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Aibin Wu Jide Liu Shaoxiong Qin Ping Mei 《Monatshefte für Chemie / Chemical Monthly》2010,21(3):95-99
Abstract
A series of mono and bis-2-(2-(dimethylamino)-ethyl)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-diones with different amino side chains, a novel family of antitumor agents, has been designed and synthesized. Their antitumor activity was evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8, and A375 cancer cell lines in vitro. Preliminary results showed that most of the derivatives had antitumor activity comparable with that of mitonafide, with IC 50 values of 10−6–10−5 M. More importantly, the derivatives had distinct antitumor selectivity against different cancer cell lines. This work provided a novel class of mitonafide-based lead compounds with improved antitumor selectivity against cancer cell lines for further optimization. 相似文献3.
N. B. Patel A. I. Gandhi R. D. Sharma 《Monatshefte für Chemie / Chemical Monthly》2010,46(2):1123-1133
Abstract
6-(Substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones were prepared from β-aryl glutaconic acid, which, on fusion with aniline, results in 4-(4-ethoxyphenyl)-1-phenylpyridine-2,6(1H,5H)-dione. This, on further treatment with phosphorus oxychloride gave 6-chloro-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinone, and further treatment with secondary amines yielded 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones. These were subjected to azo coupling with different aryldiazonium chlorides furnishing two isomers, which were separated by column chromatography. All compounds were characterized by elemental analysis, and use of IR and NMR spectral data, and were evaluated for antimicrobial activity. 相似文献4.
A. G. Majouga E. K. Beloglazkina S. Z. Vatsadze N. A. Frolova N. V. Zyk 《Russian Chemical Bulletin》2004,53(12):2850-2855
Three procedures were used for the synthesis of -, , and -pyridyl-substituted (5Z)-3-phenyl-5-(pyridylmethylene)-2-thiohydantoins: the reaction of 2-thiohydantoin with the corresponding aldehyde in AcOH in the presence of AcONa, the two-step one-pot synthesis with the use of the same starting compounds, and three-component condensation of aryl isothiocyanate, glycine, and aldehyde in AcOH. Alkylation of the resulting thiohydantoins with iodomethane in the presence of a base afforded the corresponding S-methylated derivatives, viz., 2-methylthio-3-phenyl-5-(pyridylmethylene)-3,5-dihydro-4H-imidazol-4-ones. The structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thioxoimidazolin-4-one and (5Z)-2-methylthio-3-phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one were established by X-ray diffraction analysis.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2734–2739, December, 2004. 相似文献
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V. N. Britsun A. N. Esipenko A. N. Chernega M. O. Lozinskii 《Russian Journal of Organic Chemistry》2005,41(1):108-113
3-Aryl-1,2,4-triazole-5-thiones react with dimethyl acetylenedicarboxylate and methyl 3-phenyl-propynoate to afford the corresponding 5-substituted 2-aryl-7H-[1,2,4]triazolo[3,2-b][1,3]thiazin-7-ones. Treatment of 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones with alkalies leads to formation of 3-(benzimidazol-2-ylsulfanyl)-3-arylpropionic acids, their reaction with methyl p-toluenesulfonate yields 1-(3-methyl-2-thioxo-2,3-dihydro-1N-benzimidazol-1-yl)-3-phenyl-2-propen-1-one, and oxidation with hydrogen peroxide gives benzimidazole-2-sulfonic acid and 3-aryl-2-propenoic acids.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 109–114.Original Russian Text Copyright © 2005 by Britsun, Esipenko, Chernega, Lozinskii. 相似文献
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Prashant P. Thakare Yogesh Walunj Abhijit Chavan Vivek D. Bobade Dhiman Sarkar Pravin C. Mhaske 《Journal of heterocyclic chemistry》2020,57(11):3918-3929
A new series of 4-(4-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-3-yl)quinoline ( 6a-t ) have been synthesized by a click reaction of 4-(4-ethynyl-1-phenyl-1H-pyrazol-3-yl)quinoline ( 4a-d ) with a substituted benzyl azide ( 5a-e ). The starting alkyne derivatives 4a-d are obtained from Bestmann-Ohira reaction of 1-phenyl-3-(quinolin-4-yl)-1H-pyrazole-4-carbaldehyde and dimethyl(1-diazo-2-oxopropyl)phosphonate. The newly synthesized compounds are screened against M. tuberculosis H37Ra dormant and active, Escherichia coli, Pseudomonas fluorescence, Staphylococcus aureus and Bacillus subtilis strains at 30 μg/mL concentration. Most of the screened compounds showed good to moderate antibacterial activity against S. aureus, B. subtilis, and Mycobacterium tuberculosis H37Ra strains. The synthesized derivatives of quinolinyl-pyrazole-4-carbaldehyde and quinolinyl-pyrazole-4-ethyne reportd good to moderate activity against both strains of M. tuberculosis H37Ra. Ten derivatives of quinolinyl-pyrazole presented good activity against B. subtilis. These results suggested that further optimization and development of quinolinyl-pyrazolyl-1,2,3-triazole moeity could serve as lead compounds for antimycobacterial activity. 相似文献
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Shubhangi C. Joshi Kunjbihari N. Trivedi 《Monatshefte für Chemie / Chemical Monthly》1992,123(6-7):557-564
Summary The Claisen rearrangement of 7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 a) gave 7-hydroxy-8-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (3 a) and 2,3-dihydro-2,6-diphenyl-3-methyl-(7H)furo[2,3-h]-1-benzopyran-7-one (7 a). 2-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 b) afforded4 b and7 b. 8-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (12) gave only the alkali soluble product 7-hydroxy-8-methyl-6-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (13).3 a,4 b, and13 were further cyclized in acidic medium to9 a,10 b, and14 followed by dehydrogenation.This paper is dedicated to Dr. F. M. Dean, Department of Organic Chemistry, Robert Robinson Laboratories, University of Liverpool, Liverpool, U. K., on his retirement 相似文献
8.
Ashraf A Aly 《Tetrahedron》2003,59(32):6067-6073
Reaction of 4-arylidene-2-phenyl-5(4H)-1,3-oxazolones with benzyne afforded predominantly, 3-arylidene-7-hydroxy-7-phenyl-1,4(H)-benzoxazepine-2-ones in addition to their N-phenyl derivatives. However, the reaction of the target oxazolones with an excess of benzyne gave only the N-phenyl derivatives of 1,4(H)-benzoxazepine-2-ones in good yields. The reaction mechanism describing product formation is also explained. Arylation of 1,4(H)-benzoxazepine-2-ones with benzyne proceeded successfully to give the N-phenyl products. 相似文献
9.
Leila S. Boulos Mona H. N. Arsanious El-Sayed M. A. Yakout 《Monatshefte für Chemie / Chemical Monthly》2007,41(9):979-984
The reaction of 3-amino-2-phenyl-4(3H)-quinazolinone with oxovinylidenetriphenylphosphorane afforded 5-phenylpyrazolo[1,5-c] quinazoline-2(3H)-one and triphenylphosphine oxide. On the other hand, when quinazolinone reacts with phosphorus ylides, the corresponding
phosphorane adducts were obtained. Moreover, quinazolinone reacts with trisdialkylaminophosphines to give the new (dialkylamino)oxophosphonium
dipolar products. Possible reaction mechanisms are considered and the structural assignments are based on analytical and spectroscopic
results. 相似文献
10.
N-(1,3-Thiazol-5(4H)-ylidene)amines via 1,3-Dipolar Cycloaddition of Azides and 1,3-Thiazol-5(4H)-thiones Organic azides 5 and 4,4-dimethyl-2-phenyl-1,3-thiazol-5(4H)-thione ( 2 ) in toluene at 90° react to give the corresponding N-(1,3-thiazol-5(4H)-ylidene)amines (= 1,3-thiazol-5(4H)-imines) 6 in good yield (Table). A reaction mechanism for the formation of these scarcely investigated thiazole derivatives is formulated in Scheme 3: 1,3-Dipolar azide cycloaddition onto the C?S group of 2 leads to the 1:1 adduct C . Successive elimination of N2 and S yields 6 , probably via an intermediate thiaziridine E . 相似文献
11.
Tukaram S. Choudhare Devendra S. Wagare Vijay T. Kadam Prashant D. Netankar 《Journal of heterocyclic chemistry》2021,58(8):1637-1644
The present investigation describe the synthesis of 8-(benzyloxy)-5-(2-[1,3-diphenyl-1H-pyrazol-4-yl]thiazol-4-yl)quinolin-2(1H)-one derivatives. Quinolin-8-ol was transformed by five step synthetic procedures into 8-Benzyloxy-5-(2-bromo-acetyl)-1H-quinolin-2-one. Subsequently, 8-Benzyloxy-5-(2-bromo-acetyl)-1H-quinolin-2-one condensed with 1,3-Diphenyl-1H-pyrazole-4-carbothioic acid amide in the presence of acetonitrile to afford 8-(benzyloxy)-5-(2-[1,3-diphenyl-1H-pyrazol-4-yl]thiazol-4-yl)quinolin-2(1H)-one derivatives. Synthesized compounds were screened for their antimicrobial activity against gram-positive and gram-negative bacteria. Most of the synthesized compounds are found to be active against tested bacterial strains and fungal strain. 相似文献
12.
Faouzi Guenadil Hocine Aichaoui Coco N. Kapanda Didier M. Lambert Christopher R. McCurdy Jacques H. Poupaert 《Monatshefte für Chemie / Chemical Monthly》2011,27(7):67-80
Abstract
A simpler and efficient “green” method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. 相似文献13.
6,7-Dimethoxy-2-phenyl-4-1,3-benzothiazine (1) and 6,7-dimethoxy-4-phenyl-2-1,3-benzothiazine (2) react with substituted acetyl chlorides to give linearly, and new angularly condensed β-lactam derivatives (4,5). Heating of the latter compounds with hydrogen chloride in anhydrous ethanol leads to the formation of the corresponding 4- and 2-1,3-benzothiazinium chloride, respectively. The configurations of these compounds (the mutual positions of the substituents relative to the β-lactam ring) were determined by 1H and 13C studies, also making use of the aromatic solvent-induced shifts. 相似文献
14.
A series of α-[3-alkyl-3,4-dihydro-2-oxo-2H-1,3-benzoxazin-4-yl]-β-keto ester derivatives 1 (Table I) were synthesized by the condensation of 3-alkyl-3,4-dihydro-4-hydroxy-2H-1,3-benzoxazine-2-ones 3 (2) with β-keto esters 4 in the presence of traces of mineral acids under azeotropic conditions. Condensation of 1 with hydrazines 5 gave pyrazolone derivatives 2 (Table II). Condensation of β-diketone derivatives 6 with hydrazines 5 and with 1,2-benzenediamine ( 8 ) resulted in the formation of pyrazoles ( 7a-c ) and diazepine derivatives 12 (Table III) and 13 , respectively. 相似文献
15.
N. T. Pokhodylo R. D. Savka V. S. Matiichuk N. D. Obushak 《Russian Journal of General Chemistry》2009,79(2):309-314
By cycloaddition of arylazides to acetylacetone are obtained derivatives of 1,2,3-triazole. In the reaction of 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) and 1-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] ethanones (VIIa-VIIe) with isatin are obtained 2-[1-(R-phenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids (IIIa–IIIe) and 2-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] -4-quinolinecarboxylic acids (IXa, IXb), respectively. We found that 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) readily transform into [5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] acetic acids (IVa–IVc) by the method of Wilgerodt-Kindler. The (5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)acetic acid reacts with 5-phenyl-4-amino-4H-1,2,4-triazol-3-thiol affording 6-[(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) methyl]-3-phenyl[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazole (VI).
Original Russian Text ? N.T. Pokhodylo, R.D. Savka, V.S. Matiichuk, N.D. Obushak, 2009, published in Zhurnal Obshchei Khimii,
2009, vol. 79, no. 2, pp. 320–325. 相似文献
16.
Summary The title compounds (5) were prepared by addition of 2-phenyl-1,3-dithiane anion (2-lithiated10) to adequately substituted N-alkyl-3,4-dihydroisoquinolinium salts (7a–7g). Cleavage of compounds5 with HgO/BF3 affords S-benzoyl-1,3-propanedithiol (4a) and the corresponding disulfide4c, benzaldehyde, and Hg(I) ions. In contrast to the title compounds, 2-(-dialkylaminobenzyl)-2-phenyl-1,3-dithianes (6) yield benzil under these conditions.In commemoration of the late Prof. Dr. Dr. h.c. mult.Horst Böhme, Marburg/Germany, an outstanding representative of Pharmaceutical Chemistry 相似文献
17.
Formation of Methyl 5,6-Dihydro-l, 3(4H)-thiazine-4-carboxyiates from 4-Allyl-l, 3-thiazol-5(4H)-ones . The reaction of N-[1-(N, N-dimethylthiocarbamoyl)-1-methyl-3-butenyl]benzamid ( 1 ) with HCl or TsOH in MeCN or toluene yields a mixture of 4-allyl-4-methyl-2-phenyl-1,3-thiazol-5(4H)-one ( 5a ) and allyl 4-methyl-2-phenyl-1,3-thiazol-2-yl sulfide ( 11 ; Scheme 3). Most probably, the corresponding 1,3-oxazol-5(4H)-thiones B are intermediates in this reaction. With HCl in MeOH, 1 is transformed into methyl 5,6-dihydro-4,6-dimethyl-2-phenyl-1,3(4H)-thiazine-4-carboxylate ( 12a ). The same product 12a is formed on treatment of the 1,3-thiazol-5(4H)-one 5a with HCl in MeOH (Scheme 4). It is shown that the latter reaction type is common for 4-allyl-substituted 1,3-thiazol-5(4H)-ones. 相似文献
18.
5-Amino-3-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-7-phenyl-7H-thiazolo[3,2-a]pyrimidine-6-carbonitrile was synthesized via the reaction of 4-(2-aminothiazol-4-yl)-3-methyl-1-phenyl-2-pyrazolin-5-one with benzylidene malononitrile and was then transformed
to related fused heterocyclic systems. The antifungal and antibacterial studies revealed in some cases excellent biocidal
properties. 相似文献
19.
《Tetrahedron: Asymmetry》1999,10(1):153-167
(R)-Monomethyl 2-methyl-2-(2-nitrophenoxy)malonates obtained by PLE catalyzed hydrolysis of the corresponding dimethyl malonates undergo solvent-dependent enantioselective cyclization to afford (R)-methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acids, respectively. These compounds are easily converted to enantiomerically and diastereomerically pure carboxamides, which are used as peptidomimetic building blocks. 相似文献
20.
5-(Trifluoromethanesulfonyloxy)-4H-1,3-dioxin (3) participates in a variety of nucleophilic substitution reactions with cuprate reagents or in palladium catalyzed cross-coupling reactions to provide 5-substituted-4H-1,3-dioxins 5. Upon thermolysis, these compounds undergo facile retrocycloaddition reactions to generate the corresponding 2-substituted acroleins which, if necessary, can be trapped in situ with dienes or heterodienophiles. In particular, the heretofore unknown 2-acylacroleins can be generated using this methodology and trapped with enol ethers to afford 5-acyl-3,4-dihydro-2H-pyrans (6g,h), a substructural unit common to many natural products. 相似文献