Some scientific research about Phthalazine

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Selective cobalt nanoparticles for catalytic transfer hydrogenation of N-heteroarenes

Nitrogen modified cobalt catalysts supported on carbon were prepared by pyrolysis of the mixture generated from cobalt(ii) acetate in aqueous solution of melamine or waste melamine resins, which are widely used as industrial polymers. The obtained nanostructured materials catalyze the transfer hydrogenation of N-heteroarenes with formic acid in the absence of base. The optimal Co/Melamine-2@C-700 catalyst exhibits high activity and selectivity for the dehydrogenation of formic acid into molecular hydrogen and carbon dioxide and allows for the reduction of diverse N-heteroarenes including substrates featuring sensitive functional groups.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N104 – PubChem

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Synthesis and cytotoxicity evaluation of some new 6-nitro derivatives of thiazole-containing 4-(3H)-quinazolinone

Quinazolinones are a group of fused heterocyclic compounds which have valuable biological properties including cytotoxic, antibacterial and antifungal activities. Thiazole group-containing compounds have been also reported to have a wide range of biological activities such as antitumor, anti-inflammatory, analgesic and antibacterial effects. Due to valuable cytotoxic effects of both thiazole groups and quinazoline derivatives, in this study a series of quinazolinone-thiazole hybrids were synthesized and evaluated for their cytotoxic effects on three cell lines including MCF-7, HT-29, and PC-3. Among tested compounds (quinazolinones and three intermediates), k5 and k6 showed highest cytotoxic activities against PC3 cell line. K6 and C were most active compounds against MCF7 and K6 showed best cytotoxicity on HT-29 cell line.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N190 – PubChem

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Isolation and X-ray characterization of {[phthalazinium](CuCl 2)}?: A new example of a dichlorocuprate(I) presenting a rare staircase Chain structure

Air-sensitive complexes [Cu2(mu-phtz)3(PR 3)2][CF3SO3]2 (phtz = C8H6N2), 3 (R = phenyl) and 4 (R = benzyl) have been synthesized from {[Cu(CF3SO3)]2 C 6H5Me} (1) at room temperature, in acetonitrile solution, after successive additions of stoichiometric amounts of phthalazine (phtz) and triphenylphosphine and tribenzylphosphine, respectively. The dissolution of 4 in an excess of benzyl chloride gave rise to the slow formation of orange needles, characterized by an X-ray crystallographic analysis as the title compound, {[phthalazinium](CuCl2)}? (5). The solid-state structure of 5 can be described as a one-dimensional anionic chain, [(CuCl2) -]?, presenting a rare staircase shape with terminal chloride ligands. The negative charges are compensated by monoprotonated phthalazinium cations [phtzH]+ which are stacked through pi-pi interactions between N-heterocyclic rings, and are also in N-H hydrogen bonding interaction with the terminal chloride ligands of the anionic chain. The formation of 5 was unexpected and can be explained by the dechlorination of benzyl chloride molecules.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N341 – PubChem

Extended knowledge of Phthalazine

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Pyrimidine, pyridazine, quinazoline, phthalazine, and triazine coordination polymers of copper(I) halides

The coordination of diazine and triazine bridging ligands (B = pyrimidine (Pym), quinazoline (Qnz), pyridazine (Pdz), phthalazine (Ptz), and 1,3,5-triazine (Trz)) with CuX and CuXL (X = Cl, Br, I; L = PPh3, P(OPh)3) has been investigated. Products without phosphorus(III) ligands include [CuXB] (B = Qnz, Pdz, Ptz), [(CuX)2B] (B = Pym, Qnz, Pdz, Ptz, Trz), [(CuX)3B2] (B = Ptz, Trz), and [(CuX)3B] (B = Trz). Only CuX-Trz and CuI-Pdz afford more than one product stoichiometry. Products with phosphorus ligands are of the types [(CuXL)B] (B = Pdz, Ptz), [(CuXL)2B] (B = Pym, Qnz, Pdz, Ptz, Trz), and [(CuXL)3B] (B = Trz). Thermogravimetic analyses of the complexes typically show step-wise losses of B and L, ultimately yielding CuX. The X-ray crystal structure of [CuBr(Qnz)] features copper atoms bridged by Br and Qnz, forming 2D sheets of fused rectangular Cu4Br2(Qnz)2 units. The X-ray structures of [(CuBr(PPh3))2B] (B = Pym, Trz) show 1D chains formed from rhomboidal (CuL)2Br2 units linked by the B ligand. The structure of [CuCl(PPh3)(Pdz)] is shown by X-ray to be a simple halide-bridged dimer. The X-ray structure of [(CuCl(P(OPh)3))3(Trz)] is a hexamer, having an oblate spheroid core. The core is composed of a Cu6Cl6 macrocycle capped with two Trz ligands.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N274 – PubChem

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Dioxygen-Mediated Decarbonylative C-H Alkylation of Heteroaromatic Bases with Aldehydes

An operationally simple and economical method for the direct alkylation of heteroaromatic bases employing readily available aldehydes as alkyl radical precursors and molecular oxygen as a reagent is presented. This simple transformation demonstrates a broad substrate scope with respect to aldehydes and nitrogen heterocycles, enabling the introduction of several medicinally important yet challenging alkyl moieties, such as ethyl, isopropyl, tert-butyl, and cyclohexyl to the different classes of heterocyclic bases in good to excellent yields. A simple method for the direct alkylation of heteroaromatic bases with aldehydes as inexpensive alkyl radical precursors and molecular oxygen as a reagent is presented. This transformation demonstrates a broad substrate scope with respect to aldehydes and nitrogen heterocycles, enabling the introduction of various alkyl moieties to heterocyclic bases (>40 examples) in good to excellent yields.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N337 – PubChem

More research is needed about Phthalazine

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Design, synthesis, cytotoxicity and 3D-QSAR analysis of new 3,6-disubstituted-1,2,4,5-tetrazine derivatives as potential antitumor agents

We synthesized two new series of 3-substituted-6-(2,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazines and analysed them for a potential role as antitumor agents. Twenty-two compounds were obtained, and four molecular structures were determined by X-ray diffraction analysis. Using flow cytometry and MTT assay, potential action on cell toxicity was determined for each of the compounds for four cancer cell lines. The potency and selectivity demonstrated by these compounds are dependent on the cancer cell line, where the following compounds were found the most promising agents against certain cell lines: compounds 1i and 1j for HL-60 cells, 1a and 1b on HCT116 cells, 1f on Hela cells and 2h on H1975 cells. The action exerted by these compounds is comparable to the well-known cancer treatment drug etoposide and higher than vatalanib. To arrive at the structural requirements for activity on each cell line, a SAR and 3D-QSAR analysis was carried out. From the 3D-QSAR models, steric and electronic features were identified in the aromatic centres, and were key components for cytotoxic activity on HL-60 cell lines. The cytometry results suggest that some tetrazine derivatives induce apoptosis on HCT116 cells.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N97 – PubChem

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Recent advances in oxasteroids chemistry

The continuous interest in the field of oxasteroids mainly arises from the fascinating aspects associated with their peculiar stereochemical features and their promising and sometimes unexpected biological activities. The recent development in the partial and total syntheses of oxasteroids are herein described.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N197 – PubChem

Discovery of Phthalazine

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Medicinal Chemistry, Pharmacology, and Clinical Implications of TRPV1 Receptor Antagonists

Transient receptor potential vanilloid 1 (TRPV1) is an ion channel expressed on sensory neurons triggering an influx of cations. TRPV1 receptors function as homotetramers responsive to heat, proinflammatory substances, lipoxygenase products, resiniferatoxin, endocannabinoids, protons, and peptide toxins. Its phosphorylation increases sensitivity to both chemical and thermal stimuli, while desensitization involves a calcium-dependent mechanism resulting in receptor dephosphorylation. TRPV1 functions as a sensor of noxious stimuli and may represent a target to avoid pain and injury. TRPV1 activation has been associated to chronic inflammatory pain and peripheral neuropathy. Its expression is also detected in nonneuronal areas such as bladder, lungs, and cochlea where TRPV1 activation is responsible for pathology development of cystitis, asthma, and hearing loss. This review offers a comprehensive overview about TRPV1 receptor in the pathophysiology of chronic pain, epilepsy, cough, bladder disorders, diabetes, obesity, and hearing loss, highlighting how drug development targeting this channel could have a clinical therapeutic potential. Furthermore, it summarizes the advances of medicinal chemistry research leading to the identification of highly selective TRPV1 antagonists and their analysis of structure?activity relationships (SARs) focusing on new strategies to target this channel.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N21 – PubChem

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Benzoquinolines and chloride secretion in murine colonic epithelium

1. In all, 27 compounds related chemically to phenanthrolines were investigated for their ability to stimulate electrogenic chloride secretion in murine colonic epithelia under short circuit current conditions. A total of 11 compounds, not previously examined, were shown to have substantial activity. Cumulative concentration – response relations were obtained in the presence of amiloride to inhibit electrogenic sodium absorption and Ba2+ to prevent potassium secretion. 2. Single- or double-ring substitutions in 1,10 phenanthroline (EC50 = 612 muM) produced only modest increases in affinity of between 0.7- and 2.1-fold. 3. Naphthalenes with either one or two ring nitrogens showed some activity but had very low affinity, yet some (e.g. isoquinoline, EC50 = 700 muM) were able to produce maximal responses. 4. Removal of one nitrogen from 1,10-phenanthroline or from 4,7-phenanthroline gave, respectively, 7,8-benzoquinoline and 5,6-benzoquinoline. These two were the most active compounds found, the EC50 for 5,6-benzoquinoline being 29 muM. 5. Most concentration – response curves were steep with Hill slopes of approximately 3. At high concentration, some compounds inhibited the response, producing a characteristic bell shape. 6. 5,6- and 7,8-benzoquinoline may be useful starting points for the synthesis of more potent agents by the addition of ring substituents.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N117 – PubChem

Brief introduction of Phthalazine

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Low temperature X-ray structure analyses combined with NBO studies of a new heteroleptic octa-coordinated Holmium(III) complex with N,N,N-tridentate hydrazono-phthalazine-type ligand

The new heteroleptic [HoL(H2O)5]Br3 complex, L is hydrazono-phthalazine ligand, is synthesized and its molecular structure aspects were analyzed using single crystal X-ray structure (SCXRD), Hirshfeld (HF) analysis, quantum theory of atoms in molecules (QTAIM) and natural bond orbital (NBO) method. The SCXRD showed that the Ho is octa-coordinated with one N,N,N-tridentate ligand L and five water molecules. The HF analysis is used to analyze the molecular packing in the [HoL(H2O)5]Br3crystal structure. The complex cations are connected via strong O?H?Br and N?H?Br H-bonding interactions which have greater importance than the C?H?Br contacts. Also, all the Ho?N and Ho?O bonds have the characteristics of closed shell interactions using QTAIM. The natural orbitals included in these interactions were analyzed using NBO method. The alpha LP*(8)Ho and beta LP*(4)Ho which have mainly s-orbital characters are the most important anti-bonding natural orbitals included in all Ho-N and Ho?O bonds. The rest of the Ho anti-bonding orbitals which have either p or d-orbital characters shared partially in the Ho-ligands interactions. Natural charges analysis revealed the presence of significant amount of electron density (0.9225?0.9300 e) transferred from the ligands to Ho (2.0700?2.0775 e). Spherical spin density with ?4.0 e is predicted over the Ho atom.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N415 – PubChem