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Relevant bibliographies by topics / Pyrrolo [2,3-b]pyridine

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Academic literature on the topic 'Pyrrolo [2,3-b]pyridine'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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Journal articles on the topic "Pyrrolo [2,3-b]pyridine"

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Huang, Ping-Hsin, Yuh-Sheng Wen, and Jiun-Yi Shen. "2-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 31, 2012): o1943. http://dx.doi.org/10.1107/s1600536812023690.

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Vadlakonda, Rajashekar, Sreenivas Enaganti, and Raghunandan Nerella. "INSILICO DISCOVERY OF HUMAN AURORA B KINASE INHIBITORS BY MOLECULAR DOCKING, PHARMACOPHORE VALIDATION AND ADMET STUDIES." Asian Journal of Pharmaceutical and Clinical Research 10, no. 2 (February 1, 2017): 165. http://dx.doi.org/10.22159/ajpcr.2017.v10i2.14974.

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Objectives: To predict the anticancer potentiality of some newly designed azaindole derivatives gainst human Aurora B kinase and to identify the critical features important for their activity.Methods: Initially, the derivatives of azaindoles, (Z)-2-(oxo-1 H-pyrrolo [2,3-b] pyridine-3 (2H)-ylidene)-N-(p-substituted) hydrazine carbothioamide (scaffold A), (E)-3-((E)-substituted benzylidene hydrazono)-1H-pyrrolo[2,3-b]pyridine-2(3H)-one (scaffold B), and 1-(2-substituted acetyl)-1H- pyrrolo [2,3-b]pyridine-2,3-dione are synthesized and sketched using ACD/ChemSketch (12.0). With the 3D converted compounds, docking into the active site of the retrieved protein Aurora B kinase is carried out using LibDock module of discovery studio (DS). Further absorption, distribution, metabolism, excretion and toxicity (ADMET) properties, ligand, and structure-based pharmacophore modeling are applied using DS.Results: Through docking and pharmacophore studies, it is revealed that compound C13 (N-{(Z)-2-[4-(dimethylamino)phenyl]ethenyl}-1H- pyrrolo[2,3-b]pyridine-3-carboxamide) shows the highest binding affinity and good pharmacophoric features with acceptable fit values of both ligand and structure-based pharmacophore models. Furthermore, the calculated ADMET properties are reliable.Conclusion: These studies suggest that the compound C13 (N-{(Z)-2-[4-(dimethylamino)phenyl]ethenyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxamide)may act as a potent target in the anticancer therapy.Keywords: Aneuploidy, Aurora B kinase, Azaindole, Cancer, Cell cycle, Genome stability.

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Huang, Ping-Hsin, Yuh-Sheng Wen, and Jiun-Yi Shen. "4-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine." Acta Crystallographica Section E Structure Reports Online 69, no. 5 (April 10, 2013): o674. http://dx.doi.org/10.1107/s1600536813008672.

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Karpov, Sergey, Arthur Grigor’ev, Yakov Kayukov, Iuliia Gracheva, and Victor Tafeenko. "Cascade Regioselective Heterocyclization of 2-Acyl-1,1,3,3-tetracyanopropenides: Synthesis of Pyrrolo[3,4-c]pyridine and Pyrrolo[3,4-d]thieno[2,3-b]pyridine Derivatives." Synlett 28, no. 13 (May 2, 2017): 1592–95. http://dx.doi.org/10.1055/s-0036-1588823.

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2-Acyl-1,1,3,3-tetracyanopropenides (ATCN) undergo cascade heterocyclization under the action of aliphatic thiols, resulting in the formation of 6-(alkylthio)-4-amino-1-aryl(alkyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles. The involvement of methyl mercaptoacetate to this reaction leads to the formation of the methyl 4,8-diamino-1-aryl-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-d]thieno[2,3-b]pyridine-7-carboxylates, containing a new fused heterocyclic scaffold.

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Meade, Eric A., and Lilia M. Beauchamp. "The synthesis of 4-benzylamino-6-methyl-1H-pyrrolo[3, 2-c]pyridine and 4-benzylamino-6-methyl-1H-pyrrolo[2, 3-b]pyridine." Journal of Heterocyclic Chemistry 33, no. 2 (March 1996): 303–8. http://dx.doi.org/10.1002/jhet.5570330215.

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Selig, Roland, Dieter Schollmeyer, Wolfgang Albrecht, and Stefan Laufer. "2-(3,4,5-Trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridine." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (November 14, 2009): o3097. http://dx.doi.org/10.1107/s1600536809047540.

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van Es, Theodorus, Benjamin Staskun, and Manuel A. Fernandes. "Preparation, X-ray Structure and Propylaminolysis of 7,7-dichloro-5,7-dihydro-thieno[3,4-b]pyridin-5-one." Journal of Chemical Research 2007, no. 6 (June 2007): 373–76. http://dx.doi.org/10.3184/030823407x225392.

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Refluxing 2-methylpyridine-3-carboxylic acid with thionyl chloride for 6–7 h gave (∼50%) title compound dichlorothienolactone 2 as was confirmed by a X-ray structure analysis. The propylaminolysis of 2 provides a new and convenient access to highly functionalised pyrrolo[3,4- b]pyridine derivatives.

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Yang, Haozhe, Simone Budow, Henning Eickmeier, Hans Reuter, and Frank Seela. "1,7-Dideaza-2′-deoxy-6-nitronebularine: a pyrrolo[2,3-b]pyridine nucleoside with an intramolecular hydrogen bond stabilizing thesynconformation." Acta Crystallographica Section C Crystal Structure Communications 69, no. 8 (July 9, 2013): 892–95. http://dx.doi.org/10.1107/s0108270113016922.

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The title compound [systematic name: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-nitro-1H-pyrrolo[2,3-b]pyridine], C12H13N3O5, forms an intramolecular hydrogen bond between the pyridine N atom as acceptor and the 5′-hydroxy group of the sugar residue as donor. Consequently, the N-glycosylic bond exhibits asynconformation, with a χ torsion angle of 61.6 (2)°, and the pentofuranosyl residue adopts a C2′-endoenvelope conformation (2E,S-type), withP= 162.1 (1)° and τm= 36.2 (1)°. The orientation of the exocyclic C4′—C5′ bond is +sc(gauche,gauche), with a torsion angle γ = 49.1 (2)°. The title nucleoside forms an ordered and stacked three-dimensional network. The pyrrole ring of one layer faces the pyridine ring of an adjacent layer. Additionally, intermolecular O—H...O and C—H...O hydrogen bonds stabilize the crystal structure.

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Mosiagin, Ivan P., Olesya A. Tomashenko, Dar’ya V. Spiridonova, Mikhail S. Novikov, Sergey P. Tunik, and Alexander F. Khlebnikov. "Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings." Beilstein Journal of Organic Chemistry 17 (June 23, 2021): 1490–98. http://dx.doi.org/10.3762/bjoc.17.105.

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A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o-bromophenyl-substituted pyrrolylpyridinium salts using the (TMS)3SiH/AIBN system. The cyclization provides generally good yields of pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline hydrobromides having no additional radical-sensitive substituents. The free bases can be obtained from the synthesized hydrobromides in quantitative yield by basification at room temperature. The selectivity control of intramolecular arylation was achieved by replacing the halogen: the use of 1-(2-(ortho-bromophenyl)-4-(ortho-iodophenyl)pyrrol-3-yl)pyridinium bromide makes it possible to obtain a monocyclization product, and the bicyclization product from the dibromo derivative. The procedure is also applicable to obtain 3-arylpyrido[2,1-a]pyrrolo[3,2-c]isoquinoline derivatives including 2-unsubstituted skeletons that are inaccessible via Pd-catalyzed cyclization.

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Vrábel, Viktor, Štefan Marchalín, and Jozef Kožišek. "Isopropyl 2-methyl-4-(3-nitrophenyl)-5,7-dioxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,4-b]pyridine-3-carboxylate." Acta Crystallographica Section E Structure Reports Online 59, no. 10 (September 30, 2003): o1570—o1571. http://dx.doi.org/10.1107/s1600536803021020.

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Dissertations / Theses on the topic "Pyrrolo [2,3-b]pyridine"

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Hichour, Mohammed. "Synthèse et réactivité de 1-[2-(1H-pyrrolo[2,3-b]pyridin-3-yl)éthyl]pipéridines : application à la synthèse de 11-azaindoloquinolizidines." Montpellier 1, 1996. http://www.theses.fr/1996MON13503.

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Tber, Zahira. "L'imidazo[1,2-a]pyridine : fonctionnalisation et synthèse des nouveaux polyhétérocycles." Thesis, Orléans, 2016. http://www.theses.fr/2016ORLE2021.

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Les préparations de composés comportant un noyau imidazo[1,2-a]pyridinique constituent un thème de recherche important en synthèse organique, compte tenu des nombreuses activités biologiques qu’ils peuvent présenter. Dans la première partie, nous nous sommes concentrés sur le développement de nouvelles stratégies rapides et efficaces basées sur l’utilisation de cuivre et de fer pour fonctionnaliser la position 6 du cycle imidazo[1,2-a]pyridine avec diverses amines et divers thiols. Ensuite, nous avons appliqué avec succès cette procédure pour la préparation de thioéthers symétriques et dissymétriques en utilisant le 2-mercaptobenzooxasole, réactif économique qui ne présente aucun risque chimique. Dans le dernier volet de ce travail, nous nous sommes intéressés au développement de nouvelles réactions multicomposants en vue de synthétiser divers pyrrolo[3',2':4,5]imidazo[1,2-a]pyridines et 5-aminopyrido[2’,1’:2,3]imidazo[4,5-c]isoquinoléines
The preparations of imidazo[1,2-a]pyridine is one of important research topic in organic synthesis, This entitie present some interesting biological activities. First, we devoleped a new rapid and efficient strategies to functionalize position 6 of the imidazo[1,2-a]pyridine with various amines and thiols catalysed by copper and iron. Then we applied this procedure to the preparation of symmetric and asymmetric thioethers using 2 mercaptobenzooxasole, which is an economical reagent and which presents no chemical risk. The last part of this work concerns the development of new multicomponent reactions for the synthesis of various pyrrolo[3',2':4,5]imidazo[1,2-a]pyridine and 5-amino pyrido[2’,1’:2,3] imidazo [4,5-c]isoquinoléines

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Chaulet, Charlotte. "Synthèse et étude du mécanisme d'action de nouveaux analogues de la thalidomide, dérivés du noyau 1H-pyrrolo (2, 3-b) pyridine, sur la modulation des cellules NK et la production des cytokines TNF-a et IL-6." Thesis, Tours, 2010. http://www.theses.fr/2010TOUR3802/document.

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La thalidomide est un sédatif hypnotique mis sur le marché pour la première fois en Allemagne en octobre 1957 et largement vendu par la suite dans 46 pays sous 51 noms commerciaux différents. Il fut également utilisé comme antiémétique chez les femmes enceintes et, dès le jour de Noël de l’année 1956, un premier enfant atteint de phocomélie naissait, six mois avant la mise sur le marché. La thalidomide fut retirée de la vente fin 1961, du fait de ses effets dévastateurs sur le développement fœtal. De nombreux mécanismes d’action de la thalidomide dans l’embryopathie ont été rapportés, notamment un effet antiangiogénique avec inhibition de la neurovascularisation au cours du développement des membres durant la vie fœtale. Par la suite, la thalidomide s’est imposée comme traitement dans un grand nombre de pathologies. Il a également été démontré qu’elle était capable d’induire une augmentation ou une inhibition de l’expression de chimiokines ou de facteur de croissance.L’élaboration de nouvelles molécules analogues plus efficaces reste au centre de nombreuses études de recherche. Sur la base des travaux effectués sur la régulation de la production de cytokines et de la modulation des lymphocytes NK par la thalidomide et ses analogues, nous avons travaillé autour du noyau 1H-pyrrolo[2,3-b]pyridine. Cette étude a permis de fonctionnaliser ce noyau sur diverses positions par différents types de synthèse organique : désulfonylation, réactions d’addtion 1,4 de type Michael, couplage peptidique, … et d’élaborer des molécules originales. Les composés synthétisés ont fait l’objet d’études pharmacologiques
Thalidomide is a sedative hypnotic on the market for the first time in Germany in October 1957 and subsequently sold widely in the 46 countries under 51 different trade names. It was also used as antiemetic in pregnant women and from the Christmas Day of 1956, a first child with phocomelia born, six months before placing on the market. Thalidomide was withdrawn from the market in late 1961, because of its devastating effects on fetal development. Many mechanisms of action of thalidomide embryopathy have been reported, including an antiangiogenic effect with inhibition of neurovascularisation during limb development during fetal life. Subsequently, thalidomide has emerged as a treatment of many diseases. It was also demonstrated its ability to induce an increase or inhibition of expression of chemokines or growth factor. The development of new molecules like more effective remains the focus of many research studies. Based on studies on the regulation of cytokines production and modulation of NK cells by thalidomide and its analogs, we worked on the 1H-pyrrolo [2,3-b] pyridine. This study led us to functionalize 7-azaindole on various positions and by different organic synthesis: desulfonylation, Michael addition, peptide coupling… These synthetized compounds have been tested in pharmacologic studies

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Kuleshova, Olena. "2-azahetaryl-3-enaminonitriles cycliques pour la synthèse d'azahétérocycles fonctionnalisés, la complexation de métaux et la conception de sondes optiques." Thesis, Toulouse 3, 2018. http://www.theses.fr/2018TOU30127/document.

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Les recherches effectuées au cours de ce travail de thèse sont centrées sur les dérivés cycliques de type 2-azahetaryl-3-énaminonitrile qui représentent une structure d'intérêt du fait de son nombre élevé de sites réactifs potentiels. La fonctionnalisation régiosélective de chaque site donne en effet accès à des une grande diversité structurelle de composés azoté et substitué par un azahétérocycle. Un atout majeur des 2-azahetaryl-2-(1-R-pyrrolidin-2-ylidene)acétonitriles est leur grande accessibilité à partir de matières premières simples et bon marché. Nous avons pu étudier leur emploi dans la synthèse des pyrazoles (isoxazoles). Ils jouent alors le rôle de diélectrophiles 1,3. L'action d'hydrazine (hydroxylamine) conduit à des 5-amino-4- azahetaryl-3-(ω-aminopropyl)-1H-pyrazole (isoxazole) formés avec une régiosélectivité complète et de bons rendements 50-85%. Ceci établit une approche en deux étapes efficace et facilement reproductible à des amino-pyrazoles substitués par des hétérocycles à partir d'acétonitriles hétérocycliques. Des transformations subséquentes ont été réalisées donnant accès à des polyamino-azoles dérivatisés régiosélectivement, à des composés tétracycliques jusqu'à un rendement global de 45% et à des pyrazoles arylés jusqu'à 71% de rendement par diazotation suivie d'une arylation par couplage croisé Suzuki-Miyaura ou C-H activation. Nous avons illustré une protection de l'azote efficace sous forme de nitrosamine pendant le couplage croisé catalysé par Pd. Nous avons également effectué la quaternarisation de l'azote de l'hétérocycle pour étudier l'effet d'une moitié cationique sur la régiosélectivité de la réaction de tels dérivés 2-azahetaryl-3-énaminonitrile avec des 1,2-binucléophiles. L'augmentation de la demande en électrons sur l'hétérocycle a induit un changement de chemin réactionnel qui a conduit à un produit issu de l'ouverture du cycle azole. Une différence de réactivité entre les dérivés du benzoxazole et du benzimidazole d'une part et du benzothiazole d'autre part a été observée. Alors que les premiers suivent la voie d'ouverture de cycle, le second suit une transformation "classique" puis une substitution nucléophile au centre C-2 du benzothiazole conduisant à la formation du cycle de l'azépine. Dans le cas des énaminonitriles substitués par un benzoxazolyle dans les mêmes conditions, les deux régioisomères sont formés. La réaction de formylation du 2-(benzo[d]thiazol-2-yl)-2-(pyrrolidin-2-ylidène) acétonitrile avec le N,N-diméthylformamide diméthylacétal (DMF DMA), suivie d'une amination et d'une cyclisation dans des conditions basiques a engendré à la pyrrolo[3,2-c]pyridine-6-imine, un composé qui présente un rendement quantique fluorescent élevé (Φ = 61%) et s'est révélé très sensible à la protonation. Les deux caractéristiques devraient être utiles pour développer un test de détection d'eau originaux pour les solvants aprotiques. Nous avons démontré qu'une telle méthode fluorométrique pour déterminer la teneur en eau dans le DMSO présente une limite de détection de 0,068%
The research carried out in the course of this PhD work is centered on cyclic 2-azahetaryl-3-enaminonitrile derivatives which represent an attractive scaffold due to its high number of potential reactive sites. Regioselective functionalization of each site may give access to various structurally different Nitrogen-containing moieties featuring an azaheterocycle substituent. One first application in heterocyclic synthesis of 2-azahetaryl-2-(1-R-pyrrolidin-2-ylidene)acetonitriles, readily accessed from available and cheap starting materials, is their involvement in Knorr-type synthesis of pyrazoles (isoxazoles) where they play the role of the 1,3-dielectrophiles. Thus 4-azahetaryl-3-(ω-aminopropyl)-1H-pyrazole (isoxazole)-5-amines are formed with complete regioselectivity in good yields 50-85%. This establishes an efficient and easily reproducible two-step approach to heterocycle- substituted amino-pyrazoles from heterocyclic acetonitriles. Unprecedented subsequent transformations were carried out providing an access to regioselectively derivatized polyamino azoles, tetracyclic compounds in up to 45% overall yield and arylated pyrazoles in up to 71% yield through diazotization, followed by arylation through Suzuki-Miyaura cross-coupling or C-H activation. We illustrated the unprecedented but efficient nitrogen protection as a nitrosamine during the Pd-catalyzed cross-coupling. Also the possibility of pyrazoles C-H activation in order to get densely substituted pyrazoles was shown for the first time. We also performed the quaternarization of the nitrogen of the heterocycle to investigate the effect of a cationic moiety on the regioselectivity of the reaction of such azahetaryl-3-enaminonitrile derivatives with 1,2-binucleophiles. The increased electron demand on the heterocycle induced a reaction path shift that produced the azole ring- opened product. Derivatives of benzoxazole and benzimidazole form second way products straight away, while the one of benzothiazole undergoes the "classical" transformation pathway and subsequent nucleophilic substitution at C-2 center of benzothiazole leading to azepine cycle formation. In the case of benzoxazolyl substituted enaminonitriles under the same conditions both regioisomers are formed. Formylation reaction of 2-(benzo[d]thiazol-2-yl)-2-(pyrrolidin-2-ylidene) acetonitrile with N,N-dimethylformamide dimethyl acetal (DMF DMA), followed by further reamination and cyclization under basic conditions gave rise to pyrrolo[3,2-c]pyridine-6-imine, a compound that exhibits a high fluorescent quantum yield (Φ = 61%) and proved to be very sensitive to protonation. Both characteristics are expected to be useful to develop an unprecedented water detection test for aprotic solvents. We have demonstrated that such a fluorometric method for determining water content in DMSO presents a limit of detection of 0.068%. From other enaminonitriles reactions with DMF DMA provided either a mixture of methylated and formylated products, or only methylated products (few adducts also shown non reactivity). These observations prompted us to assume that the presence of easily accessible NH group is essential in formylation of the C-3 center of pyrrolidine allowing to propose a mechanism for this uncommon reaction. 2-Azahetaryl-2-(pyrrolidin-2-ylidene)acetonitriles and their 3-oxo-benzo- analogues were also used to create: a) visible spectrophotometric probes for Zn(II) b) water stable BF2-rigidified complexes that overcome the limitations of BODIPY-dyes and have Stokes shifts up to 9000 cm-1, emission at violet-blue range, fluorescence both in solution (Φ up to 90%) and crystalline state; c) films of polymeric composites exhibiting photovoltaic effect

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Laube, Markus. "Synthese von Cyclooxygenase-2-Inhibitoren als Grundlage für die funktionelle Charakterisierung der COX-2-Expression mittels PET." Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2015. http://nbn-resolving.de/urn:nbn:de:bsz:14-qucosa-160091.

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Eine erhöhte COX-2-Expression wird bei Krankheiten wie rheumatoider Arthritis aber auch Parkinson, Alzheimer und Krebs beobachtet. Die nichtinvasive Visualisierung und Quantifizierung der COX 2-Expression in vivo mittels Positronen-Emissions-Tomographie (PET) könnte wertvolle Beiträge zur Diagnose dieser Krankheiten liefern. Zur Nutzung der PET-Technik werden geeignete COX-2-adressierende Radiotracer benötigt, deren Entwicklung auch die Identifizierung neuer, der Radiomarkierung zugänglicher COX-2-Inhibitoren als Leitstrukturen voraussetzt. Ziel dieser Arbeit war die Synthese von selektiven, der Radiomarkierung zugänglichen COX 2-Inhibitoren und deren In-vitro-Evaluierung, um Verbindungen zu identifizieren, die für eine weitere Entwicklung zu COX-2-adressierenden Radiotracern geeignet sind. Im Rahmen dieser Arbeit wurden ausgehend von literaturbekannten COX-2-Inhibitoren zwei grundlegende Strategien verfolgt: die Derivatisierung an der Peripherie sowie der Austausch von Strukturelementen im Grundgerüst der COX-2-selektiven Inhibitoren. In dieser Arbeit wird zum einen die Synthese der Zielverbindungen (Diphenyl-substituierte Indol-, Pyrazolo[1,5-b]pyridazin-, 1,2-Dihydropyrrolo[3,2,1-hi]indol- und Pyrrolo[3,2,1-hi]indol-Derivate sowie 2-Carbaboranyl-substituierte Indol-Derivate) und deren strukturanalytische Charakterisierung vorgestellt. Es konnte die McMurry-Cyclisierung als neuer Zugang für die Synthese von Carbaboranyl-substituierten Verbindungen und 1,2-Dihydropyrrolo[3,2,1-hi]indol-Derivaten sowie die Dehydrogenierung mittels DDQ als neue Variante zur Synthese von Pyrrolo[3,2,1-hi]indol-Derivaten etabliert werden. Durch Röntgeneinkristallstrukturanalyse wurde die Molekülstruktur von sechs Zwischenverbindungen und neun Zielverbindungen aufgeklärt. Zum anderen erfolgte die Charakterisierung der Verbindungen in vitro, wobei die COX-inhibitorischen Eigenschaften mit einem Fluoreszenz-basierten, einem Enzymimmunoassay (EIA)-basierten und einem [14C]Arachidonsäure-basierten COX-Assay bestimmt und zudem viele Verbindungen hinsichtlich ihrer Redoxeigenschaften untersucht wurden. Im Besonderen die hergestellten Indol-Derivate besitzen antioxidative Eigenschaften, die bei der Untersuchung der COX inhibitorischen Eigenschaften beachtet werden müssen. Die Derivatisierung an der Peripherie der bekannten Inhibitoren führte zur Identifizierung von zwei Aminosulfonyl-substituierten Indol-Derivaten und einem Fluorethoxy-substituierten Pyrazolo[1,5 b]pyridazin-Derivat, die grundsätzlich geeignete Kandidaten für eine weitere Entwicklung zum Radiotracer darstellen. Das Fluorethoxy-substituierte Pyrazolo[1,5 b]pyridazin-Derivat wurde im Rahmen dieser Arbeit mit Fluor-18 markiert und die initiale Charakterisierung des Radiotracers in vitro durchgeführt. Der Austausch von Strukturelementen im Grundgerüst der literaturbekannten COX-2-Inhibitoren mit voluminöseren Gruppen führte zum einen bei Austausch eines Phenylrings gegen einen Carbaboranyl-Cluster zum Verlust der COX-inhibitorischen Eigenschaften, was eine weitere Entwicklung dieser Verbindungen zum Radiotracer ausschließt. Zum anderen wurde ausgehend von 2,3-Diphenyl-1H-indol-Derivaten die bicyclische auf eine tricyclische Kernstruktur vergrößert. Dies lieferte hoch affine und selektive COX-2-Inhibitoren. Unter den hergestellten Verbindungen wurden ein 1,2-Dihydropyrrolo[3,2,1-hi]indol- und drei Pyrrolo[3,2,1-hi]indol-Derivate als vielversprechende Kandidaten für die weitere Entwicklung zum Radiotracer identifiziert.

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Letellier, Marie-Anne. "Synthèse et évaluation pharmacologique de dérivés des noyaux 4,4-dyméthil-3,4-dihydro-1H-quinoléin-2-one et 1H-pyrrolo[2,3-b]pyridin-2(3H)-one en tant qu'inhibiteurs de la Rho-kinase en vue d'un traitement contre l'hypertension." Tours, 2007. http://www.theses.fr/2007TOUR3803.

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L’hypertension artérielle (HTA) touche dans les pays industrialisés près de 15% de la population adulte. Lorsqu’on ne peut déceler de cause à l’élévation de la pression artérielle dans les vaisseaux, on parle d’HTA essentielle ou primaire. Une contraction normale du muscle lisse, dont le mécanisme fait intervenir la petite protéine G Rho et sa cible Rho-kinase, entraîne le rétrécissement du diamètre des vaisseaux et provoque une élévation de la pression artérielle. Ainsi, des inhibiteurs de Rho-kinase pourraient se révéler utiles dans le traitement de l’hypertension. Les objectifs fixés consistaient en la conception et l’élaboration de nouveaux inhibiteurs de la Rho-kinase en termes de sélectivité, de biodisponibilité et d’originalité structurale. Ainsi, des dérivés des noyaux 4,4-diméthyl-3,4-dihydro-1H-quinoléin-2-one et 1H-pyrrolo[2,3-b]pyridin-2(3H)-one ont été synthétisés et ont fait l’objet d’études pharmacologiques effectuées par les laboratoires SERVIER
Over a billion people are suffering from arterial hypertension, a disease defined by a rise in the blood pressure in the arteries due to the abnormal contraction of the smooth-muscle. The contraction is regulated by the cytosolic calcium concentration to which the Rho/Rho-kinase intracellular pathway is associated. Designing compounds that inhibit the enzyme is of great interest. We have elaborated new potential Rho-kinase inhibitors. Various molecules were synthesized based on the 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one and the 1H-pyrrolo[2,3-b]pyridin-2(3H)-one chemistry. The new compounds were then studied by our collaborators, les laboratories SERVIER, for their activity on Rho-kinase inhibition

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7

Hajbi, Youssef. "Application de la réaction de Diels-Alder à demande électronique inverse à la synthèse de nouveaux composés oxygénés et azotés à visée thérapeutique." Phd thesis, Université d'Orléans, 2007. http://tel.archives-ouvertes.fr/tel-00151105.

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Cette thèse s'inscrit dans une volonté de développer de nouvelles architectures hétéroaromatiques susceptible de montrer un potentiel thérapeutique. Pour cela la synthèse de dihydrofuro[2,3-b]pyridines et dihydropyrano[2,3-b]pyridines hautement et diversement fonctionnalisées est apparue particulièrement intéressante notamment en vue de l'obtention de nouveaux analogues sérotoninergiques. L'accès à ces nouveaux squelettes a été réalisé via une réaction intramoléculaire de Diels-Alder à demande électronique inverse avec des 1,2,4-triazines.

Pour ce faire, des 3-méthylsulfanyl-1,2,4-triazines ont été mis à réagir avec différents nucléophiles permettant l'introduction d'alcynes convenablement substitués. La réactivité de ces alcynes selon une réaction de Diels-Alder à demande électronique inverse a été explorée. L'activation par micro-ondes de la réaction de cycloaddition s'est avérée très efficace. Des dihydrofuro[2,3-b]pyridines diversement substituées en position 2, 3, 4, et/ou 6 et des dihydropyrano[2,3-b]pyridines substituées en position 3, 4, 5 et/ou 7 ont été synthétisées avec de bons rendements.

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Book chapters on the topic "Pyrrolo [2,3-b]pyridine"

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Hirota, E., K. Kuchitsu, T. Steimle, J. Vogt, and N. Vogt. "117 C7H6N2 1H-Pyrrolo[2,3-b]pyridine." In Molecules Containing Three or Four Carbon Atoms and Molecules Containing Five or More Carbon Atoms, 290. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-642-41504-3_248.

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Hirota, E., K. Kuchitsu, T. Steimle, J. Vogt, and N. Vogt. "112 C7H6ArN2 1H-Pyrrolo[2,3-b]pyridine – argon (1/1)." In Molecules Containing Three or Four Carbon Atoms and Molecules Containing Five or More Carbon Atoms, 285. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-642-41504-3_243.

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Liu, Yan, Tianyi Shang, Chuanming Xu, Hui Yang, Peng Yu, and Kui Lu. "A Novel One-Pot Five-Component Synthesis of Tetrahydro-pyrrolo[3,4-b]pyridine-5-one via Ugi/Aza-Diels–Alder Tandem Reaction." In Lecture Notes in Electrical Engineering, 461–66. Berlin, Heidelberg: Springer Berlin Heidelberg, 2015. http://dx.doi.org/10.1007/978-3-662-46318-5_48.

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Ragan, John A. "Development and Scale-Up of a Heterocyclic Cross-Coupling for the Synthesis of 5-[2-(3-Methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridine-7-yl] amino-2-methyl-1H-indole." In Fundamentals of Early Clinical Drug Development, 21–36. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2006. http://dx.doi.org/10.1002/0470043407.ch2.

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Taber, Douglass F. "The Harran Synthesis of (+)-Roseophilin." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0107.

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Ansa-bridged prodiginines include (+)-roseophilin B 3 and streptorubin B. The observation that streptorubin B potentiated apoptopic signaling in cell culture led to the development of obatoclax, currently being evaluated for the treatment of leukemia. Patrick G. Harran of UCLA devised (J. Am. Chem. Soc. 2013, 135, 3788) what promises to be a general route to the prodiginines, a key step of which was the cyclization of 1 to 2. In planning the synthesis of 1, the authors took advantage of the relative inertness of a monosubstituted alkene. Friedel-Crafts acylation of 5 proceeded smoothly without affecting the distal double bond. Reduction then completed the preparation of 7. The preparation of 1 continued from the pyrrole 9, prepared from the pyridine 8. Addition of the derived enoate to the aldehyde 10 proceeded smoothly, to give, after oxidation and acid-mediated rearrangement, the furan 12. Selective metalation followed by carboxylation gave the acid 13, which was combined with 7 to give 15. Deprotonation of 15 gave an intermediate that reacted primarily on the pyrrole N. This intermediate was then reacted with diethylchlorophosphite to give, after oxidation, the phosphoramide 16. Advantage was then taken of the organometallic reactivity of the monosubstituted alkene of 16, as Ru-mediated cross metathesis with 17 followed by reduction completed the preparation of 1. The diheteroaryl ketone of 1 is not enolizable. On exposure to KHMDS, the dialkyl ketone will be deprotonated reversibly. Either enolate could add to the diheteroaryl ketone, but only the adduct from deprotonation of the methylene could go on to alkene formation. This net dehydration may likely be driven by phosphoryl transfer to the intermediate alkoxide. The enone 2 is prochiral. Hydrogenation with an enantiopure catalyst proceeded with high de and 67% ee. Remediated intramolecular Friedel-Crafts addition of the dialkyl ketone to the pyrrole followed by acid-mediated rearrangement then delivered (+)-roseophilin 3. There are several points along this synthesis at which diversity could be introduced. This should enable detailed structure–activity studies of the prodiginines.

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Taber, Douglass F. "Heteroaromatic Construction: The Jia Synthesis of (-)- cis -Clavicipitic Acid." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0065.

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Simultaneously, Aaran Aponick of the University of Florida (Organic Lett. 2009, 11, 4624) and Shuji Akai of the University of Shizuoka (Organic Lett. 2009, 11, 5002) reported the Au-mediate conversion of a propargylic diol such as 1 to the furan 2. Pyrroles can also be prepared using the same protocol. Jason K. Sello of Brown University developed (Organic Lett. 2009, 11, 2984) the direct aldol condensation of an acetoacetate 3 with the protected 1,3-dihydroxy acetone 4 to give 5, the methyl ester of a methylenomycin furan (MMF) bacterial-signaling molecule from Streptomyces coelicolor. Nobuharu Iwasawa of the Tokyo Institute of Technology demonstrated (Angew. Chem. Int. Ed. 2009, 48, 8318) that the imine 6 was sufficiently nucleophilic to react with the Rh vinylidene derived from the alkyne 7, leading to the pyrrole 8. Min Shi of the Shanghai Institute of Organic Chemistry extended (J. Org. Chem. 2009, 74, 5983) the reactivity of methylene cyclopropanes to the condensation of the aldehyde 9 with an acyl hydrazide, to give the pyrrole 11. Xue-Long Hou, also of the Shanghai Institute of Organic Chemistry, described (Tetrahedron Lett. 2009, 50, 6944) the Au-mediated reorganization of the alkynyl aziridine 12 to the pyrrole 13. Masahiro Yoshida of the University of Tokushima carried out (Tetrahedron Lett. 2009, 50, 6268) a similar rearrangement under oxidative conditions, giving the iodinated pyrrole 15. André M. Beauchemin of the University of Ottawa showed (Angew. Chem. Int. Ed. 2009, 48, 8325) that under acid catalysis, the oxime 16 cyclized to the pyridine 17. Shunsuke Chiba of Nanyang Technological University developed (J. Am. Chem. Soc. 2009, 131, 12570) the Mn(III)-mediated fusion of a cyclopropanol 18 with an alkenyl azide 19 to deliver the pyridine 20. Kazuaki Shimada of Iwate University found (Tetrahedron Lett. 2009, 50, 6651) that an isotellurazole such as 21, easily prepared from the corresponding alkyne, condensed with another alkyne 22, delivering the pyridine 23 with high regiocontrol. Christopher J. Moody of the University of Nottingham devised (Organic Lett. 2009, 11, 3686) a new route to the 1,2,4-triazine 24 from an α-diazoacetoacetate. He carried 24 on to the pyridine 26 by condensation with norbornadiene 25.

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Taber, Douglass F. "Heteroaromatic Construction: The Sato Synthesis of (–)-Herbindole." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0067.

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Troels Skrydstrup of Aarhus University devised (Angew. Chem. Int. Ed. 2012, 51, 4681) a gold-catalyzed protocol for the condensation of 1 with 2 to deliver the furan 3. Thomas A. Moss of AstraZeneca Mereside found (Tetrahedron Lett. 2012, 53, 3056) that readily-available α-chloroaldehydes such as 4 could be combined with 5 to make the furan 6. This same approach can be used to assemble pyrroles. Yong-Qiang Tu and Shao-Hua Wang of Lanzhou University developed (J. Org. Chem. 2012, 77, 4167) a Pd-cascade cyclization that transformed the ester 7 into the pyrrole 8. Cheol-Min Park of the Nanyang Technological University rearranged (Chem. Commun. 2012, 48, 3996; J. Am. Chem. Soc. 2012, 134, 4104) the oxime ether 10 to the pyrrole 11. Glenn C. Micalizio of Scripps/Florida established (J. Am. Chem. Soc. 2012, 134, 1352) a Ti-mediated coupling of 12 with an aromatic aldehyde to deliver the pyridine 13. Yoichiro Kuninobu, now at the University of Tokyo, and Kazuhiko Takai of Okayama University observed (Org. Lett. 2012, 14, 3182) high regioselectivity in the Re-mediated condensation of 14 with 15 to give the pyridine 16. Douglas M. Mans of GlaxoSmithKline, King of Prussia, cyclized (Org. Lett. 2012, 14, 1604) the amide 17 to the oxazole (not illustrated), leading, after intramolecular 4+2 cycloaddition, to the pyridine 18. Karl Hemming of the University of Huddersfield combined (Org. Lett. 2012, 14, 126) the cyclopropenone 20 with the imine 19 to construct the pyridine 21. Shu-Jiang Tu of Xuzhou University and Guigen Li of Texas Tech University condensed (Org. Lett. 2012, 14, 700) enamine 22 with the aldehyde hydrate 23 to give the pyrrole 24, which should be readily aromatized to the corresponding indole. Biaolin Yin of the South China University of Technology cyclized (Org. Lett. 2012, 14, 1098) the furan 25 to the indole 26. Richmond Sarpong of the University of California, Berkeley rearranged (J. Am. Chem. Soc. 2012, 134, 9946) the alkynyl cyclopropane 27 to an intermediate that was aromatized to the indole 28. Stefan France of Georgia Tech uncovered (Angew. Chem. Int. Ed. 2012, 51, 3198) an In catalyst that rearranged the cyclopropene 29 to the indole 30.

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Taber, Douglass. "Preparation of Heteroaromatics." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0068.

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Masahiro Yoshida of the University of Tokushima described (Tetrahedron Lett. 2008, 49, 5021) the Pt-mediated rearrangement of alkynyl oxiranes such as 1 to the furan 2. Roman Dembinski of Oakland University reported (J. Org. Chem. 2008, 73, 5881) a related zinc-mediated rearrangement of propargyl ketones to furans. The cyclization of aryloxy ketones such as 3 to the benzofuran 4 developed (Tetrahedron Lett. 2008, 49, 6579) by Ikyon Kim of the Korea Research Institute of Chemical Technology is likely proceeding by a Friedel-Crafts mechanism. Sandro Cacchi and Giancarlo Fabrizi of Università degli Studi “La Sapienza”, Roma, observed (Organic Lett. 2008, 10, 2629) that base converted the enamine 5 to the pyrrole 6. Alternatively, oxidation of 5 with CuBr led to a pyridine. Zhuang-ping Zhuan of Xiamen University prepared (Adv. Synth. Cat. 2008, 350, 2778) pyrroles such as 9 by condensing an alkynyl carbinol 7 with a 1,3-dicarbonyl compound. Richard C. Larock of Iowa State University found (J. Org. Chem. 2008, 73, 6666) that combination of an alkynyl ketone 10 with 11 followed by oxidation with I-Cl led to the pyrazole 12. The “click” condensation of azides with alkynes, leading to the 1,4-disubstituted 1,2,3- triazole, has proven to be a powerful tool for combinatorial synthesis. Valery V. Fokin of Scripps/La Jolla and Zhenyang Lin and Guochen Jia of the Hong Kong University of Science and Technology have developed (J. Am. Chem. Soc. 2008, 130, 8923) a complementary approach, using Ru catalysts to prepare 1,5-disubstituted 1,2,3- triazoles. Remarkably, internal alkynes participate, and, as in the conversion of 13 to 15, propargylic alcohols direct the regioselectivity of the cycloaddition. A variety of methods have been put forward for functionalizing pyridines. Sukbok Chang of KAIST described (J. Am. Chem. Soc. 2008, 130, 9254) the direct oxidative homologation of a pyridine N -oxide 16 to give the unsaturated ester 18. Jonathan Clayden of the University of Manchester observed (Organic Lett. 2008, 10, 3567) that metalation of 19 gave an anion that rearranged to 20 with complete retention of enantiomeric excess. Shigeo Katsumura of Kwansei Gakuin University developed (Tetrahedron Lett. 2008, 49, 4349) an intriguing three-component coupling, combining 21, 22, and methanesulonamide 23 to give the pyridine 24.

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9

Taber, Douglass F. "Heteroaromatic Construction: The Fukuyama Synthesis of Tryprostatin A." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0067.

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Alessandro Palmieri of the University of Camerino developed (Synlett 2010, 2468) the condensation of a nitro acrylate 1 with a 1,3-dicarbonyl partner 2 to give the furan 3. Chaozhong Li of the Shanghai Institute of Organic Chemistry showed (Tetrahedron Lett. 2010, 51, 3678) that an alkenyl halide 4 could be cyclized to the furan 5. Ayhan S. Demir of Middle East Technical University established (Chem. Commun. 2010, 46, 8032) that a Au catalyst could catalyze the addition of an amine 7 to a cyanoester 6 to give the pyrrole 8 . Bruce A. Arndtsen of McGill University effected (Org. Lett. 2010, 12, 4916) the net three-component coupling of an imine 9, an acid chloride 10, and an alkyne 11 to deliver the pyrrole 12. Bernard Delpech of CNRS Gif-sur-Yvette prepared (Org. Lett. 2010, 12, 4760) the pyridine 15 by combining the diene 13 with the incipient carbocation 14. Max Malacria, Vincent Gandon, and Corinne Aubert of UPMC Paris optimized (Synlett 2010, 2314) the internal Co-mediated cyclization of a nitrile alkyne 5 to the tetrasubstituted pyridine 17. Yoshiaki Nakao of Kyoto University and Tamejiro Hiyama, now at Chuo University, effected (J. Am. Chem. Soc. 2010, 132, 13666) selective substitution of a preformed pyridine 18 at the C-4 position by coupling with an alkene 19. We showed (J. Org. Chem. 2010, 75, 5737) that the anion from deprotonation of a pyridine 21 could be added in a conjugate sense to 22 to give 23. Other particularly useful strategies for further substitution of preformed pyridines have been described by Olafs Daugulis of the University of Houston (Org. Lett. 2010, 12, 4277), by Phil S. Baran of Scripps/La Jolla (J. Am. Chem. Soc. 2010, 132, 13194), and by Robert G. Bergmann of the University of California, Berkeley, and Jonathan A. Ellman of Yale University (J. Org. Chem. 2010, 75, 7863). K. C. Majumdar of the University of Kalyani developed (Tetrahedron Lett. 2010, 51, 3807) the oxidative Pd-catalyzed cylization of 24 to the indole 25. Nan Zheng of the University of Arkansas showed (Org. Lett. 2010, 12, 3736) that Fe could be used to catalyze the rearrangement of the azirine 26 to the indole 27.

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Taber, Douglass F. "Heteroaromatic Synthesis: The Tokuyama Synthesis of (−)-Rhazinilam." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0066.

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Mei-Huey Lin of the National Changhua University of Education rearranged (J. Org. Chem. 2014, 79, 2751) the initial allene derived from 1 to the γ-chloroenone. Displacement with acetate followed by hydrolysis led to the furan 2. A. Stephen K. Hashmi of Ruprecht-Karls-Universität Heidelberg showed (Angew. Chem. Int. Ed. 2014, 53, 3715) that the Au-catalyzed conversion of the bis alkyne 3, mediated by 4, proceeded selectively to give 5. Tehshik P. Yoon of the University of Wisconsin used (Angew. Chem. Int. Ed. 2014, 53, 793) visible light with a Ru catalyst to rearrange the azide 6 to the pyrrole 7. Cheol-Min Park, now at UNIST, found (Chem. Sci. 2014, 5, 2347) that a Ni catalyst reorganized the methoxime 8 to the pyrrole 9. A Rh catalyst converted 8 to the corresponding pyridine (not illustrated). In the course of a synthesis of opioid ligands, Kenner C. Rice of the National Institute on Drug Abuse optimized (J. Org. Chem. 2014, 79, 5007) the preparation of the pyridine 11 from the alcohol 10. Vincent Tognetti and Cyrille Sabot of the University of Rouen heated (J. Org. Chem. 2014, 79, 1303) 12 and 13 under microwave irradiation to give the 3-hydroxy pyridine 14. Tomislav Rovis of Colorado State University prepared (J. Am. Chem. Soc. 2014, 136, 2735) the pyridine 17 by the Rh-catalyzed combination of 15 with 16. Fabien Gagosz of the Ecole Polytechnique rearranged (Angew. Chem. Int. Ed. 2014, 53, 4959) the azirine 18, readily available from the oxime of the β-keto ester, to the pyridine 19. Matthias Beller of the Universität Rostock used (Chem. Eur. J. 2014, 20, 1818) a Zn catalyst to mediate the opening of the epoxide 21 with the aniline 20. A Rh catalyst effected the oxidation and cyclization of the product amino alcohol to the indole 22. Sreenivas Katukojvala of the Indian Institute of Science Education & Research showed (Angew. Chem. Int. Ed. 2014, 53, 4076) that the diazo ketone 23 could be used to anneal a benzene ring onto the pyrrole 24, leading to the 2,7-disubstituted indole 25.

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Conference papers on the topic "Pyrrolo [2,3-b]pyridine"

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Fathima, K. Saiadali, M. Vasumathi, and K. Anitha. "Synthesis and structural study of 4-(2-chlorophenyl)-2-ethoxy-5,6,7,8,9,10-hexahydrocycloocta[B]pyridine-3-carbonitrile." In DAE SOLID STATE PHYSICS SYMPOSIUM 2015. Author(s), 2016. http://dx.doi.org/10.1063/1.4948008.

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Dotsenko, Victor, and Sergey Krivokolysko. "Diversity-oriented Cascade Synthesis of Pyrido[2\',3\':4,5]thieno[2,3-b]pyridine Derivatives." In The 15th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00727.

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Huang, Cheng-Cheng, Xin-Hua Li, Ge Zhan, and Hong-Ping Xiao. "One-pot Synthesis of 6-Methyl-bis[1]benzothieno[3,2-b:2',3'-e]pyridine." In 2015 International Conference on Medicine and Biopharmaceutical. WORLD SCIENTIFIC, 2016. http://dx.doi.org/10.1142/9789814719810_0139.

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Hussein, Ola, Feras Alali, Ala-Eddin Al Moustafa, and Ashraf Khalil. "Design, Synthesis and Biological Evaluation of Novel Chalcone Analogs as Potential Therapeutic Agents for Castration-Resistant Prostate Cancer." In Qatar University Annual Research Forum & Exhibition. Qatar University Press, 2020. http://dx.doi.org/10.29117/quarfe.2020.0179.

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Prostate cancer (PCa) is the second most frequently diagnosed malignancy, as well as a leading cause of cancer-related mortality in men globally. Despite the initial response to hormonal targeted therapy, the majority of patients ultimately progress to a lethal form of the disease, termed as castration-resistant prostate cancer (CRPC), which currently lacks curative therapeutic options and is associated with poor prognosis. Therefore, the development of novel treatment modalities for PCa is urgently needed. Chalcones, also known as 1,3-diphenyl-2-propen-1-ones, are among the highly attractive scaffolds being investigated for their antitumor activities. Three series of 18 cyclic (tetralone-based) and two acyclic chalcone analogs, in which ring B was either substituted with nitrogen mustard or replaced by pyrrole or pyridine heterocyclic rings, were designed, synthesized and evaluated as potential therapies for CRPC. Compounds were synthesized by Claisen-Schmidt condensation reaction, purified using columnchromatography or recrystallization and characterized by 1H-NMR, 13C-NMR and LC-MS. The compounds' in-vitro cytotoxicity was evaluated against three prostate cancer cell lines (PC3, DU145, and LNCaP). Among the tested compounds, OH14, OH19 and OH22 showed potent antiproliferative activities at low micromolar levels with IC50 values ranging between 4.4 and 10 µM against PC3 and DU145 cell lines. Detailed biological studies of the lead molecule OH19 revealed that it significantly induces apoptosis through upregulation of Bax and downregulation of BCL-2. In addition, OH19 potently inhibits colony formation and reduces cell migration of androgen-independent PCa cell lines (PC3 and DU145). The molecular pathway analysis show that the anticancer activity of OH19 is associated with attenuation in the phosphorylation of Akt and ERK. Furthermore, OH19 inhibits blood vessel formation in the chick chorioallantoic membrane (CAM) model as compared to control. These results indicate that OH19 could serve as a potential promising lead molecule for the treatment of CRPC and thus, further in-vitro and invivo studies are warranted.

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Wan, Yanlingxue, Ryan Hayes, Joshua Li, Kristin Ferrer, Padma T. Uppula, and Brian Yuen Yau Wong. "Abstract 5091: Inhibition of mutagenicity of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine ( PhIP) by aqueous extract (crude) and organic extract (pulegone) ofCalamintha nepeta." In Proceedings: AACR Annual Meeting 2019; March 29-April 3, 2019; Atlanta, GA. American Association for Cancer Research, 2019. http://dx.doi.org/10.1158/1538-7445.sabcs18-5091.

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Wan, Yanlingxue, Ryan Hayes, Joshua Li, Kristin Ferrer, Padma T. Uppula, and Brian Yuen Yau Wong. "Abstract 5091: Inhibition of mutagenicity of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine ( PhIP) by aqueous extract (crude) and organic extract (pulegone) ofCalamintha nepeta." In Proceedings: AACR Annual Meeting 2019; March 29-April 3, 2019; Atlanta, GA. American Association for Cancer Research, 2019. http://dx.doi.org/10.1158/1538-7445.am2019-5091.

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Queiroz, Maria-João, Bruna Silva, Cristina Xavier, and M. Helena Vasconcelos. "Synthesis and evaluation of the antitumor potential of novel methyl 3-(hetero)arylthieno[3,2-<em>b</em>]pyridine-2-carboxylates." In 6th International Electronic Conference on Medicinal Chemistry. Basel, Switzerland: MDPI, 2020. http://dx.doi.org/10.3390/ecmc2020-07454.

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