☆ 4.7 Article

Synthesis and structure-activity relationships of N-{1-[(6-fluoro-2-naphthyl)methyllpiperidin-4-yl}benzamide derivatives as novel CCR3 antagonists

BIOORGANIC & MEDICINAL CHEMISTRY (2008)

期刊

BIOORGANIC & MEDICINAL CHEMISTRY

卷 16, 期 1, 页码 144-156

出版社

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.bmc.2007.10.003

关键词

-

类别

Biochemistry & Molecular Biology Chemistry, Medicinal Chemistry, Organic

向作者/读者索取更多资源

Protocol

Reagent

摘要

A novel class of potent CCR3 receptor antagonists were designed and synthesized starting from N-1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-yl}benzamide (1),which was found by subjecting our chemical library to high throughput screening (HTS). The CCR3 inhibitory activity of the synthesized compounds against eotaxin-induced Ca2+ influx was evaluated using CCR3-expressing preB cells. Systematic chemical modifications of I revealed that the 6-fluoro-2-naphthylmethyl moiety was essential for CCR3 inhibitory activity in this new series of CCR3 antagonists. Further structural modifications of the benzamide and piperidine moieties of 1 led to the identification of N-{8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3- yl} biphenyl-2-carboxamide (31) as a potent CCR3 antagonist with an IC50 value of 0.020 mu M. (C) 2007 Elsevier Ltd. All rights reserved.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Organic

Design, Synthesis of Some NewN-(2-fluoro-4-morpholin-4-yl-phenyl)-Substituted-Benzamide Derivatives and Screening of Their Microbial Activities

Murtaza A. Patharia, Santosh V. Raut, Bharat K. Dhotre, Mohammad Arif Pathan

Summary: This study presents an efficient synthesis method for novel fluorinated Morpholine containing benzamide derivatives and evaluates their microbial activities. The synthetic process is simple, with high yields, low cost, short reaction time, mild reaction conditions, and environmentally friendly advantages.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

Design, Synthesis, Molecular Docking Analysis and Biological Evaluations of 4-[(Quinolin-4-yl)amino]benzamide Derivatives as Novel Anti-Influenza Virus Agents

Chao Zhang, Yun-Sang Tang, Chu-Ren Meng, Jing Xu, De-Liang Zhang, Jian Wang, Er-Fang Huang, Pang-Chui Shaw, Chun Hu

Summary: In this study, a series of novel anti-influenza agents were designed and synthesized. The compound G07 demonstrated significant anti-influenza activity against multiple influenza virus strains and showed inhibition of ribonucleoprotein and the PA-PB1 subunit of RNA polymerase. These results indicate the potential of 4-[(quinolin-4-yl)amino]benzamide derivatives as candidates for anti-influenza agents.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2022)

添加到收藏夹

Article Chemistry, Medicinal

Discovery of N-((3S,4S)-4-(3,4-Difluorophenyl)piperidin-3-yl)-2-fluoro-4-(1-methyl-1H-pyrazol-5-yl)benzamide (Hu7691), a Potent and Selective Akt Inhibitor That Enables Decrease of Cutaneous Toxicity

Jinxin Che, Xiaoyang Dai, Jian Gao, Haichao Sheng, Wenhu Zhan, Yang Lu, Dan Li, Zizheng Gao, Zegao Jin, Binhui Chen, Peihua Luo, Bo Yang, Yongzhou Hu, Qiaojun He, Qinjie Weng, Xiaowu Dong

Summary: Inhibiting Akt2 isozyme may lead to keratinocyte apoptosis, driving the search for new selective Akt inhibitors with improved cutaneous safety. After optimization, Hu7691 shows promising selectivity, low apoptosis induction in keratinocytes, and excellent anticancer cell proliferation potency, leading to its approval by NMPA for clinical trials.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Engineering, Chemical

The fabrication, characterization, and pervaporation performance of poly (ether-block-amide) membranes blended with 4-(trifluoromethyl)-N(pyridine-2-yl)benzamide and 4-(dimethylamino)-N(pyridine-2-yl)benzamide fillers

Asmaa Selim, Katarzyna Knozowska, Borys Osmialowski, Joanna Kujawa, Peter Mizsey, Wojciech Kujawski

Summary: Novel PEBA membranes containing new organic fillers F1 and F2 were fabricated and evaluated for pervaporation performance in ethanol/water mixtures, with the membrane composition of 2.5% F1 and 10% F2 showing the best efficiency. Incorporation of organic fillers improved both permeate flux and separation factor of the membranes.

SEPARATION AND PURIFICATION TECHNOLOGY (2021)

添加到收藏夹

Article Chemistry, Physical

Synthesis, comprehensive spectroscopic investigation and molecular docking studies of (6-Fluoro-2-oxo-2H-chromen-4-yl) methyl morpholine-4-carbodithioate

Bessy Mary Philip, Jerin Susan John, Merin George, K. Mahesh Kumar, M. Vinduvahini, Hemanth H. S. Kumar, H. C. Devarajegowda, O. Kotresh, Tressia Alias Princy Paulose, D. Sajan

Summary: Experimental and theoretical investigations were performed to study the structure of a novel coumarin derivative. The compound was characterized using single crystal X-ray analysis, spectroscopic characterizations, and density functional theory calculations. The pharmacokinetic features of the compound were determined, and its inhibition efficiency against carcinoma-type proteins was identified through molecular docking.

JOURNAL OF MOLECULAR STRUCTURE (2022)

添加到收藏夹

Article Agriculture, Multidisciplinary

Synthesis and Biological Activity of Novel Pyrazol-5-yl-benzamide Derivatives as Potential Succinate Dehydrogenase Inhibitors

Wei Wang, Jianhua Wang, Furan Wu, Huan Zhou, Dan Xu, Gong Xu

Summary: A series of novel pyrazol-5-yl-benzamide derivatives were designed, synthesized, and evaluated for their antifungal activities. Compound 5IIc showed excellent in vitro and in vivo fungicidal activities, demonstrating its potential as a promising fungicide candidate. Additionally, molecular docking simulation and enzymatic inhibition assay provided insights into the mechanism of action of compound 5IIc.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Synthesis, Antifungal Activity, DFT Study and Molecular Dynamics Simulation of Novel 4-(1,2,4-Oxadiazol-3-yl)-N-(4-phenoxyphenyl)benzamide Derivatives

Zihui Yang, Qingsong Liu, Yue Sun, Xuebao Sun, Linlin Chen, Lu Sun, Wen Gu

Summary: The newly designed benzamide derivatives 3a-j exhibited promising antifungal activity in preliminary assays, with compound 3e showing significant inhibition against multiple fungi. In vivo experiments further demonstrated the excellent inhibitory effect of compound 3e against Botrytis cinerea. Molecular dynamics simulation revealed that compound 3e could effectively bind to the active site of class II histone deacetylase (HDAC).

CHEMISTRY & BIODIVERSITY (2021)

添加到收藏夹

Article Agriculture, Multidisciplinary

Discovery of Novel Pyrazol-5-yl-benzamide Derivatives Containing a Thiocyanato Group as Broad-Spectrum Fungicidal Candidates

Yantao Li, Han Yang, Yidan Ma, Yuan Cao, Dan Xu, Xili Liu, Gong Xu

Summary: In this study, a series of novel benzamide derivatives incorporating a thiocyanato group into the pyrazole ring were synthesized and evaluated for their fungicidal activities against various fungi and pathogens. Compound A36 showed the highest antifungal activity against Valsa mali, while compound B6 exhibited the best anti-oomycete activity against Phytophthora capsici. Compound A27 displayed broad-spectrum inhibitory activities against multiple fungi and pathogens.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

New potent steroid sulphatase inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives

Olga Ciupak, Mateusz Dasko, Karol Biernacki, Janusz Rachon, Maciej Maslyk, Konrad Kubinski, Aleksandra Martyna, Sebastian Demkowicz

Summary: A new class of potent steroid sulphatase inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives has been reported in this study. Compound 3L exhibited the highest activity in enzymatic assay, inhibiting STS activity to 7.98% at 0.5 μM concentration. Cell line experiments confirmed the effectiveness of 3L in passing through cellular membrane, making it a promising candidate for further preclinical investigations with an IC50 value of 15.97 nM.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Cytotoxic and Antitumoral Activity of N-(9H-purin-6-yl) Benzamide Derivatives and Related Water-soluble Prodrugs

Emeline Cros-Perrial, Steve Saulnier, Muhammad Zawwad Raza, Remi Charmelot, David Egron, Charles Dumontet, Laurent Chaloin, Suzanne Peyrottes, Lars Petter Jordheim

Summary: The study synthesized a series of chemically related N-(9H-purin-6-yl) benzamide derivatives and evaluated their activity on cancer cell models, finding some compounds to be active against cancer cells. Additionally, the lead compound and its prodrug showed synergistic activity with fludarabine.

CURRENT MOLECULAR PHARMACOLOGY (2022)

添加到收藏夹

Article Chemistry, Organic

Synthesis of (2-Aminopyrimidin-4-yl)(pyridin-4-yl)methanone and Derivatives

Francis Giraud, Beatrice Josselin, Sandrine Ruchaud, Fabrice Anizon, Pascale Moreau

Summary: The impact of planarity of a heterocyclic system on protein kinase inhibition was studied by synthesizing and evaluating new compounds.

SYNTHESIS-STUTTGART (2023)

添加到收藏夹

Article Chemistry, Medicinal

Design, synthesis and biological evaluation of novel 2-(4-(1H-indazol-6-yl)-1H-pyrazol-1-yl)acetamide derivatives as potent VEGFR-2 inhibitors

Xing-Rong Wang, Shuai Wang, Wen-Bo Li, Kai-Yan Xu, Xue-Peng Qiao, Xue-Li Jing, Zi-Xiao Wang, Chang-jiang Yang, Shi-Wu Chen

Summary: A series of novel VEGFR-2 inhibitors were designed and synthesized in this study, with compound W13 showing excellent inhibitory effects on tumor cell proliferation, potentially serving as a promising anticancer agent for gastric cancer therapy.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Development and Validation of an Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry Method for Quantitative Determination of N-((3S,4S)-4-(3,4-Difluorophenyl)piperidin-3-yl)-2-fluoro-4-(1-methyl-1H-pyrazol-5-yl)benzamide in Dog Plasma

Li Ping, Xinwei Dong, Minjuan Zuo, Yawen Hong, Difeng Zhu

Summary: This study developed a method for measuring Hu7691 in dog plasma, a selective AKT inhibitor developed at Zhejiang University. The method utilized ultra-performance liquid chromatography-tandem mass spectrometry for fast and efficient drug quantification. The results showed that Hu7691 exhibited high bioavailability in dogs, providing a basis for its clinical application.

APPLIED SCIENCES-BASEL (2022)

添加到收藏夹

Article Chemistry, Medicinal

Discovery of (S)-N-(2-Amino-4-fluorophenyl)-4-(1-(3-(4-((dimethylamino)methyl)phenyl)-6-oxopyridazin-1(6H)-yl)ethyl)benzamide as Potent Class I Selective HDAC Inhibitor for Oral Anticancer Drug Candidate

Daqiang Li, Zhuo Zhang, Yalei Li, Xinyi Wang, Hanyue Zhong, Huajie Yang, Yong Xi, Hongchun Liu, Aijun Shen, Youhong Hu

Summary: A series of novel benzamide derivatives were designed and synthesized from the pyridazinone scaffold. Among them, (S)-17b showed potent inhibitory activity against human class I HDAC isoforms and human myelodysplastic syndrome (SKM-1) cell line in vitro. Furthermore, (S)-17b demonstrated excellent in vivo antitumor activity in SKM-1 xenograft models, and showed better efficacy on mouse models with intact immune system compared to those with thymus deficiencies. This novel compound (S)-17b may serve as a promising drug candidate for further investigation.

JOURNAL OF MEDICINAL CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct Synthesis, Characterization and Theoretical Studies of N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)benzamide Derivatives

Tushar Das, Amit Ranjan, Leslaw Sieron, Waldemar Maniukiewicz, Subrata Das

Summary: A coherent synthesis method for the generation of amides with high yield and reproducibility has been developed, showing potential biological properties. Among the synthesized compounds, compound 3 f exhibited the most prominent properties and was identified as an ideal drug candidate through computational analysis.

CHEMISTRYSELECT (2021)

添加到收藏夹

暂无数据

暂无数据

© Peeref 2019-2024. All rights reserved.