Extracurricular laboratory:new discovery of Phthalazine

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Organocatalysis in Inert C-H Bond Functionalization

As two coexisting and fast-growing research fields in modern synthetic chemistry, the merging of organocatalysis and C-H bond functionalization is well foreseeable, and the joint force along this line has been demonstrated to be a powerful approach in making inert C-H bond functionalization more viable, predictable, and selective. In this review, we provide a comprehensive summary of organocatalysis in inert C-H bond functionalization over the past two decades. The review is arranged by types of inert C-H bonds including alkane C-H, arene C-H, and vinyl C-H as well as those activated benzylic C-H, allylic C-H, and C-H bonds alpha to the heteroatom such as nitrogen and oxygen. In each section, the discussion is classified by the explicit organocatalytic mode involved.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N352 – PubChem

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Syntheses of substituted 2,4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors

A series of 2,4-dioxo-thieno[2,3-d], [3,2-d] and [3,4-d]pyrimidin-1-acetic acids (2) with a benzyl moiety at the N-3 position were prepared and tested in vitro for aldose reductase inhibitory activity against partially purified enzyme from rat lens. Some of these compounds were also evaluated for inhibition of sorbitol accumulation in the sciatic nerve or lens of streptozotocin-induced diabetic rats in vivo. Among the synthesized compounds, several showed potent aldose reductase inhibitory activity with IC50s in the 10-8 M range. Particularly, the potencies of non-substituted thieno- (2a and 2aa), 5-methylthieno- (2c), 5,6-dimethylthieno- (2g), 6-isopropylthieno- (2j and 2k), 6-chlorothienopyrimidine (2q) and benzothienopyrimidine (2ac) analogs were approximately equipotent ot FK-366 (1A) and Ponalrestat (1B) as references. Although most compounds were inactive in vivo, 2 compounds, 2k and 2q, possessed moderate in vivo activity.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N898 – PubChem

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A ‘push-pull’ tropylium-fused aminoporphyrazine

Crossover Linstead macrocyclization of cycloheptatrienylmaleonitrile and (dimethylamino)-maleonitrile gave access to an unsymmetrical (A3B) porphyrazine bearing six peripheral amino substituents and a fused cycloheptatrienyl ring. Subsequent hydride abstraction gave a tropylium-fused aminoporphyrazine, which contains both strongly electron-donating and withdrawing groups and thus can be labelled as a ‘push-pull’ macrocycle. Detailed structural studies of this novel porphyrazine are described.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N373 – PubChem

Extended knowledge of Phthalazine

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Surgical Cleavage of Unstrained C(sp3)?C(sp3) Bonds in General Alcohols for Heteroaryl C?H Alkylation and Acylation

We reported herein a predictable and surgical cleavage of carbon-carbon bond in alcohols. A wide range of 1, 2 and 3 alcohols including sugars and steroids without ring strain or steric hindrance were all compatible with this system. Also it offered a green and practical strategy for generation of alkyl/acyl radicals using alcohols as the sources. Besides, the features of visible-light-initiation, catalyst and metal free, excellent selectivity and mild conditions make it valuable and attractive. (Figure presented.).

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Phthalazine – Wikipedia,
Phthalazine | C8H6N476 – PubChem

Brief introduction of Phthalazine

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Comparative study on the interaction of two binuclear Pt (II) complexes with human serum albumin: Spectroscopic and docking simulation assessments

Human serum albumin (HSA) principally tasks as a transport carrier for a vast variety of natural compounds and pharmaceutical drugs. In the present study, two structurally related binuclear Pt (II) complexes containing cis, cis-[Me2Pt (mu-NN) (mu-dppm) PtMe2] (1), and cis, cis-[Me2Pt(mu-NN)(mu dppm) Pt((CH2)4)] (2) in which NN?=?phthalazine and dppm?=?bis (diphenylphosphino) methane were used to investigate their interaction with HSA, using UV?Vis absorption spectroscopy, fluorescence, circular dichroism and molecular dynamic analyses. The spectroscopic results suggest that upon binding to HSA, the binuclear Pt (II) complexes could effectively induce structural alteration of this protein. These complexes can bind to HSA with the binding affinities of the following order: complex 2?>?complex 1. Moreover, the thermodynamic parameters of binding between these complexes and HSA suggested the existence of entropy-driven spontaneous interaction, which mostly dominated with the hydrophobic forces. The ANS fluorescence results also indicated that two binuclear Pt (II) complexes were competing for the binding to the hydrophobic regions on HSA. In addition, competitive displacement assay and docking simulation study revealed that complexes 1 and 2 bind to the drug binding sites II and I on HSA, respectively. Furthermore, complex 2, with the higher binding affinity for HSA, shows more denaturing effect on this protein. Considering the protein structural damages in the pathway of harmful side effects of platinum drugs, complex 1 with the moderate binding affinity and low denaturing effect might be of high significance.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N397 – PubChem

Archives for Chemistry Experiments of 763114-26-7

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PHTHALAZINONE COMPOUND

4-(4-Fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)phthalazin-1(2H)-one as crystalline Form C.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N744 – PubChem

Brief introduction of 253-52-1

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Investigations of reactions of selected azaarenes with radicals in water. 2. Chlorine and bromine radicals

The halogen radicals that react with azaarenes are produced by the photooxidation of halogenide anions with hydroxyl and sulfate radicals and exist as complexes of the radical and the respective halogenide anion in the aqueous phase. The main reaction products of the reactions are identified, and in the case of the bromine radicals, the second order rate constants are determined. Oxidation takes place according to the different redox potentials of the two reactants and is especially observed for chlorine radicals. A typical product spectrum comparable with that in reactions with hydroxyl and sulfate radicals has been found. The formation of some oxidation products in reactions of bromine radicals is in contradistinction to the oxidation potentials of the azaarenes and can be understood only by the reaction of their excited states. The halogenation is the main reaction of the azaarenes. Halogenation products of both, the benzene and the pyridine/diazine rings, have been found. The halogenation of the pyridine/diazine ring again requires the reaction of excited states. The majority of derivatives is halogenated in substitution reactions, but in the reaction of benzo[h]quinoline, addition is also observed. The resonance energy per electron is responsible for the change in the halogenation mechanism from substitution to addition.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N66 – PubChem

Extended knowledge of 2-(3-(4-Bromo-2-fluorobenzyl)-4-oxo-3,4-dihydrophthalazin-1-yl)acetic acid

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Aldose reductase as a drug target for treatment of diabetic nephropathy: Promises and challenges

Diabetic nephropathy (DN) is one of the most serious microvascular complications of diabetes mellitus and the leading cause of end stage renal disease. One of the key pathways activated in DN is the polyol pathway, in which glucose is converted to sorbitol (a relatively nonmetabolizable sugar) by the enzyme aldose reductase (AR). Shunting of glucose into this pathway causes disruption to glucose metabolism and subsequently damages the tissues via increased oxidative stress, protein kinase c activation and production of advanced glycation end products (AGE) in the kidney. This review aims to provide a comprehensive overview of the AR enzyme structure, substrate specificity and topology in normal physiology; to elaborate on the deleterious effects of AR activation in DN; and to summarize the potential therapeutic benefits and major challenges associated with AR inhibition in patients with DN.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N863 – PubChem

Simple exploration of Phthalazine

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Laser ablation: Preparation of ‘chemically pure’ Ag colloids for surface-enhanced Raman scattering spectroscopy

Chemically pure’ Ag colloids as active surfaces for surface-enhanced Raman scattering (SERS) spectroscopy were prepared by laser ablation of an Ag foil in pure water, in the presence of Cl-anions, and in the presence of an adsorbate. SERS-activity of the ablated colloids was proved using 2,2′-bipyridine [bpy] and phtalazine [pht] as adsorbates. Moreover, a SERS-active Ag colloid/adsorbate system was prepared by laser ablation of Ag foil immersed in an aqueous solution of pht. SERS spectra of phi obtained from this system are identical with those of phi added to Ag colloid ablated in pure water. The possibility of preparing a SERS-active system by laser ablation of Ag in the presence of an adsorbate was thus demonstrated. Furthermore, Ag colloid-bpy films were prepared from the laser ablated colloids and their SERS activity proved by obtaining a good quality SERS spectra of bpy.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N350 – PubChem

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Synthesis of novel dual target inhibitors of PARP and HSP90 and their antitumor activities

Poly (ADP-ribose) polymerase (PARP) inhibitors have achieved great success in clinical application, especially for the prolonged survival of cisplatin-sensitive ovarian cancer patients. However, there are still many patients who do not respond to PARP inhibitors. Novel PARP inhibitors with higher activity are urgently needed. Herein we report a series of compounds by molecular hybridization PARP-1 inhibitor Olaparib (Ola) with HSP90 inhibitor C0817 (one curcumin derivative). All synthesized compounds were evaluated for their antiproliferative activity in vitro, and some were further assessed for their inhibitory activities of the PARP enzyme and HSP90 affinity. Our results indicated that compound 4 could bind to HSP90 and cause static quenching, indicating that compound 4 was able to bind to HSP90, moreover, downstream molecular breast cancer 1 (BRAC-1) was reduced. In conclusion, dual target inhibitors of PARP and HSP90 exhibited stronger selective cytotoxicities against cancer.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N785 – PubChem