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1

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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2

HUSAIN, Asif, Aftab AHMAD, Anil BHANDARI, and Veerma RAM. "ANTITUBERCULAR ACTIVITY OF SOME NEWER 6-PYRIDAZINONE DERIVATIVES." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 19, no. 19 (December 20, 2011): 17–23. http://dx.doi.org/10.48141/sbjchem.v19.n19.2011.22_2011.pdf.

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Two series of 6-pyridazinone derivatives (17-30) were synthesized and evaluated for antitubercular activities against the Mycobacterium tuberculosis H37Rv strain. The results indicated that among the synthesized compounds, 5-( 4-hydroxy-3-methoxybenzyl}-3-phenyl-1,6-dihydro-6-pyridazinone (23) showed good antitubercular activity. Three more compounds, (18, 25 & 27) were significant in their antitubercular action. The present study reveals the antitubercular potential of 6-pyridazinones.
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3

Rodriguez, Christina, Rachel Kiriakopoulos, Lana K. Hiscock, Zachary Schroeder, and Louise N. Dawe. "Pyridazinones from maleic hydrazide: a new substrate for the Mitsunobu reaction." Canadian Journal of Chemistry 98, no. 6 (June 2020): 273–77. http://dx.doi.org/10.1139/cjc-2019-0474.

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Crystal engineered organic frameworks assembled using hydrogen bonding are known, and examples constructed from hydroxypyridine/pyridone as the dominant source of hydrogen bonding have been reported. Less explored are analogous systems based on maleic hydrazide. Herein, a two-step route (Mitsunobu followed by Schiff base reactions) to asymmetrically substituted pyridazinones from maleic hydrazide (step 1) is reported with 2-, 3-, or 4-pyridinecarboxaldehyde (step 2). Upon reaction with 4-pyridinecarboxaldehyde, single crystals suitable for analysis via X-ray diffraction were obtained. Careful examination of this solid state structure and comparison with a large number of related structures in the Cambridge Structural Database revealed a pyridazinone (vs. pyridazinol) core and persistent [Formula: see text] “head-to-tail” hydrogen bonded dimers. Although these pyridazinones were originally considered suitable for use as ligands for metal cation coordination, challenges in achieving this outcome were encountered.
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4

Rimaz, Mehdi, Jabbar Khalafy, and Peyman Najafi Moghadam. "A Regioselective One-Pot, Three Component Synthesis of 6-Aryl-4-cyano-3(2H)-pyridazinones in Water." Australian Journal of Chemistry 63, no. 9 (2010): 1396. http://dx.doi.org/10.1071/ch09602.

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A series of 4-cyano-3(2H)-pyridazinones bearing different aryl substituents in the 6-position of the pyridazinone ring was synthesized regioselectively using a novel efficient one-pot three component reaction of alkyl 2-cyanoacetates with arylglyoxals in the presence of hydrazine hydrate at room temperature in water.
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5

Asif, Mohammad. "Some Conventional and Convenient Process for Functionalization of 6-Phenyl-4,5-Dihydropyridazinone Compounds." Asian Journal of Chemistry and Pharmaceutical Sciences 1, no. 1 (November 21, 2016): 41. http://dx.doi.org/10.18311/ajcps/2016/8375.

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The pyridazinone derivatives, particularly those bearing substituted different group or atom at a different position, have attracted considerable attention due to their characteristic pharmacological and other anticipated activities. These activities promoted the synthesis of a large number of substituted pyridazinone derivatives in order to explore the usefulness of this heterocyclic system. In the present review, various synthetic methods have been studied for the synthesis of substituted pyridazinone derivatives. The behaviour of the pyridazinone toward formaldehyde/piperidine, ethyl chloroacetate, chloroacetic acid, benzene sulfonyl chloride, bromine/acetic acid and aromatic aldehydes has also been studied. However, the reactions of the chloro derivative resulting from the reaction of pyridazinone with phosphorus oxychloride (POCl<sub>3</sub>). The behavior of chloropyridazine toward hydrazines, thiourea, sodium azide, anthranilic acid, aromatic amines and sulfa compounds have also been taken into consideration. Thethiopyridazinone derivativeswere prepared from the reaction of pyridazinone with phosphorus pentasulphide (P<sub>2</sub>S<sub>5</sub>). All the structures of were established on the based of spectroscopic data.<p> </p><p><strong> </strong></p>
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6

Widell, Karl-Olof, Christer Sundqvist, and Hemming I. Virgin. "Characterization of SAN 9789-Stimulated Lettuce (Lactuca sativa) Seed Germination." Weed Science 33, no. 2 (March 1985): 160–64. http://dx.doi.org/10.1017/s0043174500082023.

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Dark germination of light-requiring lettuce seeds (Lactuca sativaL. ‘Grand Rapids’) was stimulated by SAN 9789 [4-chloro-5-(methylamino-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone] and to a minor degree by BASF 13761 [4-chloro-5-methoxy-2-phenyl-3(2H)-pyridazinone] and BASF 44521 [4-chloro-5-methoxy-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone], but not by’ pyrazon [5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone], SAN 9785 [4-chloro-5-(dimethylamino)-2-phenyl-3 (2H)-pyridazinone], SAN 9774 [5-amino-4-chloro-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone], or SAN 6706 [4-chloro-5-(dimethylamino)-2-(α,α,α-trifluoro-m-tolyl)-3(2H)-pyridazinone]. SAN 9789 stimulation was inhibited by cis-4-cyclohexene-1,2-dicarboximide (CHDC), and abscisic acid (ABA) at 1 × 10-4M. Red light nullified the inhibitory effect of CHDC (1 × 10-4M) but not the inhibitory effect of ABA (1 × 10-4M) on SAN 9789 stimulated germination. Gibberellic acid (GA3) and kinetin (6-furfurylaminopurine) increased the germination stimulatory effect of SAN 9789 in darkness. Temperatures above 25 C decreased the effect of SAN 9789, with a temperature of 35 C completely inhibiting germination. The inhibitory effect of CHDC was strongly decreased at temperatures below 20 C. SAN 9789-induced germination in darkness was always the same (25 to 26% units increase in germination) even though the red light-stimulated germination differed with the seed batch.
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7

Li, Hong Sen, Lin Jing Zhao, Jia Rong Tang, Yi Zhe Cheng, Jie Chen, Zhi Yi Zheng, and Hai Lin Sun. "Study on New 3-(2H)-Pyridazinones Derivtives." Advanced Materials Research 524-527 (May 2012): 1751–54. http://dx.doi.org/10.4028/www.scientific.net/amr.524-527.1751.

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A series of novel pyridazinone derivatives was designed and synthesized. Insecticide activities of 7 pyridazinone derivatives were evaluated. The Preliminary bioassy test showed that compounds exhibited mild activity or moderate activity against Oriental armyworm at 200mg L-1
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8

El Kalai, Fouad, Cemile Baydere, Said Daoui, Rafik Saddik, Necmi Dege, Khalid Karrouchi, and Noureddine Benchat. "Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate." Acta Crystallographica Section E Crystallographic Communications 75, no. 6 (May 24, 2019): 892–95. http://dx.doi.org/10.1107/s2056989019007424.

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The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C—H...O hydrogen bonds generate dimers with R 2 2(10) and R 2 2(24) ring motifs which are linked by C—H...O interactions, forming chains extending parallel to the c-axis direction. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H...H (44.5%), C...H/H...C (18.5%), H...O/H...O (15.6%), Cl...H/H...Cl (10.6%) and C...C (2.8%) contacts.
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9

Wasfy, Ashraf A. F., Mohamed M. H. Arief, Mahassen S. Amine, Shafey G. Donia, and Aly A. Aly. "γ-Oxo Carboxylic Acids in Heterocyclic Synthesis, III. Synthesis of Biologically Active 4-Benzylamino-6-(5,5-dioxodibenzothiophen- 2-yl)-2,3,4,5-tetrahydropyridazin-3-ones." Zeitschrift für Naturforschung B 57, no. 6 (June 1, 2002): 668–76. http://dx.doi.org/10.1515/znb-2002-0613.

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α-Benzylamino-β-(5,5-dioxodibenzothiophen-2-carbonyl)propionic acid (1) has been synthesized by treating the corresponding β-aroylacrylic acid with benzylamine in dry benzene. On treatment with hydrazine hydrate the keto acid 1 furnishes the corresponding pyridazinone derivative 2. The behaviour of 2 towards carbon electrophiles, namely, ethyl chloroacetate, acrylonitrile, formaldehyde and secondary amines (under Mannich reaction conditions), aromatic aldehydes and carbon nucleophiles, namely, POCl3/PCl3 and P2S5 has been investigated. The 3-chloropyridazine derivative 13 reacts with hydrazine hydrate to give the 3-hydrazino derivative 14. On treatment with ethyl acetoacetate and/or acetylacetone the hydrazine 14 undergoes cyclization to afford pyrazolone derivative 16 and 3-(3,5-dimethylpyrazol- 1-yl)pyridazine derivative 17, respectively. On reaction with acetylhydrazine in boiling butanol and/or sodium azide in DMF the 3-chloropyridazine derivative 13 affords the triazolo[4,3-b]pyridazine 18 and the tetrazolo[1,5-b]pyridazine 19, respectively. The anti-microbial activity of the synthesized derivatives has been investigated.
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10

Costas-Lago, María Carmen, Tamara Costas, Noemí Vila, and Pedro Besada. "4-[(tert-Butyldiphenylsilyloxy)methyl]pyridazin-3(2H)-one." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (November 30, 2013): o1859—o1860. http://dx.doi.org/10.1107/s1600536813032212.

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In the title compound, C21H24N2O2Si, the carbonyl group of the heterocyclic ring and the O atom of the silyl ether group are placed toward opposite sides and thetert-butyl and pyridazinone moieties areanti-oriented across the Si—O bond [torsion angle = −168.44 (19)°]. In the crystal, molecules are assembled into inversion dimers through co-operative N—H...O hydrogen bonds between the NH groups and O atoms of the pyridazinone rings of neighbouring molecules. The dimers are linked by π–π interactions involving adjacent pyridazinone rings [centroid–centroid distance = 3.8095 (19) Å], generating ladder-like chains along theb-axis direction. The chains are further linked into a two-dimensional network parallel to theabplane through weak C—H...π interactions.
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11

Hu, Zilun, Cailan Wang, Wei Han, Karen A. Rossi, Jeffrey M. Bozarth, Yiming Wu, Steven Sheriff, et al. "Pyridazine and pyridazinone derivatives as potent and selective factor XIa inhibitors." Bioorganic & Medicinal Chemistry Letters 28, no. 6 (April 2018): 987–92. http://dx.doi.org/10.1016/j.bmcl.2018.02.049.

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12

Tao, Jing. "Synthesis of Aldehyde Hydrazones Containing Pyridazinone." Advanced Materials Research 361-363 (October 2011): 2008–11. http://dx.doi.org/10.4028/www.scientific.net/amr.361-363.2008.

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The reaction of 1,4,5,6-tetrahydro-6-pyridazinone-3-carboxylic acid hydrazides (1) and 1,6-dihydro-6-pyridazinone-3-carboxylic acid hydrazides (2) with four kind of substituted 3-formyl chromones (3a-3d) and five kind of 1-phenyl-3-aryl-4-formylpyrazoles (3e-3i) afforded the new compounds aldehyde hydrazones (4a-4i) and (5a-5i). Their structures were established by IR, 1H NMR and elemental analysis.
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13

Samanta, Kartick Chandra, Mohd Asif, Pooja, Vikas Garg, Priyanka Sharma, and Ravinder Singh. "Synthesis of Different Substituted Pyridazinone Derivatives and Their Anticonvulsant Activity." E-Journal of Chemistry 8, no. 1 (2011): 245–51. http://dx.doi.org/10.1155/2011/873470.

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6-Phenyl(3᾽-imino-benzylidene)-2,3,4,5-tetrahydro pyridazin-3-one derivatives were synthesized from 6-(3᾽-aminophenyl)-2,3,4,5-tetrahydro pyridazin-3-one by reaction with different aldehydes. The respective pyridazinone was prepared by cyclization of appropriateβ-(aminophenyl) propionic acid with hydrazine hydrate. The pyridazinone derivatives were tested for anticonvulsant activity by MES (maximal electro shock) method and found that few of them have shown significant anticonvulsant activity.
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14

Daoui, Said, Emine Berrin Cinar, Necmi Dege, Tarik Chelfi, Fouad El Kalai, Abdulmalik Abudunia, Khalid Karrouchi, and Noureddine Benchat. "Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one." Acta Crystallographica Section E Crystallographic Communications 77, no. 1 (January 1, 2021): 23–27. http://dx.doi.org/10.1107/s205698902001573x.

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The title pyridazinone derivative, C19H14Cl2N2O, an important pharmacophore with a wide variety of biological applications is not planar, the chlorophenyl and pyridazinone rings being almost perpendicular, subtending a dihedral angle of 85.73 (11)°. The phenyl ring of the styryl group is coplanar with the pyridazinone ring [1.47 (12)°]. In the crystal, N—H...O hydrogen bonds form inversion dimers with an R 2 2(8) ring motif and C—H...Cl hydrogen bonds also occur. The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (37.9%), C...H/H...C (18.7%), Cl...H/ H...Cl (16.4%) and Cl...C/C...Cl (6.7%) contacts.
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15

Daoui, Said, Cemile Baydere, Fouad El Kalai, Lhassane Mahi, Necmi Dege, Khalid Karrouchi, and Noureddine Benchat. "Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[5-(4-methylbenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetic acid." Acta Crystallographica Section E Crystallographic Communications 75, no. 12 (November 26, 2019): 1925–29. http://dx.doi.org/10.1107/s2056989019015317.

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The title pyridazinone derivative, C20H18N2O3, is not planar. The phenyl ring and the pyridazine ring are inclined to each other by 10.55 (12)°, whereas the 4-methylbenzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)°. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers with an R 2 2(14) ring motif. The dimers are linked by C—H...O hydrogen bonds, generating ribbons propagating along the c-axis direction. The intermolecular interactions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. They revealed that the most significant contributions to the crystal packing are from H...H (48.4%), H...O/O...H (21.8%) and H...C/C...H (20.4%) contacts. Molecular orbital calculations providing electron-density plots of HOMO and LUMO molecular orbitals and molecular electrostatic potentials (MEP) were also computed, both with the DFT/B3LYP/6–311 G++(d,p) basis set.
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16

Walker, Scott S., Yiming Xu, Ilias Triantafyllou, Michelle F. Waldman, Cara Mendrick, Nathaniel Brown, Paul Mann, et al. "Discovery of a Novel Class of Orally Active Antifungal β-1,3-d-Glucan Synthase Inhibitors." Antimicrobial Agents and Chemotherapy 55, no. 11 (August 15, 2011): 5099–106. http://dx.doi.org/10.1128/aac.00432-11.

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ABSTRACTThe echinocandins are a class of semisynthetic natural products that target β-1,3-glucan synthase (GS). Their proven clinical efficacy combined with minimal safety issues has made the echinocandins an important asset in the management of fungal infection in a variety of patient populations. However, the echinocandins are delivered only parenterally. A screen for antifungal bioactivities combined with mechanism-of-action studies identified a class of piperazinyl-pyridazinones that target GS. The compounds exhibitedin vitroactivity comparable, and in some cases superior, to that of the echinocandins. The compounds inhibit GSin vitro, and there was a strong correlation between enzyme inhibition andin vitroantifungal activity. In addition, like the echinocandins, the compounds caused a leakage of cytoplasmic contents from yeast and produced a morphological response in molds characteristic of GS inhibitors. Spontaneous mutants ofSaccharomyces cerevisiaewith reduced susceptibility to the piperazinyl-pyridazinones had substitutions inFKS1. The sites of these substitutions were distinct from those conferring resistance to echinocandins; likewise, echinocandin-resistant isolates remained susceptible to the test compounds. Finally, we present efficacy and pharmacokinetic data on an example of the piperazinyl-pyridazinone compounds that demonstrated efficacy in a murine model ofCandida glabratainfection.
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17

Hovakimyan, S. A., A. V. Babakhanyan, V. S. Voskanyan, V. E. Karapetian, G. A. Panosyan, and S. T. Kocharian. "Synthesis of Pyridazinone Derivatives." Chemistry of Heterocyclic Compounds 40, no. 8 (August 2004): 1047–51. http://dx.doi.org/10.1023/b:cohc.0000046696.37815.62.

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18

Moniot, Aurélie, Julien Braux, Camille Bour, Christine Guillaume, Fabien Lamret, Ingrid Allart-Simon, Sandra Audonnet, et al. "Pyridazinone Derivatives Limit Osteosarcoma-Cells Growth In Vitro and In Vivo." Cancers 13, no. 23 (November 28, 2021): 5992. http://dx.doi.org/10.3390/cancers13235992.

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Osteosarcoma is a rare primary bone cancer that mostly affects children and young adults. Current therapeutic approaches consist of combining surgery and chemotherapy but remain unfortunately insufficient to avoid relapse and metastases. Progress in terms of patient survival has remained the same for 30 years. In this study, novel pyridazinone derivatives have been evaluated as potential anti-osteosarcoma therapeutics because of their anti-type 4 phosphodiesterase activity, which modulates the survival of several other cancer cells. By using five—four human and one murine osteosarcoma—cell lines, we demonstrated differential cytotoxic effects of four pyridazinone scaffold-based compounds (mitochondrial activity and DNA quantification). Proapoptotic (annexin V positive cells and caspase-3 activity), anti-proliferative (EdU integration) and anti-migratory effects (scratch test assay) were also observed. Owing to their cytotoxic activity in in vitro conditions and their ability to limit tumor growth in a murine orthotopic osteosarcoma model, our data suggest that these pyridazinone derivatives might be hit-candidates to develop new therapeutic strategies against osteosarcoma.
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19

TAKAYA, Masahiro, and Makoto SATO. "Studies on Pyridazinone Derivatives. XVI. Analgesic-Antiinflammatory Activities of 3 (2H)-Pyridazinone Derivatives." YAKUGAKU ZASSHI 114, no. 2 (1994): 94–110. http://dx.doi.org/10.1248/yakushi1947.114.2_94.

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20

Ismail, Magda M. F., Dalia H. S. Soliman, Mona H. Abd Elmoniem, and Ghehad A. R. Abdel Jaleel. "Synthesis, Molecular Modeling of Novel Substituted Pyridazinones and their Vasorelaxant Activities." Medicinal Chemistry 17, no. 2 (December 30, 2020): 171–86. http://dx.doi.org/10.2174/1573406416666200327191100.

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Background: Hypertension, one of the most common cardiovascular diseases that can cause coronary disease, stroke, myocardial infarction, and sudden death, it is the major contributor to cardiac failure as well as renal insufficiency. Objectives: As there are many cardio-active pyridazinone-base derivatives in clinical use, therefore, we aimed to synthesize a new series of pyridazin-3-ones and evaluate their vasorelaxant activity. Methods: A new series of synthesized compounds were carried out first by the synthesis of 6- flouroarylpyridazinones by cyclization of 3-(4-flourobenzoyl) propionic acid with hydrazine hydrate or arylhydrazines to provide the corresponding pyridazinone derivatives 2a-d. Mannich reaction was performed using morpholine or piperidine formaldehyde to obtain compounds 3a,b. On the other hand, reaction of 2a with various chloroacetamide intermediates, in dimethylformamide and potassium carbonate as a catalyst, afforded the target compounds 5a-c. The aromatic acid hydrazide intermediates 6a-g were prepared in 50-90% yield, by reacting to the prepared esters with hydrazine hydrate under reflux in ethanol. The two compounds 8a,b were prepared via condensation of 7a,b with ethyl chloroacetate in dry acetone. Finally, the target 2,4,6-trisubstituted pyridazinones 9a-c derivatives were obtained by the reaction of 7a with the appropriate aromatic aldehyde or substituted acetophenones. The new compounds were then evaluated for their vasorelaxant properties using isolated thoracic rat aortic rings. In addition, a homology model was built and molecular modeling simulation of these compounds into the active sites of the newly created α1a-adrenoceptor model was performed in order to predict and rationalize their affinities toward this receptor. Results: Among these compounds; 5a was the most potent, it exhibited approximately two-times the activity of prazosin (IC50 = 0.250, 0.487 mmol, respectively) also, fourteen compounds were more potent than prazosin.
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21

Zvirgzdins, Alvis, Mara Delina, Anatoly Mishnev, and Andris Actins. "Pimobendan B from powder diffraction data." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (October 19, 2013): o1677. http://dx.doi.org/10.1107/s1600536813028353.

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The title molecule, C19H18N4O2{systematic name: (RS)-6-[2-(4-methoxyphenyl)-1H-benzimidazol-5-yl]-5-methyl-4,5-dihydropyridazin-3(2H)-one}, adopts an extended conformation. The dihedral angles between the central benzimidazole ring sytem and the pendant methoxyphenyl and pyridazinone residues are 1.41 (18) and 9.7 (3)°, respectively. In the crystal, N—H...N hydrogen bonds link the imadazole groups into [001] chains, and pairs of N—H...O hydrogen bonds link the pyridazinone groups into dimers. Together, these generate a two-dimensional supramolecular structure parallel to (010). The layers are linked by C—H...π interactions.
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22

Li, Wei, Zhoulong Fan, Kaijun Geng, Youjun Xu, and Ao Zhang. "Late-stage diversification of biologically active pyridazinones via a direct C–H functionalization strategy." Organic & Biomolecular Chemistry 13, no. 2 (2015): 539–48. http://dx.doi.org/10.1039/c4ob02061h.

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23

Combs, D. W. "Bemoradan and related pyridazinone cardiotonics." Drugs of the Future 18, no. 2 (1993): 139. http://dx.doi.org/10.1358/dof.1993.018.02.202017.

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24

Akhtar, Wasim, M. Shaquiquzzaman, Mymoona Akhter, Garima Verma, Mohemmed Faraz Khan, and M. Mumtaz Alam. "The therapeutic journey of pyridazinone." European Journal of Medicinal Chemistry 123 (November 2016): 256–81. http://dx.doi.org/10.1016/j.ejmech.2016.07.061.

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25

TAKAYA, MASAHIRO. "Studies on Pyridazinone Derivatives. XI. Synthesis and Antifungal Activity of Amino Derivatives of Pyridazinone." YAKUGAKU ZASSHI 107, no. 10 (1987): 819–22. http://dx.doi.org/10.1248/yakushi1947.107.10_819.

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26

Graf, Josef A., Reto J. Strasser, and Ulrich Kull. "Structure-Function-Relationship in Thylakoids Influenced by the Pyridazinone BAS 13–338 (SAN 9785)." Zeitschrift für Naturforschung C 42, no. 6 (June 1, 1987): 808–12. http://dx.doi.org/10.1515/znc-1987-0628.

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The pyridazinone BAS 13-338 (SAN 9785) inhibits the desaturation sequence leading to polyunsaturated fatty acids, mainly of glycolipids. Parallel to the inhibition of fatty acid desaturation in the presence of the pyridazinone, changes in energy-distribution parameters have been observed. These data indicate that the amount of polyunsaturated fatty acids in glycolipids is strongly correlated with excitation, trapping, grouping and dissipation, but not with spillover. Functional changes in energy distribution induced by BAS 13-338 are interpreted as a consequence of structural changes in the lipid matrix, which may imply a structure-function relationship between pigment protein complexes and the surrounding lipid environment in thylakoids.
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27

Graf, Josef A., Reto J. Strasser, and Ulrich Kuli. "Structure-Function-Relationship in Thylakoids Influenced by the Pyridazinone BAS 13—338 (SAN 9785)." Zeitschrift für Naturforschung C 42, no. 7-8 (August 1, 1987): 808–12. http://dx.doi.org/10.1515/znc-1987-7-811.

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The pyridazinone BAS 13-338 (SAN 9785|) inhibits the desaturation sequence leading to polyunsaturated fatty acids, mainly of glycolipids. Parallel to the inhibition of fatty acid desaturation in the presence of the pyridazinone, changes in energy-distribution parameters have been observed. These data indicate that the amount of polyunsaturated fatty acids in glycolipids is strongly correlated with excitation, trapping, grouping and dissipation, but not with spillover. Functional changes in energy distribution induced by BAS 13-338 are interpreted as a consequence of structural changes in the lipid matrix, which may imply a structure-function relationship between pigment protein complexes and the surrounding lipid environment in thylakoids.
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28

Allart-Simon, Ingrid, Aurélie Moniot, Nicolo Bisi, Miguel Ponce-Vargas, Sandra Audonnet, Marie Laronze-Cochard, Janos Sapi, Eric Hénon, Frédéric Velard, and Stéphane Gérard. "Pyridazinone derivatives as potential anti-inflammatory agents: synthesis and biological evaluation as PDE4 inhibitors." RSC Medicinal Chemistry 12, no. 4 (2021): 584–92. http://dx.doi.org/10.1039/d0md00423e.

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29

Ramadan, Sayed K., Doaa R. Abdel Haleem, Hisham S. M. Abd-Rabboh, Nourhan M. Gad, Wael S. I. Abou-Elmagd, and David S. A. Haneen. "Synthesis, SAR studies, and insecticidal activities of certain N-heterocycles derived from 3-((2-chloroquinolin-3-yl)methylene)-5-phenylfuran-2(3H)-one against Culex pipiens L. larvae." RSC Advances 12, no. 22 (2022): 13628–38. http://dx.doi.org/10.1039/d2ra02388a.

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A new series of N-heterocycles including pyridazinone, oxadiazole, triazolopyridazinone, and triazole derivatives were synthesized from the acid hydrazide via its reaction with certain carbon electrophiles.
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30

Sotelo, Eddy, Enrique Raviña, and Isabel Estevez. "Pyridazine derivatives.XIX: Functionalization studies at the5position in the 6-phenyl-3(2H)-pyridazinone system." Journal of Heterocyclic Chemistry 36, no. 4 (July 1999): 985–90. http://dx.doi.org/10.1002/jhet.5570360426.

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31

Youssef, A. SA, M. I. Marzouk, H. MF Madkour, A. MA El-Soll, and M. A. El-Hashash. "Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-yl-pyridazin-3-one." Canadian Journal of Chemistry 83, no. 3 (March 1, 2005): 251–59. http://dx.doi.org/10.1139/v05-045.

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6-Aryl-4-pyrazol-1-yl-pyridazin-3-one (1) reacted with a PCl5–POCl3 mixture to give the 3-chloropyridazine derivative 3. Reaction of 3 with 2-hydroxybenzoylhydrazide and semicarbazide hydrochloride afforded 4 and 5. Reaction of 1 with ethyl chloroacetate gave 8. Reaction of 8 with hydrazine hydrate yielded the hydrazide 9. The hydrazide 9 condensed with the acetylenic ketones and esters 10a–10d and acetylacetone to give the adducts 11a, 11b, 12, 13, and 14. Reacting 1 with formaldehyde and piperidine, morpholine, or piperazine, 3-bromopropanoic acid, acetic anhydride, p-toluenesulphonyl chloride, succinyl chloride, oxalyl chloride, ethanolamine, or ethyl chloroacetate gave the adducts 15–22. The structures of all newly synthesized compounds were evidenced from their spectral and microanalytical data. Key words: 6-aryl-4-pyrazol-1-yl-pyridazinone derivative, 6-aryl-3-chloropyridazine derivative, 3,6-diaryl-1,2,4-triazino[4,3-b]pyridazine derivative, 6-aryl-3-ethoxycarbonylmethoxypyridazine derivative, 6-aryl-3-(ω-benzoylacetophenone)hydrazinocarbonylmethoxypyridazine.
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32

Yadav, Priyanka, Abhineet Verma, Vishal Prasad Sharma, Rashmi Singh, Tarun Yadav, Ranjeet Kumar, Shiv Pal, Hariom Gupta, Satyen Saha, and Ashish K. Tewari. "The development of a robust folded scaffold as a fluorescent material using butylidine-linked pyridazinone-based systems via aromatic π⋯π stacking interactions." New Journal of Chemistry 46, no. 12 (2022): 5830–38. http://dx.doi.org/10.1039/d2nj00083k.

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Fluorescence-capable robust folded pyridazinone-based homo- and heterodimers linked with butylidine linkers, whose crystals exhibit fluorescence with quantum yields of 11% (1CN) and 28% (2CN) due to intramolecular stacking, were synthesized.
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33

Dundar, Yasemin, Ozge Kuyrukcu, Gokcen Eren, F. Sezer Senol Deniz, Tijen Onkol, and Ilkay Erdogan Orhan. "Novel pyridazinone derivatives as butyrylcholinesterase inhibitors." Bioorganic Chemistry 92 (November 2019): 103304. http://dx.doi.org/10.1016/j.bioorg.2019.103304.

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34

Bulka, E., and H. Gille. "Pyridazinone-(6) und deren Azomethine [1]." Zeitschrift für Chemie 5, no. 10 (September 2, 2010): 374–75. http://dx.doi.org/10.1002/zfch.19650051005.

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35

Becker, Heinz Georg Osmar, Dieter Nagel, and Hans-Joachim Timpe. "Photolyse zwitterionischer s-Triazolo[4,3b]pyridazinone." Zeitschrift für Chemie 13, no. 6 (September 1, 2010): 213. http://dx.doi.org/10.1002/zfch.19730130603.

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36

TAKAYA, MASAHIRO. "Studies on Pyridazinone Derivatives. XII. Synthesis and Analgesic Activity of 2-Phenyl-3(2H)-pyridazinone Derivatives." YAKUGAKU ZASSHI 107, no. 11 (1987): 910–13. http://dx.doi.org/10.1248/yakushi1947.107.11_910.

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37

TAKAYA, Masahiro. "Studies on Pyridazinone Derivatives. XV. Oxydative Reactions and Antibacterial Antifungal Activity of Sulfur Derivatives of Pyridazinone." YAKUGAKU ZASSHI 113, no. 9 (1993): 676–81. http://dx.doi.org/10.1248/yakushi1947.113.9_676.

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38

Zhang, Binliang, Xiaobo Liu, Hehua Xiong, Qian Zhang, Xin Sun, Zunhua Yang, Shan Xu, Pengwu Zheng, and Wufu Zhu. "Discovery of [1,2,4]triazolo[4,3-a]pyrazine derivatives bearing a 4-oxo-pyridazinone moiety as potential c-Met kinase inhibitors." New Journal of Chemistry 44, no. 21 (2020): 9053–63. http://dx.doi.org/10.1039/d0nj00575d.

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We disclosed the preparation and biological evaluation of a series of [1,2,4]triazolo[4,3-a]pyrazine derivatives bearing 4-oxo-pyridazinone moieties, which demonstrated potent inhibition of c-Met kinase, culminating in the discovery of 22i.
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39

Deeb, Ali Abdel Hamid, Fatma Abdel Rahman El-Mariah, and Heba Kamal Abd El-Mawgoud. "Pyridazine and its related compounds: Part 38. Pyrimido[1,2-b]pyridazinone, synthesis and some reactions." European Journal of Chemistry 6, no. 2 (June 30, 2015): 204–10. http://dx.doi.org/10.5155/eurjchem.6.2.204-210.1252.

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40

Saeed, Makarem M., Nadia A. Khalil, Eman M. Ahmed, and Kholoud I. Eissa. "Synthesis and anti-inflammatory activity of novel pyridazine and pyridazinone derivatives as non-ulcerogenic agents." Archives of Pharmacal Research 35, no. 12 (December 2012): 2077–92. http://dx.doi.org/10.1007/s12272-012-1205-5.

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41

Zhou, Yuefen, Lian-Sheng Li, Jingjing Zhao, Peter Dragovich, Nebojsa Stankovic, Thomas Bertolini, Douglas Murphy, et al. "Synthesis of New Pyridazinone Derivatives: 2,6-Disubstituted 5-Hydroxy-3(2H)-pyridazinone-4-carboxylic Acid Ethyl Esters." Synthesis 2007, no. 21 (November 2007): 3301–8. http://dx.doi.org/10.1055/s-2007-990823.

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42

Piaz, V. Dal, G. Ciciani, and M. P. Giovannoni. "5-Acetyl-2-methyl-4-nitro-6-phenyl-3(2H)-pyridazinone: Versatile Precursor to Hetero-Condensed Pyridazinones." Synthesis 1994, no. 07 (1994): 669–71. http://dx.doi.org/10.1055/s-1994-25540.

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43

Alagöz, Mehmet Abdullah, Zeynep Özdemir, Mehtap Uysal, Simone Carradori, Marialucia Gallorini, Alessia Ricci, Susi Zara, and Bijo Mathew. "Synthesis, Cytotoxicity and Anti-Proliferative Activity against AGS Cells of New 3(2H)-Pyridazinone Derivatives Endowed with a Piperazinyl Linker." Pharmaceuticals 14, no. 3 (February 25, 2021): 183. http://dx.doi.org/10.3390/ph14030183.

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Novel twenty-three 3(2H)-pyridazinone derivatives were designed and synthesized based on the chemical requirements related to the anti-proliferative effects previously demonstrated within this scaffold. The introduction of a piperazinyl linker between the pyridazinone nucleus and the additional (un)substituted phenyl group led to some compounds endowed with a limited cytotoxicity against human gingival fibroblasts (HGFs) and good anti-proliferative effects against gastric adenocarcinoma cells (AGS) as evaluated by MTT and LDH assays, using doxorubicin as a positive control. Successive analyses revealed that the two most promising representative compounds (12 and 22) could exert their effects by inducing oxidative stress as demonstrated by the hydrogen peroxide release and the morphological changes (cell blebbing) revealed by light microscopy analysis after the haematoxylin-eosin staining. Moreover, to further assess the apoptotic process induced by compounds 12 and 22, Bax expression was measured by flow cytometry. These findings enlarged our knowledge of the structural requirements in this scaffold to display valuable biological effects against cancerous cell lines.
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44

HUSAIN, ASIF, AFTAB AHMAD, ANIL BHANDARI, and VEERMA RAM. "SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF PYRIDAZINONE DERIVATIVES." Journal of the Chilean Chemical Society 56, no. 3 (2011): 778–80. http://dx.doi.org/10.4067/s0717-97072011000300013.

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45

Helm, Matthew D., Andrew Plant, and Joseph P. A. Harrity. "A novel approach to functionalised pyridazinone arrays." Organic & Biomolecular Chemistry 4, no. 23 (2006): 4278. http://dx.doi.org/10.1039/b613223e.

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46

Sundar, Babu G., Thomas Bailey, Edward Bacon, Lisa Aimone, Zeqi Huang, Jacquelyn Lyons, Rita Raddatz, and Robert Hudkins. "Amine-constrained pyridazinone histamine H3 receptor antagonists." Bioorganic & Medicinal Chemistry Letters 21, no. 18 (September 2011): 5543–46. http://dx.doi.org/10.1016/j.bmcl.2011.06.094.

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47

Murineddu, Gabriele, Francesco Deligia, Giulio Ragusa, Laura García-Toscano, María Gómez-Cañas, Battistina Asproni, Valentina Satta, et al. "Novel sulfenamides and sulfonamides based on pyridazinone and pyridazine scaffolds as CB 1 receptor ligand antagonists." Bioorganic & Medicinal Chemistry 26, no. 1 (January 2018): 295–307. http://dx.doi.org/10.1016/j.bmc.2017.11.051.

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48

Darwish, Elham S., Mahmoud A. Abdelrahman, and Abdellatif M. Salaheldin. "Enamines in Heterocyclic Synthesis: A Novel Simple and Efficient Route to Condensed Pyridazines." Zeitschrift für Naturforschung B 66, no. 6 (June 1, 2011): 597–602. http://dx.doi.org/10.1515/znb-2011-0607.

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An efficient and easy preparation of enamine derivatives, via active methyl and methylene compounds by in situ-generated 1-(diethoxymethyl)piperidine, produced from the mixture of triethyl orthoformate/piperidine/DMF, are described. Some new pyridazinone derivatives have been synthesized from the reaction of enamines with hydrazine hydrate and cyanoacid hydrazide.
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49

Saini, Minaxi, Dinesh Kumar Mehta, and Rina Das. "Biological Evaluation and Molecular Docking Studies of Synthesized 5-Substituted-2-chlorophenyl-4-chloro Derivatives Bearing Pyridazinone Moiety." Letters in Organic Chemistry 17, no. 3 (February 19, 2020): 170–83. http://dx.doi.org/10.2174/1570178616666190705152605.

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Chemical modification of pyridazinone may lead to a potent therapeutic agent. In this study, biological properties of pyridazinone derivatives were evaluated by assessing their antimicrobial and in-vitro antioxidant activities. The reaction of a mucochloric acid and 3-chloro-phenylhydrazine hydrochloride led to the formation of 5-aryl-4-chloro-2-(3-chloro-phenyl)-2H-pyridazin-3-one derivatives 2(a-j). The target compounds were synthesized using nucleophilic substitution reaction. In-silico molecular docking studies of the synthesized compounds were carried out with the help of V-Life Science MDS 4.6 software using GRIP batch docking method to find out which derivative had a better docking. The newly synthesized compounds were characterized by FTIR, 1HNMR, 13C-NMR, MS, and elemental analysis. Antimicrobial and in-vitro antioxidant activity study of the novel synthesized compounds were screened. Compounds 2f and 2g showed good antimicrobial having an MIC 12.5 μg/mL against Staphylococcus aureus and Candida albicans and in-vitro antioxidant activities having an IC50 50.84. The experimental results were further supported by molecular docking analysis with better interaction patterns.
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50

TAKAYA, MASAHIRO. "Studies on Pyridazinone Derivatives. XIV. : Nucleophilic Replacement Reactions of 4, 5-Dichloro-3(2H)-pyridazinones with Hydrobromic Acid." YAKUGAKU ZASSHI 108, no. 9 (1988): 911–15. http://dx.doi.org/10.1248/yakushi1947.108.9_911.

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