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Journal articles on the topic 'Phthalazine'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Mourad, Asmaa Kamal, Abdelmoneim Abdelsalam Makhlouf, Ahmed Yousef Soliman, and Samar Ahmed Mohamed. "Phthalazines and phthalazine hybrids as antimicrobial agents: Synthesis and biological evaluation." Journal of Chemical Research 44, no. 1-2 (October 29, 2019): 31–41. http://dx.doi.org/10.1177/1747519819883840.

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Phthalazine and phthalazinone derivatives are important owing to their significant biological activities and pharmacological properties. Herein, a benzoic acid derivative (2), a benzoxazin-1-one derivative (3), and an oxophthalazin-2(1 H)-yl)acetohydrazide (13) are utilized as precursors to construct a novel series of phthalazinones bearing various valuable functional groups in excellent yields via several simple and promising approaches. Finally, the antimicrobial activity of the newly synthesized phthalazines is screened against different microbial strains; namely, Gram-negative and Gram-positive bacteria utilizing Amoxicillin as a standard drug.

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2

Wasfy, A. A. F. "Fused Heterocycles. Part I. Synthesis of Some Annelated 1,2,4-Triazole Systems from [4-(1H-Benzimidazol-2-yl)-Phthalazin-1-Yl]Hydrazine." Journal of Chemical Research 2003, no. 8 (August 2003): 457–58. http://dx.doi.org/10.3184/030823403103174786.

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Substituted 6-(1 H-benzimidazol-2-yl)-[1,2,4]triazolo[3,4- a]phthalazine derivatives containing alkyl, aryl, hydroxyl, mercapto, methylthio and formyl substituents at position 3 have been synthesised. Di-[6-(1 H-benzimidazol-2-yl)-3-[1,2,4]triazolo[3,4- a]phthalazin-3-yl]alkanes have been obtained by the use of dicarboxylic acids or their esters in the above condensations. Methylation reactions of the triazolo-phthalazine system are reported.

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3

Xu, Jing. "Research on Synthesis of Triazine Ring and its Isomerization." Applied Mechanics and Materials 686 (October 2014): 26–30. http://dx.doi.org/10.4028/www.scientific.net/amm.686.26.

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This paper designed and synthesized a series of different chain length of phthalonitrile-terminated oligo (phthalazinone imide), it has good water solubility, and can be under normal atmospheric pressure to form the s-triazine rings-containing thermosetting oligo (phthalazine imide). Compared with the traditional thermosetting resin, the resin has the advantages of high temperature resistance, high strength, flame retardant, resistance to chemical corrosion.

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4

Plasseraud, Laurent, Hélène Cattey, and Philippe Richard. "Self-assembly Through Non-coordinating Intermolecular Forces, Part 2 [1]. Synthesis, Crystal Structure and Packing of [Cu2(μ-phthalazine)3(phthalazine)2][CF3SO3]2." Zeitschrift für Naturforschung B 63, no. 10 (October 1, 2008): 1169–74. http://dx.doi.org/10.1515/znb-2008-1005.

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Abstract Treatment of the copper(I) trifluoromethanesulphonate toluene complex {[Cu(CF3SO3)]2 · C6H5Me} (1) with phthalazine (phtz, C8H6N2) in dichloromethane-acetonitrile solution yielded, via the bis(acetonitrile)tris(μ-phthalazine)dicopper(I) trifluoromethanesulphonate intermediate (2), the novel bis(phthalazine)tris(μ-phthalazine)dicopper(I) trifluoromethanesulphonate salt (3). Compound 3 was completely characterised and the molecular structure determined by single-crystal X-ray diffraction. Complex 3 crystallises in the monoclinic system, space group C2/c, with a = 26.9527(10), b = 10.9558(7), c = 19.2104(10) Å , β = 127.268(2)◦, V = 4514.3(4) Å3 and Z = 4. The copper(I) coordination geometry is tetrahedral, each copper centre being linked to four phthalazine molecules. Dicationic units of 3 which present an unusual paddle wheel-like shape constitute appropriate organometallic building blocks for the construction of a supramolecular solid-state architecture. The analysis of the packing of the molecules of 3 in the crystal revealed an unprecedented 2-dimensional network, resulting from intermolecular π-π and electrostatic interactions.

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5

Habibi, Davood, Nosratollah Mahmoudi, and Omid Marvi. "Green Procedure for the Synthesis of Phthalazino[2,3‐b]phthalazine‐5,7,12,14‐tetraones." Synthetic Communications 37, no. 18 (September 1, 2007): 3165–71. http://dx.doi.org/10.1080/00397910701545247.

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6

Habibi, Davood, Nosratollah Mahmoodi, and Omid Marvi. "Montmorillonite K-10 clay as reusable heterogeneous catalyst for the microwave-mediated solventless synthesis of phthalazinetetraones." Canadian Journal of Chemistry 85, no. 2 (February 1, 2007): 81–84. http://dx.doi.org/10.1139/v06-189.

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Different phthalazino[2,3-b]phthalazine-5,7,12,14-tetraones were synthesized in a simple and environmentally benign method from the reaction of some phthalic anhydrides with semicarbazide or thiosemicarbazide using montmorillonite K-10 clay as solid heterogeneous acidic catalyst and microwaves under solvent-free conditions in good yields and short reaction times. The present method has many obvious advantages compared with those reported in the literature, including high efficiency, higher yield, operational simplicity, environmental benignity, and the possibility of recycling the solid clay. The solid clay catalyst used in the first cycle of the reactions was successfully recovered and reused in the second cycle, showing a gradual decrease in activity.Key words: montmorillonite K-10 clay, microwave, solvent-free condition, phthalazinetetraones, semicarbazide, thiosemicarbazide.

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7

Çelik, Ömer, Semra İde, Mustafa Kurt, and Şenay Yurdakul. "Dichlorobis(phthalazine)zinc(II)." Acta Crystallographica Section E Structure Reports Online 60, no. 8 (July 17, 2004): m1134—m1136. http://dx.doi.org/10.1107/s1600536804016915.

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8

Cai, Mingjian. "5-Bromophthalazine hemihydrate." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (July 10, 2012): o2421. http://dx.doi.org/10.1107/s1600536812030358.

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The title compound, C8H5BrN2·0.5H2O, is a phthalazine derivative synthesized from 3-bromobenzene-1,2-dicarbaldehyde and hydrazine. The molecule is essentially planar, the deviation from the mean plane of the phthalazine ring being 0.015 (3) Å. The O atom of the solvent water molecule is situated on a twofold rotation axis. In the crystal, O—H...N hydrogen bonds and short N...Br [2.980 (3) Å] contacts lead to the formation of a two-dimensional network parallel to (101).

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9

Soliman, Saied M., Raghdaa A. Massoud, Hessa H. Al-Rasheed, and Ayman El-Faham. "Molecular and Supramolecular Structures of Cd(II) Complexes with Hydralazine-Based Ligands; A New Example for Cyclization of Hydrazonophthalazine to Triazolophthalazine." Crystals 11, no. 7 (July 15, 2021): 823. http://dx.doi.org/10.3390/cryst11070823.

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Molecular and supramolecular structures of two polymeric and one trinuclear Cd(II) complex with hydralazine-type ligands were presented. Self-assembly of E-1-(2-(thiophen-2-ylmethylene)hydrazinyl)phthalazine (HL) and CdCl2 gave the 1D coordination polymer [Cd(H2L)Cl3]n*H2O, 1, in which the Cd(II) ion is hexa-coordinated with one cationic monodentate ligand (H2L+) and five chloride ions, two of them acting as connectors between Cd(II) centers, leading to the formation of a 1D coordination polymer along the a-direction. Using DFT calculations, the cationic ligand (H2L+) could be described as a protonated HL with an extra proton at the hydrazone moiety. Repeating the same reaction by heating under reflux conditions in the presence of 1 mL saturated aqueous KSCN solution, the ligand HL underwent cyclization to the corresponding [1,2,4]triazolo[3,4-a]phthalazine-3(2H)-thione (TPT) followed by the formation of [Cd(TPT)(SCN)2]n*H2O, 2, a 1D coordination polymer. In this complex, the Cd(II) is coordinated with one NS-donor TPT bidentate chelate and two bridged μ(1,3)-thiocyanate ions connecting the Cd(II) centers forming the 1D polymer array along the b-direction. Heating E-2-(1-(2-(phthalazin-1-yl)hydrazono)ethyl)phenol HLOH with CdCl2 under reflux condition gave the trinuclear complex [Cd3(Hydralazine)2(H2O)2Cl6], 3, indicating the hydrolysis of the hydrazonophthalazine ligand HLOH during the course of the reaction. Due to symmetry considerations, there are only two different Cd(II) centers having CdN2Cl3O and CdN2Cl4 coordination environments. Hirshfeld topology analysis was used to analyze the solid-state supramolecular structure of the studied complexes.

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10

Çelik, Ömer, Semra İde, Mustafa Kurt, and Şenay Yurdakul. "Dibromobis(phthalazine-κN2)zinc(II)." Acta Crystallographica Section E Structure Reports Online 60, no. 4 (March 20, 2004): m424—m425. http://dx.doi.org/10.1107/s1600536804004908.

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11

Patil, Smita, Rahul Patil, Umesh Fegade, Banashree Bondhopadhyay, Umesh Pete, Suban K. Sahoo, Narinder Singh, Anupam Basu, Ratnamala Bendre, and Anil Kuwar. "A novel phthalazine based highly selective chromogenic and fluorogenic chemosensor for Co2+ in semi-aqueous medium: application in cancer cell imaging." Photochemical & Photobiological Sciences 14, no. 2 (2015): 439–43. http://dx.doi.org/10.1039/c4pp00358f.

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12

Vuong, Thi Minh Ha, Jennifer Weimmerskirch-Aubatin, Jean-François Lohier, Nathalie Bar, Sophie Boudin, Christophe Labbé, Fabrice Gourbilleau, Hien Nguyen, Tung Thanh Dang, and Didier Villemin. "Blue highly fluorescent boron difluoride complexes based on phthalazine–pyridine." New Journal of Chemistry 40, no. 7 (2016): 6070–76. http://dx.doi.org/10.1039/c6nj00726k.

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13

Hiiuk, Volodymyr M., Sergiu Shova, Aurelian Rotaru, Alexander A. Golub, Igor O. Fritsky, and Il'ya A. Gural'skiy. "Spin crossover in 2D iron(ii) phthalazine cyanometallic complexes." Dalton Transactions 49, no. 16 (2020): 5302–11. http://dx.doi.org/10.1039/d0dt00783h.

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14

Martins, Felipe Terra, Lauro June Queiroz Maia, Gisane Gasparotto, Ana Karoline Silva Medanha Valdo, José Antônio Nascimento Neto, Leandro Ribeiro, Yuri de Freitas Rego, Cleiton Moreira da Silva, and Ângelo de Fátima. "Phthalazine-trione as a blue-green light-emitting moiety: crystal structures, photoluminescence and theoretical calculations." New Journal of Chemistry 43, no. 3 (2019): 1313–21. http://dx.doi.org/10.1039/c8nj02976h.

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15

Liu, Hai-Jie, Marcos Gil-Sepulcre, Laia Francàs, Pau Nolis, Teodor Parella, Jordi Benet-Buchholz, Xavier Fontrodona, et al. "Mononuclear ruthenium compounds bearing N-donor and N-heterocyclic carbene ligands: structure and oxidative catalysis." Dalton Transactions 46, no. 9 (2017): 2829–43. http://dx.doi.org/10.1039/c6dt04729g.

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16

Plasseraud, Laurent, Andreas Scheurer, and Frank Hampel. "Self-Assembly Of 1D- And 3D-Networks Through Non-Coordination Intermolecular Forces: Synthesis And Crystal Structures Of Copper(I) Complexes Based On Pyridazine-Type Ligands." Zeitschrift für Naturforschung B 62, no. 6 (June 1, 2007): 799–806. http://dx.doi.org/10.1515/znb-2007-0608.

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Reaction of [Cu2(H3CCN)2(μ-pydz)3][PF6]2 (1) with an excess of pyridazine or phthalazine yielded the novel dinuclear complexes [Cu2(μ-pydz)3(pydz)2][PF6]2 (2) and [Cu2 (μ- pydz)(μ-phtz)2(phtz)2][PF6]2 (5), respectively. Depolymerisation of the coordination polymer 1∞ {[Cu(μ-pydz)2][PF6]} (3) in dichloromethane by addition of an excess of benzo[c]cinnoline afforded the dinuclear copper(I) salt [Cu2(μ-pydz)2(pydz)2(benzo[c]cinnoline)2][PF6]2 (4). Furthermore, a new route for the preparation of bis(benzonitrile)tris(μ-phthalazine)dicopper(I) bis(trifluoromethanesulfonate), [Cu2(C6H5CN)2(μ-phtz)3][CF3SO3]2 (7), was established from {[Cu(CF3SO3)]2 ・C6H5Me}, phthalazine and benzonitrile via the very air-sensitive intermediate [Cu2(CF3SO3)2(μ-phtz)3] (6). Copper(I) compounds 2, 4, and 7 were completely characterised and the molecular structures confirmed in the solid state by single-crystal X-ray structure determination. The analysis of the packing of the molecules in crystals of 4 and 7 revealed a self-assembly of oneand three-dimensional frameworks, respectively, resulting from intermolecular π-π stacking interactions between pyridazine-type ligands

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17

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

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

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18

Xin, Lijun, Jie Xue, Gangtie Lei, and Juan Qiao. "Efficient near-infrared-emitting cationic iridium complexes based on highly conjugated cyclometalated benzo[g]phthalazine derivatives." RSC Advances 5, no. 53 (2015): 42354–61. http://dx.doi.org/10.1039/c5ra04511h.

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19

Hwang, Jong Yeon, Hyung-Sub Choi, and Young-Dae Gong. "Solid-phase synthesis of [1,2,4]triazolo[3,4-a]phthalazine and tetrazolo[5,1-a]phthalazine derivatives." Tetrahedron Letters 46, no. 17 (April 2005): 3107–10. http://dx.doi.org/10.1016/j.tetlet.2005.02.154.

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20

Carbonell, E., A. Martinez-Camarena, C. Galiana-Rosello, M. Inclan, R. Tejero, M. J. R. Yunta, P. Navarro, et al. "Acid–base behaviour and binding to double stranded DNA/RNA of benzo[g]phthalazine-based ligands." New Journal of Chemistry 43, no. 2 (2019): 700–708. http://dx.doi.org/10.1039/c8nj05039b.

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21

Simijonović, Dušica, Zorica D. Petrović, Vesna M. Milovanović, Vladimir P. Petrović, and Goran A. Bogdanović. "A new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic products." RSC Advances 8, no. 30 (2018): 16663–73. http://dx.doi.org/10.1039/c8ra02702a.

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22

Lee, Jae Jun, Ye Won Choi, Ga Rim You, Sun Young Lee, and Cheal Kim. "A phthalazine-based two-in-one chromogenic receptor for detecting Co2+ and Cu2+ in an aqueous environment." Dalton Transactions 44, no. 29 (2015): 13305–14. http://dx.doi.org/10.1039/c5dt00957j.

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23

Khazaei, Ardeshir, Mohammad Ali Zolfigol, Fatemeh Karimitabar, Iraj Nikokar, and Ahmad Reza Moosavi-Zare. "N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media." RSC Advances 5, no. 87 (2015): 71402–12. http://dx.doi.org/10.1039/c5ra10730j.

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24

Zhou, Jian, Chuanliu Yin, Tianshuo Zhong, Xiangyun Zheng, Xiao Yi, Junyu Chen, and Chuanming Yu. "A direct synthesis method towards spirocyclic indazole derivatives via Rh(iii)-catalyzed C–H activation and spiroannulation." Organic Chemistry Frontiers 8, no. 18 (2021): 5024–31. http://dx.doi.org/10.1039/d1qo00805f.

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A rhodium(iii)-catalyzed [4 + 1] spiroannulation of N-aryl phthalazine-diones (pyridazine-diones) with diazo compounds to construct spirocyclic indazole derivatives with diverse structures is described.

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25

El-Helby, Abdel-Ghany A., Helmy Sakr, Rezk R. A. Ayyad, Khaled El-Adl, Mamdouh M. Ali, and Fathalla Khedr. "Design, Synthesis, In Vitro Anti-cancer Activity, ADMET Profile and Molecular Docking of Novel Triazolo[3,4-a]phthalazine Derivatives Targeting VEGFR-2 Enzyme." Anti-Cancer Agents in Medicinal Chemistry 18, no. 8 (December 28, 2018): 1184–96. http://dx.doi.org/10.2174/1871520618666180412123833.

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Background: Extensive studies were reported in the synthesis of several phthalazine derivatives as promising anticancer agents as potent VEGFR-2 inhibitors. Vatalanib (PTK787) was the first anilinophthalazine published derivative as a potent inhibitor of VEGFR. The discovery of vatalanib as a clinical candidate led to the design and synthesis of different anilinophthalazine derivatives as potent inhibitors for VEGFR-2. The objective of present research work is the synthesis of new agents with the same essential pharmacophoric features of the reported and clinically used VEGFR-2 inhibitors (e.g vatalanib and sorafenib). The main core of our molecular design rationale comprised bioisosteric modification strategies of VEGFR-2 inhibitors at four different positions. </P><P> Material and Methods: A correlation between structure and biological activity of our designed phthalazines was established using molecular docking and VEGFR-2 kinase assay. Results and Discussion: In view of their expected anticancer activity, novel triazolo[3,4-a]phthalazine derivatives 5-6a-o and 3-substituted-bis([1,2,4]triazolo)[3,4-a:4',3'-c]phthalazines 9a-b were designed, synthesized and evaluated for their anti-proliferative activity against two human tumor cell lines HCT-116 human colon adenocarcinoma and MCF-7 breast cancer. It was found that, compound 6o the most potent derivative against both HCT116 and MCF-7 cancer cell lines. Compounds 6o, 6m, 6d and 9b showed the highest anticancer activities against HCT116 human colon adenocarcinoma with IC50 of 7±0.06, 13±0.11, 15±0.14 and 23±0.22 µM respectively while compounds 6o, 6d, 6a and 6n showed the highest anticancer activities against MCF-7 breast cancer with IC50 of 16.98±0.15, 18.2±0.17, 57.54±0.53 and 66.45±0.67 µM respectively. Sorafenib as a highly potent VEGFR-2 inhibitor was used as a reference drug with IC50 of 5.47±0.3 and 7.26±0.3 µM respectively. Nine compounds were further evaluated for their VEGFR-2 inhibitory activity. Compounds 6o, 6m, 6d and 9b emerged as the most active counterparts against VEGFR-2 with IC50 values of 0.1±0.01, 0.15±0.02, 0.28±0.03 and 0.38±0.04 µM, respectively comparable to that of sorafenib (IC50 = 0.1±0.02) µM. Furthermore, molecular docking studies were carried out for all synthesized compounds to investigate their binding pattern and predict their binding affinities towards VEGFR-2 active site. In silico ADMET studies were calculated for the tested compounds. Most of our designed compounds exhibited good ADMET profile. Conclusion: The obtained results showed that, the most active compounds could be useful as a template for future design, optimization, adaptation and investigation to produce more potent and selective VEGFR-2 inhibitors with higher anticancer analogs.

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26

Sakthivel, Karuppusamy, Kannupal Srinivasan, and Sampath Natarajan. "1-Benzoyl-4-(4-methylphenyl)phthalazine." Acta Crystallographica Section E Structure Reports Online 67, no. 12 (November 30, 2011): o3497. http://dx.doi.org/10.1107/s1600536811050641.

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27

Armarego, W. L. F. "Improved preparation of phthalazine and quinazoline." Journal of Applied Chemistry 11, no. 2 (May 4, 2007): 70–72. http://dx.doi.org/10.1002/jctb.5010110207.

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28

Sutherland, John B., James P. Freeman, Anna J. Williams, and Joanna Deck. "Biotransformation of phthalazine byFusarium moniliformeandCunninghamella elegans." Mycologia 91, no. 1 (January 1999): 114–16. http://dx.doi.org/10.1080/00275514.1999.12060998.

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29

Alinasab Amiri, Ali, Shahrzad Javanshir, Zahra Dolatkhah, and Mohammad G. Dekamin. "SO3H-functionalized mesoporous silica materials as solid acid catalyst for facile and solvent-free synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-trione derivatives." New Journal of Chemistry 39, no. 12 (2015): 9665–71. http://dx.doi.org/10.1039/c5nj01733e.

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30

Dam, Binoyargha, Mithu Saha, Ramen Jamatia, and Amarta Kumar Pal. "Nano-ferrite supported glutathione as a reusable nano-organocatalyst for the synthesis of phthalazine-trione and dione derivatives under solvent-free conditions." RSC Advances 6, no. 60 (2016): 54768–76. http://dx.doi.org/10.1039/c6ra06376d.

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Nano-organocatalyzed one-pot four-component reactions for the synthesis of phthalazine-trione/dione derivatives have been devised for the first time from easily accessible starting materials under solvent-free conditions.

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31

Fallah-Ghasemi Gildeh, Sara, Morteza Mehrdad, Hossein Roohi, Khatereh Ghauri, Sahar Fallah-Ghasemi Gildeh, and Kurosh Rad-Moghadam. "Experimental and DFT mechanistic insights into one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones under catalysis of DBU-based ionic liquids." New Journal of Chemistry 44, no. 38 (2020): 16594–601. http://dx.doi.org/10.1039/d0nj03478a.

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32

Savić, Nada D., Biljana Đ. Glišić, Hubert Wadepohl, Aleksandar Pavic, Lidija Senerovic, Jasmina Nikodinovic-Runic, and Miloš I. Djuran. "Silver(i) complexes with quinazoline and phthalazine: synthesis, structural characterization and evaluation of biological activities." MedChemComm 7, no. 2 (2016): 282–91. http://dx.doi.org/10.1039/c5md00494b.

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New silver(i) complexes with quinazoline and phthalazine have been synthesized, characterized and evaluated for their antimicrobial activity and their effect on the viability of fibroblasts and the development of zebrafish embryos.

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33

Yuan, Chunhao, Leijie Zhou, Zhanhu Sun, and Hongchao Guo. "Phosphine-catalyzed [3 + 2] cycloaddition of phthalazinium dicyanomethanides with allenoates: highly efficient synthesis of 1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine derivatives." RSC Advances 6, no. 81 (2016): 77931–36. http://dx.doi.org/10.1039/c6ra13643e.

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The phosphine-catalyzed [3 + 2] cycloaddition has been achieved at room temperature, providing novel heterocyclic compounds, 1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine derivatives, as single (Z)-isomers in excellent yields (88–99% yield).

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34

Bashti, Aigin, Ali Reza Kiasat, and Babak Mokhtari. "Synthesis and characterization of dicationic 4,4′-bipyridinium dichloride ordered mesoporous silica nanocomposite and its application in the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives." RSC Advances 5, no. 33 (2015): 25816–23. http://dx.doi.org/10.1039/c4ra17067a.

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Application of SBA@BiPy²⁺ 2Cl⁻ nanocomposite as a novel environmentally safe heterogeneous nanoreactor for the one-pot solvent-free synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives.

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35

Tong, Bihai, and Qunying Mei. "1-(2,6-Diisopropylphenoxy)-4-phenylphthalazine." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (July 28, 2012): o2578. http://dx.doi.org/10.1107/s1600536812033296.

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In the title molecule, C26H26N2O, the phenyl and phenoxy rings form dihedral angles of 54.66 (7) and 84.83 (6)°, respectively, with the phthalazine mean plane. The crystal packing exhibits weak C—H...π interactions.

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36

Shao, Xin, Jun Tian, Weimin Liu, Qunji Xue, and Chunlin Ma. "Tribological properties of SiO2 nanoparticle filled-phthalazine ether sulfone/phthalazine ether ketone (50/50 mol %) copolymer composites." Journal of Applied Polymer Science 85, no. 10 (June 14, 2002): 2136–44. http://dx.doi.org/10.1002/app.10780.

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37

Ryu, Chung-Kyu, Rae-Eun Park, Mi-Young Ma, and Ji-Hee Nho. "Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones." Bioorganic & Medicinal Chemistry Letters 17, no. 9 (May 2007): 2577–80. http://dx.doi.org/10.1016/j.bmcl.2007.02.003.

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38

El-Gazzar, Marwa G., and Hala M. Aly. "Anticancer Evaluation and Docking Study of New Bifunctional Phthalazine Derivatives." Current Organic Synthesis 15, no. 3 (April 27, 2018): 414–22. http://dx.doi.org/10.2174/2211556006666170927155809.

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Aims and Objective: A series of novel phthalazine derivatives was synthesized with versatile, readily accessible electrophilic and nucleophilic reagents. The newly synthesized compounds were confirmed by the results of spectroscopic measurements. Hence, their potential clinical application investigated in particular for cancer treatment. Materials and Methods: The newly synthesized compounds were characterized by spectroscopic measurements and were tested for their in vitro anticancer activity by MTT assay against human liver cancer cell line. Docking study of all the synthesized compounds was performed within the active site of the enzyme VEGFR-2 (Vascular Endothelial Growth Factor Receptor-2). Results: The quinazoline derivative 12 emerged as the most potent compound in this study with an IC50 value of 5.4 µM. Docking study showed that the synthesized compounds were fit in the VEGFR-2 active site almost at the same position of sorafenib and vatalanib with comparable docking scores (-15.20 to -8.92 was kcal/mol). Conclusion: we have synthesized a novel series of phthalazine derivatives and evaluated their potential anticancer activity against HEPG2 cell line. The quinazoline derivative 12 emerged as the most potent compound in this study with an IC50 value of 5.4 µM. The SAR and docking studies pointed out that rigidification of the structure resulted in better activity and better binding within the active site of VEGFR-2 as in compounds 3, 5, 6 and 12. These results introduced new phthalazine derivatives having promising activity which could lead to the development of more potent anticancer agents.

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Berber, Nurcan, Mustafa Arslan, Emre Yavuz, Cigdem Bilen, and Nahit Gencer. "Synthesis and Evaluation of New Phthalazine Urea and Thiourea Derivatives as Carbonic Anhydrase Inhibitors." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/742178.

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A new series of phthalazine substituted urea and thiourea derivatives were synthesized, and their inhibitory effects on the activity of purified human carbonic anhydrases (hCAs I and II) were evaluated. 2H-Indazolo[2,1-b]phthalazine-trione derivative(1)was prepared with 4-nitrobenzaldehyde, dimedone, and phthalhydrazide in the presence of TFA in DMF, and nitro group was reduced to amine derivative(2)with SnCl2·2H2O. The compound was reacted with isocyanates and isothiocyanates to get the final products(3a–p). The results showed that all the synthesized compounds inhibited the CA isoenzymes activity.3a(IC50= 6.40 µM for hCA I and 6.13 µM for hCA II) has the most inhibitory effect. The synthesized compounds are very bulky to be able to bind near the zinc ion, and they much more probably bind as the coumarin derivatives.

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40

Pisal, Parshuram M., Vinod T. Kamble, Ravi Varala, and Pradip B. Gujarathi. "Efficient one-pot three-component synthesis of 2H-indazole [2,1-b]phthalazine-1,6,11(13H)-triones at room temperature." Organic Communications 13, no. 4 (December 26, 2020): 194–201. http://dx.doi.org/10.25135/acg.oc.85.20.08.1768.

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Tetrabutylammonium bromide (TBAB) and cesium carbonate (Cs2O3) catalyzed, one-pot three-component synthesis of 2H-indazole[2,1b]phthalazine-1,6,11(13H)-triones was developed at room temperature in ethanol. Both electron donating and withdrawing groups are compatible under the optimized reaction parameters.

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Inoue, Hiroyasu, Tadamitsu Sakurai, Koichi Tomiyama, Ryo Sano, Masahiro Oshio, Toshihiko Hoshi, and Jun Okubo. "Photochemical Reactions of Phthalazine in 2-Propanol." Bulletin of the Chemical Society of Japan 61, no. 3 (March 1988): 893–98. http://dx.doi.org/10.1246/bcsj.61.893.

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42

Elce, Edmund, and Allan S. Hay. "Highly phenylated poly(aryl ether phthalazine)s." Journal of Polymer Science Part A: Polymer Chemistry 34, no. 10 (July 30, 1996): 1897–905. http://dx.doi.org/10.1002/(sici)1099-0518(19960730)34:10<1897::aid-pola7>3.0.co;2-m.

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43

LANDELLE, Henriette, Anne-Marie GODARD, Daniel LADUREE, Edith CHENU, and Max ROBBA. "Synthesis of Benzofuro(3,2-f)phthalazine Derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 39, no. 11 (1991): 3057–60. http://dx.doi.org/10.1248/cpb.39.3057.

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44

Lande, S. S., M. T. Elnabarawy, E. A. Reiner, A. N. Welter, and R. R. Robideau. "Laboratory assessment of environmental impact of phthalazine." Bulletin of Environmental Contamination and Toxicology 38, no. 2 (February 1987): 332–36. http://dx.doi.org/10.1007/bf01606683.

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45

Ouakki, Moussa, Hoyam Chahmout, Sarra Sibous, Mouhsine Galai, Zakaria Benzakri, Saïd Boukhris, Abdelaziz Souizi, and Mohammed Cherkaoui. "Novel pyrazole derivatives as inhibitors of stainless steel in 2.0M H2SO4 media: Electrochemical Study." Mediterranean Journal of Chemistry 10, no. 3 (March 16, 2020): 239–52. http://dx.doi.org/10.13171/mjc02003161235mo.

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Metallic materials are well known and widely used in various industrial sectors. However, they can be easily corroded in various aggressive environments. The protective action of stainless steel by two organic pyrazole compounds: {1-amino-5,10-dioxo-3-(p-tolyl)-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile} and {1-amino-3-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b] phthalazine-2-carbonitrile} in H2SO4 2.0M medium was studied using the electrochemical technics (Electrochemical Impedance Spectroscopy (EIS), potentiodynamic polarization), Scanning Electron Microscopy (SEM) and Energy Dispersion X-ray spectroscopy (EDX). Polarization curves indicate that both compounds act as anodic inhibitors. A suitable equivalent electrical circuit model was used to calculate the impedance parameters. The adsorption study showed that these compounds are adsorbed to the steel surface according to the adsorption isotherm of Langmuir. Effect of temperature was also investigated and activation parameters were evaluated.

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46

Wang, Xiao, Guangzhou Lu, Weiwei Ma, and Liqzang Wu. "Molecular Iodine: A Versatile Catalyst for the Synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione Derivatives in Ethanol." E-Journal of Chemistry 8, no. 3 (2011): 1000–1005. http://dx.doi.org/10.1155/2011/231939.

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An efficient method for the synthesis of 2H-indazolo[2,1-b] phthalazine-1,6,11(13H)-trione derivatives by a three-component condensation reaction of dimedone, aromatic aldehydes and phthalhydrazide in the presence of a catalytic amount of molecular iodine in ethanol is described.

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47

Deshpande, Megha S., Sudesh M. Morajkar, Bikshandarkoil R. Srinivasan, Mini Bharati Ahirwar, and Milind M. Deshmukh. "Effect of the electronic structure on the robustness of ruthenium(ii) bis-phenanthroline compounds for photodissociation of the co-ligand: synthesis, structural characterization, and density functional theory study." New Journal of Chemistry 45, no. 12 (2021): 5437–51. http://dx.doi.org/10.1039/d0nj05921h.

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Photodissociation of co-ligand in cis-[Ru(phen)₂(L)₂](PF₆)₂ (phen = 1,10-phenanthroline, L = isoquinoline 1; phthalazine 2), upon blue light irradiation was investigated via both experimental and DFT studies.

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Izuogu, David Chukwuma, Jonnie Niyi Asegbeloyin, Mukesh M. Jotani, and Edward R. T. Tiekink. "2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study." Acta Crystallographica Section E Crystallographic Communications 76, no. 5 (April 21, 2020): 697–702. http://dx.doi.org/10.1107/s2056989020005101.

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The X-ray crystal structure of the title phthalazin-1-one derivative, C17H16N2O3S {systematic name: 2-[(2,4,6-trimethylbenzene)sulfonyl]-1,2-dihydrophthalazin-1-one}, features a tetrahedral sulfoxide-S atom, connected to phthalazin-1-one and mesityl residues. The dihedral angle [83.26 (4)°] between the organic substituents is consistent with the molecule having the shape of the letter V. In the crystal, phthalazinone-C6-C—H...O(sulfoxide) and π(phthalazinone-N2C4)–π(phthalazinone-C6) stacking [inter-centroid distance = 3.5474 (9) Å] contacts lead to a linear supramolecular tape along the a-axis direction; tapes assemble without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of the C—H...O and π-stacking interactions but, also H...H and C—H...C contacts. The calculation of the interaction energies indicate the importance of dispersion terms with the greatest energies calculated for the C—H...O and π-stacking interactions.

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ELTAMANY, E. H. "ChemInform Abstract: Reactivity of 1-Chlorobenzo[g]phthalazinone and 1,4-Dichlorobenzo[g]phthalazine Towards Some Nucleophilic Reagents." ChemInform 29, no. 26 (June 21, 2010): no. http://dx.doi.org/10.1002/chin.199826188.

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Zhao, Xiao-Na, Guo-Fei Hu, Meng Tang, Tai-Tai Shi, Xiao-Li Guo, Tao-Tao Li, and Zhan-Hui Zhang. "A highly efficient and recyclable cobalt ferrite chitosan sulfonic acid magnetic nanoparticle for one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones." RSC Adv. 4, no. 93 (2014): 51089–97. http://dx.doi.org/10.1039/c4ra09984b.

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A novel magnetical cobalt ferrite chitosan sulfonic acid (CoFe₂O₄-CS-SO₃H) was prepared and identified as an efficient catalyst for synthesis of 2H-indazolo[2,1-b]phthalazine-triones by one-pot, four-component reaction.

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