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4-Aminoquinoline Compound

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https://www.readbyqxmd.com/read/28360437/introducing-new-antimalarial-analogues-of-chloroquine-and-amodiaquine-a-narrative-review
#1
REVIEW
Arezoo Rafiee Parhizgar, Azar Tahghighi
Antimalarial drugs with the 4-aminoquinoline scaffold such as the important drugs, chloroquine (CQ) and amodiaquine (AQ), have been used to prevent and treat malaria for many years. The importance of these drugs is related to their simple usage, high efficacy, affordability, and cost-effectiveness of their synthesis. In recent years, with the spread of parasite resistance to CQ and cross-resistance to its other analogues have decreased their consumption in many geographical areas. On the other hand, AQ is an effective antimalarial drug which its usage has been restricted due to hepatic and hematological toxicities...
March 2017: Iranian Journal of Medical Sciences
https://www.readbyqxmd.com/read/28350449/long-chained-4-aminoquinolines-as-quorum-sensing-inhibitors-in-serratia-marcescens-and-pseudomonas-aeruginosa
#2
Ivana Aleksić, Sandra Šegan, Filip Andric, Mario Zlatović, Ivana Moric, Dejan M Opsenica, Lidija Senerovic
Antibiotic resistance has become serious global threat to public health; therefore, the improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (MIC > 400 μM). Through detailed structure-activity study we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 μM and 63 μM in S...
March 28, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28315598/n-piperonyl-substitution-on-aminoquinoline-pyrimidine-hybrids-effect-on-the-antiplasmodial-potency
#3
Rohit Kholiya, Shabana I Khan, Aparna Bahuguna, Mohit Tripathi, Diwan S Rawat
A series of 4-aminoquinoline-piperonyl-pyrimidine hybrids were synthesized with the aim of identifying compounds with enhanced antimalarial activity. All the synthesized molecules were evaluated in vitro against cultured Plasmodium falciparum W2 and D6 strains and exhibited potent antiplasmodial activities with IC50 values in the range of 0.02-5.16 μM. Out of the 22 synthesised hybrids, 12 were found to be better (up to eight-fold more active) than chloroquine (CQ), particularly against the CQ-resistant W2 strain of P...
March 11, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28274627/three-component-one-pot-synthesis-of-anthranilamide-schiff-bases-bearing-4-aminoquinoline-moiety-as-mycobacterium-tuberculosis-gyrase-inhibitors
#4
Preeti S Salve, Shankar G Alegaon, Dharmarajan Sriram
An efficient three-component, one-pot protocol is described for the synthesis of biologically interesting 2-(benzylideneamino)-N-(7-chloroquinolin-4-yl)benzohydrazide derivatives from isatoic anhydride, 7-chloro-4-hydrazinylquinoline and aromatic and/or hetero aromatic aldehydes under catalyst free condensation by using water as reaction media. All synthesized compounds were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis (MTB) and cytotoxicity activity against normal VERO cell lines...
February 17, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28261884/modulation-of-antimalarial-activity-at-a-putative-bisquinoline-receptor-in-vivo-using-fluorinated-bisquinolines
#5
Alistar John Fielding, Valentina Lukinovic, Philip Evans, Said Alizadeh, Roger Bisby, Mike Drew, Alessio Del Casino, James Dunn, Laura Randle, Nicola Dempster, Nahar Lutfun, Sarker Satyajit, Fabián G Cantú Reinhard, Sam P de Visser, Mike Dascombe, Fyaz Ismail
Antimalarials can interact with heme covalently, by - interactions or hydrogen bonding. Consequently, the prototropy of 4-aminoquinolines and quinoline methanols was investigated using quantum mechanics. Calculations showed mefloquine protonated preferentially at the piperidine and was impeded at the endocyclic nitrogen due to electronic rather than steric factors. In gas phase calculations, 7-substituted mono- and bis-4-aminoquinolines were preferentially protonated at the endocyclic quinoline nitrogen...
March 6, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28222317/synthesis-antimalarial-activity-heme-binding-and-docking-studies-of-n-substituted-4-aminoquinoline-pyrimidine-molecular-hybrids
#6
Shiv Shyam Maurya, Shabana I Khan, Aparna Bahuguna, Deepak Kumar, Diwan S Rawat
A series of novel N-substituted 4-aminoquinoline-pyrimidine hybrids have been synthesized via simple and economic route and evaluated for their antimalarial activity. Most compounds showed potent antimalarial activity against both CQ-sensitive and CQ-resistant strains with high selectivity index. All the compounds were found to be non-toxic to the mammalian cell lines. The most active compound 7b was analysed for heme binding activity using UV-spectrophotometer. Compound was found to interact with heme and a complex formation between compound and heme in a 1:1 stoichiometry ratio was determined using job plots...
March 31, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28215783/synthesis-and-biological-evaluation-of-potential-inhibitors-of-the-cysteine-proteases-cruzain-and-rhodesain-designed-by-molecular-simplification
#7
Saulo Fehelberg Pinto Braga, Luan Carvalho Martins, Elany Barbosa da Silva, Policarpo Ademar Sales Júnior, Silvane Maria Fonseca Murta, Alvaro José Romanha, Wai Tuck Soh, Hans Brandstetter, Rafaela Salgado Ferreira, Renata Barbosa de Oliveira
Analogues of 8-chloro-N-(3-morpholinopropyl)-5H-pyrimido[5,4-b]indol-4-amine 1, a known cruzain inhibitor, were synthesized using a molecular simplification strategy. Five series of analogues were obtained: indole, pyrimidine, quinoline, aniline and pyrrole derivatives. The activity of the compounds was evaluated against the enzymes cruzain and rhodesain as well as against Trypanosoma cruzi amastigote and trypomastigote forms. The 4-aminoquinoline derivatives showed promising activity against both enzymes, with IC50 values ranging from 15 to 125µM...
February 9, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/27936446/design-synthesis-and-evaluation-of-4-aminoquinoline-purine-hybrids-as-potential-antiplasmodial-agents
#8
P Linga Reddy, Shabana I Khan, Prija Ponnan, Mohit Tripathi, Diwan S Rawat
A novel series of 4-aminoquinoline-purine hybrids were synthesized and assessed for their antiplasmodial activity against CQ-sensitive and CQ-resistant strains of P. falciparum. It was envisaged that linking of the 4-aminoquinoline pharmacophore (targeting heme-detoxification pathway of malarial parasite) with the purine functionality (targeting plasmodial HG(X)PRT enzyme) will produce a hybrid antiplasmodial agent with increased potency. The synthesized hybrids displayed good antiplasmodial activities against both the sensitive and resistant strains of P...
January 27, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27908538/antimalarial-activity-of-novel-4-aminoquinolines-active-against-drug-resistant-strains
#9
Srinivasarao Kondaparla, Awakash Soni, Ashan Manhas, Kumkum Srivastava, Sunil K Puri, S B Katti
In the present study we have synthesized a new class of 4-aminoquinolines and evaluated against Plasmodium falciparum in vitro (3D7-sensitive strain & K1-resistant strain) and Plasmodium yoelii in vivo (N-67 strain). Among the series, eleven compounds (5, 6, 7, 8, 9, 11, 12, 13, 14, 15 and 21) showed superior antimalarial activity against K1 strain as compared to CQ. In addition, all these analogues showed 100% suppression of parasitemia on day 4 in the in vivo mouse model against N-67 strain when administered orally...
November 23, 2016: Bioorganic Chemistry
https://www.readbyqxmd.com/read/27896925/design-synthesis-and-in-vitro-antiplasmodial-activity-of-some-bisquinolines-against-chloroquine-resistant-strain
#10
Srinivasarao Kondaparla, Pooja Agarwal, Kumkum Srivastava, Sunil K Puri, Seturam B Katti
A series of novel bisquinoline compounds comprising N(1) -(7-chloroquinolin-4-yl) ethane-1,2-diamine and 7-chloro-N-(2-(piperazin-1-yl)ethyl)quinolin-4-amine connected with 7-chloro-4-aminoquinoline containing various amino acids is described. We have bio-evaluated the compounds against both chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum in vitro. Among the series, compounds 4 and 7 exhibited 1.8- and 10.6-fold superior activity as compared to chloroquine (CQ; IC50  = 0...
November 29, 2016: Chemical Biology & Drug Design
https://www.readbyqxmd.com/read/27787977/synthesis-of-1-4-benzodiazepine-2-5-diones-by-base-promoted-ring-expansion-of-3-aminoquinoline-2-4-diones
#11
Filip Křemen, Martin Gazvoda, Stanislav Kafka, Karel Proisl, Anna Srholcová, Antonin Klasek, Damijana Urankar, Janez Košmrlj
An unprecedented reactivity of 3-aminoquinoline-2,4-diones is reported. Under basic conditions these compounds undergo molecular rearrangement to furnish 1,4-benzodiazepine-2,5-diones. The transformations take place under mild reaction conditions by using 1,1,3,3-tetramethylguanidine (TMG), NaOEt, or benzyltrimethylammonium hydroxide (Triton B) as a base. A proposed mechanism of the rearrangement and the conformational equilibrium of 1,4-benzodiazepine-2,5-dione rings are discussed.
October 27, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27743972/aminoquinoline-compounds-effect-of-7-chloro-4-quinolinylhydrazone-derivatives-against-leishmania-amazonensis
#12
Luciana Maria Ribeiro Antinarelli, Isabela de Oliveira Souza, Nicolas Glanzmann, Ayla das Chagas Almeida, Gabriane Nascimento Porcino, Eveline Gomes Vasconcelos, Adilson David da Silva, Elaine Soares Coimbra
In this study, we have investigated the antileishmanial activity of ten 7-chloro-4-quinolinylhydrazone derivatives. Among the compounds tested, compounds 2a and 2j presented activity against promastigotes (IC50 values of 52.5 and 21.1 μM, respectively) and compounds 2a and 2c were active against intracellular amastigotes (IC50 of 8.1 and 15.6 μM, respectively) of Leishmania amazonensis. The majority of compounds did not show toxicity against murine macrophages. Compound 2a exhibited low cytotoxicity to human erythrocytes and induced an oxidative imbalance in promastigote forms, reflected by an increase in the formation of reactive oxygen species (ROS) and a reduction of mitochondrial membrane potential...
December 2016: Experimental Parasitology
https://www.readbyqxmd.com/read/27704851/amine-mediated-transimination-and-aromatization-triggered-domino-reaction-in-the-synthesis-of-polyfunctionalized-4-aminoquinolines
#13
Runzhe Song, Zhaomeng Han, Qiuqin He, Renhua Fan
Dearomatization provides numerous possibilities for the development of new transformative modes of aromatic compounds. A conceptually novel metal-free multicomponent domino reaction of the dearomatized products of 2-alkynylanilines is developed. The reaction involves the secondary amine-mediated transimination with α-amino nitriles and subsequent aromatization-triggered cascade rearrangement, nucleophilic cyclization, and retro-Strecker reaction. This process provided a new practical method for the rapid synthesis of polyfunctionalized 4-aminoquinolines from readily available starting materials...
October 5, 2016: Organic Letters
https://www.readbyqxmd.com/read/27692831/7-chloro-4-aminoquinoline-%C3%AE-hydroxy-%C3%AE-lactam-derived-tetramates-as-a-new-family-of-antimalarial-compounds
#14
Nicolas Chopin, Shinya Iikawa, Julien Bosson, Adeline Lavoignat, Guillaume Bonnot, Anne-Lise Bienvenu, Stéphane Picot, Jean-Philippe Bouillon, Maurice Médebielle
In this Letter we report on an efficient and short 2-3 steps synthesis of γ-hydroxy-γ-lactam derived-tetramates bearing a 7-chloro-4-aminoquinoline skeleton and their evaluation as potent antimalarials. These molecules were obtained through ring opening-ring closure (RORC) process of γ-ylidene-tetronate derivatives in the presence of 7-chloro-4-aminoquinoline-derived amines. In vitro antimalarial activity of these new γ-lactams was evaluated against Plasmodium falciparum clones of variable sensitivity (3D7 and W2) and they were found to be active in the range of 14-827nM with generally good resistance index...
September 15, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27591008/synthesis-and-biological-evaluation-of-n-cyanoalkyl-n-aminoalkyl-and-n-guanidinoalkyl-substituted-4-aminoquinoline-derivatives-as-potent-selective-brain-permeable-antitrypanosomal-agents
#15
Irene Sola, Albert Artigas, Martin C Taylor, F Javier Pérez-Areales, Elisabet Viayna, M Victòria Clos, Belén Pérez, Colin W Wright, John M Kelly, Diego Muñoz-Torrero
Current drugs against human African trypanosomiasis (HAT) suffer from several serious drawbacks. The search for novel, effective, brain permeable, safe, and inexpensive antitrypanosomal compounds is therefore an urgent need. We have recently reported that the 4-aminoquinoline derivative huprine Y, developed in our group as an anticholinesterasic agent, exhibits a submicromolar potency against Trypanosoma brucei and that its homo- and hetero-dimerization can result in to up to three-fold increased potency and selectivity...
November 1, 2016: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/27590574/design-synthesis-and-evaluation-of-3-quinoline-carboxylic-acids-as-new-inhibitors-of-protein-kinase-ck2
#16
Anatolii R Syniugin, Olga V Ostrynska, Maksym O Chekanov, Galyna P Volynets, Sergiy A Starosyla, Volodymyr G Bdzhola, Sergiy M Yarmoluk
In this article, the derivatives of 3-quinoline carboxylic acid were studied as inhibitors of protein kinase CK2. Forty-three new compounds were synthesized. Among them 22 compounds inhibiting CK2 with IC50 in the range from 0.65 to 18.2 μM were identified. The most active inhibitors were found among tetrazolo-quinoline-4-carboxylic acid and 2-aminoquinoline-3-carboxylic acid derivatives.
2016: Journal of Enzyme Inhibition and Medicinal Chemistry
https://www.readbyqxmd.com/read/27572396/metabolomics-based-screening-of-the-malaria-box-reveals-both-novel-and-established-mechanisms-of-action
#17
Darren J Creek, Hwa H Chua, Simon A Cobbold, Brunda Nijagal, James I MacRae, Benjamin K Dickerman, Paul R Gilson, Stuart A Ralph, Malcolm J McConville
High-throughput phenotypic screening of chemical libraries has resulted in the identification of thousands of compounds with potent antimalarial activity, although in most cases, the mechanism(s) of action of these compounds remains unknown. Here we have investigated the mode of action of 90 antimalarial compounds derived from the Malaria Box collection using high-coverage, untargeted metabolomics analysis. Approximately half of the tested compounds induced significant metabolic perturbations in in vitro cultures of Plasmodium falciparum In most cases, the metabolic profiles were highly correlated with known antimalarials, in particular artemisinin, the 4-aminoquinolines, or atovaquone...
November 2016: Antimicrobial Agents and Chemotherapy
https://www.readbyqxmd.com/read/27534744/3d-qsar-pharmacophore-and-molecular-docking-studies-of-known-inhibitors-and-designing-of-novel-inhibitors-for-m18-aspartyl-aminopeptidase-of-plasmodium-falciparum
#18
Madhulata Kumari, Subhash Chandra, Neeraj Tiwari, Naidu Subbarao
BACKGROUND: The Plasmodium falciparum M18 Aspartyl Aminopeptidase (PfM18AAP) is only aspartyl aminopeptidase which is found in the genome of P. falciparum and is essential for its survival. The PfM18AAP enzyme performs various functions in the parasite and the erythrocytic host such as hemoglobin digestion, erythrocyte invasion, parasite growth and parasite escape from the host cell. It is a valid target to develop antimalarial drugs. In the present work, we employed 3D QSAR modeling, pharmacophore modeling, and molecular docking to identify novel potent inhibitors that bind with M18AAP of P...
2016: BMC Structural Biology
https://www.readbyqxmd.com/read/27490082/interactions-between-4-aminoquinoline-and-heme-promising-mechanism-against-trypanosoma-cruzi
#19
Guilherme Curty Lechuga, Júlio Cesar Borges, Claudia Magalhães Calvet, Humberto Pinheiro de Araújo, Aline Araujo Zuma, Samara Braga do Nascimento, Maria Cristina Machado Motta, Alice Maria Rolim Bernardino, Mirian Claudia de Souza Pereira, Saulo Cabral Bourguignon
Chagas disease is a neglected tropical disease caused by the flagellated protozoan Trypanosoma cruzi. The current drugs used to treat this disease have limited efficacy and produce severe side effects. Quinolines, nitrogen heterocycle compounds that form complexes with heme, have a broad spectrum of antiprotozoal activity and are a promising class of new compounds for Chagas disease chemotherapy. In this study, we evaluated the activity of a series of 4-arylaminoquinoline-3-carbonitrile derivatives against all forms of Trypanosoma cruzi in vitro...
December 2016: International Journal for Parasitology, Drugs and Drug Resistance
https://www.readbyqxmd.com/read/27472314/hybrid-molecules-containing-a-7-chloro-4-aminoquinoline-nucleus-and-a-substituted-2-pyrazoline-with-antiproliferative-and-antifungal-activity
#20
Alba Montoya, Jairo Quiroga, Rodrigo Abonia, Marcos Derita, Maximiliano Sortino, Alfredo Ornelas, Susana Zacchino, Braulio Insuasty
Twenty-four new hybrid analogues (15-38) containing 7-chloro-4-aminoquinoline and 2-pyrazoline N-heterocyclic fragments were synthesized. Twelve of the new compounds were evaluated against 58 human cancer cell lines by the U.S. National Cancer Institute (NCI). Compounds 25, 30, 31, 36, and 37 showed significant cytostatic activity, with the most outstanding GI50 values ranging from 0.05 to 0.95 µM. The hybrid compounds (15-38) were also evaluated for antifungal activity against Candida albicans and Cryptococcus neoformans...
July 27, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
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