Bioorganic & Medicinal Chemistry

Items from 1 to 20 out of 29 results

article

1,2,4-Triazolo[1,5-a]quinoxaline derivatives and their simplified analogues as adenosine A3 receptor antagonists. Synthesis, structure–affinity relationships and molecular modeling studies

Daniela Catarzi, Flavia Varano, Daniela Poli, Lucia Squarcialupi, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 9-21

The 1,2,4-triazolo[1,5-a]quinoxaline (TQX) scaffold was extensively investigated in our previously reported studies and recently, our attention was focused at position 5 of the tricyclic nucleus where different acyl and carboxylate moieties were introduced (compounds 2–15). This study produced some interesting compounds endowed with good hA ₃ receptor affinity and selectivity. In addition,...

article

Synthesis and antimycobacterial evaluation of 5-alkylamino-N-phenylpyrazine-2-carboxamides

Jan Zitko, Barbora Servusová, Alena Janoutová, Pavla Paterová, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 174-183

Substitution of chlorine in 5-chloro-N-phenylpyrazine-2-carboxamide (1) with simple n-alkylamines yielded a series of 5-alkylamino-N-phenylpyrazine-2-carboxamides (propylamino to octylamino derivatives), which possessed similar or increased activity against Mycobacterium tuberculosis H37Rv compared to parent 5-chloro derivative (1), with MIC ranging from 2.5 to 12.2μM. 5-Butylamino to 5-heptylamino...

article

Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity

Tara Man Kadayat, Chanmi Park, Kyu-Yeon Jun, Til Bahadur Thapa Magar, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 160-173

For the development of potential anticancer agents, we designed and synthesized 30 new 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives containing aryl moiety such as furyl, thienyl, pyridyl, and phenyl at 2- and 4-position of 5H-indeno[1,2-b]pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines. Among prepared 30 compounds,...

article

Synthesis, biological evaluation and 3D-QSAR study of novel 4,5-dihydro-1H-pyrazole thiazole derivatives as BRAFV600E inhibitors

Meng-Yue Zhao, Yong Yin, Xiao-Wei Yu, Chetan B. Sangani, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 46-54

Many reports implied that the BRAF serine/threonine kinase was mutated in various types of human tumors, which were related with cell growth, survival and differentiation. To provide new therapeutic opportunities, a series of novel 4,5-dihydro-1H-pyrazole derivatives (6a–10d) containing thiazole moiety as potential V600E mutant BRAF kinase (BRAF ^V600E ) inhibitors were designed and synthesized...

article

Synthesis and biological evaluation of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists

Xuekun Wang, Tianxiao Zhao, Baowei Yang, Zheng Li, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 132-140

Free fatty acid receptor 1 (FFA1) is a new potential drug target for the treatment of type 2 diabetes because of its role in amplifying glucose-stimulated insulin secretion in pancreatic β-cell. In the present studies, we identified phenoxyacetic acid derivative (18b) as a potent FFA1 agonist (EC ₅₀ =62.3nM) based on the structure of phenylpropanoic acid derivative 4p. Moreover, compound 18b...

article

Synthesis and biological evaluation of pyridinone analogues as novel potent HIV-1 NNRTIs

Yuanyuan Cao, Yu Zhang, Shaotong Wu, Quanzhi Yang, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 149-159

A novel 2-pyridinone scaffold was rationally designed and synthesized based on the active anti-HIV agent 1 (LAM-trans) via an efficient method. The biological results revealed that some target compounds inhibited HIV-1 reverse transcriptase in the lower micromolar concentration range (IC ₅₀ 0.089–0.68μm). Notably, the most promising compound 25b exhibited extremely potent inhibitory activity...

article

Retraction notice to “3-Benzhydryl-4-piperidones as novel neurokinin-1 receptor antagonists and their efficient synthesis” [Bioorg. Med. Chem. 19 (2011) 5175–5182]

Junya Shirai, Minoru Nakamura, Naoki Tarui, Tadatoshi Hashimoto, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 272

article

Identification of a novel glycan processing enzyme with exo-acting β-allosidase activity in the Golgi apparatus using a new platform for the synthesis of fluorescent substrates

Wataru Hakamata, Kazuki Miura, Takako Hirano, Toshiyuki Nishio

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 73-79

The majority of eukaryotic proteins undergo post-translational modifications (PTMs) involving the attachment of complex glycans, predominantly through N-glycosylation and O-glycosylation. PTMs play important roles in virtually all cellular processes, and aberrant regulation of protein glycosylation and glycan processing has been implicated in various diseases. However, glycan processing on proteins...

article

Design, synthesis and biological activity of a novel Rutin analogue with improved lipid soluble properties

Anna Baldisserotto, Silvia Vertuani, Alessia Bino, Daniela De Lucia, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 264-271

Recent interest in flavonoids has increased greatly due to their biological and pharmacological activities. Flavonoids, consist of a large group of low molecular weight polyphenolic substances, naturally occurring in fruits, vegetables, tea, and wine, and are an integral part of the human diet.Rutin is a common dietary flavonoid that is widely consumed worldwide from plant-derived beverages and foods...

article

Bioactive metabolites from Chaetomium aureum: Structure elucidation and inhibition of the Hsp90 machine chaperoning activity

Fatima Zahra Kabbaj, Su Lu, My El Abbés Faouzi, Bouchra Meddah, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 126-131

Chemical investigation of the EtOAc extract of the fungus Chaetomium aureum, an endophyte of the Moroccan medicinal plant Thymelaea lythroides, afforded one new resorcinol derivative named chaetorcinol, together with five known metabolites. The structures of the isolated compounds were determined on the basis of one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry as well...

article

Synthesis and biological evaluation of novel chiral diazepine derivatives as bombesin receptor subtype-3 (BRS-3) agonists incorporating an antedrug approach

Tetsuyoshi Matsufuji, Kousei Shimada, Shozo Kobayashi, Masanori Ichikawa, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 89-104

Novel compounds based on the lead BRS-3 agonists from our HTS compounds 2a and 2b have been synthesized with the focus on obtaining peripheral BRS-3 agonists. To identify potent anti-obesity compounds without adverse effects on the central nerve system, a labile carboxylic ester with an antedrug functionality was introduced onto the terminal position. Through the extensive synthetic exploration and...

article

Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities

Haruhisa Kikuchi, Toshiyuki Suzuki, Masato Ogura, Miwako K. Homma, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 66-72

Mitochondrial uncoupling is one of the therapeutic strategies used to control energy metabolism in various metabolic diseases and in obesity. Ppc-1 (1), a prenylated quinolinecarboxylic acid isolated from cellular slime molds, shows uncoupling activity in vitro and anti-obesity activity in vivo. In this study, we synthesized Ppc-1 (1) and its derivatives, and revealed the structure–activity relationship...

article

Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors

Young Hun Lee, Min Cheol Shin, Yong Don Yun, Seo Young Shin, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 231-240

Alzheimer’s disease (AD), a progressive and neurodegenerative disorder of the brain, is the most common cause of dementia among elderly people. To date, the successful therapeutic strategy to treat AD is maintaining the levels of acetylcholine by inhibiting acetylcholinesterase (AChE). In the present study, aurone derivatives were designed and synthesized as AChE inhibitors based on the lead structure...

article

Synthesis of novel 10-hydroxycamptothecin derivatives utilizing topotecan hydrochloride as ortho-quinonemethide precursor

Hanyi Tan, Guolin Wang, Jiajun Li, Guangrong Meng, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 118-125

A series of 9-(alkylthiomethyl)-10-hydroxycamptothecins and pyrano-fused camptothecin derivatives were synthesized via the reaction of topotecan hydrochloride with various thiols and alkyl vinyl ethers respectively. In the reactions, topotecan hydrochloride was utilized as ortho-quinonemethide (o-QM) precursor. The configuration of 19 was determined by ¹ H NMR and NOESY spectra as syn-isomers,...

article

Modified 2,4-diaminopyrimidine-based dihydrofolate reductase inhibitors as potential drug scaffolds against Bacillus anthracis

Baskar Nammalwar, Christina R. Bourne, Nancy Wakeham, Philip C. Bourne, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 203-211

The current Letter describes the synthesis and biological evaluation of dihydrophthalazine-appended 2,4-diaminopyrimidine (DAP) inhibitors (1) oxidized at the methylene bridge linking the DAP ring to the central aromatic ring and (2) modified at the central ring ether groups. Structures 4a–b incorporating an oxidized methylene bridge showed a decrease in activity, while slightly larger alkyl groups...

article

Antidepressant- and anxiolytic-like activity of 7-phenylpiperazinylalkyl-1,3-dimethyl-purine-2,6-dione derivatives with diversified 5-HT1A receptor functional profile

Anna Partyka, Grażyna Chłoń-Rzepa, Anna Wasik, Magdalena Jastrzębska-Więsek, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 212-221

Continuing our earlier study in a group of purine-2,6-dione derivatives of long chain arylpiperazines (LCAPs), a series of 8-unsubstituted 7-phenylpiperazin-4-yl-alkyl (4–14) and 7-tetrahydroisoquinolinyl-alkyl (15–17) analogues were synthesized and their serotonin 5-HT _1A , 5-HT _2A , 5-HT ₆ , 5-HT ₇ and dopamine D ₂ receptor affinities were determined. The...

article

Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists

Matteo Gianella-Borradori, Ivy Christou, Carole J.R. Bataille, Rebecca L. Cross, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 241-263

The cannabinoid receptor 2 (CB ₂ R) has been linked with the regulation of inflammation, and selective receptor activation has been proposed as a target for the treatment of a range of inflammatory diseases such as atherosclerosis and arthritis. In order to identify selective CB ₂ R agonists with appropriate physicochemical and ADME properties for future evaluation in vivo, we first...

article

A dual inhibitor of matrix metalloproteinases and a disintegrin and metalloproteinases, [18F]FB-ML5, as a molecular probe for non-invasive MMP/ADAM-targeted imaging

Nathalie Matusiak, Riccardo Castelli, Adriaan W. Tuin, Herman S. Overkleeft, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 192-202

Numerous clinical studies have shown a correlation between increased matrix metalloproteinase (MMP)/a disintegrin and metalloproteinase (ADAM) activity and poor outcome of cancer. Various MMP inhibitors (MMPIs) have been developed for therapeutic purposes in oncology. In addition, molecular imaging of MMP/ADAM levels in vivo would allow the diagnosis of tumors. We selected the dual inhibitor of MMPs...

article

Clofazimine analogs with antileishmanial and antiplasmodial activity

Anna Barteselli, Manolo Casagrande, Nicoletta Basilico, Silvia Parapini, more

Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > 55-65

A set of novel riminophenazine derivatives has been synthesized and evaluated for in vitro activity against chloroquine–sensitive (CQ-S) and chloroquine–resistant (CQ-R) strains of Plasmodium falciparum and against different species of Leishmania promastigotes. Most of the new compounds inhibited the growth of Leishmania promastigotes as well as CQ-S and CQ-R strains of P. falciparum with IC ₅₀...

article

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Bioorganic & Medicinal Chemistry > 2015 > 23 > 1 > IFC

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23
Year:
2015

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CYTOTOXICITY (3)
APOPTOSIS (2)
INFLAMMATION (2)
10-HYDROXYCAMPTOTHECIN DERIVATIVES (1)
2,4-DIARYL-5H-INDENO[1,2-B]PYRIDINE (1)
4(Α-L-RHAMNOSYLOXY)-BENZYL ISOTHIOCYANATE (1)
4,5-DIHYDRO-1H-PYRAZOLE (1)
5-HT1A RECEPTOR AGONIST/ANTAGONIST (1)
5-HT2A RECEPTOR ANTAGONIST (1)
5-HT7 RECEPTOR ANTAGONIST (1)
ABSCISIC ACID (1)
ABSCISIC ACID ANALOGS (1)
ACETYLCHOLINESTERASE INHIBITOR (1)
ADAMS (1)
ADENOSINE RECEPTOR ANTAGONISTS (1)
AGONIST (1)
AKT (1)
ALKYLAMINO DERIVATIVES (1)
ALZHEIMER’S DISEASE (1)
ANTEDRUG (1)
ANTI-OBESITY (1)
ANTI-OBESITY DRUGS (1)
ANTIBIOTICS (1)
ANTICANCER ACTIVITY (1)
ANTICANCER AGENTS (1)
ANTIFOLATES (1)
ANTIFUNGAL (1)
ANTILEISHMANIAL ACTIVITY (1)
ANTIMICROBIAL AGENTS (1)
ANTIMICROBIALS (1)
ANTIOXIDANT (1)
ANTIPLASMODIAL ACTIVITY (1)
ANTIPROLIFERATION (1)
ANTIPROLIFERATIVE (1)
ANTITUBERCULARS (1)
ANTIVIRAL (1)
ANXIETY (1)
AURONE (1)
BACILLUS ANTHRACIS INHIBITION (1)
BIOACTIVE METABOLITES (1)
BOMBESIN RECEPTOR SUBTYPE-3 (BRS-3) (1)
BRAFV600E INHIBITION (1)
BRAIN PENETRATION (1)
CAMP (1)
CANNABINOID RECEPTOR 1 (1)
CANNABINOID RECEPTOR 2 (1)
CARBOCYCLIC NUCLEOSIDES (1)
CARBOHYDRATES (1)
CAULERPA RACEMOSA (1)
CELLULITE (1)
CHAETOMIUM AUREUM (1)
CLOFAZIMINE (1)
CLOFAZIMINE ANALOGS (1)
CONFIGURATION DETERMINATION (1)
COUPE ROSE (1)
CYCLOADDITION (1)
CYTOTOXIC ACTIVITY (1)
DEPRESSION (1)
DERMO-COSMETIC (1)
DIAZEPINE (1)
DIHYDROFOLATE REDUCTASE (1)
DOPAMINE TRANSPORTER (1)
DRUG RESISTANCE (1)
ENZYME INHIBITORS (1)
ENZYME MYROSINASE (1)
EYE BAGS (1)
FFA1 AGONIST (1)
FLUORESCENT SUBSTRATE (1)
G PROTEIN-COUPLED RECEPTORS (1)
GALANTAMINE (1)
GLUCOMORINGIN (1)
GLYCAN PROCESSING (1)
GOLGI APPARATUS (1)
GRANULOCYTES (1)
HIV-1 (1)
HSP90 (1)
HT1080 XENOGRAFT MOUSE MODEL (1)
HYDROXAMATE (1)
IN VITRO BINDING (1)
INFLAMMATORY DISEASE (1)
LIGAND-BASED SCREENING (1)
LIGAND–RECEPTOR MODELING STUDIES (1)
LONG-CHAIN ARYLPIPERAZINES (1)
MAPK P38 (1)
MEMORY ENHANCING (1)
METABOLIC DISEASES (1)
METASTASIS (1)
MITOCHONDRIAL UNCOUPLING (1)
MMP/ADAM INHIBITOR (1)
MMPS (1)
MOLECULAR DOCKING (1)
MORINGA OLEIFERA (1)
NEUROPROTECTIVE ACTIVITY (1)
NNRTIS (1)
NON-SMALL CELL LUNG CANCER (1)
NORBORNANE (1)
NOVEL DRUGS (1)
NUCLEIC ACIDS (1)
NUCLEOPHILIC ADDITION (1)
OLIGONUCLEOTIDES (1)
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INFONA - science communication portal

Bioorganic & Medicinal Chemistry

1,2,4-Triazolo[1,5-a]quinoxaline derivatives and their simplified analogues as adenosine A3 receptor antagonists. Synthesis, structure–affinity relationships and molecular modeling studies

Synthesis and antimycobacterial evaluation of 5-alkylamino-N-phenylpyrazine-2-carboxamides

Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity

Synthesis, biological evaluation and 3D-QSAR study of novel 4,5-dihydro-1H-pyrazole thiazole derivatives as BRAFV600E inhibitors

Synthesis and biological evaluation of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists

Synthesis and biological evaluation of pyridinone analogues as novel potent HIV-1 NNRTIs

Retraction notice to “3-Benzhydryl-4-piperidones as novel neurokinin-1 receptor antagonists and their efficient synthesis” [Bioorg. Med. Chem. 19 (2011) 5175–5182]

Identification of a novel glycan processing enzyme with exo-acting β-allosidase activity in the Golgi apparatus using a new platform for the synthesis of fluorescent substrates

Design, synthesis and biological activity of a novel Rutin analogue with improved lipid soluble properties

Bioactive metabolites from Chaetomium aureum: Structure elucidation and inhibition of the Hsp90 machine chaperoning activity

Synthesis and biological evaluation of novel chiral diazepine derivatives as bombesin receptor subtype-3 (BRS-3) agonists incorporating an antedrug approach

Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities

Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors

Synthesis of novel 10-hydroxycamptothecin derivatives utilizing topotecan hydrochloride as ortho-quinonemethide precursor

Modified 2,4-diaminopyrimidine-based dihydrofolate reductase inhibitors as potential drug scaffolds against Bacillus anthracis

Antidepressant- and anxiolytic-like activity of 7-phenylpiperazinylalkyl-1,3-dimethyl-purine-2,6-dione derivatives with diversified 5-HT1A receptor functional profile

Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists

A dual inhibitor of matrix metalloproteinases and a disintegrin and metalloproteinases, [18F]FB-ML5, as a molecular probe for non-invasive MMP/ADAM-targeted imaging

Clofazimine analogs with antileishmanial and antiplasmodial activity

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