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Journal articles on the topic 'Azaindole'

Author: Grafiati

Published: 4 June 2021

Last updated: 21 February 2023

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1

Belasri, Khadija, Ferenc Fülöp, and István Szatmári. "Solvent-Free C-3 Coupling of Azaindoles with Cyclic Imines." Molecules 24, no. 19 (October 4, 2019): 3578. http://dx.doi.org/10.3390/molecules24193578.

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By direct coupling 7-azaindole and cyclic imines, such as 3,4-dihydroisoquinoline, 6,7-dihydrothieno[3,2-c]pyridine, 3,4-dihydro-β-carboline, and 4,5-dihydro-3H-benz[c]azepine, new 3-substituted 7-azaindole derivatives have been synthesized. The reaction was extended to 4-azaindoles and 6-azaindoles, as electron-rich aromatic compounds. The lowest reactivity was observed in the case of C-3 substitution of 5-azaindole. In this case, the aza-Friedel-Crafts reaction took place by using 10 mol % of p-toluenesulfonic acid (p-TSA) as the catalyst. The role of the acid catalyst can be explained by the different pKa values of the azaindoles. All reactions were performed in solvent-free conditions by using both classical heating and microwave irradiation. In all cases, microwave heating proved to be more convenient to synthesize new C-3-substituted azaindole derivatives.

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2

Sharma, Neha, and Anurag. "7-Azaindole Analogues as Bioactive Agents and Recent Results." Mini-Reviews in Medicinal Chemistry 19, no. 9 (May 6, 2019): 727–36. http://dx.doi.org/10.2174/1389557518666180928154004.

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Azaindoles have been accepted as important structures having various biological activities in medicinal chemistry in novel drug discovery. Various azaindole derivatives have been used commercially and newer analogues are synthesized continuously. As in literature, azaindole is a very potent moiety, its derivatives displayed a number of biological activities such as kinase inhibitors, cytotoxic agents, anti-angiogenic activity, CRTh2 receptor antagonists, melanin agonists, nicotine agonists, effectiveness in alzheimer disease, cytokinin analogs, Orai inhibitors in asthma and chemokine receptor- 2 (CCR2) antagonists. This review consists of biological activities of various azaindole analogs, reported so far, and their structure activity relations, along with future perspectives in this field.

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3

Pan, Changduo, Yun Wang, Chao Wu, and Jin-Tao Yu. "Iridium-catalyzed C–H phosphoramidation of N-aryl-7-azaindoles with phosphoryl azides." Organic & Biomolecular Chemistry 16, no. 20 (2018): 3711–15. http://dx.doi.org/10.1039/c8ob00776d.

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4

Chong, Delano P. "Computational Study of the Electron Spectra of Vapor-Phase Indole and Four Azaindoles." Molecules 26, no. 7 (March 30, 2021): 1947. http://dx.doi.org/10.3390/molecules26071947.

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After geometry optimization, the electron spectra of indole and four azaindoles are calculated by density functional theory. Available experimental photoemission and excitation data for indole and 7-azaindole are used to compare with the theoretical values. The results for the other azaindoles are presented as predictions to help the interpretation of experimental spectra when they become available.

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5

Noble, Jennifer A., Ernesto Marceca, Claude Dedonder, and Christophe Jouvet. "Influence of the N atom and its position on electron photodetachment of deprotonated indole and azaindole." Physical Chemistry Chemical Physics 22, no. 46 (2020): 27290–99. http://dx.doi.org/10.1039/d0cp03609a.

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6

Nowak, Maciej J., Igor Reva, Hanna Rostkowska, and Leszek Lapinski. "UV-induced hydrogen-atom transfer and hydrogen-atom detachment in monomeric 7-azaindole isolated in Ar and n-H2 matrices." Physical Chemistry Chemical Physics 19, no. 18 (2017): 11447–54. http://dx.doi.org/10.1039/c7cp01363a.

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Upon UV excitation, the N1H form of 7-azaindole isolated in an Ar matrix transforms into N7H, C3H tautomers and the 7-azaindolyl radical; whereas only C3H and 7-azaindolyl radical products are photogenerated in solid H₂ environment.

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7

Poitras, Jacques, and André L. Beauchamp. "Reactions of 7-azaindole with niobium and tantalum pentachlorides and coupling to the azaindolyl-azaindolium cation." Canadian Journal of Chemistry 72, no. 7 (July 1, 1994): 1675–83. http://dx.doi.org/10.1139/v94-211.

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The reaction of NbCl5 and TaCl5 with 7-azaindole (Haza) at room temperature in benzene or dichloromethane yielded MCl5(Haza) addition compounds. Under more severe conditions, the same compound was obtained with TaCl5. For NbCl5, some reduction to Nb(IV) was observed and NbCl5(Haza), NbCl4(Haza)2, and the (H2aza)+ ion were identified in the reaction mixture by infrared spectroscopy. Oxidative coupling of two azaindole units via N7—C6 also took place during the reaction, since the 7-(azaindol-6-yl)azaindolium cation was found as counter-ion in the crystal structures of two complex salts. In the crystals of (H2aza-aza)[NbOCl4(Haza)]•0.5CH2Cl2([Formula: see text]a = 7.255 Å, b = 12.412 Å, c = 14.277 Å, α = 89.03°, β = 85.60°, γ = 76.66°, Z = 2, R = 0.062), the anion is the roughly octahedral [NbOCl4(azaindole)]− species containing a neutral N7-coordinated azaindole trans to the Nb=O bond. The [NbOCl5]2− salt ([Formula: see text]a = 7.527 Å, b = 10.168 Å, c = 10.467 Å, α = 66.41°, β = 84.07°, γ = 85.51°, Z = 1, R = 0.037) contains the distorted octahedral [NbOCl5]2− ion disordered over two orientations. The infrared spectra suggest monomeric octahedral structures for the MCl5(Haza) and NbCl4(Haza)2 complexes. 1H NMR spectroscopy shows that NbCl5(Haza) is not dissociated in CD2Cl2.

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8

Dufour, Pascal, Yves Dartiguenave, Michèle Dartiguenave, Nathalie Dufour, Anne-Marie Lebuis, Francine Bélanger-Gariépy, and André L. Beauchamp. "Crystal structures of 7-azaindole, an unusual hydrogen-bonded tetramer, and of two of its methylmercury(II) complexes." Canadian Journal of Chemistry 68, no. 1 (January 1, 1990): 193–201. http://dx.doi.org/10.1139/v90-025.

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Crystals of 7-azaindole ([Formula: see text], a = 11.312(4), b = 14.960(6), c = 15.509(5) Å, α = 102.86(3), β = 108.78(3), γ = 90.71(3)°, Z = 16, R = 0.052) contain tetrameric units of approximate S4 symmetry, in which the molecules are associated by means of four complementary N—H … N hydrogen bonds. [CH3Hg(7-azaindole)]NO3 ([Formula: see text], a = 7.818(3), b = 7.884(3), c = 9.135(4) Å, α = 97.89(3), β = 109.13(3), γ = 103.28(3)°, Z = 2, R = 0.039) contains well-separated nitrate ions and complex cations in which the methylmercury group is linearly bonded to the pyridine nitrogen atom, whereas the five-membered ring remains protonated. In the neutral [CH3Hg(azaindolate)] complex ([Formula: see text], a = 10.926(10), b = 11.333(8), c = 11.647(10) Å, α = 92.13(8), β = 104.83(9), γ = 111.86(7)°, Z = 6, R = 0.048), methylmercury groups have substituted the N—H proton in the five-membered ring for the three symmetry-independent molecules. Intermolecular secondary Hg … N bonds are found with pyridine nitrogens. Keywords: azaindole, methylmercury, crystal structure.

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9

Bilodeau, Denis, and André L. Beauchamp. "Methyl- and phenylmercury complexes of azaindolyl–azaindole." Inorganica Chimica Acta 261, no. 1 (August 1997): 7–13. http://dx.doi.org/10.1016/s0020-1693(96)05571-5.

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10

Poitras, Jacques, and André L. Beauchamp. "Preparation and characterization of azaindolyl-azaindole and structure of its halogen-free dicationic cluster containing the µ4-oxotetracopper(II) core." Canadian Journal of Chemistry 72, no. 11 (November 1, 1994): 2339–47. http://dx.doi.org/10.1139/v94-298.

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Refluxing NbCl5 and excess 7-azaindole (Haza) in benzene yielded a solid mixture containing NbCl5(Haza), NbCl4(Haza)2, the azaindolium ion (H2aza)+, and the azaindolyl-azaindolium ion (H2aza-aza)+. The neutral (Haza-aza) molecule was obtained from the hydrolysed mixture and shown by X-ray diffraction (monoclinic, P21/c, a = 10.025, b = 13.758, c = 8.416 Å, β = 102.89°, Z = 4, R = 0.035) to result from the coupling of two azaindole units via N7—C6′. This compound was the only oxidation product detected, but concurrent formation of other niobium- and (or) azaindole-containing products keeps the yield of Haza-aza low. Dark green crystals of [Cu4O(aza-aza)4]Cl2•6.5H2O were obtained from (Haza-aza) and CuCl2 in wet methanol. The crystal structure (monoclinic, C2/c, a = 17.704, b = 25.240, c = 14.457 Å, β = 116.14°, Z = 4, R = 0.051) shows the presence of a tetranuclear dicationic cluster consisting of a µ4-oxide ion surrounded by a tetrahedron of Cu(II) atoms. A distorted square-planar coordination is achieved about each copper atom by (aza-aza)− ligands each bridging two copper atoms and providing a third nitrogen donor to one of them. For each such cation, the unit cell also includes two chloride ions and 6.5 disordered lattice water molecules. The 1H NMR and infrared spectroscopy data are discussed.

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11

You, Zhen, Bei Li, Jun Gao, Jiong Lu, and Ruihua Xu. "Azaindole inhibits liver cancer cell proliferation in vitro and in vivo by targeting the expression of kinesin family member C1." Tropical Journal of Pharmaceutical Research 20, no. 2 (January 13, 2022): 359–64. http://dx.doi.org/10.4314/tjpr.v20i2.20.

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Purpose: To investigate the effect of azaindole on proliferation of liver cancer cells, as well as the underlying mechanism. Methods: Colony forming and 3-(4,5-dimethylthiazole-2-yl)-2,5-biphenyl tetrazolium bromide (MTT) assays were used to determine the effect of azaindole on cell proliferation. A tumor model was established through subcutaneous administration of HEPG2 cells to rats. Thereafter, in vivo tumor development was measured using Vernier caliper. Results: The proliferation potential of HEPG2 and SNU-398 cells was markedly and dose-dependently suppressed by treatment with azaindole at doses of 2, 4, 8, 16 and 20 μM (p < 0.05). The expression levels of Ki67 and PCNA levels were significantly down-regulated in HEPG2 and SNU-398 cells on treatment with 20 μM azaindole. Moreover, azaindole significantly suppressed mRNA and protein expressions of KIFC1 in HEPG2 and SNU-398 cells (p < 0.05). Tumor volume in azaindole-treated rats on day 21 was greatly reduced, while KIFC1 expression in azaindole-treated rat tumor tissue was significantly down-regulated, when compared to the model group (p < 0.05). Conclusion: Azaindole targets proliferation of liver cancer cells in vitro and inhibits tumor growth in vivo through a mechanism involving down-regulation of KIFCI expression. Thus, azaindole is a potential therapeutic candidate for liver cancer.

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12

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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13

Ameur Messaoud, Mohamed Yacine Ameur, Ghenia Bentabed-Ababsa, Ziad Fajloun, Monzer Hamze, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Thierry Roisnel, Vincent Dorcet, and Florence Mongin. "Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties." Molecules 26, no. 20 (October 19, 2021): 6314. http://dx.doi.org/10.3390/molecules26206314.

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Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The reactivity of the substrate was discussed in light of the calculated atomic charges and the pKa values. The behavior of the 1-arylated 7-azaindoles in direct iodination was then studied, and the results explained by considering the HOMO orbital coefficients and the atomic charges. Finally, some of the iodides generated, generally original, were involved in the N-arylation of indole. While crystallographic data were collected for fifteen of the synthesized compounds, biological properties (antimicrobial, antifungal and antioxidant activity) were evaluated for others.

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14

Pankey, Edward A., Ryuk J. Byun, William B. Smith, Manish Bhartiya, Franklin R. Bueno, Adeleke M. Badejo, Johannes-Peter Stasch, Subramanyam N. Murthy, Bobby D. Nossaman, and Philip J. Kadowitz. "The Rho kinase inhibitor azaindole-1 has long-acting vasodilator activity in the pulmonary vascular bed of the intact chest rat." Canadian Journal of Physiology and Pharmacology 90, no. 7 (July 2012): 825–35. http://dx.doi.org/10.1139/y2012-061.

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Responses to a selective azaindole-based Rho kinase (ROCK) inhibitor (azaindole-1) were investigated in the rat. Intravenous injections of azaindole-1 (10–300 µg/kg), produced small decreases in pulmonary arterial pressure and larger decreases in systemic arterial pressure without changing cardiac output. Responses to azaindole-1 were slow in onset and long in duration. When baseline pulmonary vascular tone was increased with U46619 or L-NAME, the decreases in pulmonary arterial pressure in response to the ROCK inhibitor were increased. The ROCK inhibitor attenuated the increase in pulmonary arterial pressure in response to ventilatory hypoxia. Azaindole-1 decreased pulmonary and systemic arterial pressures in rats with monocrotaline-induced pulmonary hypertension. These results show that azaindole-1 has significant vasodilator activity in the pulmonary and systemic vascular beds and that responses are larger, slower in onset, and longer in duration when compared with the prototypical agent fasudil. Azaindole-1 reversed hypoxic pulmonary vasoconstriction and decreased pulmonary and systemic arterial pressures in a similar manner in rats with monocrotaline-induced pulmonary hypertension. These data suggest that ROCK is involved in regulating baseline tone in the pulmonary and systemic vascular beds, and that ROCK inhibition will promote vasodilation when tone is increased by diverse stimuli including treatment with monocrotaline.

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15

Poitras, Jacques, and André L. Beauchamp. "Preparation and structure of chloro-copper(II) complexes of 7-azaindole." Canadian Journal of Chemistry 70, no. 12 (December 1, 1992): 2846–55. http://dx.doi.org/10.1139/v92-362.

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The light green trans-CuCl2(Haza)2 adduct precipitates immediately from mixtures of CuCl2•2H2O with excess 7-azaindole (Haza) in methanol. Upon standing in azaindole-rich solution, this solid is replaced by a deep green Cu2Cl4(Haza)6 compound, whose crystal structure (orthorbombic, Fdd2, a = 26.558, b = 23.750, c = 12.727 Ǻ, Z = 8, R = 0.068, Rw = 0.066) shows the presence of square-planar [Cu(Haza)4]2+ and trans-[CuCl2(Haza)2] units connected by bridging Cl− ions, making each Cu atom (4 + 2)-coordinated. Azaindole is bonded to the metal via the pyridine N7 site, whereas the five-membered ring retains its N1—H proton. The azaindole ligands are disordered over two orientations in the [CuCl2(Haza)2] unit. The square-planar Cu species and apical Cl− ions lie on a twofold axis and define along c an infinite chain based on the [Formula: see text] pattern. Equimolar mixtures of azaindole and CuCl2•2H2O yield a brown Cu4OCl6(Haza)4 compound. The crystal structure of its ethyl acetate solvate (monoclinic, P21/c, a = 11.661, b = 22.415, c = 15.077 Ǻ, β = 109.85°, Z = 4, R = 0.048, Rw = 0.054) shows the presence of a tetranuclear cluster consisting of a μ4-oxide ion surrounded by a tetrahedron of Cu(II) atoms bridged in pairs by chlorine atoms. The trigonal-bipyramidal coordination of each copper atom is completed by a monodentate N7-bonded azaindole molecule hydrogen bonded to bridging chlorines via N1—H. The influence of complexation on the infrared spectrum of azaindole is discussed.

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16

Sánchez-Obregón, Rubén, Alex G. Fallis, and Arthur G. Szabo. "Syntheses of a potential fluorescence probe, (−)-(R)-7-azatryptophan, via alkylation of the (1R,4R)-camphor imine of tert-butylgycinate." Canadian Journal of Chemistry 70, no. 5 (May 1, 1992): 1531–36. http://dx.doi.org/10.1139/v92-188.

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The synthesis of (−)-(R)-7-azatryptophan (2) from commercially available 7-azaindole (4) is described. The key step involved the diastereoselective alkylation of tert-butyl [(1R,4R)-bornylideneamino]acetate (3) with 1-(tert-butyloxycarbonyl-3-(iodomethyl)-7-azaindole (19) derived from 3-formyl-7-azaindole (14). The alkylation, conducted at −100 °C in a THF/HMPA solvent using potassium hexamethyldisilazide as the base, afforded 7 in greater than 98% diastereomeric excess. Hydrolysis and deprotection gave (−)-(R)-7-azatryptophan.

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17

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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18

Motati, Damoder Reddy, Radhika Amaradhi, and Thota Ganesh. "Azaindole therapeutic agents." Bioorganic & Medicinal Chemistry 28, no. 24 (December 2020): 115830. http://dx.doi.org/10.1016/j.bmc.2020.115830.

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19

Lebuis, Anne-Marie, and André L. Beauchamp. "Preparation and structure of oxo-rhenium(V) complexes with 7-azaindole." Canadian Journal of Chemistry 71, no. 12 (December 1, 1993): 2060–69. http://dx.doi.org/10.1139/v93-256.

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Four Re(V) oxo compounds were obtained from 7-azaindole (Haza) and ReOCl3(PPh3)2: the oxo-bridged dimer Re2O3Cl4(Haza)4 (1), the oxo–ethoxo monomers ReO(OEt)Cl2(Haza)2 (2) and ReO(OEt)Cl2(Haza)(PPh3) (3), and the dioxo [ReO2(Haza)4]Cl salt (4a). [ReO2(Haza)4]I (4b) was also prepared from ReO2I(PPh3)2. The ReO(OEt)Cl2(Haza)2 complex was shown by X-ray diffraction (C2/c, a = 16.292, b = 9.395, c = 12.104 Å, β = 101.47°, R = 0.041) to consist of individual molecules of the trans-trans isomer in which azaindole is N7-bonded. Crystals of [Formula: see text] (C2/m a = 15.422, b = 13.055, c = 9.086 Å, β = 91.13°, R = 0.059) contain well separated Cl− anions and trans-dioxo cations. The N7-bonded azaindole ligands are held parallel to the O=Re=O direction by intramolecular [Formula: see text] hydrogen bonds, but the relative orientation of the four ligands cannot be determined because of disorder. Characteristic Re—oxygen vibrations are observed in infrared for each type of compounds. The 1H and 13C NMR spectra are discussed in relation with the azaindole binding mode.

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20

Chatterji, Monalisa, Radha Shandil, M. R. Manjunatha, Suresh Solapure, Vasanthi Ramachandran, Naveen Kumar, Ramanatha Saralaya, et al. "1,4-Azaindole, a Potential Drug Candidate for Treatment of Tuberculosis." Antimicrobial Agents and Chemotherapy 58, no. 9 (June 23, 2014): 5325–31. http://dx.doi.org/10.1128/aac.03233-14.

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ABSTRACTNew therapeutic strategies against multidrug-resistant (MDR) and extensively drug-resistant (XDR)Mycobacterium tuberculosisare urgently required to combat the global tuberculosis (TB) threat. Toward this end, we previously reported the identification of 1,4-azaindoles, a promising class of compounds with potent antitubercular activity through noncovalent inhibition of decaprenylphosphoryl-β-d-ribose 2′-epimerase (DprE1). Further, this series was optimized to improve its physicochemical properties and pharmacokinetics in mice. Here, we describe the short-listing of a potential clinical candidate, compound 2, that has potent cellular activity, drug-like properties, efficacy in mouse and rat chronic TB infection models, and minimalin vitrosafety risks. We also demonstrate that the compounds, including compound 2, have no antagonistic activity with other anti-TB drugs. Moreover, compound 2 shows synergy with PA824 and TMC207in vitro, and the synergy effect is translatedin vivowith TMC207. The series is predicted to have a low clearance in humans, and the predicted human dose for compound 2 is ≤1 g/day. Altogether, our data suggest that a 1,4-azaindole (compound 2) is a promising candidate for the development of a novel anti-TB drug.

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21

Liu, Chen-Fei, Guo-Tai Zhang, Jun-Shu Sun, and Lin Dong. "Access to π-conjugated azaindole derivatives via rhodium(iii)-catalyzed cascade reaction of azaindoles and diazo compounds." Organic & Biomolecular Chemistry 15, no. 14 (2017): 2902–5. http://dx.doi.org/10.1039/c7ob00059f.

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22

Gebre, Tesfaye Tadesse, Teshome Abute Lilisho, and Birhanu Bekele Gosa. "DFT Study on the Molecular Mechanism, Thermodynamic and Kinetic Parameters of Cycloaddition Reaction of Aziridine with CO2 in the Presence of Organocatalysts (TBD and 7-Azaindole)." Trends in Sciences 20, no. 3 (December 26, 2022): 6520. http://dx.doi.org/10.48048/tis.2023.6520.

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The catalytic conversions of CO2 into value added chemicals have attracted the interest of many visionary researchers. In this work, the coupling reaction of aziridine with CO2 has been investigated in the absence and presence of organocatalysts (TBD and 7-azaindole) computationally using density functional theory method. The kinetic and thermodynamic parameters of each mechanism were calculated at B3LYP/6-31G (d) level. The results show that, the TBD and 7-azaindole catalyzed reactions of aziridine with CO2 have significantly lower the energy barrier compared to a single step concerted non-catalyzed one. In TBD catalyzed reaction, mechanism I in which the TBD catalyst first interact with CO2 to form TBD-CO2 adduct (zwitterion) and then the zwitterion formed facilitated the ring opening of aziridine to form intermediate is the favorable path. In the case of 7-azaindole catalyzed reaction, mechanism 1 is the most favorable pathway in both gas phase and water phase. However, these parameters were significantly affected in the presence of water using Solvent Model Density (SMD).

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Zhang, Haofan, Fengming He, Guiping Gao, Sheng Lu, Qiaochu Wei, Hongyu Hu, Zhen Wu, Meijuan Fang, and Xiumin Wang. "Approved Small-Molecule ATP-Competitive Kinases Drugs Containing Indole/Azaindole/Oxindole Scaffolds: R&D and Binding Patterns Profiling." Molecules 28, no. 3 (January 17, 2023): 943. http://dx.doi.org/10.3390/molecules28030943.

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Kinases are among the most important families of biomolecules and play an essential role in the regulation of cell proliferation, apoptosis, metabolism, and other critical physiological processes. The dysregulation and gene mutation of kinases are linked to the occurrence and development of various human diseases, especially cancer. As a result, a growing number of small-molecule drugs based on kinase targets are being successfully developed and approved for the treatment of many diseases. The indole/azaindole/oxindole moieties are important key pharmacophores of many bioactive compounds and are generally used as excellent scaffolds for drug discovery in medicinal chemistry. To date, 30 ATP-competitive kinase inhibitors bearing the indole/azaindole/oxindole scaffold have been approved for the treatment of diseases. Herein, we summarize their research and development (R&D) process and describe their binding models to the ATP-binding sites of the target kinases. Moreover, we discuss the significant role of the indole/azaindole/oxindole skeletons in the interaction of their parent drug and target kinases, providing new medicinal chemistry inspiration and ideas for the subsequent development and optimization of kinase inhibitors.

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24

Zhu, Yan‐Ying, Hui‐Bei Xu, Jing Zhang, Yi Luo, and Lin Dong. "Ru(II)‐Catalyzed Difluoromethylations of 7‐Azaindoles: Access to Novel Fluoro‐7‐Azaindole Derivatives." Asian Journal of Organic Chemistry 10, no. 6 (April 28, 2021): 1410–13. http://dx.doi.org/10.1002/ajoc.202100159.

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25

Chang, Guanjun, Li Yang, Junxiao Yang, Yawen Huang, Ke Cao, Jiajun Ma, and Dapeng Wang. "A nitrogen-rich, azaindole-based microporous organic network: synergistic effect of local dipole–π and dipole–quadrupole interactions on carbon dioxide uptake." Polymer Chemistry 7, no. 37 (2016): 5768–72. http://dx.doi.org/10.1039/c6py01154c.

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26

Martin, Cristina, Carlos Borreguero, Koen Kennes, Mark Van der Auweraer, J. Hofkens, Gustavo de Miguel, and Eva M. García-Frutos. "Bipolar luminescent azaindole derivative exhibiting aggregation-induced emission for non-doped organic light-emitting diodes." Journal of Materials Chemistry C 7, no. 5 (2019): 1222–27. http://dx.doi.org/10.1039/c8tc05476b.

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27

Catalán, Javier, Cristina Díaz, and José L. G. de Paz. "Excited-state proton phototransfer in the (3-methyl-7-azaindole)-(7-azaindole) heterodimer." Chemical Physics Letters 419, no. 1-3 (February 2006): 164–67. http://dx.doi.org/10.1016/j.cplett.2005.11.072.

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28

Noble, Jennifer A., Ernesto Marceca, Claude Dedonder, Witchaya Phasayavan, Geraldine Féraud, Burapat Inceesungvorn, and Christophe Jouvet. "Influence of the N atom position on the excited state photodynamics of protonated azaindole." Physical Chemistry Chemical Physics 22, no. 46 (2020): 27280–89. http://dx.doi.org/10.1039/d0cp03608k.

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29

Kannaboina, Prakash, Krishanu Mondal, Joydev K. Laha, and Parthasarathi Das. "Recent advances in the global ring functionalization of 7-azaindoles." Chemical Communications 56, no. 79 (2020): 11749–62. http://dx.doi.org/10.1039/d0cc04264a.

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30

Gong, Shan Shan, and Qi Sun. "A Practical Synthesis of 4-Azaindole." Advanced Materials Research 859 (December 2013): 353–56. http://dx.doi.org/10.4028/www.scientific.net/amr.859.353.

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An improved method for practical synthesis of 4-azaindole from 2-chloro-3-nitropyridine has been developed. In the key step, decarboxylation with acetic acid afforded 3-nitro-2-pyridylacetonitrile in high yield.

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31

Kim, Yechan, and Sungwoo Hong. "Rh(iii)-catalyzed 7-azaindole synthesis via C–H activation/annulative coupling of aminopyridines with alkynes." Chemical Communications 51, no. 56 (2015): 11202–5. http://dx.doi.org/10.1039/c5cc03497c.

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32

Cash, Michael T., Peter R. Schreiner, and Robert S. Phillips. "Excited state tautomerization of azaindole." Organic & Biomolecular Chemistry 3, no. 20 (2005): 3701. http://dx.doi.org/10.1039/b506652b.

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33

Gordon, Mark S. "Hydrogen Transfer in 7-Azaindole." Journal of Physical Chemistry 100, no. 10 (January 1996): 3974–79. http://dx.doi.org/10.1021/jp952851c.

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34

Immadi, Sri Sujana, Rachel Dopart, Zhixing Wu, Boqiao Fu, Debra A. Kendall, and Dai Lu. "Exploring 6-Azaindole and 7-Azaindole Rings for Developing Cannabinoid Receptor 1 Allosteric Modulators." Cannabis and Cannabinoid Research 3, no. 1 (December 2018): 252–58. http://dx.doi.org/10.1089/can.2018.0046.

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35

Pracharova, Jitka, Tereza Radosova Muchova, Eva Dvorak Tomastikova, Francesco P. Intini, Concetta Pacifico, Giovanni Natile, Jana Kasparkova, and Viktor Brabec. "Anticancer potential of a photoactivated transplatin derivative containing the methylazaindole ligand mediated by ROS generation and DNA cleavage." Dalton Transactions 45, no. 33 (2016): 13179–86. http://dx.doi.org/10.1039/c6dt01467d.

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36

Poitras, Jacques, Martin Leduc, and André L. Beauchamp. "Preparation and structure of 7-azaindolium salts containing unusual chloro-copper(II) anionic units." Canadian Journal of Chemistry 71, no. 4 (April 1, 1993): 549–60. http://dx.doi.org/10.1139/v93-077.

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Dark-red crystals of (H2aza)5[Cu5Cl14(H2O)4]Cl were obtained by addition of HCl to equimolar amounts of 7-azaindole (Haza) and CuCl2•2H2O in methanol. They were shown by X-ray diffraction (triclinic, [Formula: see text] a = 9.396(1), b = 9.894(1), c = 15.958(1), Å, α = 106.10(1)°, β = 98.25(1)°, γ = 105.56(1)°, Z = 1, R = 0.031) to contain infinite chains in which the basic [Cu5Cl14(H2O)4]4− pattern is built up from trans-CuCl2(H2O)2, [CuCl3(H2O)]−, and dichlorobridged [Cu2Cl6]2− species. In the idealized chain, these units occur in the 1:2:1 ratio, but disorder is present and some of the CuCl2(H2O)2 units are randomly replaced by [CuCl3(H2O)]−. The Cu atoms have a roughly square-planar primary coordination, and connection along the chain is achieved by weaker apical Cu–Cl bridging interactions. All azaindole molecules are present as uncoordinated N7-protonated monocations. A related (H2aza)3[Cu3Cl8(H2O)3]Cl salt was obtained as a side-product of the reaction of 7-azaindole with excess CuCl2•2H2O in methanol without acid. In these brown crystals (triclinic, [Formula: see text] a = 9.308(1), b = 9.964(1), c = 19.212(4) Å, α = 76.67(1)°, β = 79.35(1)°, γ = 75.27(1)°, Z = 2, R = 0.046), the [Cu6Cl16(H2O)6]4− pattern of the chain contains the same three building units as above, but in the 2:2:1 ratio. In both salts, the polymeric chloro-copper chains are parallel and separated by azaindolium cations stacked along the same direction. The structures are stabilized by networks of hydrogen bonds involving the azaindolium cations, the chlorine atoms, and water molecules in the chloro-copper chain, and a noncoordinated Cl− ion. Most of the azaindolium cations are disordered. The influence of N7-protonation on the infrared spectrum of azaindole is discussed.

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37

Gallou, Fabrice, Jonathan T. Reeves, Zhulin Tan, Jinhua J. Song, Nathan K. Yee, Scot Campbell, Paul-James Jones, and Chris H. Senanayake. "Regioselective Halogenation of 6-Azaindoles: Efficient Synthesis of 3-Halo-2,3-disubstituted-6-azaindole Derivatives." Synlett, no. 15 (2005): 2400–2402. http://dx.doi.org/10.1055/s-2005-872680.

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38

Li, Chaozheng, Yonggang Yang, Donglin Li, and Yufang Liu. "A theoretical study of the potential energy surfaces for the double proton transfer reaction of model DNA base pairs." Physical Chemistry Chemical Physics 19, no. 6 (2017): 4802–8. http://dx.doi.org/10.1039/c6cp07716a.

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39

Surasani, Rajendra, Dipak Kalita, A. V. Dhanunjaya Rao, and K. B. Chandrasekhar. "Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols." Beilstein Journal of Organic Chemistry 8 (November 19, 2012): 2004–18. http://dx.doi.org/10.3762/bjoc.8.227.

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Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

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40

Dongare, Sakharam B., Babasaheb P. Bandgar, Pravin S. Bhale, Sadanand N. Shringare, and Hemant V. Chavan. "Design, Synthesis, and Spectroscopic Study of 7-Azaindolyl Hydrazones with Anti-Breast Cancer Activity." Croatica chemica acta 92, no. 1 (2019): 1–9. http://dx.doi.org/10.5562/cca3418.

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A series of 7-azaindolyl hydrazones were prepared by reacting of hydrazides of 7-azaindole-3-acetic acids with aromatic aldehydes and N-substituted indolyl-3-carboxyaldehydes. Structure of all the synthesized compounds were satisfactorily correlated by IR, 1H NMR, 13C NMR and mass spectroscopic evidences. The synthesized compounds were evaluated for their possible anticancer potential against MCF-7 induced breast carcinoma. It is worth mentioning that most of the compounds were considerably active against MCF-7 cell line with GI50 values ranging from 22.3–81.0 μM. The hydrazones of N-1-substituted indole-3-carboxyaldehydes 9f, 9g, 9h, 9c, and 9j were active against MCF-7 cell line with GI50 values less than 40 μM (GI50 = 22.3 and 24.9, 29.6, 30.2 and 37.8 μM respectively) with moderate TGI values (TGI = 56.6, 59.5, 65.5, 70.7 and 94.6 μM respectively). The active compounds were also screened against the normal Vero monkey cell line, which showed moderate selectivity against inhibition of cancer cells.

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41

Santos, A., Ana Mortinho, and M. Marques. "Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization." Molecules 23, no. 10 (October 17, 2018): 2673. http://dx.doi.org/10.3390/molecules23102673.

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Azaindoles are rare in nature but extremely attractive for drug discovery programs. Azaindoles can be obtained by diverse methods, including those involving metal-catalyzed reactions. This important core has been fascinating the scientific community due to their challenging synthesis and relevant bioactivity. This paper highlights the diverse synthetic methodologies developed to date involving metal-catalyzed reaction to attain azaindoles and its functionalization.

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42

Lande, Duc, Conrad Kunick, and Johann Grünefeld. "2,3,4-Trioxo-1-(1H-pyrrolo[2,3-b]pyridin-7-ium-7yl)-cyclobutan-1-ide." Molbank 2018, no. 4 (October 12, 2018): M1026. http://dx.doi.org/10.3390/m1026.

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43

Yu, Xue-fang, Shohei Yamazaki, and Tetsuya Taketsugu. "Solvent effects on the excited-state double proton transfer mechanism in the 7-azaindole dimer: a TDDFT study with the polarizable continuum model." Physical Chemistry Chemical Physics 19, no. 34 (2017): 23289–301. http://dx.doi.org/10.1039/c7cp04942k.

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44

Nakajima, A., M. Hirano, R. Hasumi, K. Kaya, H. Watanabe, C. C. Carter, J. M. Williamson, and Terry A. Miller. "High-Resolution Laser-Induced Fluorescence Spectra of 7-Azaindole−Water Complexes and 7-Azaindole Dimer." Journal of Physical Chemistry A 101, no. 4 (January 1997): 392–98. http://dx.doi.org/10.1021/jp9614411.

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45

Catalán, J. "On the phosphorescence of 7-azaindole C2h dimer: The case of 3-bromo-7-azaindole." Chemical Physics Letters 423, no. 4-6 (June 2006): 395–400. http://dx.doi.org/10.1016/j.cplett.2006.04.003.

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46

Sharma, Hayden A., M. Todd Hovey, and Karl A. Scheidt. "Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes." Chemical Communications 52, no. 59 (2016): 9283–86. http://dx.doi.org/10.1039/c6cc04735a.

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47

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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48

Li, Shuai-Shuai, Chen-Fei Liu, Ying-Qi Xia, Wei-Huan Li, Guo-Tai Zhang, Xiao-Mei Zhang, and Lin Dong. "A unique annulation of 7-azaindoles with alkenyl esters to produce π-conjugated 7-azaindole derivatives." Organic & Biomolecular Chemistry 14, no. 23 (2016): 5214–18. http://dx.doi.org/10.1039/c6ob00730a.

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49

Liu, Bin, Ridong Li, Wei Zhan, Xin Wang, Zemei Ge, and Runtao Li. "Rh(iii)-catalyzed C–H oxidative ortho-olefination of arenes using 7-azaindole as a directing group and utilization in the construction of new tetracyclic heterocycles containing a 7-azaindole skeleton." RSC Advances 6, no. 53 (2016): 48205–11. http://dx.doi.org/10.1039/c6ra07478b.

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A wide range of Rh(iii)-catalyzed ortho-olefinated 7-azaindole derivatives as well as novel tetracyclic heterorings were achieved, which could served as useful starting materials for the construction of biological molecules.

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50

Le, Yi, Zhisong Yang, Yumei Chen, Dongmei Chen, Longjia Yan, Zhenchao Wang, and Guiping Ouyang. "Microwave-assisted synthesis of 7-azaindoles via iron-catalyzed cyclization of an o-haloaromatic amine with terminal alkynes." RSC Advances 9, no. 68 (2019): 39684–88. http://dx.doi.org/10.1039/c9ra08742g.

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An efficient and practical procedure was developed to prepare 7-azaindole, starting from an o-haloaromatic amine and corresponding terminal alkynes under microwave irradiation and the scope was demonstrated with a number of examples.

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