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Excited state absorption spectra and intersystem crossing kinetics in diazanaphthalenes

Picosecond time-resolved, excited state absorption spectra in the visible following excitation at 355 nm are discussed for room temperature solutions of four diazanaphthalenes (DN)-quinoxaline (1,4-DN), quinazoline (1,3-DN), cinnoline (1,2-DN), and phthalazine (2,3-DN).Kinetics of singlet state decay are obtained by monitoring the decay of Sn <*> S1 bands.The intersystem crossing rate constant (kisc) is found to vary as kisc(1,4-DN)>kisc(1,3-DN)>kisc(1,2-DN).The kisc in phthalazine could not be determined from the weak, visible Sn<*>S1 absorption.Assuming rapid singlet vibrational relaxation and only minor effects due to energy gap variations, these experimental results agree with statistical limit predictions for the relative nonradiative rate.Calculations of the spin-orbit coupling matrix element betael = <*>so<*>T1(3??*)>, using INDO wave functions, give the ordering betael(1,4-DN)>betael(2,3-DN)>betael(1,3-DN)>betael(1,2-DN).

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Phthalazine | C8H6N394 – PubChem

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Direct selective oxidative cross-coupling of simple alkanes with heteroarenes

A dream reaction: An efficient and practical method for the oxidative cross-coupling of heteroaromatic compounds and simple alkanes has been developed. The desired products are smoothly and regioselectively formed under mild reaction conditions at ambient temperature in a hypervalent-iodine-mediated transformation. The method allows for preferential transformation of stronger C sp 3-H bonds in the presence of weaker C sp 3-H bonds under metal-free conditions.

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From Thorium to Plutonium: Trends in Actinide(IV) Chloride Structural Chemistry

A series of eighteen tetravalent actinide (An = Th, U, Pu) compounds were synthesized from acidic aqueous solutions containing thorium, uranium, or plutonium and a series of protonated nitrogen heterocycles. The compounds were characterized using Raman, IR, and optical absorption spectroscopies. The structures were determined using single-crystal X-ray diffraction and found to consist of [An(H2O)xCly]4-y (x = 4-7 and y = 2-4) or AnCl62- molecular units. Breaks in the structural chemistry of the early actinides were observed, with Th adopting exclusively Th-aquo-chloro species and Pu forming only PuCl62- U crystallized as both U-aquo-chloro and UCl62-. The relationship between the solid-state structural units and the solution species was interrogated using UV-vis-near-IR absorption spectroscopy. A comparison of the solution and solid-state spectra suggested that, although prevalent in the solid state, particularly for U and Pu, AnCl62- does not exist to an appreciable extent in the reaction solution. Despite the identification of U-aquo-chloro species in solution, there are limited reports of these complexes in the solid state. Isolation of these unique actinide(IV) chlorides as reported in this work may point to the importance of nonbonding interactions in the stabilization and precipitation of AnIV structural units.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N463 – PubChem

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Synthesis and cytotoxic evaluation of some new 3-(2-(2-phenylthiazol-4-yl) ethyl)-quinazolin-4(3H) one derivatives with potential anticancer effects

Quinazolinones are a group of heterocyclic compounds that have important biological activities such as cytotoxicity, anti-bacterial, and anti-fungal effects. Thiazole-containing compounds have also many biological effects including antitumor, antibacterial, anti-inflammatory, and analgesic activities. Due to significant cytotoxic effects of both quinazoline and thiazole derivatives, in this work a group of quinazolinone-thiazol hybrids were prepared and their cytotoxic effects on three cell lines were evaluated using MTT assay. Compounds A3, A2 , B4 , and A1 showed highest cytotoxic activities against PC3 cell line. Compounds A3 , A5 , and A2 were most active against MCF-7 and A3 , A5 , and A6 showed good cytotoxic effect on HT-29 cell line. According to the results, A3 efficiently inhibited all cell growth tested in a dose dependent manner. The IC 50 of A3 was 10 M, 10 muM, and 12muM on PC3, MCF-7, and HT-29 cells, respectively.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N191 – PubChem

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Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N471 – PubChem

Extracurricular laboratory:new discovery of Phthalazine

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Synthesis, Structure, and Biological Activity of New Azine-Bridged Dinuclear Platinum(II) Complexes – A New Class of Anticancer Compounds

A recently described new class of dinuclear platinum anticancer compounds, represented so far by the isomeric azine-bridged complexes [{cis-Pt(NH 3)2Cl}2(mu-pzn)]Cl2 (1) (pzn = pyrazine), [{cis-Pt(NH3)2Cl)2(mu-pmn)]Cl 2 (2) (pmn = pyrimidine) and [{cis-Pt(NH3) 2Cl}2(mu-pdn)](NO3)2 (3) (pdn = pyridazine), has been added to. Three new dinuclear complexes of this type, [{cis-Pt(NH3)2Cl}2(mu-2,5pzn)]Cl2 (4) (2,5pzn = 2,5-dimethylpyrazine), [{cis-Pt(NH3) 2Cl)2(mu-qzn)]Cl2 (5) (qzn = quinazoline), and [{cis-Pt(NH3)2Cl}2(mu-pht)](NO 3)2 (6) (pht = phthalazine), have been newly synthesized and characterized by 1H and 195Pt NMR spectroscopy. The interaction of the new compounds with 2 equiv. of 9EtG in D2O at 310 K has been investigated. Complexes 4 and 5 undergo substitution of both chloride ligands by 9EtG similarly to the related complexes 1 and 2, respectively. The methyl substituents on the pyrazine ring induce steric hindrance in 4 resulting in a slower reaction rate as compared to 1. Similarly to the case of 3, interaction of complex 6 with 9EtG results in cleavage of the Pt-N(pht) bond and subsequent formation of the polymeric species. A cytotoxicity assay of 4-6 has been performed on seven human tumor cell lines and on L1210 murine leukemia cell lines, sensitive and resistant to cisplatin. Compounds 4 and 5 exhibit lower cytotoxicity than the analogous complexes with unsubstituted azines. Complex 6 is more active: its cytotoxicity in the L1210 cell lines is similar to that of cisplatin. Analysis of nuclear DNA fragmentation in L1210 cells treated with the azine-bridged complexes 1-6 has been carried out. The results clearly indicate induction of apoptosis by all the compounds, implying considerable anticancer potential. The structure-activity relationship for this class of dinuclear platinum(ii) complexes is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N218 – PubChem

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Development of anti-angiogenic tyrosine kinases inhibitors: Molecular structures and binding modes

Purpose Since the hypothesis that solid tumors cause angiogenesis by secreting pro-angiogenic factors was introduced, research on angiogenesis has proceeded continuously. Development of inhibitors targeting the angiogenic tyrosine kinases, to block downstream signal transduction pathways, has become an important approach to cancer therapy. Our goal was to study the development and mechanism of anti-angiogenic tyrosine kinases inhibitors. Methods We researched data on discovery of the inhibitors and their binding modes using the PubMed, Web of Science, Food and Drug Administration (FDA), and Clinical Trials Web sites. Results In the last decade, many small molecule inhibitors targeting angiogenesis have been designed and synthesized with many now entering the clinic or gaining FDA approval. Advances in understanding regulatory mechanisms of angiogenesis have enabled development of these drugs. The development of inhibitors up to Phase 3 clinical trials and, for many, FDA approval has helped leading to the discovery of additional compounds. The structures, activities, and binding modes of these inhibitors are discussed in this review. Conclusions Though the angiogenesis inhibitors have different chemical structures, they share similar binding modes. Their interactions with the hinge region of receptor tyrosine kinases (RTKs) are critical to their effectiveness as inhibitors. In addition, as we review here, different drugs, when bound, induce different conformations of RTKs.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N508 – PubChem

Top Picks: new discover of Phthalazine

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REISSERT COMPOUND STUDIES. LIII. A NEW SYNTHESIS OF REISSERT COMPOUNDS USING TRI-n-BUTYLTIN CYANIDE

Reissert compounds were prepared by the reaction of the heterocyclic base and acyl halide with tri-n-butyltin cyanide in methylene chloride.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N349 – PubChem

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Cynomolgus monkey liver aldehyde oxidase: Extremely high oxidase activity and an attempt at purification

Aldehyde oxidase (EC 1.2.3.1) in monkey (Macaco fascicularis) liver was characterized. Liver cytosol exhibited extremely high benzaldehyde and phthalazine oxidase activities based on aldehyde oxidase, compared with those of rabbits, rats, mice and guinea pigs. Monkey liver aldehyde oxidase showed broad substrate specificity distinct from that of the enzyme from other mammals. Purified aldehyde oxidase from monkey liver cytosol showed two major bands and two minor bands in sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). These bands were also observed in Western blotting analysis using anti-rat aldehyde oxidase. The molecular mass of the enzyme was estimated to be 130-151 kDa by SDS-PAGE, and to be about 285 kDa by HPLC gel nitration. The results suggest that isoforms of aldehyde oxidase exist in monkey livers. 2000 Elsevier Science Inc. All rights reserved.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N423 – PubChem

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Visible-Light-Triggered, Metal- and Photocatalyst-Free Acylation of N-Heterocycles

A photoinduced acylation of N-heterocycles is explored. This visible-light triggered reaction occurs not only under extremely mild reaction conditions, but also does not require the presence of a photosensitizer. The mechanistic studies suggest formation of EDA complexes prompt to harness the energy from visible-light. Compatibility with a large panel of alpha-keto acids as acyl precursors and an array of N-heterocycles clearly showcase the synthetic potential of this handy and green acylation protocol. (Figure presented.).

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N174 – PubChem