
O'Reilly, Molly,Kirkwood, Nerissa K.,Kenyon, Emma J.,Huckvale, Rosemary,Cantillon, Daire M.,Waddell, Simon J.,Ward, Simon E.,Richardson, Guy P.,Kros, Corné J.,Derudas, Marco
, p. 5312 - 5329 (2019/06/07)
Aminoglycosides (AGs) are broad-spectrum antibiotics used for the treatment of serious bacterial infections but have use-limiting side effects including irreversible hearing loss. Here, we assessed the otoprotective profile of carvedilol in mouse cochlear cultures and in vivo zebrafish assays and investigated its mechanism of protection which, we found, may be mediated by a block of the hair cell's mechanoelectrical transducer (MET) channel, the major entry route for the AGs. To understand the full otoprotective potential of carvedilol, a series of 18 analogues were prepared and evaluated for their effect against AG-induced damage as well as their affinity for the MET channel. One derivative was found to confer greater protection than carvedilol itself in cochlear cultures and also to bind more tightly to the MET channel. At higher concentrations, both carvedilol and this derivative were toxic in cochlear cultures but not in zebrafish, suggesting a good therapeutic window under in vivo conditions.
With chiral center carbazolyl isopropanolamine derivatives of the preparation method and application of (by machine translation)
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Paragraph 0056; 0057; 0062; 0067, (2019/05/04)
The invention relates to a with chiral center carbazolyl isopropanolamine derivatives of the preparation method and application. This compound has the general formula (I) indicated by the structure: The compound such as [...] Phaeosphaeria, tobacco wilt b
Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of Enterococcus faecalis
Zhang, Yuan,Tangadanchu, Vijai Kumar Reddy,Cheng, Yu,Yang, Ren-Guo,Lin, Jian-Mei,Zhou, Cheng-He
supporting information, p. 244 - 249 (2018/03/21)
A series of isopropanol-bridged carbazole azoles as potential antimicrobial agents were designed and synthesized from commercial carbazoles. Bioassay revealed that 3,6-dichlorocarbazolyl triazole 3f could effectively inhibit the growth of E. faecalis with minimal inhibitory concentration of 2 μg/mL. The active molecule 3f showed lower propensity to trigger the development of resistance in bacteria than norfloxacin and exerted rapidly bactericidal ability. Compound 3f also exhibited low cytotoxicity to normal mammalian RAW264.7 cells. Further mechanism exploration indicated that conjugate 3f was membrane active against E. faecalis and could form 3f-DNA complex by intercalating into DNA of resistant E. faecalis, which might be responsible for its antimicrobial action. Molecular docking showed an efficient binding of triazole derivative 3f with DNA gyrase enzyme through noncovalent interactions.
Polymer dye-containing nanocomposites as photocatalysts
Linnik, Oksana,Nadtoka, Oksana
, p. 106 - 114 (2017/02/15)
A significant improvement of photocatalytic efficiency is achieved by the synthesis of TiO2/SiO2 nanocomposites where silica matrix provides the transport of reagents to TiO2 nanoparticles via porous structure, generation of the new active sites and thermal stability. The semiconductive films contained 10 or 30% of TiO2 in silica matrix are synthesized by sol-gel method using concentrated anatase titania colloid. The complex composites consisted of i) the Acridine Yellow dye molecules and the polyepoxypropyl carbazole; ii) the azobenzene containing polymer covered onto the titania/silica films are obtained as photocatalytic materials. Photocatalytic activity of the composites is tested via the reduction of dichromate ions.
Sulfonamido-derivatives of unsubstituted carbazoles as BACE1 inhibitors
Bertini, Simone,Ghilardi, Elisa,Asso, Valentina,Minutolo, Filippo,Rapposelli, Simona,Digiacomo, Maria,Saccomanni, Giuseppe,Salmaso, Veronica,Sturlese, Mattia,Moro, Stefano,Macchia, Marco,Manera, Clementina
supporting information, p. 4812 - 4816 (2017/10/17)
A novel series of variously substituted N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-arylsulfonamides has been synthesized and assayed for β-Secretase (BACE1) inhibitory activity. BACE1 is a widely recognized drug target for the prevention and treatment of Alzheimer's Disease (AD). The introduction of benzyl substituents on the nitrogen atom of the arylsulfonamide moiety has so far led to the best results, with three derivatives showing IC50 values ranging from 1.6 to 1.9 μM. Therefore, a significant improvement over the previously reported series of N-carboxamides (displaying IC50's ≥ 2.5 μM) has been achieved, thus suggesting an active role of the sulfonamido-portion in the inhibition process. Preliminary molecular modeling studies have been carried out to rationalize the observed structure-activity relationships.
Novel carbazole aminoalcohols as inhibitors of β-hematin formation: Antiplasmodial and antischistosomal activities
Wang, Weisi,Li, Qiang,Wei, Yufen,Xue, Jian,Sun, Xiao,Yu, Yang,Chen, Zhuo,Li, Shizhu,Duan, Liping
, p. 191 - 199 (2017/04/13)
Malaria and schistosomiasis are two of the most socioeconomically devastating parasitic diseases in tropical and subtropical countries. Since current chemotherapeutic options are limited and defective, there is an urgent need to develop novel antiplasmodials and antischistosomals. Hemozoin is a disposal product formed from the hemoglobin digestion by some blood-feeding parasites. Hemozoin formation is an essential process for the parasites to detoxify free heme, which is a reliable therapeutic target for identifying novel antiparasitic agents. A series of novel carbazole aminoalcohols were designed and synthesized as potential antiplasmodial and antischistosomal agents, and several compounds showed potent in?vitro activities against Plasmodium falciparum 3D7 and Dd2 strains and adult and juvenile Schistosoma japonicum. Investigations on the dual antiparasitic mechanisms showed the correlation between inhibitory activity of β-hematin formation and antiparasitic activity. Inhibiting hemozoin formation was identified as one of the mechanisms of action of carbazole aminoalcohols. Compound 7 displayed potent antiplasmodial (Pf3D7 IC50?=?0.248?μM, PfDd2 IC50?=?0.091?μM) and antischistosomal activities (100% mortality of adult and juvenile schistosomes at 5 and 10?μg/mL, respectively) and exhibited low cytotoxicity (CC50?=?7.931?μM), which could be considered as a promising lead for further investigation. Stoichiometry determination and molecular docking studies were also performed to explain the mode of action of compound 7.
