Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations.

Abstract:

:The synthesis, antimicrobial activity evaluations, biomolecule-binding properties (DNA), and absorption and emission properties of a new series of (Z)-1,1,1-trichloro-4-alkyl(aryl)amino-4-arylbut-3-en-2-ones (4, 5) and 2,2-difluoro-3-alkyl(aryl)amino-4-aryl-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides (6, 7) in which 3(4)-alkyl(aryl) = H, Me, iso-propyl, n-butyl, C6H5, 4-CH3C6H4, 4-CH3OC6H4, 4-NO2C6H4, 4-FC6H4, 4-BrC6H4, 2-naphthyl, is reported. A series of β-enaminoketones (4, 5) is synthesized from the O,N-exchange reaction of some amines (3) with (Z)-1,1,1-trichloro-4-methoxy-4-aryl-but-3-en-2-ones (1, 2) at 61-90% yields. Subsequently, reactions of the resulting β-enaminoketones with an appropriate source of boron (BF3.OEt2) gave the corresponding oxazaborinine derivatives (6, 7) at 50-91% yields. UV-Vis and emission properties of biomolecule-binding properties for the DNA of these new BF2-β-enamino containing CCl3 units were also evaluated. Some compounds from the present series also exhibited potent antimicrobial effects on various pathogenic microorganisms at concentrations below those that showed cytotoxic effects. Compounds 4d, 4e, 6e, and 6f showed the best results and are very significant against P. zopfii, which causes diseases in humans and animals.

journal_name

Front Pharmacol

authors

Rosa WC,Rocha IO,Rodrigues MB,Coelho HS,Denardi LB,Ledur PC,Zanatta N,Acunha TV,Iglesias BA,Bonacorso HG

doi

10.3389/fphar.2020.01328

subject

Has Abstract

pub_date

2020-09-02 00:00:00

pages

1328

issn

1663-9812

journal_volume

11

pub_type

杂志文章
  • MOF Regulates TNK2 Transcription Expression to Promote Cell Proliferation in Thyroid Cancer.

    abstract::MOF is a well-known histone acetyltransferase to catalyze acetylation of histone H4 lysine 16 (K16), and it is relevant to diverse biological processes, such as gene transcription, cell cycle, early embryonic development and tumorigenesis. Here, we identify MOF as an oncogene in most thyroid cancer. It is found that e...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2020.607605

    authors: Li D,Yang Y,Chen B,Guo X,Gao S,Wang M,Duan M,Li X

    更新日期:2020-12-08 00:00:00

  • Obesity: A New Adverse Effect of Antibiotics?

    abstract::Since the introduction of antibiotics, they have been used freely, with their prescription occurring almost always when they were not necessary. The other major form of contact between humans and antibiotics, now unintentionally, is with the large amount of these drugs in the environment and in our food. The relations...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章,评审

    doi:10.3389/fphar.2018.01408

    authors: Del Fiol FS,Balcão VM,Barberato-Fillho S,Lopes LC,Bergamaschi CC

    更新日期:2018-12-03 00:00:00

  • Therapeutic Anabolic and Anticatabolic Benefits of Natural Chinese Medicines for the Treatment of Osteoporosis.

    abstract::Osteoporosis is a bone disease characterized by increasing osseous fragility and fracture due to the reduced bone mass and microstructural degradation. Primary pharmacological strategies for the treatment of osteoporosis, hormone replacement treatment (HRT), and alendronate therapies may produce adverse side-effects a...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章,评审

    doi:10.3389/fphar.2019.01344

    authors: He J,Li X,Wang Z,Bennett S,Chen K,Xiao Z,Zhan J,Chen S,Hou Y,Chen J,Wang S,Xu J,Lin D

    更新日期:2019-11-25 00:00:00

  • Prospects for the Use of New Technologies to Combat Multidrug-Resistant Bacteria.

    abstract::The increasing use of antibiotics is being driven by factors such as the aging of the population, increased occurrence of infections, and greater prevalence of chronic diseases that require antimicrobial treatment. The excessive and unnecessary use of antibiotics in humans has led to the emergence of bacteria resistan...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2019.00692

    authors: Lima R,Del Fiol FS,Balcão VM

    更新日期:2019-06-21 00:00:00

  • Proanthocyanidin Polymer-Rich Fraction of Stryphnodendron adstringens Promotes in Vitro and in Vivo Cancer Cell Death via Oxidative Stress.

    abstract::Cervical cancer is the fourth most common cancer that affects women, mainly through human papilloma virus (HPV) infection with high-risk HPV16 and HPV18. The present study investigated the in vitro anticancer activity and mechanism of action of a proanthocyanidin polymer-rich fraction of Stryphnodendron adstringens (F...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2018.00694

    authors: Kaplum V,Ramos AC,Consolaro MEL,Fernandez MA,Ueda-Nakamura T,Dias-Filho BP,Silva SO,de Mello JCP,Nakamura CV

    更新日期:2018-07-03 00:00:00

  • ORY-1001 Suppresses Cell Growth and Induces Apoptosis in Lung Cancer Through Triggering HK2 Mediated Warburg Effect.

    abstract::ORY-1001, an inhibitor of covalent lysine (K)-specific demethylase 1A (KDM1A), has been used as a therapy for the treatment of acute leukemia. However, the underlying mechanisms of anticancer are still not fully elucidated. Here, we report that KDM1A is highly expressed in lung cancers, where it appears to drive aggre...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2018.01411

    authors: Lu Z,Guo Y,Zhang X,Li J,Li L,Zhang S,Shan C

    更新日期:2018-12-04 00:00:00

  • IL-6 but Not TNFα Levels Are Associated With Time to Pregnancy in Female Rheumatoid Arthritis Patients With a Wish to Conceive.

    abstract::Fertility issues are common amongst women with rheumatoid arthritis (RA). Interleukin 6 (IL-6) and tumor necrosis factor alpha (TNFα), known key players in RA pathogenesis, have been associated with reproductive disorders. This study investigates the role of these cytokines in decreased fertility in women with active ...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2020.604866

    authors: Bongenaar M,Smeele HTW,Lubberts E,Dolhain RJEM

    更新日期:2020-12-10 00:00:00

  • Steroidal Pyrimidines and Dihydrotriazines as Novel Classes of Anticancer Agents against Hormone-Dependent Breast Cancer Cells.

    abstract::Most breast and prostate tumors are hormone-dependent, making it possible to use hormone therapy in patients with these tumors. The design of effective endocrine drugs that block the growth of tumors and have no severe side effects is a challenge. Thereupon, synthetic steroids are promising therapeutic drugs for the t...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2017.00979

    authors: Scherbakov AM,Komkov AV,Komendantova AS,Yastrebova MA,Andreeva OE,Shirinian VZ,Hajra A,Zavarzin IV,Volkova YA

    更新日期:2018-01-10 00:00:00

  • CUMYL-4CN-BINACA Is an Efficacious and Potent Pro-Convulsant Synthetic Cannabinoid Receptor Agonist.

    abstract::Synthetic cannabinoid receptor agonists (SCRAs) are the largest class of new psychoactive substances (NPS). New examples are detected constantly, and some are associated with a series of adverse effects, including seizures. CUMYL-4CN-BINACA (1-(4-cyanobutyl)-N-(2-phenylpropan-2-yl)indazole-3-carboxamide) is structural...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2019.00595

    authors: Kevin RC,Anderson L,McGregor IS,Boyd R,Manning JJ,Glass M,Connor M,Banister SD

    更新日期:2019-05-29 00:00:00

  • Ion Fluxes through KCa2 (SK) and Cav1 (L-type) Channels Contribute to Chronoselectivity of Adenosine A1 Receptor-Mediated Actions in Spontaneously Beating Rat Atria.

    abstract::Impulse generation in supraventricular tissue is inhibited by adenosine and acetylcholine via the activation of A1 and M2 receptors coupled to inwardly rectifying GIRK/KIR3.1/3.4 channels, respectively. Unlike M2 receptors, bradycardia produced by A1 receptors activation predominates over negative inotropy. Such diffe...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2016.00045

    authors: Bragança B,Oliveira-Monteiro N,Ferreirinha F,Lima PA,Faria M,Fontes-Sousa AP,Correia-de-Sá P

    更新日期:2016-03-07 00:00:00

  • The Use of Beta Blockers in Takotsubo Syndrome as Compared to Acute Coronary Syndrome.

    abstract:Background:Takotsubo syndrome (TTS) and acute coronary syndrome (ACS) patients have a similar mortality rate. In this study, we sought to determine the short- and long-term outcome of TTS patients as compared to ACS patients both treated with beta-blockers. Objectives:In the present study we described the data of 5 ye...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2020.00681

    authors: Kummer M,El-Battrawy I,Gietzen T,Ansari U,Behnes M,Lang S,Zhou X,Borggrefe M,Akin I

    更新日期:2020-05-14 00:00:00

  • Calcium Handling Defects and Cardiac Arrhythmia Syndromes.

    abstract::Calcium ions (Ca2+) play a major role in the cardiac excitation-contraction coupling. Intracellular Ca2+ concentration increases during systole and falls in diastole thereby determining cardiac contraction and relaxation. Normal cardiac function also requires perfect organization of the ion currents at the cellular le...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章,评审

    doi:10.3389/fphar.2020.00072

    authors: Kistamás K,Veress R,Horváth B,Bányász T,Nánási PP,Eisner DA

    更新日期:2020-02-25 00:00:00

  • Pulmonary Deposition of Radionucleotide-Labeled Palivizumab: Proof-of-Concept Study.

    abstract:Objective:Current prevention and/or treatment options for respiratory syncytial virus (RSV) infections are limited as no vaccine is available. Prophylaxis with palivizumab is very expensive and requires multiple intramuscular injections over the RSV season. Here we present proof-of-concept data using nebulized palivizu...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2020.01291

    authors: Rajapaksa AE,Do LAH,Suryawijaya Ong D,Sourial M,Veysey D,Beare R,Hughes W,Yang W,Bischof RJ,McDonnell A,Eu P,Yeo LY,Licciardi PV,Mulholland EK

    更新日期:2020-08-19 00:00:00

  • Mifepristone for Treatment of Metabolic Syndrome: Beyond Cushing's Syndrome.

    abstract::A growing body of research indicates that cortisol, the glucocorticoid product of the activation of the hypothalamic-pituitary-adrenal axis, plays a role in the pathophysiology of metabolic syndrome. In this regard, chronic exposure to cortisol is associated with risk factors related to metabolic syndrome like weight ...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2020.00429

    authors: Díaz-Castro F,Monsalves-Álvarez M,Rojo LE,Del Campo A,Troncoso R

    更新日期:2020-04-24 00:00:00

  • Canthin-6-One Accelerates Alpha-Synuclein Degradation by Enhancing UPS Activity: Drug Target Identification by CRISPR-Cas9 Whole Genome-Wide Screening Technology.

    abstract::Parkinson's disease (PD) is the second most common neurodegenerative disorder characterized by the accumulation of protein aggregates (namely Lewy bodies) in dopaminergic neurons in the substantia nigra region of the brain. Alpha-synuclein (α-syn) is the major component of Lewy bodies in PD patients, and impairment of...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2019.00016

    authors: Yuan NN,Cai CZ,Wu MY,Zhu Q,Su H,Li M,Ren J,Tan JQ,Lu JH

    更新日期:2019-01-28 00:00:00

  • Cysteine Proteases: Modes of Activation and Future Prospects as Pharmacological Targets.

    abstract::Proteolytic enzymes are crucial for a variety of biological processes in organisms ranging from lower (virus, bacteria, and parasite) to the higher organisms (mammals). Proteases cleave proteins into smaller fragments by catalyzing peptide bonds hydrolysis. Proteases are classified according to their catalytic site, a...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章,评审

    doi:10.3389/fphar.2016.00107

    authors: Verma S,Dixit R,Pandey KC

    更新日期:2016-04-25 00:00:00

  • Mitochondrial Defunctionalization Supresses Tim-3-Galectin-9 Secretory Pathway in Human Colorectal Cancer Cells and Thus Can Possibly Affect Tumor Immune Escape.

    abstract::The Tim-3-galectin-9 secretory pathway is known to protect various types of cancer cells against host immune surveillance. We found that pharmacologically induced mitochondrial dysfunction leads to a reduced galectin-9 expression/exocytosis in human colorectal cancer cells and re-distribution of this protein (the effe...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2019.00342

    authors: Sakhnevych SS,Yasinska IM,Fasler-Kan E,Sumbayev VV

    更新日期:2019-04-05 00:00:00

  • 8-Formylophiopogonanone B Antagonizes Paraquat-Induced Hepatotoxicity by Suppressing Oxidative Stress.

    abstract::Flavonoids are some of the most important natural products with a variety of physiological activities. 8-Formylophiopogonanone B (8-FOB) is a naturally existing homoisoflavonoid in Ophiopogon japonicus. Paraquat (PQ) has been widely used as a potent herbicide and has high toxicity in humans. The goal of the present st...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2019.01283

    authors: Qian JY,Deng P,Liang YD,Pang L,Wu LC,Yang LL,Zhou Z,Yu ZP

    更新日期:2019-10-24 00:00:00

  • Efficacy of Pharmacist Based Diabetes Educational Interventions on Clinical Outcomes of Adults With Type 2 Diabetes Mellitus: A Network Meta-Analysis.

    abstract::Background: Comparative efficacy of different pharmacist based interventions on glycemic control of type 2 diabetes patients is unclear. This review aimed to evaluate and compare the efficacy of different pharmacist based interventions on clinical outcomes of type 2 diabetes patients. Methods: A systematic search was ...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2018.00339

    authors: Bukhsh A,Khan TM,Lee SWH,Lee LH,Chan KG,Goh BH

    更新日期:2018-04-10 00:00:00

  • Salvinorin A Inhibits Airway Hyperreactivity Induced by Ovalbumin Sensitization.

    abstract::Salvinorin A, a neoclerodane diterpene isolated from Salvia divinorum, exerts a number of pharmacological actions which are not solely limited to the central nervous system. Recently it has been demonstrated that Salvinorin A inhibits acute inflammatory response affecting leukotriene (LT) production. Since LTs are pot...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2016.00525

    authors: Rossi A,Caiazzo E,Bilancia R,Riemma MA,Pagano E,Cicala C,Ialenti A,Zjawiony JK,Izzo AA,Capasso R,Roviezzo F

    更新日期:2017-01-13 00:00:00

  • Patient Satisfaction and Their Willingness to Pay for a Pharmacist Counseling Session in Hospital and Community Pharmacies in Saudi Healthcare Settings.

    abstract:Objective:Patient satisfaction is an indicator for quality of healthcare service and is sometimes linked to patients' willingness to pay. Willingness to pay is an economic method for estimating patient's inclination for a service in monetary terms. This study assessed satisfaction of patients from pharmacist counseling...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2020.00138

    authors: AlShayban DM,Naqvi AA,Islam MA,Almaskeen M,Almulla A,Alali M,AlQaroos A,Raafat M,Iqbal MS,Haseeb A

    更新日期:2020-03-02 00:00:00

  • In Vivo Pharmacokinetic/Pharmacodynamic Profiles of Danofloxacin in Rabbits Infected With Salmonella typhimurium After Oral Administration.

    abstract::Salmonella typhimurium is a highly transmissible pathogen in rabbits that causes significant losses. Danofloxacin shows excellent efficacy against S. typhimurium infections. However, there are few reports of the pharmacokinetic/pharmacodynamic (PK/PD) modeling of danofloxacin against this pathogen. The aim of this stu...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2018.00391

    authors: Xiao X,Pei L,Jiang LJ,Lan WX,Xiao JY,Jiang YJ,Wang ZQ

    更新日期:2018-04-17 00:00:00

  • The Humanistic Burden of Small Cell Lung Cancer (SCLC): A Systematic Review of Health-Related Quality of Life (HRQoL) Literature.

    abstract::Background: Little is known about the humanistic burden of small cell lung cancer (SCLC), specifically the impact on health-related quality of life (HRQoL). The aim of this systematic literature review was to explore the impact of SCLC on HRQoL and the patient reported outcomes (PROs) used to capture this impact. Meth...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章,评审

    doi:10.3389/fphar.2017.00339

    authors: Bennett BM,Wells JR,Panter C,Yuan Y,Penrod JR

    更新日期:2017-06-15 00:00:00

  • Hexane Extracts of Calophyllum brasiliense Inhibit the Development of Gastric Preneoplasia in Helicobacter felis Infected INS-Gas Mice.

    abstract::Objectives: Indigenous Latin American populations have used extracts from Calophyllum brasiliense, a native hardwood, to treat gastrointestinal symptoms for generations. The hexane extract of Calophyllum brasiliense stem bark (HECb) protects against ethanol-mediated gastric ulceration in Swiss-Webster mice. We investi...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2017.00092

    authors: Lemos LM,Miyajima F,Castilho GR,Martins DT,Pritchard DM,Burkitt MD

    更新日期:2017-02-27 00:00:00

  • Nonmuscle Myosin Heavy Chain ⅡA-Mediated Exosome Release via Regulation of the Rho-Associated Kinase 1/Myosin Light Chains/Actin Pathway.

    abstract::Nonmuscle myosin ⅡA, a kind of ATP-dependent molecular motor, binds actin to form the molecular motors of the cell. We found that interfering with nonmuscle myosin heavy chain (NMMHC) ⅡA could affect the exosome release from microglial cells stimulated by LPS. LPS could enhance exosome release from microglial cells by...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2020.598592

    authors: Lv Y,Chen J,Hu J,Qian Y,Kong Y,Fu L

    更新日期:2020-12-08 00:00:00

  • Chemical Composition of Scrophularia lucida and the Effects on Tumor Invasiveness in Vitro.

    abstract::A detannified methanolic extract of Scrophularia lucida L. attenuated the formation of cancer cell-induced circular chemorepellent induced defects (CCIDs) in the lymph endothelial cell barrier, which resemble entry ports for the intravasating tumor into the vasculature as a prerequisite for lymph node metastasis. Ther...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2018.00304

    authors: Lewenhofer V,Schweighofer L,Ledermüller T,Eichsteininger J,Kählig H,Zehl M,Nguyen CH,Krupitza G,Özmen A,Krenn L

    更新日期:2018-04-03 00:00:00

  • Acute Liver Failure in a Patient Treated With Metamizole.

    abstract::We report on a patient who developed acute liver failure while being treated with metamizole. After liver transplantation, the patient recovered rapidly. Liver biopsy showed massive necrosis and lobular infiltration of lymphocytes. A lymphocyte transformation test performed 20 months after transplantation was positive...

    journal_title:Frontiers in pharmacology

    pub_type:

    doi:10.3389/fphar.2019.00996

    authors: Krisai P,Rudin D,Grünig D,Scherer K,Pichler W,Terracciano L,Krähenbühl S

    更新日期:2019-09-11 00:00:00

  • The interplay between iron accumulation, mitochondrial dysfunction, and inflammation during the execution step of neurodegenerative disorders.

    abstract::A growing set of observations points to mitochondrial dysfunction, iron accumulation, oxidative damage and chronic inflammation as common pathognomonic signs of a number of neurodegenerative diseases that includes Alzheimer's disease, Huntington disease, amyotrophic lateral sclerosis, Friedrich's ataxia and Parkinson'...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章,评审

    doi:10.3389/fphar.2014.00038

    authors: Urrutia PJ,Mena NP,Núñez MT

    更新日期:2014-03-10 00:00:00

  • Selective Serotonin Reuptake Inhibitor Pharmaco-Omics: Mechanisms and Prediction.

    abstract::Selective serotonin reuptake inhibitors (SSRIs) are a standard of care for the pharmacotherapy of patients suffering from Major Depressive Disorder (MDD). However, only one-half to two-thirds of MDD patients respond to SSRI therapy. Recently, a "multiple omics" research strategy was applied to identify genetic differe...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章,评审

    doi:10.3389/fphar.2020.614048

    authors: Nguyen TTL,Liu D,Ho MF,Athreya AP,Weinshilboum R

    更新日期:2021-01-11 00:00:00

  • The Anti-neuroinflammatory Activity of Tectorigenin Pretreatment via Downregulated NF-κB and ERK/JNK Pathways in BV-2 Microglial and Microglia Inactivation in Mice With Lipopolysaccharide.

    abstract::The activation of microglia is decisively involved with the neurodegeneration observed in many neuroinflammatory pathologies, such as multiple sclerosis, Parkinson's disease, and Alzheimer's disease. Tectorigenin (TEC) is an isoflavone isolated from various medicinal plants, such as Pueraria thunbergiana Benth, Belamc...

    journal_title:Frontiers in pharmacology

    pub_type: 杂志文章

    doi:10.3389/fphar.2018.00462

    authors: Lim HS,Kim YJ,Kim BY,Park G,Jeong SJ

    更新日期:2018-05-09 00:00:00