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The invention provides a 3 – (2 – phenylethyl and five-membered heterocyclic) – 4 – (3 – dimethylamine c amino) quinoline derivatives and its preparation method and application, 3 – (2 – phenylethyl and five-membered heterocyclic) – 4 – (3 – dimethylamine c amino) quinoline derivatives of the formula is: . The compound has a good anti-tumor activity, can be applied to the preparation of anti-tumor drug. (by machine translation)

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Benzofuran – Wikipedia,
Benzofuran | C8H3518O – PubChem

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Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitors-3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC 50 = 0.3 muM) and 4-oxo-1,4-dihydrobenzo[h]quinoline-3-carboxylic acid (9) (IC50 = 1 muM), are ATP competitive (Ki values are 0.06 and 0.28 muM, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.

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Benzofuran – Wikipedia,
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The development of a clear chemical process to produce diverse value-added chemicals from low-cost raw materials is a particularly attractive concept and represents a considerable challenge in sustainable organic synthesis. Herein, two highly efficient and clear methods for the synthesis of quinolone derivatives based on a linear/branched domino protocol under sustainable conditions were established. The main advantages of these protocols are the simple experimental procedure, high bond-forming efficiency, inexpensive readily available starting materials, moderate to excellent yields with good functional group compatibility, and nonchromatographic purification, which render these methods particularly attractive for the sustainable preparation of biologically and medicinally interesting molecules. To demonstrate the practical utility of our protocol, existing pharmaceutical sarafloxacin was successfully synthesized. Furthermore, a postulated reaction pathway including condensation reaction/nucleophilic aromatic substitution/Friedel-Crafts reaction for these domino reactions is also discussed.

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Benzofuran – Wikipedia,
Benzofuran | C8H3519O – PubChem

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Ribosylation reactions of previously silylated 3-carbethoxy-8-methyl-1,4-dihydro-4-oxoquinoline (6a) and 3-carbethoxy-6-methyl-1,4-dihydro-4-oxoquinoline (6b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (7), under Lewis acid catalysis, were studied. The method using hexamethyldisilazane (HMDS)/trimethylchlorosilane (TMCS) mixture for silylation and anhydrous stannic chloride as catalyst for ribosylation failed to give any nucleoside product. On the other hand, the protected nucleoside 3-carbethoxy-6-methyl-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4- dihydro-4-oxoquinoline (8b) was obtained in good yields using bis(trimethylsilyl)trifluoroacetamide (BSTFA) containing 1% of TMCS and the same catalyst. Compound 8b was more easily isolated in higher yields with an improvement of the later method by replacing stannic chloride with trimethylsilyl trifluoromethanesulfonate (TMSOTf). De-O-benzoylation of 8b with methanolic sodium hydroxide solution afforded the free riboside 3-carbomethoxy-6-methyl-1-beta-D-ribofuranosyl-1,4-dihydro-4-oxoquinoline (9b). The structures of the obtained products were confirmed by their UV, MS, IR, 1H and 13C-NMR data.

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Benzofuran – Wikipedia,
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We report the detailed synthesis and photochemistry of two analogs (specifically 3,5-di-tert-butyl-7?-methyl- and 3,5-di-tert-butyl-7?,9?-dimethyl-1?,3?-dihydrospirocyclohexa[2,5]diene-1,2?-pyrido[4,3,2-de]quinazolin-4-one) of the perimidinespirohexadienone (3,5-di-tert-butyl-1?,3?-dihydrospirocyclohexa[2,5]diene-1,2?-perimidin-4-one) family of photochromes in which the naphthalene moiety of the parent is replaced by a quinoline, and compare them to the parent compound. Molar absorptivities of both the short wavelength spirocyclic isomer (SW) and long wavelength quinonimine isomer (LW) of each were determined by a combination of proton NMR and UV-vis spectroscopy in solvents of varying polarity. Quantum yield measurements for photoisomerization of SW to LW are reported in those same solvents, with qualitative extrapolation to additional solvents. The position and rate of the thermal equilibrium reverting LW to SW is estimated for these compounds. The 9?-methyl in SW (6-methyl in LW) is found to be essential for complete reversion of LW to SW in the dark. Finally one-dimensional NOE NMR spectroscopy was used to conclusively determine the structure of LW for the quinoline analogs as the 4-(5-aminoquinolin-4-ylimino)-2,6-di-tert-butylcyclohexa-2,5-dienone resulting from opening toward the quinoline nitrogen, rather than the 4-(4-aminoquinolin-5-ylimino) structure that would result from spirocyclic ring opening away from the quinoline nitrogen which had been initially proposed by Minkin et al. for very similar compounds [V.I. Minkin, V.N. Komissarov, V.A. Kharlanov, Perimidinespirocyclohexadienones, in: J.C. Crano, R.J. Guglielmetti (Eds.), Organic Photochromic and Thermochromic Compounds, vol. 1, Plenum Press, New York, 1999, pp. 315-340, and references therein].

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Benzofuran – Wikipedia,
Benzofuran | C8H3527O – PubChem

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A series of substituted 1,3,4-oxadiazole, 1,2,4-triazole, and 1,3,4-thiadiazole derivatives of the substituted 3-carboethoxy-1,4-dihydro-4- oxoquinoline have been synthesized through the reaction of the key intermediate thiosemicarbazide derivatives with different reagents. N?-Arylidene-4-oxo- 1,4-dihydroquinoline-3-carbohydrazides were also synthesized through the condensation reaction of the corresponding hydrazides with the appropriate aldehydes. Antimicrobial activity of some of the synthesized compounds was evaluated.

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Benzofuran – Wikipedia,
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Regiocontrolled nitration of 4-quinolone, the highly privileged scaffold, has been developed at ambient conditions. The nitro group can selectively be introduced at diverse positions simply by tuning the reactivity of the moiety. Discrimination is being achieved through the selective functionalization of the free N-H group. The functional group has been screened theoretically with the help of Fukui function and local softness calculation. Theoretical predictions are synchronized well with the experimental findings. Finally, this nitration technique allows quick access to the structurally diverse 4-quinolones.

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Quinolones have been discovered in our laboratory was a new class of antifilarial agents. This has led to the design, synthesis, and antifilarial evaluation of a number of N-substituted quinol-4(1H)-one-3-carboxamide derivatives 4-6. The macrofilaricidal activity of the target compounds was initially evaluated in vivo against Acanthoeilonema viteae by oral administration of 200 mg/kg x 5 days. Among all the synthesized compounds, 13 displayed activity, with the most potent compound (4a) exhibiting 100% macrofilaricidal and 90% microfilaricidal activities. Compound 4e elicited significant macrofilaricidal (80%) response while compound 5c showed 100% sterilization of female worms. Finally, the two most potent macrofilaricidal compounds, namely 4a and 4e, have been screened for their potency against DNA topoisomerase II, and it has been observed that both have the capability to interfere with this enzyme at 10 mumol/mL concentration. The structure- activity relationship (SAR) associated with position-3 and aryl ring substituents is discussed.

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Benzofuran – Wikipedia,
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A single crystal X-ray diffraction and theoretical study has been carried out on mono hydrates of three 2H-pyrazolo[4,3-c]quinolin-3(5H)-one derivatives, namely 6-methyl-2-phenylpyrazolo[4,3-c]quinolin-3-one, 3, 6-methyl-2-(4- chlorophenyl)pyrazolo[4,3-c]quinolin-3-one, 4, and 8-methyl-2-(4-nitrophenyl) pyrazolo[4,3-c]quinolin-3-one, 5. The monohydrates were obtained on recrystallization from moist solvents. While there are three tautomeric forms possible for such pyrazolo[4,3-c]quinolin-3-one molecules, the sole form isolated in the solid [(X)×(H2O)] (X = 3, 4 and 5) compounds was the quinoloid form – the one calculated to be the most stable at the M06-2X/6-311++G(d,p) level of theory. Excellent agreement was found between the calculated and X-ray determined structures. Molecule 5 in [(5)×(H 2O)] is very near planar while both molecules 3 and 4 in their respective hydrates are much less so as a consequence of angles about 24 between the two aromatic rings. In each hydrate, the pyrazolo[4,3-c]quinolin-3-one molecule is bonded to three water molecules and each water molecule is likewise H-bonded to three pyrazolo[4,3-c]quinolin-3-one molecules. While the water molecules are H-bonded to 3 and 4 via the pyridinyl N and 2x the carbonyl O atoms, in [(5)×(H2O)] the H-bonds are to pyridinyl N, carbonyl O and a nitro O atoms. Calculations indicated that the found arrangement in [(5)×(H2O)] is more stable than one using the connections as found in [(3)×(H2O)] and [(4)×(H2O)]. While each of the hydrates possess strong N-H?O and O-H?O hydrogen bonds, and weaker C-H?pi and pi?pi interactions, the supramolecular arrays are very different.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H3523O – PubChem

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A new series of quinolone-3-carboxylic acids featuring different hydrophobic groups at N-1, C-2, C-7, and C-8 positions were synthesized and evaluated for their activity against single-cycle replicable HIV NL4-3 as inhibition rate of p24 expression in Hela cells cultures. Most of the synthesized compounds showed anti-HIV activity with no significant cytotoxicity at concentration of 100 muM. The most active compounds 4h, 4k, and 4j exhibited anti-HIV activity with an inhibition rate of 55, 71, and 84 %, respectively. A docking study using the crystallographic data available for PFV integrase including its complexes with Mg2+ and Raltegravir revealed that the active compounds could occupy same space near Raltegravir and interact with the Mg2+ ions in the active site. Thus, the anti-HIV activity of the synthesized compounds might involve a metal chelating mechanism. [InlineMediaObject not available: see fulltext.]

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Benzofuran – Wikipedia,
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