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Chemical Communications (Cambridge,... Jun 2023A transition-metal-free and base-promoted one-pot synthesis of 2,3,4-trisubstituted 1--pyrroles has been developed. The reaction occurs through the [3+2] cycloaddition...
A transition-metal-free and base-promoted one-pot synthesis of 2,3,4-trisubstituted 1--pyrroles has been developed. The reaction occurs through the [3+2] cycloaddition of differently functionalized ynones and isocyanides. The reaction's advantageous features are operational simplicity, atom economy, and functional group tolerance with broad substrate scope. In addition, 1,3-bis-pyrrole formation and gram-scale synthesis were also achieved. Furthermore, the synthetic utility of the products was also investigated isocyanide insertion and pyrrole-triazole hybrid formation in good yield.
Topics: Pyrroles; Cyanides; Cycloaddition Reaction
PubMed: 37226554
DOI: 10.1039/d3cc01586f -
Alimentary Pharmacology & Therapeutics Jul 2023
Topics: Humans; Precision Medicine; Pyrroles; Sulfonamides
PubMed: 37307557
DOI: 10.1111/apt.17535 -
Molecules (Basel, Switzerland) Jun 2017This review covers the synthesis of coumarin-porphyrin, coumarin-phthalocyanine and coumarin-corrole conjugates and their potential applications. While... (Review)
Review
This review covers the synthesis of coumarin-porphyrin, coumarin-phthalocyanine and coumarin-corrole conjugates and their potential applications. While coumarin-phthalocyanine conjugates were obtained almost exclusively by tetramerization of coumarin-functionalized phthalonitriles, coumarin-porphyrin and coumarin-corrole conjugates were prepared by complementary approaches: (a) direct synthesis of the tetrapyrrolic macrocycle using formylcoumarins and pyrrole or (b) by functionalization of the tetrapyrrolic macrocycle. In the last approach a range of reaction types were used, namely 1,3-dipolar cycloadditions, hetero-Diels-Alder, Sonogashira, alkylation or acylation reactions. This is clearly a more versatile approach, leading to a larger diversity of conjugates and allowing the access to conjugates bearing one to up to 16 coumarin units.
Topics: Alkylation; Coumarins; Indoles; Isoindoles; Molecular Structure; Porphyrins; Pyrroles
PubMed: 28617340
DOI: 10.3390/molecules22060994 -
Chemical Reviews Feb 2017Sensing of metal ions and anions is of great importance because of their widespread distribution in environmental systems and biological processes. Colorimetric and... (Review)
Review
Sensing of metal ions and anions is of great importance because of their widespread distribution in environmental systems and biological processes. Colorimetric and fluorescent chemosensors based on organic molecular species have been demonstrated to be effective for the detection of various ions and possess the significant advantages of low cost, high sensitivity, and convenient implementation. Of the available classes of organic molecules, porphyrin analogues possess inherently many advantageous features, making them suitable for the design of ion chemosensors, with the targeted sensing behavior achieved and easily modulated based on their following characteristics: (1) NH moieties properly disposed for binding of anions through cooperative hydrogen-bonding interactions; (2) multiple pyrrolic N atoms or other heteroatoms for selectively chelating metal ions; (3) variability of macrocycle size and peripheral substitution for modulation of ion selectivity and sensitivity; and (4) tunable near-infrared emission and good biocompatibility. In this Review, design strategies, sensing mechanisms, and sensing performance of ion chemosensors based on porphyrin analogues are described by use of extensive examples. Ion chemosensors based on normal porphyrins and linear oligopyrroles are also briefly described. This Review provides valuable information for researchers of related areas and thus may inspire the development of more practical and effective approaches for designing high-performance ion chemosensors based on porphyrin analogues and other relevant compounds.
Topics: Cations; Colorimetry; Fluorescent Dyes; Molecular Structure; Porphyrins; Pyrroles
PubMed: 27078087
DOI: 10.1021/acs.chemrev.6b00021 -
ChemMedChem Jan 2024An overview of pyrroles as distinct scaffolds with therapeutic potential and the significance of pyrrole derivatives for drug development are provided in this article.... (Review)
Review
An overview of pyrroles as distinct scaffolds with therapeutic potential and the significance of pyrrole derivatives for drug development are provided in this article. It lists instances of naturally occurring pyrrole-containing compounds and describes the sources of pyrroles in nature, including plants and microbes. It also explains the many conventional and modern synthetic methods used to produce pyrroles. The key topics are the biological characteristics, pharmacological behavior, and functional alterations displayed by pyrrole derivatives. It also details how pyrroles are used to treat infectious diseases. It describes infectious disorders resistant to standard treatments and discusses the function of compounds containing pyrroles in combating infectious diseases. Furthermore, the review covers the uses of pyrrole derivatives in treating non-infectious diseases and resistance mechanisms in non-infectious illnesses like cancer, diabetes, and Alzheimer's and Parkinson's diseases. The important discoveries and probable avenues for pyrrole research are finally summarized, along with their significance for medicinal chemists and drug development. A reference from the last two decades is included in this review.
Topics: Humans; Pyrroles; Structure-Activity Relationship; Drug Development; Communicable Diseases
PubMed: 37926686
DOI: 10.1002/cmdc.202300447 -
Planta Medica Aug 2021Lime flowers, traditionally used for medical purposes for the treatment of symptoms of the common cold and mental stress, consist of the dried inflorescences including...
Lime flowers, traditionally used for medical purposes for the treatment of symptoms of the common cold and mental stress, consist of the dried inflorescences including the floral bracts of , or mixtures thereof. During phytochemical investigations, 6 different alkaloids - not described until now - were detected in and flowers. They have been isolated and characterized as alkaloids with a dihydro-pyrrole and a piperidine substructure, respectively. Compounds 1A: and 1B: (tiliines A and B) are characterized as 2 diastereomers containing a 2-methyl-3,4-dihydro-2-pyrrol-3-ol, connected via a C-10 alkyl chain to a -glucosylated hydroquinone moiety. Compounds 2A: and 2B: (tiliamines A and B) are diastereomers of a 2-methyl-substituted piperidin-3-ol, coupled via a C-9 alkyl chain again to an -glucosylated hydroquinone moiety. Compounds 3A: and 3B: (tilacetines A and B) are 3--acetylated derivatives of tiliamines. Quantification of the 6 alkaloids by HPLC-ESI-qTOF analysis indicated the presence of all alkaloids in flowers and flowers, bracts, and leaves, with tiliines A and B and tilacetines A and B being the major compounds. Acetone/water turned out be the best extraction solvent for the alkaloids, but ethanol and ethanol/water mixtures also can be used for effective extraction. Furthermore, the alkaloids are found in hot water extracts, which are typically used in the traditional medicine.
Topics: Alkaloids; Flowers; Piperidines; Pyrroles; Tilia
PubMed: 33434940
DOI: 10.1055/a-1340-0099 -
BMJ Open Diabetes Research & Care Sep 2020Progressive distal symmetrical axonal neuropathy, a complication of diabetes mellitus (DM), has an unknown cause. Normal physiological metabolism and diabetic...
INTRODUCTION
Progressive distal symmetrical axonal neuropathy, a complication of diabetes mellitus (DM), has an unknown cause. Normal physiological metabolism and diabetic dysmetabolism are associated with the generation of γ-diketones. γ-Diketones form pyrroles with protein amines, notably with axonal proteins required for the maintenance of nerve fiber integrity, especially elongate, large-diameter peripheral nerve fibers innervating the extremities. We tested the hypothesis that neuropathy-associated γ-diketone pyrroles are elevated in DM.
RESEARCH DESIGN AND METHODS
We measured the urinary concentration of γ-diketone pyrroles in age-matched and gender-matched elderly (60-84 years) persons with (n=267) or without (n=267) indicators of DM based in a community population (9411 community older adults aged ≥60 years) in Shenzhen city, Guangdong, China. We used statistical methods, including a generalized linear model, multivariate logistic regression analysis and restricted cubic splines, to assess linear and nonlinear relationships between urinary γ-diketone pyrroles and indicators of DM.
RESULTS
Compared with healthy controls, those with DM had significantly higher levels of fasting blood glucose, glycated hemoglobin A1c, urinary ketone bodies and urinary γ-diketone pyrroles. The median concentration of urinary γ-diketone pyrrole adducts was significantly higher (p<0.0001) in individuals with DM (7.5 (5.4) μM) compared with healthy controls (5.9 (4.3) μM). Both linear and non-linear relations were found between urinary γ-diketone pyrroles and indicators of DM.
CONCLUSIONS
Diabetic dysmetabolism includes increased generation and excretion of neuropathy-associated γ-diketone pyrroles. These findings form the foundation for studies to test whether γ-diketone pyrrole concentration correlates with quantitative sensory (vibration and temperature) and electrodiagnostic testing.
Topics: Aged; Aged, 80 and over; Axons; China; Diabetes Mellitus; Humans; Middle Aged; Peripheral Nervous System Diseases; Pyrroles
PubMed: 32912928
DOI: 10.1136/bmjdrc-2020-001575 -
Organic Letters Jun 2015The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization...
The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one carbon atom to another via the 7-endo-dig cyclization process. This transformation is unprecedented in the literature and is named an oxime-oxime rearrangement.
Topics: Catalysis; Gold; Indoles; Molecular Structure; Oximes; Pyrroles
PubMed: 25992473
DOI: 10.1021/acs.orglett.5b01041 -
Current Pharmaceutical Design 2024The escalation of cancer worldwide is one of the major causes of economy burden and loss of human resources. According to the American Cancer Society, there will be... (Review)
Review
BACKGROUND
The escalation of cancer worldwide is one of the major causes of economy burden and loss of human resources. According to the American Cancer Society, there will be 1,958,310 new cancer cases and 609,820 projected cancer deaths in 2023 in the United States. It is projected that by 2040, the burden of global cancer is expected to rise to 29.5 million per year, causing a death toll of 16.4 million. The hemostasis regulation by cellular protein synthesis and their targeted degradation is required for normal cell growth. The imbalance in hemostasis causes unbridled growth in cells and results in cancer. The DNA of cells needs to be targeted by chemotherapeutic agents for cancer treatment, but at the same time, their efficacy and toxicity also need to be considered for successful treatment.
OBJECTIVE
The objective of this study is to review the published work on pyrrole and pyridine, which have been prominent in the diagnosis and possess anticancer activity, to obtain some novel lead molecules of improved cancer therapeutic.
METHODS
A literature search was carried out using different search engines, like Sci-finder, Elsevier, ScienceDirect, RSC etc., for small molecules based on pyrrole and pyridine helpful in diagnosis and inducing apoptosis in cancer cells. The research findings on the application of these compounds from 2018-2023 were reviewed on a variety of cell lines, such as breast cancer, liver cancer, epithelial cancer, etc. Results: In this review, the published small molecules, pyrrole and pyridine and their derivatives, which have roles in the diagnosis and treatment of cancers, were discussed to provide some insight into the structural features responsible for diagnosis and treatment. The analogues with the chromeno-furo-pyridine skeleton showed the highest anticancer activity against breast cancer. The compound 5-amino-N-(1-(pyridin-4- yl)ethylidene)-1H-pyrazole-4-carbohydrazides was highly potent against HEPG2 cancer cell. Redaporfin is used for the treatment of cholangiocarcinoma, biliary tract cancer, cisplatin-resistant head and neck squamous cell carcinoma, and pigmentation melanoma, and it is in clinical trials for phase II. These structural features present a high potential for designing novel anticancer agents for diagnosis and drug development.
CONCLUSION
Therefore, the N- and C-substituted pyrrole and pyridine-based novel privileged small Nheterocyclic scaffolds are potential molecules used in the diagnosis and treatment of cancer. This review discusses the reports on the synthesis of such molecules during 2018-2023. The review mainly discusses various diagnostic techniques for cancer, which employ pyrrole and pyridine heterocyclic scaffolds. Furthermore, the anticancer activity of N- and C-substituted pyrrole and pyridine-based scaffolds has been described, which works against different cancer cell lines, such as MCF-7, A549, A2780, HepG2, MDA-MB-231, K562, HT- 29, Caco-2 cells, Hela, Huh-7, WSU-DLCL2, HCT-116, HBL-100, H23, HCC827, SKOV3, etc. This review will help the researchers to obtain a critical insight into the structural aspects of pyrrole and pyridine-based scaffolds useful in cancer diagnosis as well as treatment and design pathways to develop novel drugs in the future.
Topics: Humans; Neoplasms; Antineoplastic Agents; Pyridines; Pyrroles; Heterocyclic Compounds; Animals
PubMed: 38711394
DOI: 10.2174/0113816128280082231205071504 -
European Journal of Medicinal Chemistry Mar 2016Pyrrole derivatives comprise a class of biologically active heterocyclic compounds which can serve as promising scaffolds for antimicrobial, antiviral, antimalarial,... (Review)
Review
Pyrrole derivatives comprise a class of biologically active heterocyclic compounds which can serve as promising scaffolds for antimicrobial, antiviral, antimalarial, antitubercular, anti-inflammatory and enzyme inhibiting drugs. Due to their inimitable anticancer and anti-tubercular properties, researchers were inspired to develop novel pyrrole derivatives for the treatment of MDR pathogens. In the present review the main target is to focus on the development of pyrrole mimics, with emphasis based on their structure activity relationship (SAR). The present review is being obliging for the future development of pyrrole therapeutics.
Topics: Animals; Anti-Infective Agents; Antineoplastic Agents; Antioxidants; Drug Discovery; Enzyme Inhibitors; Humans; Pyrroles; Structure-Activity Relationship
PubMed: 26807541
DOI: 10.1016/j.ejmech.2015.12.017