☆ 4.5 Article

4,5-Dihydro-1H-pyrazolo[3,4-d] pyrimidine containing phenothiazines as antitubercular agents

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2014)

期刊

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷 24, 期 6, 页码 1493-1495

出版社

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.bmcl.2014.02.012

关键词

Dihydropyrazolo[3,4-d]pyrimidine; Phenothiazines; Biginelli multicomponent reaction; Cytotoxicity; Antitubercular activity

类别

Chemistry, Medicinal Chemistry, Organic

向作者/读者索取更多资源

Protocol

Reagent

摘要

A series of novel dihydropyrazolo[3,4-d]pyrimidine derivatives bearing a phenothiazine nucleus were synthesized in excellent yields via a modified Biginelli multicomponent reaction. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, Mass spectra and elemental analysis followed by antimycobacterial screening. Among all the screened compounds, compound 4g showed most pronounced activity against Mycobacterium tuberculosis (Mtb) with minimum inhibitory concentration (MIC) of 0.02 mu g/mL, making it more potent than first line antitubercular drug isoniazid. (C) 2014 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

4.5

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

Review Biochemistry & Molecular Biology

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

Maria Marinescu

Summary: Antimicrobial resistance was a global public health priority even before the COVID-19 pandemic. Research is currently focused on finding new organic structures with antimicrobial and antiviral properties, with the Biginelli synthesis being intensively studied for its production of therapeutic compounds with a range of medicinal properties.

MOLECULES (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Exploration of 4-aminopyrrolo[2,3-d]pyrimidine as antitubercular agents

Omobolanle Janet Jesumoroti, Richard M. Beteck, Audrey Jordaan, Digby F. Warner, Lesetja J. Legoabe

Summary: Tuberculosis (TB) is a major cause of death worldwide. In this study, a library of 7H-Pyrrolo[2,3-d]pyrimidine derivatives was synthesized to develop new anti-TB compounds. Sixteen compounds showed activity against Mycobacterium tuberculosis, with the most potent derivative having a MIC90 value of 0.488 μM and no cytotoxicity. These findings suggest that these compounds have potential for further drug development and optimization.

MOLECULAR DIVERSITY (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones via a Three-Component Biginelli Reaction

Giovanna Bosica, Fiona Cachia, Riccardo De Nittis, Nicole Mariotti

Summary: Multicomponent reactions offer economic and environmental advantages, with the Biginelli reaction being a significant method for synthesizing 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). In this study, silicotungstic acid supported on Ambelyst-15 was used as a catalyst for the Biginelli reaction under solventless conditions, resulting in improved reaction yields.

MOLECULES (2021)

添加到收藏夹

Review Chemistry, Medicinal

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

Francisco Sanchez-Sancho, Marcos Escolano, Daniel Gavina, Aurelio G. Csaky, Maria Sanchez-Rosello, Santiago Diaz-Oltra, Carlos del Pozo

Summary: The interest in 3,4-dihydropyrimidine-2(1H)-(thio)ones is growing due to their biological relevance. The classical approach to reach these structures is the Biginelli reaction, but it has limitations in product diversity. In this manuscript, two main strategies to overcome these limitations are discussed: modification of the reaction components and postmodification of the products. The modification of the keto ester counterpart is the most popular approach, and the use of Biginelli adducts for further modification is also highlighted.

PHARMACEUTICALS (2022)

添加到收藏夹

Article Chemistry, Physical

Synthesis of 3,4-Dihydropyrimidin-2(1H)-one-phosphonates by the Microwave-Assisted Biginelli Reaction

Nora Popovics-Toth, Adam Tajti, Evelyn Humpfner, Erika Balint

Summary: The synthesis of novel 3,4-dihydropyrimidin-2(1H)-one-phosphonates was achieved through microwave-assisted Biginelli reaction, optimizing reaction parameters and demonstrating a wide scope of application. By-products of the synthesis were also identified, including a previously reported impossible reaction between aliphatic aldehydes, diethyl (2-oxopropyl)phosphonate, and urea.

CATALYSTS (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Synthesis, biological evaluation, and in silico studies of new CDK2 inhibitors based on pyrazolo[3,4-d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine scaffold with apoptotic activity

Asmaa A. Mandour, Ibrahim F. Nassar, Mohammed T. Abdel Aal, Mahmoud A. E. Shahin, Wael A. El-Sayed, Maghawry Hegazy, Amr Mohamed Yehia, Ahmed Ismail, Mohamed Hagras, Eslam B. Elkaeed, Hanan M. Refaat, Nasser S. M. Ismail

Summary: A series of novel pyrazolopyrimidine derivatives were designed and synthesized as CDK2 inhibitors, showing promising anticancer activity against breast and colon cancer cells. Compound 15 exhibited the most significant inhibitory activity, causing alterations in cell cycle progression and apoptosis. Furthermore, compound 15 demonstrated low cytotoxicity in normal cells, indicating its potential therapeutic value.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Physical

Polymer-Supported Dioxidovanadium(V) Complex-Based Heterogeneous Catalyst for Multicomponent Biginelli Reaction Producing Biologically Active 3,4-Dihydropyrimidin-2-(1H)-ones

Mannar R. Maurya, Akhil Patter, Devesh Singh, Kaushik Ghosh

Summary: Diovandium(V) complex [(VO2)-O-V(sal-aebmz)] (1) immobilized on chloromethylated polystyrene (PS-Cl) has been used as catalyst in a single pot multicomponent Biginelli reaction, producing biologically active 3,4-dihydropyrimidin-2-(1H)-one (DHPM) under solvent-free conditions with H2O2 as oxidant. The optimized reaction conditions yield ca. 95% DHPMs.

CATALYSTS (2023)

添加到收藏夹

Article Chemistry, Applied

Synthesis and catalytic application of a curcumin-based bio-MOF in one-pot preparation of tetrahydroquinazolinone derivatives via Biginelli reaction

Parviz Movaheditabar, Mohammad Javaherian, Valiollah Nobakht

Summary: A new curcumin-based bidentate linker ligand, CurOAc, and its corresponding zinc-organic framework, Zn-CurOAc, were designed, synthesized and characterized. Zn-CurOAc showed excellent catalytic performance in the one-pot three-component Biginelli condensation reaction.

APPLIED ORGANOMETALLIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Trinuclear cis-[MoVIO2] complexes catalyzed efficient synthesis of 3,4-dihydropyrimidin-2(1H)-one based biomolecules via one-pot-three-components Biginelli reaction under solvent-free condition

Mannar R. Maurya, Devesh Singh, Reshu Tomar, Puneet Gupta

Summary: In this study, a series of complexes with tricompartmental ligands were synthesized, and their catalytic mechanisms were explored using density functional theory calculations and spectroscopic studies. The results showed that these complexes can catalyze the synthesis of biologically active compounds under mild and solvent-free conditions, which is of great significance for pharmaceutical research.

INORGANICA CHIMICA ACTA (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

CuBr-promoted domino Biginelli reaction for the diastereoselective synthesis of bridged polyheterocycles: Mechanism studies and in vitro anti-tumor activities

Mengting Zeng, Ying Xue, Yunan Qin, Fen Peng, Quan Li, Ming-Hua Zeng

Summary: This study investigated the low-cost CuBr-promoted domino Biginelli reaction under solvothermal conditions and successfully synthesized novel bridged polyheterocycles. The reaction mechanism was elucidated, and the antitumor activity of the synthesized compounds was evaluated. The findings suggest that the synthesized polyheterocycles have potential medicinal value and provide fragmentation rules for rapid structural identification.

CHINESE CHEMICAL LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Post-Biginelli Ugi reaction towards synthesis of novel bisamides of dihydropyrimidinones: Substrate scope, modification and mechanism

Rinkal B. Bhoraniya, Mahesh Koladiya, Shiv R. Desai, Sachin G. Modha

Summary: A Biginelli, hydrolysis and Ugi four-component reaction sequence was developed to synthesize novel dihydropyrimidinone (DHPM) bisamides. An unprecedented but moderate 1,6 asymmetric induction was observed for this compound class. A detailed study was carried out to investigate the effects of various substitutions on the diastereoselectivity. The results showed that steric congestion caused sluggish Mumm rearrangement, leading to the formation of side products by trapping the imidate intermediate with methanol.

TETRAHEDRON (2023)

添加到收藏夹

Article Chemistry, Applied

γ-Fe2O3@Cu3Al-LDH/HEPES a novel heterogeneous amphoteric catalyst for synthesis of annulated pyrazolo[3,4-d]pyrimidines

Farzaneh Ghobakhloo, Davood Azarifar, Masoud Mohammadi, Masoumeh Ghaemi

Summary: An efficient method for the immobilization of bifunctional HEPES catalyst and its application in the synthesis of Biginelli-like compounds has been developed. The catalyst demonstrated high efficacy, reusability, and easy purification of the products, making it a promising option for the Biginelli reaction.

APPLIED ORGANOMETALLIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Medicinal

Identification of Pyrido[3,4-d]pyrimidine derivatives as RIPK3-Mediated necroptosis inhibitors

Namkyoung Kim, Chan-Jung Park, Younghoon Kim, SeongShick Ryu, Hanna Cho, Yunju Nam, Myeonggil Han, Jeon-Soo Shin, Taebo Sim

Summary: We designed and synthesized pyrido[3,4-d]pyrimidine derivatives as novel necroptosis inhibitors capable of suppressing the phosphorylation of MLKL. Our SAR studies revealed that compound 20 exhibited comparable inhibitory activity against RIPK3-mediated pMLKL in HT-29 cells relative to the selective inhibitor GSK872. Furthermore, 20 demonstrated selectivity towards RIPK3 over RIPK1 and inhibited necroptosis by impeding MLKL oligomerization.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2023)

添加到收藏夹

Article Pharmacology & Pharmacy

Pyrazole[3,4-d]pyrimidine derivatives loaded into halloysite as potential CDK inhibitors

Marina Massaro, Giampaolo Barone, Viviana Barra, Patrizia Cancemi, Aldo Di Leonardo, Giancarlo Grossi, Fabrizio Lo Celso, Silvia Schenone, Cesar Viseras Iborra, Serena Riela

Summary: The study reported a new example of nanocomposites based on HNTs/Si306 and HNTs/Si113 as anticancer agents and CDK inhibitors, and evaluated their inhibitory effects on different cancer cell lines as well as their impact on the cell cycle of HCT116 cells through experiments.

INTERNATIONAL JOURNAL OF PHARMACEUTICS (2021)

添加到收藏夹

Article Crystallography

Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-d]pyrimidine

Sang Loon Tan, Yee Seng Tan, Jia Hui Ng, Anton V. Dolzhenko, Edward R. T. Tiekink

Summary: Two monoclinic polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine derivative, named α (from methanol) and β (from ethanol, n-propanol and iso-propanol), were isolated and characterized by X-ray crystallography and computational chemistry techniques. The different conformations observed in the crystals are due to the molecular packing, which is determined by geometry-optimization calculations. The β-form is found to be more stable by 11 kJ/mol based on lattice energy calculations.

CRYSTALS (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

Design, Synthesis, and Biological Evaluation of 1,4-dihydropyridine Derivatives as Potent Antitubercular Agents

Nisheeth C. Desai, Amit R. Trivedi, Hardik C. Somani, Kandarp A. Bhatt

CHEMICAL BIOLOGY & DRUG DESIGN (2015)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis and biological evaluation of 1,3,4-oxadiazole bearing dihydropyrimidines as potential antitubercular agents

N. C. Desai, A. R. Trivedi, H. V. Vaghani, H. C. Somani, K. A. Bhatt

MEDICINAL CHEMISTRY RESEARCH (2016)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis, biological evaluation and molecular docking study of some novel indole and pyridine based 1,3,4-oxadiazole derivatives as potential antitubercular agents

N. C. Desai, Hardik Somani, Amit Trivedi, Kandarp Bhatt, Laxman Nawale, Vijay M. Khedkar, Prakash C. Jha, Dhiman Sarkar

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2016)

添加到收藏夹

Article Chemistry, Medicinal

Preparation, biological evaluation and molecular docking study of imidazolyl dihydropyrimidines as potential Mycobacterium tuberculosis dihydrofolate reductase inhibitors

N. C. Desai, A. R. Trivedi, Vijay M. Khedkar

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2016)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis, biological valuation, and QSAR studies of novel pyrazole bearing pyridyl oxadiazole analogues as potential antimicrobial agents

N. C. Desai, G. M. Kotadiya, A. R. Trivedi, V. M. Khedkar, P. C. Jha

MEDICINAL CHEMISTRY RESEARCH (2016)

添加到收藏夹

Article Chemistry, Medicinal

Design, synthesis, and biological evaluation of novel fluorinated pyrazole encompassing pyridyl 1,3,4-oxadiazole motifs

Nisheeth C. Desai, Ghanshyam M. Kotadiya, Amit R. Trivedi, Vijay M. Khedkar, Prakash C. Jha

MEDICINAL CHEMISTRY RESEARCH (2016)

添加到收藏夹

Review Chemistry, Medicinal

Hybrid Bioactive Heterocycles as Potential Antimicrobial Agents: A Review

Nisheeth Desai, Amit Trivedi, Unnat Pandit, Amit Dodiya, V. Kameswara Rao, Priyanka Desai

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Organic

Synthesis, biological evaluation, and molecular docking study of pyridine clubbed 1,3,4-oxadiazoles as potential antituberculars

N. C. Desai, Amit Trivedi, Hardik Somani, Krunalsinh A. Jadeja, Darshita Vaja, Laxman Nawale, Vijay M. Khedkar, Dhiman Sarkar

SYNTHETIC COMMUNICATIONS (2018)

添加到收藏夹

Article Chemistry, Medicinal

Studies on molecular properties prediction, antitubercular and antimicrobial activities of novel quinoline based pyrimidine motifs

N. C. Desai, G. M. Kotadiya, A. R. Trivedi

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2014)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles

N. C. Desai, Nayan Bhatt, Hardik Somani, Amit Trivedi

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis and antimicrobial evaluation of novel benzo[b]thiophenes comprising β-lactam nucleus

Amit R. Trivedi, Jignesh M. Desai, Bipin H. Dholariya, Dipti K. Dodiya, Viresh H. Shah

MEDICINAL CHEMISTRY RESEARCH (2012)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis and antimicrobial evaluation of novel substituted pyrimidine scaffold

Hardik B. Ghodasara, Amit R. Trivedi, Vipul B. Kataria, Bharat G. Patel, Viresh H. Shah

MEDICINAL CHEMISTRY RESEARCH (2013)

添加到收藏夹

Article Chemistry, Medicinal

Synthesis and Characterization of 1-carboxyphenothiazine Derivatives Bearing Nitrogen Mustard as Promising Class of Antitubercular Agents

V. B. Kataria, M. J. Solanki, A. R. Trivedi, V. H. Shah

LETTERS IN DRUG DESIGN & DISCOVERY (2013)

添加到收藏夹

Article Chemistry, Organic

Advances in the Synthesis of Pyrazolo[3,4-b]Pyridines

Dipti K. Dodiya, Amit R. Trivedi, Vipul B. Kataria, Viresh H. Shah

CURRENT ORGANIC CHEMISTRY (2012)

添加到收藏夹

Article Chemistry, Medicinal

Design and synthesis of a library of C2-substituted sulfamidoadenosines to probe bacterial permeability

Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geiben, Melissa L. Boby, Bradley S. Sherborne, Derek S. Tan

Summary: Antibiotic resistance is a major threat to public health, with Gram-negative bacteria presenting unique challenges due to their low permeability and efflux pumps. Limited understanding of the chemical rules for overcoming these barriers hinders antibacterial drug discovery. Efforts to address this issue, such as screening compound libraries and using cheminformatic analysis, have led to the design of sulfamidoadenosines with diverse substituents, showing potential utility in accumulation in Escherichia coli.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2024)

添加到收藏夹

Article Chemistry, Medicinal

Design of MERS-CoV entry inhibitory short peptides based on helix-stabilizing strategies

Jichun Li, Qing Li, Shuai Xia, Jiahuang Tu, Longbo Zheng, Qian Wang, Shibo Jiang, Chao Wang

Summary: This study successfully developed a short peptide mimetic as a MERS-CoV fusion inhibitor by reproducing the key recognition features of the HR2 helix. The resulting 23-mer lipopeptide showed comparable inhibitory effect to the 36-mer HR2 peptide HR2P-M2. This has important implications for developing short peptide-based antiviral agents to treat MERS-CoV infection.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2024)

添加到收藏夹

Article Chemistry, Medicinal

Development of novel β2-adrenergic receptor agonists for the stimulation of glucose uptake - The importance of chirality and ring size of cyclic amines

Krista Jaunsleine, Linda Supe, Jana Spura, Sten van Beek, Anna Sandstrom, Jessica Olsen, Carina Halleskog, Tore Bengtsson, Ilga Mutule, Benjamin Pelcman

Summary: Beta(2)-adrenergic receptor agonists can stimulate glucose uptake by skeletal muscle cells and are therefore potential treatments for type 2 diabetes. The chirality of compounds has a significant impact on the activity of these agonists. This study found that certain synthesized compounds showed higher glucose uptake activity. These findings provide important information for the design of novel beta(2)AR agonists for T2D treatment.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2024)

添加到收藏夹

Article Chemistry, Medicinal

Conformationally constrained potent inhibitors for enhancer of zeste homolog 2 (EZH2)

Xin Xu, Jia Chen, Guan Wang, Xiaojuan Zhang, Qiang Li, Xiaobo Zhou, Fengying Guo, Min Li

Summary: The study focuses on EZH2, a promising therapeutic target for various types of cancers. Researchers designed and synthesized a series of novel derivatives aiming to enhance the EZH2 inhibition activity. Among them, compound 28 displayed potent EZH2 inhibition activity and showed high anti-proliferative effects in lymphoma cell lines and xenograft mouse models. The study suggests that compound 28 has potential as a therapeutic candidate for EZH2-associated cancers.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2024)

添加到收藏夹

Article Chemistry, Medicinal

The potential of Rhein's aromatic amines for Parkinson's disease prevention and treatment: α-Synuclein aggregation inhibition and disaggregation of preformed fibers

Wei Zhang, Wei Liu, Ya-Dong Zhao, Li-Zi Xing, Ji Xu, Rui-Jun Li, Yun-Xiao Zhang

Summary: This study developed a series of aromatic amide derivatives based on Rhein and investigated their inhibitory activity against alpha-Syn aggregation. Two of these compounds showed promising potential in treating Parkinson's disease by stabilizing alpha-Syn's conformation and disassembling alpha-Syn oligomers and fibrils.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2024)

添加到收藏夹

Article Chemistry, Medicinal

Design, synthesis and biological evaluation of novel cationic liposomes loaded with melphalan for the treatment of cancer

Mani Sharma, S. S. S. S. Sudha Ambadipudi, Neeraj Kumar Chouhan, V. Lakshma Nayak, Srihari Pabbaraja, Sai Balaji Andugulapati, Ramakrishna Sistla

Summary: Therapeutically active lipids in drug delivery systems can enhance the safety and efficacy of treatment. The liposome formulation created using synthesized biologically active lipids showed additive anti-cancer effects and reduced tumorigenic potential.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2024)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.