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Internal Medicine (Tokyo, Japan) Jan 2020Helicobacter pylori can infect the gastric mucosa and cause chronic inflammation, resulting in various diseases, including gastric cancer. Eradication of H. pylori in... (Review)
Review
Helicobacter pylori can infect the gastric mucosa and cause chronic inflammation, resulting in various diseases, including gastric cancer. Eradication of H. pylori in all infected subjects is recommended; however, the number of H. pylori strains with antibiotic resistance has increased, and the eradication rate has decreased. Vonoprazan, a potassium-competitive acid blocker, produces a stronger acid-inhibitory effect than proton pump inhibitors (PPIs). The H. pylori eradication rate with vonoprazan was found to be higher than that with PPIs. The H. pylori eradication rate with vonoprazan-based triple therapy (vonoprazan, amoxicillin, and clarithromycin) was approximately 90% and had an incidence of adverse events similar to that of PPIs. We review the current situation of H. pylori eradication in Japan, the first country in which vonoprazan was made available.
Topics: Amoxicillin; Anti-Bacterial Agents; Clarithromycin; Drug Therapy, Combination; Gastric Mucosa; Helicobacter Infections; Helicobacter pylori; Humans; Japan; Proton Pump Inhibitors; Pyrroles; Sulfonamides
PubMed: 31243237
DOI: 10.2169/internalmedicine.2521-18 -
Chemical Reviews Feb 2017A large number of porphyrinoids containing 2,2'-bipyrrole subunits have appeared since they were originally found as a component of sapphyrin and corrole, and it was... (Review)
Review
A large number of porphyrinoids containing 2,2'-bipyrrole subunits have appeared since they were originally found as a component of sapphyrin and corrole, and it was found that the bipyrrole subunit endowed macrocycles with specific geometric features and electronic properties. Synthetic methods for bipyrrole-containing precursors for porphyrinoid are summarized in this review; these include coupling reactions of pyrrole rings, pyrrole ring-forming reactions leading directly to bipyrrole units, and synthetic reactions for oligopyrrolic compounds. Some hybrid oligopyrroles having nonpyrrole (hetero)aromatic ring(s) are also included. This review also describes porphyrinoids composed of bipyrrole subunits. Interesting electronic properties derived from strong cyclo-π-conjugation are highlighted in the bipyrrole-based porphyrinoids with or without meso-like carbons. Anion-binding chemistry is one of the main topics for bipyrrole-based macrocycles with less efficient or deficient cyclo-π-conjugation, such as those linked with electronically localized aromatic ring(s), with sp carbon(s), and with amido or imine connection(s). The principal concern in this review is porphyrinoids of relatively large ring size, composed of more than five units of pyrroles and (hetero)aromatic substitutes in total, and so bipyrrole-based porphyrinoids up to five pyrrolic units, such as corroles, porphycenes, sapphyrins, and smaragdyrin, will not be covered here except for some special cases.
Topics: Crystallography, X-Ray; Molecular Conformation; Oxidation-Reduction; Porphyrins; Pyrroles
PubMed: 27802039
DOI: 10.1021/acs.chemrev.6b00430 -
Molecules (Basel, Switzerland) Mar 2023Pyrrole-2-carboxaldehyde (Py-2-C) derivatives have been isolated from many natural sources, including fungi, plants (roots, leaves, and seeds), and microorganisms. The... (Review)
Review
Pyrrole-2-carboxaldehyde (Py-2-C) derivatives have been isolated from many natural sources, including fungi, plants (roots, leaves, and seeds), and microorganisms. The well-known diabetes molecular marker, pyrraline, which is produced after sequential reactions in vivo, has a Py-2-C skeleton. Py-2-Cs can be chemically produced by the strong acid-catalyzed condensation of glucose and amino acid derivatives in vitro. These observations indicate the importance of the Py-2-C skeleton in vivo and suggest that molecules containing this skeleton have various biological functions. In this review, we have summarized Py-2-C derivatives based on their origins. We also discuss the structural characteristics, natural sources, and physiological activities of isolated compounds containing the Py-2-C group.
Topics: Molecular Structure; Glucose; Pyrroles; Fungi
PubMed: 36985566
DOI: 10.3390/molecules28062599 -
Chemical Society Reviews Nov 2021Expanded heteroporphyrins are a class of porphyrin macrocycles containing pyrrole, thiophene, furan, selenophene and other heterocyclic rings that are connected to form... (Review)
Review
Expanded heteroporphyrins are a class of porphyrin macrocycles containing pyrrole, thiophene, furan, selenophene and other heterocyclic rings that are connected to form an internal ring pathway containing a minimum of 17 atoms and more than 18 delocalized π electrons in their conjugated macrocyclic framework. Considering that expanded heteroporphyrins are large in size, these macrocycles are structurally flexible and prefer to adopt various conformations in which one or more pyrrole(s)/heterocycle(s) tend to be in an inverted conformation and pointed outward from the centre of the macrocyclic core. The inverted expanded heteroporphyrins are divided into two classes as follows: (1) -inverted expanded heteroporphyrins and (2) hetero-atom inverted expanded heteroporphyrins. Both inverted expanded heteroporphyrins show quite unique features in terms of their structure, aromaticity, and electronic and coordination properties. Sometimes, inverted expanded heteroporphyrins lead to the formation of fused expanded heteroporphyrins because of the intramolecular fusion of the pyrrole "N" with the "C" of the inverted heterocycle ring, which also exhibit unique features compared to inverted expanded heteroporphyrins. In this review, we attempt to describe the synthesis, structure, and aromatic, electronic and coordination properties of inverted and fused expanded heteroporphyrins. This review covers the synthesis, structure and properties of inverted and fused expanded heteroporphyrins containing a combination of pyrrole/heterocycle rings starting with five pyrrole/heterocycle-containing pentaphyrins, and then expanded heteroporphyrins containing six, seven, eight and more pyrrole/heterocyclic rings in their porphyrin macrocyclic framework.
Topics: Electrons; Molecular Conformation; Porphyrins; Thiophenes
PubMed: 34747949
DOI: 10.1039/d1cs00666e -
Chemical Communications (Cambridge,... Jun 2022Recent synthetic achievements have led to 4,4-disubstituted-4-bora-3a,4a-diaza--indacenes (BODIPYs) with varying substituents at the meso, pyrrolic and/or boron sites,... (Review)
Review
Recent synthetic achievements have led to 4,4-disubstituted-4-bora-3a,4a-diaza--indacenes (BODIPYs) with varying substituents at the meso, pyrrolic and/or boron sites, with each influencing photophysical properties and utility. This Feature article gives an overview of chemistry at the boron atom in BODIPYs, highlighting our contributions that evolved from synthetic curiosities and now offer this dipyrrolic skeleton potential across a wider range of applications. We first summarise preparative routes to BODIPYs through complexation of boron with the dipyrrinato ligand. The role of boron in protecting dipyrrins is then discussed, followed by strategies by which to achieve facile substitution at the boron atom.
Topics: Boron; Boron Compounds; Fluorescent Dyes; Pyrroles
PubMed: 35722959
DOI: 10.1039/d2cc02362h -
Yakugaku Zasshi : Journal of the... 2020In total and formal syntheses of dictyodendrins A, B, C, D, E and F, the key step involved the direct construction of the pyrrolo[2,3-c]carbazole core by the... (Review)
Review
In total and formal syntheses of dictyodendrins A, B, C, D, E and F, the key step involved the direct construction of the pyrrolo[2,3-c]carbazole core by the gold-catalyzed annulation of a conjugated diyne with a pyrrole to form three bonds and two aromatic rings. The subsequent introduction of substituents at the C1 (Suzuki-Miyaura coupling), C2 (acylation), N3 (alkylation) and C5 positions (Ullmann coupling) provided divergent access to dictyodendrins. Some dictyodendrin analogues exhibited inhibitory activities toward CDK2/CycA2 and GSK3.
Topics: Acylation; Alkylation; Carbazoles; Catalysis; Cyclin-Dependent Kinase 2; Diynes; Organic Chemistry Phenomena; Pyrroles
PubMed: 33132266
DOI: 10.1248/yakushi.20-00162 -
International Journal of Molecular... Feb 2023Redox imbalance or oxidative stress that results from both environmental and genetic factors is observed in patients with schizophrenia. Therefore, identifying markers... (Review)
Review
Redox imbalance or oxidative stress that results from both environmental and genetic factors is observed in patients with schizophrenia. Therefore, identifying markers of oxidative stress in the early stages of psychosis and using antioxidant treatments as an adjuvant to antipsychotics has important implications. The reaction of -,-dimethylaminobenzaldehyde (DMAB) with pyrrole moieties has been well studied for well over a century for use as a marker of oxidative stress dysregulation. Throughout this time, pyrroles have been investigated with varying veracity in urine extracts to identify elevated levels in patients diagnosed with schizophrenia. Since the 1960's, various claims have been made with respect to what causes the colour change when DMAB is added to urine extracts. Whilst the substances from this reaction have not been fully elucidated, an objective look at most studies indicates that urobilinogen is likely to be one them. Urobilinogen has also been identified as a major interferent in our results. Both pyrroles and urobilinogen condense the DMAB reaction system (form condensation products) and are quite different. The urobilinogen detected in urine forms when gut microflora chemically reduces the bilirubin content of bile acids. In comparison, evidence suggests that the pyrrole fraction originates from the fragmentation of regulatory haem by reactive oxygen species (ROS) such as hydrogen peroxide and super and nitrous oxides. Clinical studies in our laboratories have established that pyrroles as a urine biomarker have specificity in detecting schizophrenia; however, caution must be applied as the readings are subject to interference by other DMAB active compounds that are present, such as urobilinogen. This review highlights the initial chemistry in isolating pyrroles and provides recommendations for standardised laboratory testing to ensure pyrroles are correctly measured and distinguished from other by-products.
Topics: Humans; Pyrroles; Urobilinogen; Bilirubin; Oxidation-Reduction; Oxidative Stress
PubMed: 36769035
DOI: 10.3390/ijms24032712 -
Marine Drugs Sep 2021Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats... (Review)
Review
Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats but can also frequently be found as natural products in the marine environment. This review highlights the important class of marine pyrrole alkaloids, well-known for their diverse biological activities. A broad overview of the marine pyrrole alkaloids with a focus on their isolation, biological activities, chemical synthesis, and derivatization covering the decade from 2010 to 2020 is provided. With relevant structural subclasses categorized, this review shall provide a clear and timely synopsis of this area.
Topics: Alkaloids; Animals; Aquatic Organisms; Pyrroles; Structure-Activity Relationship
PubMed: 34564176
DOI: 10.3390/md19090514 -
European Journal of Medicinal Chemistry Dec 2020The discovery of novel synthetic compounds with drug-like properties is an ongoing challenge in medicinal chemistry. Natural products have inspired the synthesis of... (Review)
Review
The discovery of novel synthetic compounds with drug-like properties is an ongoing challenge in medicinal chemistry. Natural products have inspired the synthesis of compounds for pharmaceutical application, most of which are based on N-heterocyclic motifs. Among these, the pyrrole ring is one of the most explored heterocycles in drug discovery programs for several therapeutic areas, confirmed by the high number of pyrrole-based drugs reaching the market. In the present review, we focused on pyrrole and its hetero-fused derivatives with anticancer, antimicrobial, and antiviral activities, reported in the literature between 2015 and 2019, for which a specific target was identified, being responsible for their biological activity. It emerges that the powerful pharmaceutical and pharmacological features provided by the pyrrole nucleus as pharmacophore unit of many drugs are still recognized by medicinal chemists.
Topics: Anti-Infective Agents; Antineoplastic Agents; Antiviral Agents; Drug Design; Humans; Molecular Targeted Therapy; Pyrroles
PubMed: 32916311
DOI: 10.1016/j.ejmech.2020.112783 -
European Journal of Medicinal Chemistry Apr 2024In this review, we summarize pyrroloquinoline and pyrroloisoquinoline derivatives (PQs and PIQs) that act on a broad spectrum of biological targets and are used as... (Review)
Review
In this review, we summarize pyrroloquinoline and pyrroloisoquinoline derivatives (PQs and PIQs) that act on a broad spectrum of biological targets and are used as bacteriostatic, antiviral, plasmodial, anticancer, antidiabetic and anticoagulant agents. Many of these compounds play important roles in the study of DNA and its interactions, the regulation of the cell cycle and programmed cell death. This review involves twenty-five types of skeletally analogical compounds bearing pyrrole and (iso)quinoline scaffolds with different mutual annelations.
Topics: Quinolines; Pyrroles; Cell Cycle; Apoptosis; Antineoplastic Agents
PubMed: 38492334
DOI: 10.1016/j.ejmech.2024.116287