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

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Published: 4 June 2021

Last updated: 5 February 2022

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Benckova, M., A. Krutosikova, J. Pullman, and N. Pronayova. "ChemInform Abstract: Pyrrolo[2′,3′:4,5]furo[3,2-c]pyridine Derivatives. Reactions in the Pyridine and Pyrrole Ring." ChemInform 30, no. 46 (June 12, 2010): no. http://dx.doi.org/10.1002/chin.199946155.

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12

Croix, C., S. Massip, and M. C. Viaud-Massuard. "Synthesis of naphthyridin-2(1H)-one derivativesviaring expansion of 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives." Chemical Communications 54, no. 44 (2018): 5538–41. http://dx.doi.org/10.1039/c8cc01518j.

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The reaction of 3-aryl or 3-heteroaryl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives with an azide source under microwave irradiation provided 3- and 4-amino-naphthyridin-2(1H)-one derivatives through cycloaddition–rearrangement ring expansion.

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13

Huang, X. H., Q. F. Zhang, and H. H. Y. Sung. "Crystal structure of 2-propyl-1H-pyrrolo-[2,3-b]pyridine, C10H12N2." Zeitschrift für Kristallographie - New Crystal Structures 219, no. 1-4 (April 2004): 483–84. http://dx.doi.org/10.1524/ncrs.2004.219.14.483.

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14

Selig, Roland, Dieter Schollmeyer, Wolfgang Albrecht, and Stefan Laufer. "4-Chloro-7-methoxymethyl-2-phenyl-7H-pyrrolo[2,3-b]pyridine." Acta Crystallographica Section E Structure Reports Online 66, no. 4 (March 13, 2010): o822. http://dx.doi.org/10.1107/s1600536810008822.

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15

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (March 1, 1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, formamide and carbon disulphide to furnish the corresponding pyrimido[4',5' :4,5]furo[2,3-c]pyridazin-4(3 H)-one derivatives. The reaction of 1 with o-aminophenol gave 3,4-diphenyl-11-oxo-10,11-dihydro-12H -pyridazino[ 4',3' :4,5]pyrrolo[3,2-b][1,5]benzoxazepine.

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16

Selig, Roland, Dieter Schollmeyer, Wolfgang Albrecht, and Stefan Laufer. "2-(Bicyclo[2.2.1]hept-5-en-2-yl)-1H-pyrrolo[2,3-b]pyridine." Acta Crystallographica Section E Structure Reports Online 66, no. 7 (June 26, 2010): o1800. http://dx.doi.org/10.1107/s1600536810022087.

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17

Lessing, Timo, and Thomas Müller. "One-Pot Coupling–Cyclization–Alkylation Synthesis of 1,2,5-Trisubstituted 7-Azaindoles in a Consecutive Three-component Fashion." Synlett 28, no. 14 (July 24, 2017): 1743–47. http://dx.doi.org/10.1055/s-0036-1590837.

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1,2,5-Trisubstituted 7-azaindoles are rapidly and efficiently prepared in a one-pot, copper-free alkynylation–cyclization–alkylation sequence starting from unprotected 2-aminopyridyl halides in a consecutive three-component fashion. By extension to a consecutive four-component coupling–cyclization–iodination–alkylation synthesis of 3-iodo-1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine, a concise synthesis of SIS3, a selective TGF-β1 and signaling inhibitor, was realized.

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18

Ramek, Michael, and Sanja Tomić. "Ab initio Hartree–Fock investigation of 1-H-pyrrolo[3,2-b]pyridine-3-yl acetic acid." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 57, no. 10 (September 2001): 1951–57. http://dx.doi.org/10.1016/s1386-1425(01)00480-2.

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19

Bencková, Mária. "Synthesis of Pyrrolo[2',3':4,5]Furo[3,2 c ]Pyridine2Carboxylic Acids." Molecules 1, no. 10 (February 28, 1997): 163–65. http://dx.doi.org/10.1007/s007830050032.

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20

Melekhina, Valeriya G., Andrey N. Komogortsev, Boris V. Lichitsky, Vitaly S. Mityanov, Artem N. Fakhrutdinov, Arkady A. Dudinov, Vasily A. Migulin, Yulia V. Nelyubina, Elizaveta K. Melnikova, and Michail M. Krayushkin. "One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines." Beilstein Journal of Organic Chemistry 15 (November 25, 2019): 2840–46. http://dx.doi.org/10.3762/bjoc.15.277.

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The condensation of primary amines with N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamides was explored. Thus, a previously unknown recyclization of the starting material was observed in acidic ethanol in the presence of an amine, which provided the corresponding dihydropyrrolone derivative as the major reaction product. Based on this transformation, a practical and convenient one-pot synthetic method for substituted pyrrolo[3,4-b]pyridin-5-ones could be devised.

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21

Tsai, Chung-Yin, and Chin-Kang Sha. "2H-Pyrrolo[3,4-b]pyridine and 2H-pyrrolo[3,4-c]pyridine: synthesis of the parent ring system and the Diels-Alder reaction." Tetrahedron Letters 28, no. 13 (1987): 1419–20. http://dx.doi.org/10.1016/s0040-4039(00)95942-2.

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22

Abdel-Mohsen, Shawkat A., and Ahmed A. Geies. "A convenient synthesis of pyrrolo[2,3-b]pyridines and pyrido[2′,3′:5,4]pyrrolo[2,3-d]pyrimidines." Monatshefte für Chemie - Chemical Monthly 139, no. 10 (July 24, 2008): 1233–40. http://dx.doi.org/10.1007/s00706-007-0839-3.

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23

Mérour, Jean-Yves, and Eric Desarbre. "Heck Annulation on 2-Position of Indoles or 1H-Pyrrolo[2,3-b]pyridine." HETEROCYCLES 41, no. 9 (1995): 1987. http://dx.doi.org/10.3987/com-95-7102.

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24

Huang, Wenbo, Kaimei Wang, Ping Liu, Minghao Li, Shaoyong Ke, and Yanlong Gu. "Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles." Beilstein Journal of Organic Chemistry 16 (November 30, 2020): 2920–28. http://dx.doi.org/10.3762/bjoc.16.241.

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N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional N-(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.

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25

Spanò, Virginia, Daniele Giallombardo, Vincenzo Cilibrasi, Barbara Parrino, Anna Carbone, Alessandra Montalbano, Ilaria Frasson, et al. "Pyrrolo[3′,2′:6,7]cyclohepta[1,2- b ]pyridines with potent photo-antiproliferative activity." European Journal of Medicinal Chemistry 128 (March 2017): 300–318. http://dx.doi.org/10.1016/j.ejmech.2017.02.008.

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26

VIAUD, M.-C., P. JAMONEAU, and G. GUILLAUMET. "ChemInform Abstract: Synthesis of 3-Substituted Pyrrolo[2,3-b]pyridin-2-one Derivatives." ChemInform 29, no. 5 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199805143.

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27

Park, Hyunjin, Myong Yong Choi, Cheol Joo Moon, and Tae Ho Kim. "Crystal structure ofN-[2-(cyclohexylsulfanyl)ethyl]quinolinic acid imide." Acta Crystallographica Section E Crystallographic Communications 73, no. 9 (August 25, 2017): 1372–74. http://dx.doi.org/10.1107/s2056989017012142.

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The title compound, C15H18N2O2S {systematic name: 6-[2-(cyclohexylsulfanyl)ethyl]-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione}, was obtained from the reaction of pyridine-2,3-dicarboxylic anhydride (synonym: quinolinic anhydride) with 2-(cyclohexylsulfanyl)ethylamine. The dihedral angle between the mean plane of the cyclohexyl ring and the quinolinic acid imide ring is 25.43 (11)°. In the crystal, each molecule forms two C—H...O hydrogen bonds and one weak C—O...π [O...ring centroid = 3.255 (2) Å] interaction with neighbouring molecules to generate a ladder structure along theb-axis direction. The ladders are linked by weak C—O...π [O...ring centroid = 3.330 (2) Å] interactions, resulting in sheets extending parallel to theabplane. The molecular structure is broadly consistent with theoretical calculations performed by density functional theory (DFT).

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28

Dawood, Kamal M., Eman A. Ragab, and Sanaa N. Mohamed. "Synthesis of Some New Indolizine and Pyrrolo[1,2-a]quinoline Derivatives via Nitrogen Ylides." Zeitschrift für Naturforschung B 64, no. 4 (April 1, 2009): 434–38. http://dx.doi.org/10.1515/znb-2009-0413.

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Pyridine and quinoline react with 3-bromoacetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile (2) in dry benzene to give the corresponding pyridinium and quinolinium salts 3 and 9. The latter salts undergo [3+2] 1,3-dipolar cycloaddition with some acetylene and ethylene derivatives to give the corresponding indolizine and pyrrolo[1,2-a]quinoline derivatives

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29

Gao, Yongnian, and Yulin Lam. "[3 + 2] Cycloaddition Reactions in the Synthesis of Triazolo[4,5-b]pyridin-5-ones and Pyrrolo[3,4-b]pyridin-2-ones." Journal of Combinatorial Chemistry 10, no. 2 (March 2008): 327–32. http://dx.doi.org/10.1021/cc700183a.

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30

Francis, John E., and Michael A. Moskal. "A general synthesis of 5,7-diaminoimidazo[4,5-b]pyridine ribosides ("2-amino-1-deazaadenosines") from 5-amino-4-imidazolecarboxamide riboside (AICA riboside)." Canadian Journal of Chemistry 70, no. 5 (May 1, 1992): 1288–95. http://dx.doi.org/10.1139/v92-166.

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A short general synthesis of 5-substituted 5,7-diaminoimidazo[4,5-b]pyridines from 5-amino-4-imidazolecarboxamide riboside (AICA riboside) was designed to prepare isosteres of substituted 2-aminoadenosines that are selective adenosine A2 receptor agonists. AICA riboside was converted to a hydroxyl-protected 5-amino-4-imidazolecarbonitrile riboside and reacted with an N,N-disubstituted acetamide in the presence of phosphoryl chloride. Sodium hydride treatment completed the ring closure and introduced the 7-amino group. The hydroxyl protecting groups were removed under standard conditions. N-Substitution of the acetamide by one benzyl moiety led to a 5-N-substituted derivative through hydrogenolysis whereas N,N-dibenzylacetamide led to the 5,7-diamino compound. A 6-methyl analog was obtained from an N,N-disubstituted propionamide. This synthesis may be adapted to other heterocyclic systems, as illustrated by the preparation of an example of the imidazo[4,5-b]pyrrolo[3,2-e]pyridine ring system.

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31

Huang, Bao-Guo, Gregory Kubiak, John J. Shay, Clive Pemberton, James Peers, Reda G. Hanna, Matthew R. Powers, et al. "Chemical Development of the Casein Kinase I - Epsilon Inhibitor: 3-(3-Fluorophenyl)sulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic Acid Amide." Organic Process Research & Development 15, no. 5 (September 16, 2011): 1040–45. http://dx.doi.org/10.1021/op200171a.

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32

DESARBRE, E., and J. Y. MEROUR. "ChemInform Abstract: Heck Annulation on 2-Position of Indoles or 1H-Pyrrolo(2,3-b)pyridine." ChemInform 26, no. 52 (August 13, 2010): no. http://dx.doi.org/10.1002/chin.199552124.

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33

Bahekar, Rajesh H., Mukul R. Jain, Pradip A. Jadav, Vijay M. Prajapati, Dipam N. Patel, Arun A. Gupta, Ajay Sharma, et al. "Synthesis and antidiabetic activity of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines and thieno[2,3-b]pyridines." Bioorganic & Medicinal Chemistry 15, no. 21 (November 2007): 6782–95. http://dx.doi.org/10.1016/j.bmc.2007.08.005.

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34

Chung, Cheng-Yen, Ching-Chun Tseng, Sin-Min Li, Shuo-En Tsai, Hui-Yi Lin, and Fung Fuh Wong. "Structural Identification between Phthalazine-1,4-Diones and N-Aminophthalimides via Vilsmeier Reaction: Nitrogen Cyclization and Tautomerization Study." Molecules 26, no. 10 (May 13, 2021): 2907. http://dx.doi.org/10.3390/molecules26102907.

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N-Aminophthalimides and phthalazine 1,4-diones were synthesized from isobenzofuran-1,3-dione, isoindoline-1,3-dione, furo [3,4-b] pyrazine-5,7-dione, or 1H-pyrrolo [3,4-c] pyridine-1,3-dione with monohydrate hydrazine to carry out the 5-exo or 6-endo nitrogen cyclization under the different reaction conditions. Based on the control experimental results, 6-endo thermodynamic hydrohydrazination and kinetical 5-exo cyclization reactions were individually selective formation. Subsequently, Vilsmeier amidination derivatization was successfully developed to probe the structural divergence between N-aminophthalimide 2 and phthalazine 1,4-dione 3. On the other hand, the best tautomerization of N-aminophthalimide to diazinone was also determined under acetic acid mediated solution.

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35

Popa, Marcel Mirel, Emilian Georgescu, Mino R. Caira, Florentina Georgescu, Constantin Draghici, Raluca Stan, Calin Deleanu, and Florea Dumitrascu. "Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively." Beilstein Journal of Organic Chemistry 11 (June 26, 2015): 1079–88. http://dx.doi.org/10.3762/bjoc.11.121.

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The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric hindrance directs the reaction to the pyrimidinium N-ylides and, subsequently, to the formation of the pyrrolo[1,2-c]pyrimidines. The new pyrrolo[1,2-c]pyrimidines and the new indolizines were structurally characterized through NMR spectroscopy. The X-ray structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported.

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36

Seela, F., and W. Bourgeois. "Synthesis of 3,7-Dideaza-2′-deoxyadenosine and Related Pyrrolo[3,2-c]pyridine 2′-Deoxyribo- and 2′,3′-Dideoxyribonucleosides." Synthesis 1988, no. 12 (1988): 938–43. http://dx.doi.org/10.1055/s-1988-27759.

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37

Decrop, Maylis, Claire Espanel, Jerome Guillard, Elodie Boissier, Nathalie Gallay, Christian Binet, Marie-Claude Viaud-Massuard, and Olivier Herault. "Pyrrolo[2,3-b]Pyridinic Derivatives Induce Cell Growth Inhibition of the Myeloblastic HL-60 Cell Line." Blood 108, no. 11 (November 16, 2006): 4400. http://dx.doi.org/10.1182/blood.v108.11.4400.4400.

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Abstract Cytokins, N6-subsitued adenine derivatives play an important role in many different processes in plant development (Mok et al, Annu Rev Plant. Physiol Plant Mol Biol2001, 52:89–118), including the cell growth and division control, the vegetable cell differentiation with auxin and the storage of various metabolites as alkaloids (Yahia et al, Plant Science1998, 133:9–15). Furthermore, several studies suggest that cytokinins and their purin derivated are able to control mammalian cell apoptosis and differentiation of human leukemic cells (HL-60 myeloblastic cell line) into mature granulocytes (Ishii et al, Cell Growth Differ2002, 13: 19–26). All these compounds exert their biological activity via Cyclin-Dependant Kinase (CDK) inhibition and particulary CDK1 and CDK2. The aim of our study was the synthesis of new 7-azaindole derivates as cytokinin analogues and the evaluation of their biological effects on HL-60 cells. Eight analogues of 7-azaindole were prepared by the condension of (N-methyl-)4-chloropyrrolo[2,3-b]pyridine with corresponding amines using palladium-catalyzed reaction (Hartwig et al, Angew Chem IN Ed1998, 37: 2046–2067). The four derivates from 1H-pyrrolo[2,3-b]pyridine were 4-phenylamino-7-azaindole, 4-benzylamino-7-azaindole, 4-phenethylamino-7-azaindole and 4-phenylpiperazylamino-7-azaindole. The four derivates from 1-methyl-pyrrolo[2,3-b]pyridine were 4-phenylamino-N-methyl-7-azaindole, 4-benzylamino-N-methyl-7-azaindole, 4-phenetylamino-N-methyl-7-azaindole and 4-phenylpiperazylamino-N-methyl-7-azaindole. HL-60 cells were exposed to three concentrations of these compounds (10–100–500 μM) during 72h at 37°C. The number of viable cells was determined by Trypan blue exclusion, and the cell cycle was assessed by propidium iodide staining followed by flow cytometric analysis. All these compounds decreased the number of viable cells. The compounds of the NH serie were more active than their methyl-analogues, especially 4-phenylamino-N-methyl-7-azaindole and 4-phenethylamino-7-azaindole which presented an estimated IC50 of 2 μM. Moreover, when used at 10 μM, 4-phenylamino-N-methyl-7-azaindole induced apoptosis whereas 4-phenethylamino-7-azaindole promoted inhibition of the cell cycle without pro-apoptotic effect. These results suggest that cytokinin analogues derived from 1H-pyrrolo[2,3-b]pyridine may present interesting therapeutic potential as cytostatic agents. Further studies will clarify their biological effects on leukemic cells.

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Hart, Amy C., Gretchen M. Schroeder, Honghe Wan, James Grebinski, Jennifer Inghrim, James Kempson, Junqing Guo, et al. "Structure-Based Design of Selective Janus Kinase 2 Imidazo[4,5-d]pyrrolo[2,3-b]pyridine Inhibitors." ACS Medicinal Chemistry Letters 6, no. 8 (July 14, 2015): 845–49. http://dx.doi.org/10.1021/acsmedchemlett.5b00225.

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Wang, Xin, Ben Zhi, Jean Baum, Ying Chen, Richard Crockett, Liang Huang, Shawn Eisenberg, et al. "A Practical Synthesis of 2-((1H-Pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic Acid." Journal of Organic Chemistry 71, no. 10 (May 2006): 4021–23. http://dx.doi.org/10.1021/jo0602571.

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40

Galvez, Enrique, Isabel Iriepa, Antonio Lorente, Jose Miguel Mohedano, Feliciana Florencio, and Severino Garcia-Blanco. "Synthesis and structural study of aminals derived from 8-aminoquinoline and 1-aminonaphtalene." Canadian Journal of Chemistry 65, no. 4 (April 1, 1987): 687–92. http://dx.doi.org/10.1139/v87-117.

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Reaction of 8-aminoquinoline with pyridine-2-carboxaldehyde (2), pyridine-3-carboxaldehyde (3), pyridine-4-carboxaldehyde (4), and benzaldehyde (5) yields the corresponding aminals or Schiff's bases according to reaction conditions; analogous results are obtained from the reaction of 1-amino-naphtalene with pyridine-2-carboxaldehyde (6). On the other hand, reaction of 8-aminoquinoline with thiophene-2-carboxaldehyde or pyrrole-2-carboxaldehyde yields neither the aminal nor the Schiff's base. Crystals of 4 (C24H19N5) belong to the triclinic space group [Formula: see text]. Cell dimensions are a = 11.547(3), b = 11.759(2), c = 15.687(5) Å, α = 98.50(2)°, β = 101.61(2)°, γ = 107.28(2)°, V = 1942.6(9) Å3. Final R = 0.077 and Rw = 0.064; 3160 reflections were observed. The ir, 1H nmr of 2–6, the mass spectra of 4 and 5 and the X-ray analysis of 4 are described and discussed. Preparative features, ir, 1H nmr, analyses and crystal structure indicate that the formation of 2–6 are governed mainly by the nucleophilicity at the aldehyde carbon atom and the existence of the hydrogen bonds in the aminal.

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41

Bodige, Srinu, Parameshwar Ravula, Kali Charan Gulipalli, Srinivas Endoori, Purna Koteswara Rao Cherukumalli, Narendra Sharath Chandra JN, and Nareshvarma Seelam. "Design, synthesis, antitubercular and antibacterial activities of pyrrolo[3,2-b]pyridine-3-carboxamide linked 2-methoxypyridine derivatives and in silico docking studies." Synthetic Communications 49, no. 17 (May 25, 2019): 2219–34. http://dx.doi.org/10.1080/00397911.2019.1618874.

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42

SEELA, F., and R. GUMBIOWSKI. "ChemInform Abstract: 1,7-Dideaza-2′,3′-dideoxyadenosine: Syntheses of Pyrrolo(2,3-b)pyridine 2′,3′-Dideoxyribofuranosides and Participation of Purine N(1) During HIV-1 Reverse Transcriptase Inhibition." ChemInform 22, no. 43 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199143227.

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43

Teleha, Christopher A., Roger A. Greenberg, and Robert J. Chorvat. "Synthesis and unexpected reactions of 2-Hydroxy-3-pyridinylacetic hydrazides. Formation of 2H-Pyrrolo[2,3-b]pyridin-2-ones." Journal of Heterocyclic Chemistry 35, no. 1 (January 1998): 145–49. http://dx.doi.org/10.1002/jhet.5570350127.

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Vadukoot, Anish K., Swagat Sharma, Christopher D. Aretz, Sushil Kumar, Nagsen Gautam, Yazen Alnouti, Amy L. Aldrich, Cortney E. Heim, Tammy Kielian, and Corey R. Hopkins. "Synthesis and SAR Studies of 1H-Pyrrolo[2,3-b]pyridine-2-carboxamides as Phosphodiesterase 4B (PDE4B) Inhibitors." ACS Medicinal Chemistry Letters 11, no. 10 (January 24, 2020): 1848–54. http://dx.doi.org/10.1021/acsmedchemlett.9b00369.

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45

Tang, Qidong, Yongli Duan, Linxiao Wang, Min Wang, Yiqiang Ouyang, Caolin Wang, Han Mei, et al. "Synthesis and antiproliferative activity of pyrrolo[2,3-b]pyridine derivatives bearing the 1,8-naphthyridin-2-one moiety." European Journal of Medicinal Chemistry 143 (January 2018): 266–75. http://dx.doi.org/10.1016/j.ejmech.2017.11.034.

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Hilmy, Khalid Mohammed Hassan. "Synthesis of New Pyrrolo[2, 3-b]pyridines as a Potent Inhibitor of Tumour Necrosis Factor Alpha." Archiv der Pharmazie 337, no. 1 (January 2004): 15–19. http://dx.doi.org/10.1002/ardp.200300773.

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47

Osipova, Anzhelika, Elena Kaigorodova, Ekaterina Kostenko, and Nina Kosyanok. "Research of reactions of electrophillic substitution of ethyl 3-(1-pyrrolyl) thieno [2,3-b] pyridine -2- carboxylate." Proceedings of the Kuban State Agrarian University 1, no. 69 (2017): 164–70. http://dx.doi.org/10.21515/1999-1703-69-164-170.

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Parrino, Barbara, Anna Carbone, Gloria Di Vita, Cristina Ciancimino, Alessandro Attanzio, Virginia Spanò, Alessandra Montalbano, et al. "3-[4-(1H-Indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, Nortopsentin Analogues with Antiproliferative Activity." Marine Drugs 13, no. 4 (April 3, 2015): 1901–24. http://dx.doi.org/10.3390/md13041901.

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49

Seela, F., W. Bourgeois, and T. Jürgens. "Synthesis of Pyrrolo[3,2-C]Pyridine 2'-Deoxy-D-Ribo-, 2',3'-Dideoxy-D-Ribo-, and D-Arabinofuranosyl Nucleosides." Nucleosides, Nucleotides and Nucleic Acids 8, no. 5 (1989): 1089–90. http://dx.doi.org/10.1080/07328318908054293.

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50

Javzan, S., D. Selenge, Y. Jamyansan, J. Nadmid, and Yu Ouynbileg. "Alkaloids from cultivated plant of Peganum harmala L." Mongolian Journal of Chemistry 12 (September 24, 2014): 113–16. http://dx.doi.org/10.5564/mjc.v12i0.184.

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Alkaloids such as 1H-cyclopenta(b) quinoline, 2.3.5.6.7.8-hexahydro-9-amino-; Vasicinone(1H-Pyrrоlo[2.1-b]quinazolin-9-one,3-hydroxy-2.3-dihydro) and harmine were isolated from cultivated plant of P. harmala. Four unknown alkaloids were isolated from P. harmala for the first time: 2.2.6.6-Tetramethyl-4-piperidone., Quinoline, 2.3.4-trimethyl-., Pyridine, 2-phenoxy-4- amino- and 4-(3-Propynyloxy)- quinazoline. Their structures were determined by GC-MS.DOI: http://dx.doi.org/10.5564/mjc.v12i0.184 Mongolian Journal of Chemistry Vol.12 2011: 113-116

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