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Journal articles on the topic '5-Nitro indazole'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Pozo-Martínez, Josué, Vicente J. Arán, Matías Zúñiga-Bustos, et al. "In Vitro Evaluation of New 5-Nitroindazolin-3-one Derivatives as Promising Agents against Trypanosoma cruzi." International Journal of Molecular Sciences 25, no. 20 (2024): 11107. http://dx.doi.org/10.3390/ijms252011107.

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Chagas disease is a prevalent health problem in Latin America which has received insufficient attention worldwide. Current treatments for this disease, benznidazole and nifurtimox, have limited efficacy and may cause side effects. A recent study proposed investigating a wide range of nitroindazole and indazolone derivatives as feasible treatments. Therefore, it is proposed that adding a nitro group at the 5-position of the indazole and indazolone structure could enhance trypanocidal activity by inducing oxidative stress through activation of the nitro group by NTRs (nitroreductases). The study

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2

Saghdani, Nassima, Abdelali Chihab, Nabil El Brahmi, and Saïd El Kazzouli. "Synthesis and Characterization of Novel Indazole–Sulfonamide Compounds with Potential MAPK1 Inhibitory Activity for Cancer Treatment." Molbank 2024, no. 3 (2024): M1858. http://dx.doi.org/10.3390/m1858.

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Indazoles are a very important group of nitrogen-containing heterocycles with a wide range of biological and medicinal applications. These properties make them highly attractive for drug development, particularly when combined with sulfonamides to enhance their medicinal potential. In this work, we synthesized an indazole-based sulfonamide, namely the 1-((2-chloro-5-methoxyphenyl)sulfonyl)-5-nitro-1H-indazole (3). The reduction of the nitro group of 5-nitroindazole (1) to its corresponding amine was also performed to yield compound (4). Both compounds’ structures were elucidated using various

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3

Chen, Dong-Mei, Jia-Yan Liu, Ming Wei, Bing-Wei Wang, Ruo-Han Chu, and Dong-Sheng Chen. "Synthesis of indazolo[5,4-b][1,6]naphthyridine and indazolo[6,7-b][1,6]naphthyridine derivatives." Heterocyclic Communications 25, no. 1 (2019): 15–21. http://dx.doi.org/10.1515/hc-2019-0006.

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AbstractA simple method for the synthesis of the title compounds by an efficient in-situ reduction and cyclization reactions of aromatic aldehydes, tert-butyl 2,4-dioxopiperidine-1-carboxylate and 5-nitro-1H-indazole or 6-nitro-1H-indazole was developed.

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4

Chicha, Hakima, El Mostapha Rakib, Domenico Spinelli, Mohamed Saadi, and Lahcen El Ammari. "1-Allyl-3-chloro-5-nitro-1H-indazole." Acta Crystallographica Section E Structure Reports Online 69, no. 9 (2013): o1410. http://dx.doi.org/10.1107/s1600536813021995.

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5

Bui, Thi Thanh Cham, Hue Linh Luu, Thi Thanh Luong, et al. "An Alternative Method for Synthesizing N,2,3-Trimethyl-2H-indazol-6-amine as a Key Component in the Preparation of Pazopanib." Chemistry 6, no. 5 (2024): 1089–98. http://dx.doi.org/10.3390/chemistry6050063.

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Due to its application as an anti-cancer drug, pazopanib (1) has attracted the interest of many researchers, and several studies on pazopanib synthesis have been reported over the years. This paper provides a novel route for synthesizing N,2,3-trimethyl-2H-indazol-6-amine (5), which is a crucial building block in the synthesis of pazopanib from 3-methyl-6-nitro-1H-indazole (6). By alternating between the reduction and two methylation steps, compound 5 was obtained in a yield comparable (55%) to what has been reported (54%). It is noteworthy that the last step of N2-methylation also yielded N,N

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6

Boulhaoua, Mohammed, Sevgi Kansiz, Mohamed El Hafi, et al. "Crystal structure and Hirshfeld surface analysis of 5-[(5-nitro-1H-indazol-1-yl)methyl]-3-phenyl-4,5-dihydroisoxazole." Acta Crystallographica Section E Crystallographic Communications 75, no. 1 (2019): 71–74. http://dx.doi.org/10.1107/s2056989018017590.

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In the title compound, C17H14N4O3, the indazole unit is planar to within 0.0171 (10) Å and makes dihedral angles of 6.50 (6) and 6.79 (4)°, respectively, with the nitro and pendant phenyl groups. The conformation of the oxazole ring is best described as an envelope. In the crystal, oblique stacks along the a-axis direction are formed by π–π stacking interactions between the indazole unit and the pendant phenyl rings of adjacent molecules. The stacks are linked into pairs through C—H...O hydrogen bonds. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most impo

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7

Kouakou, Assoman, El Mostapha Rakib, Mohamed Chigr, Mohamed Saadi, and Lahcen El Ammari. "Crystal structure of 3-chloro-1-methyl-5-nitro-1H-indazole." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): o834—o835. http://dx.doi.org/10.1107/s2056989015018411.

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The molecule of the title compound, C8H6ClN3O2, is built up from fused five- and six-membered rings connected to a chlorine atom and to nitro and methyl groups. The indazole system is essentially planar with the largest deviation from the mean plane being 0.007 (2) Å. No classical hydrogen bonds are observed in the structure. Two molecules form a dimer organised by a symmetry centreviaa close contact between a nitro-O atom and the chlorine atom [at 3.066 (2) Å this is shorter than the sum of their van der Waals radii].

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8

Pakjoo, Vahid, Mina Roshani, Mehdi Pordel, and Toktam Hoseini. "Synthesis of new fluorescent compounds from 5-nitro-1H-indazole." Arkivoc 2012, no. 9 (2012): 195–203. http://dx.doi.org/10.3998/ark.5550190.0013.917.

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9

Pinard, Elisabeth, Nicolas Engrand, and Jacques Seylaz. "Dynamic Cerebral Microcirculatory Changes in Transient Forebrain Ischemia in Rats: Involvement of Type I Nitric Oxide Synthase." Journal of Cerebral Blood Flow & Metabolism 20, no. 12 (2000): 1648–58. http://dx.doi.org/10.1097/00004647-200012000-00004.

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The diameter of surface microvessels and the erythrocyte velocity and flux through intraparenchymal capillaries in the parietal cortex were measured during transient global cerebral ischemia and reperfusion using laser-scanning confocal fluorescence microscopy in anesthetized rats. The role of nitric oxide (NO) from neurons in the microcirculatory changes was also investigated using 7-nitro-indazole (7-NI, 25 mg/kg, IP). Wistar rats (4 per group) equipped with a closed cranial window were given fluorescein isothiocyanate (FITC)-Dextran and FITC-labeled erythrocytes intravenously to respectivel

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10

Cuartas, Crespo, Priego, et al. "Design and Synthesis of New 6-Nitro and 6-Amino-3,3a,4,5-Tetrahydro-2H-Benzo[g]indazole Derivatives: Antiproliferative and Antibacterial Activity." Molecules 24, no. 23 (2019): 4236. http://dx.doi.org/10.3390/molecules24234236.

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New substituted benzo[g]indazoles functionalized with a 6-nitro and 6-amino groups have been synthesized by the reaction of benzylidene tetralones with hydrazine in acetic acid. The resulting conformationally-constrained compounds were evaluated for their antiproliferative activity against selected cancer cell lines. The nitro-based indazoles 11a, 11b, 12a and 12b have shown IC50 values between 5–15 μM against the lung carcinoma cell line NCI-H460. Moreover, the nitro compounds were tested for antibacterial activity where compounds 12a and 13b have shown MIC values of 250 and 62.5 μg/mL agains

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11

Kouakou, Assoman, El Mostapha Rakib, Abdelghani El Malki, Mohamed Saadi, and Lahcen El Ammari. "6,6′-Dinitro-1,1′-(ethane-1,2-diyl)di(1H-indazole)." Acta Crystallographica Section E Structure Reports Online 70, no. 4 (2014): o390. http://dx.doi.org/10.1107/s1600536814004516.

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The molecule of the title compound, C16H12N6O4, is built up from two fused five- and six-membered rings linked by an ethylene group. The dihedral angle between the planes through the indazole ring systems is 39.74 (5)°. The nitro groups are tilted by 7.2 (2) and 8.5 (2)° with respect to planes of the fused-ring systems. In the crystal, molecules are linked by C—H...N and C—H...O hydrogen bonds into chains running parallel to thecaxis.

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12

Durgesh, Rudavath, Sreenivasulu Reddymasu, Rao Pinapati Srinivasa, and Ramesh Raju Rudraraju. "Synthesis and anticancer evaluation of indazole-aryl hydrazide-hydrazone derivatives." Journal of India Chemical Society Vol. 95, Apr 2018 (2018): 433–38. https://doi.org/10.5281/zenodo.5642515.

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Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, Andhra Pradesh, India E-mail: rrraju1@gmail.com Department of Chemistry, University College of Engineering (Autonomous), Jawaharlal Nehru Technological University, Kakinada-533 003, Andhra Pradesh, India <em>Manuscript received 24 February 2018, revised 01 March 2018, accepted 02 March 2018</em> A new series of hydrazide-hydrazones linked between indazole and substituted benzaldehydes were designed, synthesized and evaluated for their cytotoxicity against four human cancer cell lines (HeLa, MDAMB- 231, MCF-7 and A5

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13

Fernández, Soledad, Javier Giglio, Ana Laura Reyes, et al. "3-(Benzyloxy)-1-(5-[18F]fluoropentyl)-5-nitro-1H-indazole: a PET radiotracer to measure acetylcholinesterase in brain." Future Medicinal Chemistry 9, no. 10 (2017): 983–94. http://dx.doi.org/10.4155/fmc-2017-0023.

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14

UKHIN, L. YU, ZH I. ORLOVA, S. V. LINDEMAN, V. N. KHRUSTALEV, YU T. STRUCHKOV, and A. I. PROKOF'EV. "ChemInform Abstract: Synthesis and Properties of 2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5- nitro-indazole." ChemInform 26, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199506140.

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15

Arán, V. J., M. Stud, C. Foces-Foces, F. H. Cano, and M. Martínez-Ripoll. "Synthesis of indazole derivatives from aN,N-disubstituted 2-halobenzoic hydrazide. Crystal structure of 1,2-pentamethylene-5-nitro-1,2-dihydro-3H-indazol-3-one." Journal of Heterocyclic Chemistry 22, no. 6 (1985): 1743–45. http://dx.doi.org/10.1002/jhet.5570220655.

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16

Kumar, K. Pushpa, Pandreti Vedavathi, K. Venkata Subbaiah, D. Venkata Ramana Reddy, and C. Naga Raju. "Design, synthesis, spectral characterization and bioactivity evaluation of new sulfonamide and carbamate derivatives of 5-Nitro-1H-indazole." Organic Communications 10, no. 3 (2017): 239–49. http://dx.doi.org/10.25135/acg.oc.24.17.05.023.

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17

Toyoda, Kazunori, Kenichiro Fujii, Setsuro Ibayashi, Tetsuhiko Nagao, Takanari Kitazono, and Masatoshi Fujishima. "Role of Nitric Oxide in Regulation of Brain Stem Circulation during Hypotension." Journal of Cerebral Blood Flow & Metabolism 17, no. 10 (1997): 1089–96. http://dx.doi.org/10.1097/00004647-199710000-00011.

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We tested the hypothesis that nitric oxide (NO) plays a role in CBF autoregulation in the brain stem during hypotension. In anesthetized rats, local CBF to the brain stem was determined with laser-Doppler flowmetry, and diameters of the basilar artery and its branches were measured through an open cranial window during stepwise hemorrhagic hypotension. During topical application of 10−5 mol/L and 10−4 mol/L Nω-nitro-L-arginine (L-NNA), a nonselective inhibitor of nitric oxide synthase (NOS), CBF started to decrease at higher steps of mean arterial blood pressure in proportion to the concentrat

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18

Escott, Katherine J., John S. Beech, Kristin K. Haga, Steve C. R. Williams, Brian S. Meldrum, and Philip M. W. Bath. "Cerebroprotective Effect of the Nitric Oxide Synthase Inhibitors, 1-(2-Trifluoromethylphenyl) Imidazole and 7-Nitro Indazole, after Transient Focal Cerebral Ischemia in the Rat." Journal of Cerebral Blood Flow & Metabolism 18, no. 3 (1998): 281–87. http://dx.doi.org/10.1097/00004647-199803000-00006.

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The novel neuronal nitric oxide synthase inhibitors, 1-(2-trifluoromethylphenyl)imidazole (TRIM) and 7-nitro indazole (7-NI), were used to investigate the role of nitric oxide in a model of transient focal cerebral ischemia in vivo. In halothane-anesthetized rats, the middle cerebral artery (MCA) was occluded for 2 hours using an intravascular thread and then reperfused for 22 hours before histologic evaluation. TRIM (10, 20, or 50 mg/kg), 7-NI (60 mg/kg), TRIM (50 mg/kg) plus L-arginine (300 mg/kg), or L-arginine (300 mg/kg) alone was administered intraperitoneally, either at 5 or 90 minutes

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19

E. Kaufmann, Dieter, Viktor A. Zapol'skii, Jan C. Namyslo, and Mimoza Gjikaj. "Chemistry of Polyhalogenated Nitrobutadienes, 15: Synthesis of Novel 4-Nitro-3-amino-1H-pyrazole-5-carbaldehydes and Pyrazolo[3,4-f]indazole-4,8-diones." HETEROCYCLES 93, no. 2 (2016): 628. http://dx.doi.org/10.3987/com-15-s(t)46.

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20

Cerwinka, Wolfgang H., Dianne Cooper, Christian F. Krieglstein, Martin Feelisch, and D. Neil Granger. "Nitric oxide modulates endotoxin-induced platelet-endothelial cell adhesion in intestinal venules." American Journal of Physiology-Heart and Circulatory Physiology 282, no. 3 (2002): H1111—H1117. http://dx.doi.org/10.1152/ajpheart.00391.2001.

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Although platelets have been implicated in the pathogenesis of vascular diseases, little is known about factors that regulate interactions between platelets and the vessel wall under physiological conditions. The objectives of this study were to 1) define the contribution of nitric oxide (NO) to endotoxin (lipopolysaccharide, LPS)-induced platelet-endothelial cell (P/E) adhesion in murine intestinal venules and 2) determine whether the antiadhesive action of NO is mediated by soluble guanylate cyclase (sGC). Adhesive interactions between platelets and endothelial cells were monitored by intrav

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21

Boulhaoua, Mohammed, Mohammed Benchidmi, El Mokhtar Essassi, Mohamed Saadi, and Lahcen El Ammari. "Crystal structure of triethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tricarboxylate." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (2015): o780—o781. http://dx.doi.org/10.1107/s2056989015017235.

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In the title compound, C19H23N3O8, the 5-nitro-2H-indazol-2-yl unit is almost planar, with the maximum deviation from the mean plane being 0.024 (2) Å. The fused-ring system is nearly perpendicular to the three carboxylate groups, with dihedral angles of 90.0 (3), 83.8 (1) and 80.4 (1)°. The ethyl groups attached to both ends of the propane chain are each disordered over two sets of sites, with site-occupancy ratios of 0.425 (17):0.575 (17) and 0.302 (15):0.698 (15). In the crystal, molecules are linked by pairs of C—H...N hydrogen bonds, forming inversion dimers. The dimers are further linked

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22

Annor-Gyamfi, Joel, Krishna Gnanasekaran, and Richard Bunce. "Syntheses of 1-Aryl-5-nitro-1H-indazoles and a General One-Pot Route to 1-Aryl-1H-indazoles." Molecules 23, no. 3 (2018): 674. http://dx.doi.org/10.3390/molecules23030674.

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23

Fonseca-Berzal, Cristina, Cristiane França da Silva, Denise da Gama Jaen Batista, et al. "Activity profile of two 5-nitroindazole derivatives over the moderately drug-resistant Trypanosoma cruzi Y strain (DTU TcII): in vitro and in vivo studies." Parasitology 147, no. 11 (2020): 1216–28. http://dx.doi.org/10.1017/s0031182020000955.

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AbstractIn previous studies, we have identified several families of 5-nitroindazole derivatives as promising antichagasic prototypes. Among them, 1-(2-aminoethyl)-2-benzyl-5-nitro-1,2-dihydro-3H-indazol-3-one, (hydrochloride) and 1-(2-acetoxyethyl)-2-benzyl-5-nitro-1,2-dihydro-3H-indazol-3-one (compounds 16 and 24, respectively) have recently shown outstanding activity in vitro over the drug-sensitive Trypanosoma cruzi CL strain (DTU TcVI). Here, we explored the activity of these derivatives against the moderately drug-resistant Y strain (DTU TcII), in vitro and in vivo. The outcomes confirmed

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24

Recabarren-Gajardo, G., M. Gacitúa, I. Murueva, et al. "Synthesis, characterization, and electrochemical studies of new 5- and 6-nitro N -acyl-1H -indazoles." Journal of Physical Organic Chemistry 24, no. 12 (2011): 1179–87. http://dx.doi.org/10.1002/poc.1843.

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25

Fonseca-Berzal, Cristina, Alexandra Ibáñez-Escribano, Felipe Reviriego, et al. "Antichagasic and trichomonacidal activity of 1-substituted 2-benzyl-5-nitroindazolin-3-ones and 3-alkoxy-2-benzyl-5-nitro-2H-indazoles." European Journal of Medicinal Chemistry 115 (June 2016): 295–310. http://dx.doi.org/10.1016/j.ejmech.2016.03.036.

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26

Alipoor, Hamideh, Mehdi Pordel, and Ali Morsali. "Synthesis, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3H-benzo[a]pyrazolo[3,4-j]acridine." Journal of Chemical Research 41, no. 7 (2017): 371–75. http://dx.doi.org/10.3184/174751917x14967701766914.

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Four new fluorescent dyes derived from the 3 H-benzo[ a]pyrazolo[3,4- j]acridine system were synthesised and fully characterised by 1H NMR, 13C NMR, mass and analytical data. These new fluorophores were prepared from the reaction of 1-alkyl-5-nitro-1 H-indazoles with 1-naphthylacetonitrile via nucleophilic substitution of hydrogen, in high yields. The optical properties of the dyes were also investigated and the results revealed that, in some cases, they have higher quantum yields compared with well-known fluorescent dyes such as fluorescein. Solvent effects on the fluorescence characteristics

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27

Folch-Cano, Christian, Claudio Olea-Azar, Vicente J. Arán, and Christian Diaz-Urrutia. "ESR and electrochemical study of 1,2-disubstituted 5-nitroindazolin-3-ones and 2-substituted 3-alkoxy-5-nitro-2H-indazoles: Reactivity and free radical production capacity in the presence of biological systems." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75, no. 1 (2010): 375–80. http://dx.doi.org/10.1016/j.saa.2009.10.044.

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28

Kachi, Onkar G., Hari R. Pawar, Swati Jagdale, et al. "Design and Synthesis of 5-nitro Indazole Acetamides and Evaluation of their Antitubercular and Antifungal Activities." Current Bioactive Compounds 21 (May 16, 2025). https://doi.org/10.2174/0115734072364579250505080057.

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Aim: To design, synthesize, and evaluate 5-nitro indazole acetamide molecules for their antitubercular and antifungal activities. Background: The emergence of fungal resistance, multidrug-resistant strains of Mycobacterium tuberculosis, co-infections involving tuberculosis, and the recurrence of fungal diseases such as COVID-19 highlight the need for the design and synthesis of novel therapeutic molecules. Objective: The objective of the study is to design, synthesize, and evaluate 5-nitro indazole acetamides and evaluate them against fungi and tuberculosis. Method: Molecules were designed by

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29

Boulhaoua, Mohammed, Mohamed El Hafi, Mohammed Benchidmi, El Mokhtar Essassi, and Joel T. Mague. "1-Ethyl-5-nitro-1H-indazole." IUCrData 1, no. 4 (2016). http://dx.doi.org/10.1107/s2414314616005678.

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In the title molecule, C9H9N3O2, the nitro substituent is twisted by 4.0 (2)° out of the plane of the indazolyl moiety; the ethyl group is perpendicular to the indazolyl plane, with the N—N—C—C torsion angle being 101.4 (2)°. In the molecular packing, C—H...O hydrogen bonds lead to supramolecular chains along [001]. Globally, molecules assemble into layers in thebcplane. π–π interactions between five- and six-membered rings consolidate the three-dimensional packing [inter-centroid distance = 3.591 (1) Å]. The sample was refined as an inversion twin.

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30

Boulhaoua, Mohammed, Mohammed Mokhtar Abdelahi, Mohammed Benchidmi, El Mokhtar Essassi, and Joel T. Mague. "1-Benzyl-5-nitro-1H-indazole." IUCrData 1, no. 3 (2016). http://dx.doi.org/10.1107/s2414314616004855.

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31

Naas, Mohammed, Mohammed Benchidmi, El Mokhtar Essassi, Mohamed Saadi, and Lahcen El Ammari. "1-Methyl-5-nitro-3-phenyl-1H-indazole." IUCrData 1, no. 6 (2016). http://dx.doi.org/10.1107/s2414314616009615.

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The title compound, C14H11N3O2, crystallizes with two molecules in the asymmetric unit. The indazole ring system and the nitro group are nearly coplanar, with the largest deviations from the mean plane being 0.070 (4) Å in one molecule and 0.022 (3) Å in the second. The dihedral angle between the mean plane through the phenyl ring and the mean plane of the indazole ring system is of 23.24 (18)° in the first molecule and 26.87 (18)° in the second. In the crystal, molecules are linked by two C—H...O hydrogen bonds, forming linear zigzag tapes running along thec-axis direction, and by π–π stackin

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32

Boulhaoua, Mohammed, Mohamed El Hafi, Mohammed Benchidmi, El Mokhtar Essassi, and Joel T. Mague. "5-Nitro-1-(prop-2-yn-1-yl)-1H-indazole." IUCrData 1, no. 3 (2016). http://dx.doi.org/10.1107/s2414314616004806.

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The packing of the title molecule, C10H7N3O2, features the formation of weak dimersviapairwise C—H...O interactions across centers of symmetry. The prop-2-yn-1-yl moiety is twisted out of the plane of the indazole unit by 78.53 (17)°.

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33

Boulhaoua, Mohammed, Abdelhanine Essaghouani, Sanae Lahmidi, Mohammed Benchidmi, El Mokhtar Essassi, and Joel T. Mague. "5-Nitro-1-(prop-2-en-1-yl)-1H-indazole." IUCrData 2, no. 7 (2017). http://dx.doi.org/10.1107/s2414314617010914.

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In the crystal, the title molecule, C10H9N3O2, packs in layers approximately parallel to (100), which are formed by the association of zigzag chains constructed by weak C—H...O interactions. The allyl group is disordered over two positions, with a ratio of their occupancies close to 70:30.

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34

Yadav, Mithlesh, Rekha Rao, Sunil Kumar, and Archana Kapoor. "Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling." ChemistrySelect 8, no. 45 (2023). http://dx.doi.org/10.1002/slct.202303592.

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AbstractA new series of N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (4 a–i) and N‐(1‐(2‐chloropyrimidin‐4‐yl)‐6‐ethoxy‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (5 a–i) was synthesized via reduction of 1‐(2‐halopyrimidin‐4‐yl)‐5‐nitro‐1H‐indazole (3) with SnCl2 followed by reaction with various aryl sulphonyl chlorides in pyridine. The structures were confirmed using IR, 1H‐NMR, 13C‐NMR, and mass spectral methods. Compounds 4 a–i and 5 a–i were evaluated for antifungal and antibacterial activities against Gram‐negative and Gram‐positive bacteria. They al

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35

Nguyễn, Văn Hải, Thị Thanh Châm Bùi, Quốc Hùng Phan, et al. "Process of Preparing 3-methyl-6-nitro-1H-indazole by Scale of 180 g/batch as an Important Intermediate for the Preparation of Pazopanib." VNU Journal of Science: Medical and Pharmaceutical Sciences, October 24, 2023. http://dx.doi.org/10.25073/2588-1132/vnumps.4540.

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Pazopanib hydrochloride, marketed worldwide under the brand name Votrient, is an anti-cancer medication manufactured by Novartis. It is the first and only tyrosine kinase inhibitor currently approved for the treatment of multiple histological subtypes of soft tissue sarcoma (STS). In previous studies, we presented initial results regarding the synthesis of 3-methyl-5-nitro-2H-indazole (3) as an important indazole component on a laboratory scale (approximately 10 g/batch). In this study, we have successfully synthesized this compound (3) at a scale of 200 g/batch, achieving an overall process y

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36

Mollineda-Diogo, Niurka, Claudia Sissely Chaviano-Montes de Oca, Sergio Sifontes-Rodríguez, et al. "Antileishmanial activity of 5-nitroindazole derivatives." Therapeutic Advances in Infectious Disease 10 (January 2023). http://dx.doi.org/10.1177/20499361231208294.

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Background: Currently, there is no safe and effective vaccine against leishmaniasis and existing therapies are inadequate due to high toxicity, cost and decreased efficacy caused by the emergence of resistant parasite strains. Some indazole derivatives have shown in vitro and in vivo activity against Trichomonas vaginalis and Trypanosoma cruzi. On that basis, 20 indazole derivatives were tested in vitro against Leishmania amazonensis. Objective: To evaluate the in vitro activity of twenty 2-benzyl-5-nitroindazolin-3-one derivatives against L. amazonensis. Design: For the selection of promising

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ARAN, V. J., M. STUD, C. FOCES-FOCES, F. H. CANO, and M. MARTINEZ-RIPOLL. "ChemInform Abstract: Synthesis of Indazole Derivatives from a N,N-Disubstituted 2-Halobenzoic Hydrazide. Crystal Structure of 1,2-Pentamethylene-5-nitro-1,2-dihydro-3H-indazol-3-one." Chemischer Informationsdienst 17, no. 32 (1986). http://dx.doi.org/10.1002/chin.198632101.

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Yadav, Mithlesh, Suraj N. Mali, Bharti Sharma, and Archana Kapoor. "Exploring 5-Nitro-N-phenyl-3-(phenylamino)-1H-indazole-1-carboxamide (5-NPIC) Derivatives as Anticancer Agents: Synthesis, Docking, and Molecular Dynamics Insights." Journal of Computational Biophysics and Chemistry, October 4, 2024. http://dx.doi.org/10.1142/s2737416524500650.

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Alkorta, Ibon, Rosa M. Claramunt, José Elguero, et al. "Study of the Addition Mechanism of 1H-Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions." Journal of Organic Chemistry, April 11, 2022. http://dx.doi.org/10.1021/acs.joc.2c00154.

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Yadav, Mithlesh, Suraj N. Mali, Bharti Sharma, et al. "Synthesis, Antioxidant, Antimicrobial Activities and Molecular Modeling analysis of some 5-Nitro-N-phenyl-3-(phenylamino)-1H-indazole-1-carboxamide Derivatives: Docking, SAR, Toxicity and Molecular Dynamics Analysis." Chemical Physics Impact, August 2024, 100705. http://dx.doi.org/10.1016/j.chphi.2024.100705.

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Boulhaoua, Mohammed, Abdelhanine Essaghouani, Mohammed Benchidmi, El Mokhtar Essassi, and Joel T. Mague. "1-(5-Nitro-1H-indazol-1-yl)ethanone." IUCrData 1, no. 6 (2016). http://dx.doi.org/10.1107/s2414314616009391.

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Jagadeesan, S., and S. Karpagam. "Docking Investigation on Bis (Nitro Indazolyl) Methanes; Synthesis and Antimicrobial Activity Towards Breast Cancer Applications." Letters in Organic Chemistry 18 (February 4, 2021). http://dx.doi.org/10.2174/1570178618666210204110358.

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: Bismuth (III) nitrate pentahydrate (BN) was found to be a mild and efficient catalyst for the electrophilic condensation of 5-nitroindazole with a wide range of aldehydes to obtain Bis (5-nitro indazolyl) methanes 3 (a-h) at ambient temperature. This was structurally confirmed from FTIR, NMR, and HR-MS technique. Molecular docking studies of all compounds was carried out using breast cancer-causing human estrogen receptor (ER) from Molegro Virtual Docker software. Hydroxy Bis (nitro indazolyl) methanes (3b) were shown better binding affinities and the score obtained was -150.146 Kcal/mol com

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Boulhaoua, Mohammed, Mohammed Benchidmi, El Mokhtar Essassi, Mohamed Saadi, and Lahcen El Ammari. "2-(3-Bromo-5-nitro-1H-indazol-1-yl)-1-phenylethanone." IUCrData 2, no. 4 (2017). http://dx.doi.org/10.1107/s2414314617005594.

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The 5-nitro-1H-indazol-1-yl moiety of the title compound, C15H10BrN3O3, is approximately planar, with the largest deviation from the mean plane being 0.079 (3) Å. The fused-ring system is virtually perpendicular to the mean plane through the 1-phenylethanone group, making a dihedral angle of 89.7 (2)°. In the crystal, pairs of molecules form inversion dimersviaBr...O interactions [3.211 (2) Å]. The dimers are connected by C—H...O and C—H...N non-classical hydrogen bonds, in addition to π–π interactions [intercentroid distance = 3.6411 (12) Å], forming a three-dimensional network.

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El Hafi, Mohamed, Mohammed Boulhaoua, Sanae Lahmidi, et al. "Synthesis, X-Ray, Spectral Characterization, DFT, and Molecular Docking Calculations of 2-(5-Nitro-1- H -Indazol-1-yl) Acetic Acid." Polycyclic Aromatic Compounds, October 9, 2023, 1–17. http://dx.doi.org/10.1080/10406638.2023.2264453.

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