Bibliographies thématiques / Benzothiazepines

Littérature scientifique sur le sujet « Benzothiazepines »

Auteur : Grafiati
Publié le 25 juillet 2024

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Articles de revues sur le sujet "Benzothiazepines"

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Kandalkar, Madhuri, Priyanka Sharma et Sonika Sethi. « SYNTHESES AND ANTIMICROBIAL SCREENING OF 8- SUBSTITUTED-2,5-DIHYDRO-2-(2-NITROPHENYL/4- NITROPHENYL)-4-(2-CHLOROPHENYL)-1,5- BENZOTHIAZEPINES ». RASAYAN Journal of Chemistry 16, no 04 (2023) : 2072–77. http://dx.doi.org/10.31788/rjc.2023.1648498.

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1,5-Benzothiazepine, a novel heterocyclic moiety, is under research to assess its intriguing biological properties. Many versatile synthetic approaches allow the incorporation of structural variation within this scaffold. The target benzothiazepines,8-substituted-2,5-dihydro-2-(2-nitrophenyl/4-nitrophenyl)-4-(2-chlorophenyl)-1,5 benzothiazepines, was prepared by reacting, α,β-unsaturated heterocyclyl ketone, 3-(2-nitrophenyl/4-nitrophenyl)-1- (2-chlorophenyl)-2-propenone with 5-substituted-2-aminobenzenethiols, in different reaction conditions via Michael addition mechanism. The current research focuses on the comparative efficacy of synthetic techniques, spectral characteristics, and pharmacological profile of, 8-substituted-2,5-dihydro-2-(2-nitrophenyl/4-nitrophenyl)-4-(2- chlorophenyl)-1,5-benzothiazepines.
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Martínez, Carlos A., Dionisia Sanz, Rosa M. Claramunt et José Elguero Bertolini. « Reactivity of curcumin and curcuminoid β-diketones with o-aminothiophenol : synthesis of 1,5-benzothiazepines ». Anales de la Real Academia Nacional de Farmacia 88, no 88(05) (31 décembre 2022) : 351–67. http://dx.doi.org/10.53519/analesranf.2022.88.05.02.

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Four new 1,5-benzothiazepines were synthesized by reaction of o-aminothiophenol with curcumin and curcuminoid β-diketones, in methanol and in acetic acid. The mechanism involves a Michael addition on the CC double bond affording a benzothiazepine with two pendant groups, an aryl group adjacent to the sulfur atom and a 1-phenylethanone adjacent to the NH of the seven membered ring. 1D and 2D multinuclear NMR (1H, 13C, 15N, 119F) in solution and 13C and 15N NMR in solid state proved to be essential to elucidate the structures of these benzothiazepines, in particular their tautomerism. A secondary product has been identified that has the structure of a benzothiazole. Keywords: curcumin; β-diketones; aminothiophenol; 1,5-benzothiazepines
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Holland, Herbert L., Sudalaiyandi Kumaresan et Gingipalli Lakshmaiah. « Synthesis of steroidal [4,6-b,c]-benzothiazepines, a new class of aromatase inhibitor ». Canadian Journal of Chemistry 73, no 12 (1 décembre 1995) : 2185–89. http://dx.doi.org/10.1139/v95-271.

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Several steroidal [4,6-b,c]benzothiazepines have been prepared via base-catalyzed Michael addition of 2-aminothiophenol to 3β,17β-diacetoxyandrost-4-en-6-one. The product of this reaction has the 4β,5α stereochemistry, but cyclizes to a benzothiazepine with the steroidal 4β,5β configuration, confirmed by X-ray crystallographic analysis. 2-Aminothiophenol reacts with 3β,17β-diacetoxyandrost-4-en-6-one under acidic conditions to give a steroidal 6-spiro-benzothiazole. An androst-4-ene-3,17-dione-based [4,6]benzothiazepine has been shown to be a moderate competitive inhibitor of the human placental aromatase enzyme with IC50 = 42.3 µM. Keywords: steroid, aromatase, benzothiazepine.
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Archana. « SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME NOVEL BENZODIAZEPINE CONTAINING BENZOTHIAZEPINE/BENZOXAZEPINE DERIVATIVES AS POTENT ANTICONVULSANT AGENTS ». INDIAN DRUGS 55, no 06 (28 juin 2018) : 7–13. http://dx.doi.org/10.53879/id.55.06.11194.

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A new series of 4-benzodiazepinyl-2-( substituted phenyl)-1,5-benzothiazepines (3a-3f) and 4-benzodiazepinyl-2-(substituted phenyl)-1,5-benzoxazepines (4a-4f) were synthesised and evaluated for their anticonvulsant activity. All these compounds were screened in vivo, for their anticonvulsant activity and acute toxicity. Compound 4-benzodiazepinyl-2-(p-methoxy phenyl)-1,5-benzothiazepine 4b, was found to be most potent compoundof this series, more potent than standard drug phenytoin sodium. The homogeneity of all the compounds was checked by TLC. The structures of these compounds have been established by elemental analysis, IR and 1H NMR spectroscopy.
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Frimayanti, Neni, Fina Aryani, Nina Rishanti et Marzieh Yaeghoobi. « In Silico Analysis Towards Exploring Potential β Secretase 1 (BACE1) Inhibitors ; The Cause of Alzhemier Disease ». Journal of Physics : Conference Series 2049, no 1 (1 octobre 2021) : 012011. http://dx.doi.org/10.1088/1742-6596/2049/1/012011.

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Abstract 1,5 benzothiazepine chalcone derivative compounds were used as ligands and docked with protein target 2XFJ code from Hydrolase enzyme crystallographic structure. Molecular Operating Environment 2020.0901 (MOE) computer program was used as software to perform docking. The aim of this research is to determine the potentiality of 1,5 benzothiazepines as β secretase 1 (BACE1) inhibitors using molecular docking studies and also to predict their toxicity using SwissADME. Based on the docking results, some promising interactions were observed between 1,5 benzothiazepines and β secretase 1 (BACE1) receptors using Verubecestat as a positive control. Compounds MA2, MA4 and MA10 shown to have the potentiality as active inhibitors for the β secretase 1 (BACE1). These three compounds have binding free energy values of -4,6302 kcal/mol, -4,4268 kcal/mol, and -5,3427 kcal/mol, respectively. In addition, they also exhibited factor of binding (i. e. a measure of the probability of tested compounds to bind with the same amino acid that the positive control, Verubecestat). The predicted toxicity for these three compounds were measured using SwissADME and the results showed that MA2, MA4 and MA10 are not toxic and they can be used as reference for designing new inhibitors for β secretase 1 (BACE1).
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Shaik, Afzal B., Yejella R. Prasad, Srinath Nissankararao et Shaik Shahanaaz. « Synthesis, Biological and Computational Evaluation of Novel 2,3-dihydro-2-aryl-4-(4- isobutylphenyl)-1,5-benzothiazepine Derivatives as Anticancer and Anti-EGFR Tyrosine Kinase Agents ». Anti-Cancer Agents in Medicinal Chemistry 20, no 9 (20 août 2020) : 1115–28. http://dx.doi.org/10.2174/1871520620666200130091142.

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Background: Despite the availability of a variety of chemotherapeutic agents, cancer is still one of the leading causes of death worldwide because of the problems with existing chemotherapeutic agents like objectionable side effects, lack of selectivity, and resistance. Hence, there is an urgent need for the development of novel anticancer agents with high usefulness, fewer side effects, devoid of resistance and superior selectivity. Objective: The objective of this study is to synthesize a series of novel 1,5-benzothiazepine derivatives and evaluate their anticancer activity employing biological and computational methods. Methods: Twenty new benzothiazepines (BT1-BT20) were prepared by condensing different 1-(4- isobutylphenyl)ethanone chalcones with 2-amiothiophenol and evaluated for their anticancer activity by MTT assay against three cell lines including HT-29 (colon cancer), MCF-7 (breast cancer) and DU-145 (prostate cancer). These compounds were also tested for their inhibitory action against EGFR (Epidermal Growth Factor Receptor) tyrosine kinase enzyme by taking into account of their excellent action against colon and breast cancer cell lines. Further, the structural features responsible for the activity were identified by Pharmacophorebased modelling using Schrodinger’s PHASETM software. Results: Among the 20 benzothiazepine derivatives, three compounds viz., BT18, BT19 and BT20 exhibited promising activity against the cell lines tested and the activity of BT20 was more than the standard methotrexate. Again the above three compounds showed excellent inhibitory activity with the percentage inhibition of 64.5, 57.3 and 55.8 respectively against EGFR (Epidermal Growth Factor Receptor) tyrosine kinase. PHASE identified a five-point AHHRR model for the proposed activity and the computational studies provided insights into the structural requirements for the anticancer activity and the results were consistent with the observed in vitro activity data. Conclusion: These novel benzothiazepines will be useful as lead molecules for the further development of new cancer therapies against colon and breast cancers.
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Haroun, Michelyne, Santosh S. Chobe, Rajasekhar Reddy Alavala, Savita M. Mathure, Risy Namratha Jamullamudi, Charushila K. Nerkar, Vijay Kumar Gugulothu et al. « 1,5-Benzothiazepine Derivatives : Green Synthesis, In Silico and In Vitro Evaluation as Anticancer Agents ». Molecules 27, no 12 (10 juin 2022) : 3757. http://dx.doi.org/10.3390/molecules27123757.

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Considering the importance of benzothiazepine pharmacophore, an attempt was carried out to synthesize novel 1,5-benzothiazepine derivatives using polyethylene glycol-400 (PEG-400)-mediated pathways. Initially, different chalcones were synthesized and then subjected to a cyclization step with benzothiazepine in the presence of bleaching clay and PEG-400. PEG-400-mediated synthesis resulted in a yield of more than 95% in less than an hour of reaction time. Synthesized compounds 2a–2j were investigated for their in vitro cytotoxic activity. Moreover, the same compounds were subjected to systematic in silico screening for the identification of target proteins such as human adenosine kinase, glycogen synthase kinase-3β, and human mitogen-activated protein kinase 1. The compounds showed promising results in cytotoxicity assays; among the tested compounds, 2c showed the most potent cytotoxic activity in the liver cancer cell line Hep G-2, with an IC50 of 3.29 ± 0.15 µM, whereas the standard drug IC50 was 4.68 ± 0.17 µM. In the prostate cancer cell line DU-145, the compounds displayed IC50 ranges of 15.42 ± 0.16 to 41.34 ± 0.12 µM, while the standard drug had an IC50 of 21.96 ± 0.15 µM. In terms of structural insights, the halogenated phenyl substitution on the second position of benzothiazepine was found to significantly improve the biological activity. This characteristic feature is supported by the binding patterns on the selected target proteins in docking simulations. In this study, 1,5-benzothiazepines have been identified as potential anticancer agents which can be further exploited for the development of more potent derivatives.
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Frimayanti, Neni, Musyirna Rahmah Nasution et Elsa Etavianti. « Molecular docking and molecular dynamic simulation of 1,5-benzothiazepine chalcone derivative compounds as potential inhibitors for Zika virus helicase ». Jurnal Riset Kimia 12, no 1 (3 avril 2021) : 44–52. http://dx.doi.org/10.25077/jrk.v12i1.365.

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Zika virus caused of the emerging infections characterized by fever, Guillain-Barré syndrome (GBS) for adults. In the current work, we aimed to study the binding orientation of 1,5-benzothiazepine compounds as new potential agent against Zika virus inhibitor through molecular docking and molecular dynamic simulation. Since, 1-5-Benzothiazepines are particular interest for drug discovery and they also has some biological activities. However, their antiviral activities and in silico studies of the binding to their biological targets have not been extensively investigated. Molecular docking study of 1,5-benzothiazepine chalcone derivatives compounds with protein target 5GJB (PDB ID) and this protein was taken from the crystallographic structure. In this study, twelve 1,5-benzothiazepine chalcone derivative compounds were docked to the protein with the grid box along x, y and z radius of 26.85, 28.17 and 24.43 Å, respectively. Suramin was used as positive control. Thus, it can be used as a reference for design new inhibitors for Zika virus helicase. Based on the docking results, it is observed that compounds MA3 and MA8 are estimated to have activity as inhibitors for Zika virus helicase with binding free energy values of -4.6490 and -4.9291 kcal/mol, respectively. MA3 and MA8 were also stable during the MD simulations with the hydrogen bonding are still maintained before and after MD simulation. Furthermore, both of these compounds can be used an early stage for drug design and drug delivery process.
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L�vai, A. « Synthesis of benzothiazepines (review) ». Chemistry of Heterocyclic Compounds 22, no 11 (novembre 1986) : 1161–70. http://dx.doi.org/10.1007/bf00471794.

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Yadav, Neetu, Vijay B. Yadav, Mohd Danish Ansari, Hozeyfa Sagir, Ankit Verma et I. R. Siddiqui. « Catalyst-free synthesis of 2,3-dihydro-1,5-benzothiazepines in a renewable and biodegradable reaction medium ». New Journal of Chemistry 43, no 18 (2019) : 7011–14. http://dx.doi.org/10.1039/c8nj05611k.

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Thèses sur le sujet "Benzothiazepines"

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Tolaymat, Ibrahim [Verfasser]. « 1,4-benzothiazepines, 3-hydroxy-benzo[b]thiophene-2-carboxamides and benzothieno[2,3-e][1,3]oxazines derived from thiosalicylic acid / by Ibrahim Tolaymat ». 2009. http://d-nb.info/994097840/34.

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Brust, Andreas. « Reaktionskanäle von Zuckern zu hydrophilen N-Heterocyclen des Imidazol-, Chinoxalin-, Pyridazin-, Benzodiazepin- und Benzothiazepin-Typs sowie NMR-Spektroskopische Charakterisierung neuer Disaccharid-phosphate ». Phd thesis, 2001. http://tuprints.ulb.tu-darmstadt.de/125/1/Microsoft_Word_-_Diss.A.Brust.pdf.

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Stickstoff-Heterocyclen stellen industrielle Schlüsselprodukte dar und sind speziell im Wirkstoffbereich fundamentale und funktionale Einheiten. Die im Rahmen dieser Arbeit, ausgehend von niedermolekularen Kohlenhydraten entwickelten Reaktionskanäle, erschließen neuartige hydrophile, glycosidisch verknüpfte N-Heterocyclen mit potentiellem pharmakologischem Anwendungsprofil. Ausgehend von technisch einfach zugänglichen Disacchariden wie Isomaltulose, Leucrose, Maltose, Cellobiose und Lactose wurden "Eintopfverfahren" zur Darstellung von Tetrahydroxybutyl-substituierten Imidazolen und Chinoxalinen mit variablem Glycosylierungsmuster erarbeitet. Die zweite verfolgte Synthesestrategie zur Darstellung von N-Heterocyclen ging von a-Glucosyloxymetylfurfural (GMF) aus. Durch Etablierung geeigneter Reaktionssequenzen und Oxidationsverfahren wurde GMF in zahlreiche 1,4-Dicarbonyl-Synthesebausteine übergeführt, welche zum Aufbau von Zucker-substituierten Pyridazinen, Imidazolen, Benzodiazepinen und Benzothiazepinen genutzt wurden. Im zweiten Thema der Arbeit wurden die, vom Bakterium Klebsiella pneumoniae, produzierten Monophosphate verschiedener a-Glucosyl-verknüpfter Disaccharide (z.B. Saccharose, Isomaltulose u.a.) untersucht. Mittels 1- und 2-dimensionaler 1H und 13C-NMR spektroskopischer Methoden wurde bewiesen, das Klebsiella pneumoniae regiospeziefisch die primäre Alkoholfunktion des a-Glucosylrestes phosphoryliert. Desweiteren konnten die Tautomerenverteilungen der Disaccharid-phosphate ermittelt werden.
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Brust, Andreas [Verfasser]. « Reaktionskanäle von Zuckern zu hydrophilen N-Heterocyclen des Imidazol-, Chinoxalin-, Pyridazin-, Benzodiazepin- und Benzothiazepin-Typs sowie NMR-spektroskopische Charakterisierung neuer Disaccharid-Phosphate / vorgelegt von Andreas Brust ». 2001. http://d-nb.info/962736708/34.

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Chapitres de livres sur le sujet "Benzothiazepines"

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Chimirri, A., R. Gitto, S. Grasso, A. M. Monforte et M. Zappalà. « Annelated 1,5-Benzothiazepines ». Dans Advances in Heterocyclic Chemistry, 61–101. Elsevier, 1995. http://dx.doi.org/10.1016/s0065-2725(08)60472-9.

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Ulrich, H. « From 1,5-Benzothiazepines ». Dans Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-011-01101.

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lvarez, M., et J. A. Joule. « From 1,4-Benzothiazepines ». Dans Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-015-01276.

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Ulrich, H. « Of Pyrimido[1,5]benzothiazepines ». Dans Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles, 1. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-017-00306.

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Akbarzadeh, Elaheh. « Pharmaceutical applications of 1,5-benzothiazepines ». Dans Benzodiazepine-Based Drug Discovery, 295–321. Elsevier, 2022. http://dx.doi.org/10.1016/b978-0-12-824516-3.00002-1.

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Zamani, Farzad, et Esmail Doustkhah. « An introduction to benzodiazepines and benzothiazepines ». Dans Benzodiazepine-Based Drug Discovery, 1–8. Elsevier, 2022. http://dx.doi.org/10.1016/b978-0-12-824516-3.00007-0.

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Zamani, Farzad, Ramin Javahershenas, Fatemeh M. Arlan, Christopher J. T. Hyland et Esmail Doustkhah. « Synthesis of 1,4-benzodiazepines and 1,4-benzothiazepines ». Dans Benzodiazepine-Based Drug Discovery, 35–77. Elsevier, 2022. http://dx.doi.org/10.1016/b978-0-12-824516-3.00004-5.

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Zamani, Farzad, Esmail Doustkhah, Fatemeh Ahmadi et Rajender S. Varma. « Synthesis of 1,5-benzodiazepines and 1,5-benzothiazepines ». Dans Benzodiazepine-Based Drug Discovery, 199–249. Elsevier, 2022. http://dx.doi.org/10.1016/b978-0-12-824516-3.00003-3.

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Zamani, Farzad, Nasrin Zamani, Takayoshi Suzuki et Esmail Doustkhah. « Biological behavior of 1,4-benzodiazepines and 1,4-benzothiazepines ». Dans Benzodiazepine-Based Drug Discovery, 77–125. Elsevier, 2022. http://dx.doi.org/10.1016/b978-0-12-824516-3.00010-0.

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Heidarizadeh, Mohammad, Saeedeh Mohammadi, Arash Janaty, Abtin Tavakoli, Nasrin Zamani, Esmail Doustkhah et Farzad Zamani. « Biological behavior of 1,5-benzodiazepines and 1,5-benzothiazepines ». Dans Benzodiazepine-Based Drug Discovery, 249–82. Elsevier, 2022. http://dx.doi.org/10.1016/b978-0-12-824516-3.00001-x.

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Actes de conférences sur le sujet "Benzothiazepines"

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Ghodke, Mangesh, Suvarna Wagh, Anna Pratima Nikalje et Julio Seijas Vázquez. « Ultrasound assisted synthesis of 2, 4-substituted 1, 5- benzothiazepine derivatives ». Dans The 23rd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland : MDPI, 2019. http://dx.doi.org/10.3390/ecsoc-23-06704.

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