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1.
Reactions of hydrogen sulfates of quino‐ and diquino‐annelated 1,4‐dithiins 11 and 2 with DMF/hydroxylamine‐O‐sulfonic acid/Fe++ ion system took place at the α‐quinolinyl positions and led to N,N‐dimethylcarbamoyl and N‐methyl‐N‐formylaminomethyl derivatives 6 , 8 , 12 and 7 , 9 , 13 , respectively. The 1H and 13C NMR spectra of N‐methyl‐N‐formylaminomethyl derivatives 7 , 9 , 13 showed the presence of rotational isomers E and Z regarding to the N‐methyl‐N‐formylaminomethyl substituent. The spectra of 6 , 7 , 8 , 12 and 13 were completely assigned with the use of 1D and 2D NMR techniques. In the case of rotational isomers 7a and 7b , the crucial correlations came from the NOE interaction between the methylene and methyl protons from CH2N(CH3)CHO groups and benzene‐rings protons. Synthesis of 2,3‐dihydro‐1,4‐dithiino[6,5‐e]quinoline 4‐oxide 14 was presented as well. 相似文献
2.
The starting material O‐protected glycosyl isothiocyanate ( 1?3 ) was refluxed with 1,4‐diaminobenzene in CHCl3 under nitrogen atmosphere to give 1,4‐bis(N‐glycosyl)thioureidobenzene ( 4?6 ). Then 1,4‐bis[N‐(4/6‐substituted benzothiazole‐2‐yl)‐N′‐glycosylguanidino]benzenes ( 8a?8e , 9a?9e , 10a?10e ) were obtained in good yield by reaction of compounds ( 4?6 ) with 2‐amino‐4/6‐benzothizoles ( 7a?7e ) and HgCl2 in the presence of TEA in DMF. The structures of all 18 new compounds were confirmed by IR, 1H NMR, LC‐MS and elemental analysis. The bioactivity of anti‐HIV‐1 protease (HIV‐1 PR) and against angiotensin converting enzyme (ACE) have been evaluated. 相似文献
3.
Synthesis,Antiviral, and Antimicrobial Activity of N‐ and S‐Alkylated Phthalazine Derivatives
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Ahmed H. Moustafa Hassan A. El‐Sayed Rasha A. Abd El‐Hady Abdelfattah Z. Haikal Maher El‐Hashash 《Journal of heterocyclic chemistry》2016,53(3):789-799
A series of N‐alkylphthalazinone were synthesized by the reaction of phthalazin‐1(2H)‐one derivatives 1a , 1b , 1c with alkylating agents namely, propargyl, allyl bromide, epichlorohydrin, 1,3‐dichloro‐2‐propanol, 4‐bromobutylacetate, and 1‐(bromomethoxy)ethyl acetate to give the corresponding N‐alkylphthalazinone 2a , 2b , 2c , 3a , 3b , 3c , 5a , 5b , 5c , 6a , 6b , 6c , 7a , 7b , 7c , and 9a , 9b , 9c . Alkylation of phthalazin‐1(2H)‐thione to give a series from S‐alkylphthalazine 12 , 13 , 14 and thioglycosides 15 and 17 was performed. Deprotection of compounds 7a , 7b , 7c , 9a , 9b , 9c , 15 , and 17 resulted in the formation of the corresponding products 8a , 8b , 8c , 10a , 10b , 10c , 16 , and 18 . The structure of newly synthesized compounds was assigned by IR, 1H, 13C NMR, and elemental analysis. Some of these compounds were screened for antiviral and antimicrobial activity. 相似文献
4.
Yoshihisa Kurasawa Kiminari Yoshida Naoki Yamazaki Eisuke Kaji Kenji Sasaki Yoshito Zamami Yasuhiro Sakai Takatoshi Fujii Hideyuki Ito 《Journal of heterocyclic chemistry》2012,49(2):288-292
The reaction of the 6‐substituted 1‐methyl‐4‐quinolone‐3‐carboxylates 10a , 10b with hydrazine hydrate gave the 3‐carbohydrazides 7a , 7b , respectively, whose reaction with 2‐, 3‐, and 4‐pyridinecarbaldehydes afforded the 3‐(N2‐pyridylmethylene)carbohydrazides 8a , 8b , 8c and 9a , 9b , 9c . The Curtius rearrangement of compound 7b provided the N,N′‐bis(4‐quinolon‐3‐yl)urea 14 presumably via the 3‐carboazide 11 and then 3‐isocyanate 12 . Compounds 7a , 8a , and 9a were found to possess antimalarial activity from the in vitro screening data. J. Heterocyclic Chem.,(2011). 相似文献
5.
A series of 7‐fluorinated 7‐deazapurine 2′‐deoxyribonucleosides related to 2′‐deoxyadenosine, 2′‐deoxyxanthosine, and 2′‐deoxyisoguanosine as well as intermediates 4b – 7b, 8, 9b, 10b , and 17b were synthesized. The 7‐fluoro substituent was introduced in 2,6‐dichloro‐7‐deaza‐9H‐purine ( 11a ) with Selectfluor (Scheme 1). Apart from 2,6‐dichloro‐7‐fluoro‐7‐deaza‐9H‐purine ( 11b ), the 7‐chloro compound 11c was formed as by‐product. The mixture 11b / 11c was used for the glycosylation reaction; the separation of the 7‐fluoro from the 7‐chloro compound was performed on the level of the unprotected nucleosides. Other halogen substituents were introduced with N‐halogenosuccinimides ( 11a → 11c – 11e ). Nucleobase‐anion glycosylation afforded the nucleoside intermediates 13a – 13e (Scheme 2). The 7‐fluoro‐ and the 7‐chloro‐7‐deaza‐2′‐deoxyxanthosines, 5b and 5c , respectively, were obtained from the corresponding MeO compounds 17b and 17c , or 18 (Scheme 6). The 2′‐deoxyisoguanosine derivative 4b was prepared from 2‐chloro‐7‐fluoro‐7‐deaza‐2′‐deoxyadenosine 6b via a photochemically induced nucleophilic displacement reaction (Scheme 5). The pKa values of the halogenated nucleosides were determined (Table 3). 13C‐NMR Chemical‐shift dependencies of C(7), C(5), and C(8) were related to the electronegativity of the 7‐halogen substituents (Fig. 3). In aqueous solution, 7‐halogenated 2′‐deoxyribonucleosides show an approximately 70% S population (Fig. 2 and Table 1). 相似文献
6.
Mohamed G. Assy Mohamed H. Sherif Abd El‐Galil E. Amr Osama I. Abdelsalam Mohamed A. Al‐Omar Mohamed M. Abdalla Islam Ragab 《Journal of heterocyclic chemistry》2013,50(4):766-773
In continuation of our previous work, a series of novel thiophene derivatives 4 , 5 , 6 , 8 , 9 , 9a , 9b , 9c , 9d , 9e , 10 , 10a , 10b , 10c , 10d , 10e , 11 , 12 , 13 , 14 , 15 , 16 were synthesized by the reaction of ethyl 2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carboxylate ( 1 ) or 2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile ( 2 ) with different organic reagents. Fusion of 1 with ethylcyanoacetate or maleic anhydride afforded the corresponding thienooxazinone derivative 4 and N‐thienylmalimide derivative 5 , respectively. Acylation of 1 with chloroacetylchloride afforded the amide 6 , which was cyclized with ammonium thiocyanate to give the corresponding N‐theinylthiazole derivative 8 . On the other hand, reaction of 1 with substituted aroylisothiocyanate derivatives gave the corresponding thiourea derivatives 9a , 9b , 9c , 9d , 9e , which were cyclized by the action of sodium ethoxide to afford the corresponding N‐substituted thiopyrimidine derivatives 10a , 10b , 10c , 10d , 10e . Condensation of 2 with acid anhydrides in refluxing acetic acid afforded the corresponding imide carbonitrile derivatives 11 , 12 , 13 . Similarly, condensation of 1 with the previous acid anhydride yielded the corresponding imide ethyl ester derivatives 14 , 15 , 16 , respectively. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, MS spectral data, and elemental analysis. The detailed synthesis, spectroscopic data, LD50, and pharmacological activities of the synthesized compounds are reported. 相似文献
7.
8.
Jií Hanusek Pavel Drabina Milo Sedlk Pavel Rosa 《Journal of heterocyclic chemistry》2006,43(5):1281-1285
9.
Bis(1,3,4‐oxadiazoles) 4 , 5 and bis(1,2,4‐triazoles) 6a , 6b have been prepared from 3,6‐dioxa‐1,8‐octanedithiol 1 through a multistep reaction sequence. Compound 4 reacted with the appropriate alkyl halide in the presence of potassium carbonate in refluxing acetone to give the corresponding bis(S‐alkylated‐1,3,4‐oxadiazoles) 7a , 7b . The title compound 8 was prepared by condensing 4 with benzoyl bromide in the presence of triethylamine. Further, 6,9‐dioxa‐3,12‐dithiotetradecanedihydrazide 3 was converted to bis{N′‐(phenylaminocarbonyl) hydrazides} and bis{N′‐(phenylaminocarbonothioyl)hydrazides} 9a , 9b using phenylisocyanate and phenylthioisocyanate, respectively, which underwent cyclization in alkaline medium to produce 6,9‐dioxa‐3,12‐dithiotetradecane bis(4‐phenyl‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐one) and their 3‐thio analogs 10a , 10b . The new compounds 4 , 5 , 6 , 7 , 8 , 9 , 10 were characterized by their IR, 1H‐NMR, 13C‐NMR, MS, and elemental analyses. 相似文献
10.
The reactions of diethylaminoethynyl(trimethyl)silane (1), bis(diethylaminoethynyl)methylsilane (2), diethylaminoethynyl(trimethyl)germane (3), dimethylaminoethynyl(triethyl)germane (4), diethylaminoethynyl(trimethyl)stannane (5) and methyl(phenyl)aminoethynyl(trimethyl)stannane (6) with trialkylboranes [BEt3 (7b), BPr3 (7c), BiPr3 (7d) and 9‐alkyl‐9‐borabicyclo[3.3.1]nonanes 9‐Me‐9‐BBN (8a) and 9‐Et‐9‐BBN (8b)] were studied. The alkynes 1 and 2 did not react even with boiling BEt3, whereas the reactions of 3–6 afforded mainly novel enamines [(E)‐1‐amino‐1‐trialkylgermyl‐2‐dialkylboryl‐alkenes (9, 10), (E)‐1‐diethylamino‐1‐trimethylstannyl‐2‐dialkylboryl‐alkenes (11, 12), (E)‐1‐methyl(phenyl)amino‐1‐trimethylstannyl‐2‐dialkylboryl‐alkenes (13, 14)]. This particular stereochemistry is unusual for products from 1,1‐organoboration reactions, indicating a special influence of the amino group. The starting materials and products were characterized by multinuclear magnetic resonance spectroscopy (1H, 11B, 13C, 15N, 29Si, 119Sn NMR). Copyright © 2003 John Wiley & Sons, Ltd. 相似文献
11.
Inga Susvilo Algirdas Brukstus Sigitas Tumkevicius 《Journal of heterocyclic chemistry》2006,43(2):267-276
12.
N‐acetyl‐4‐nitrotryptophan methyl ester (2), N‐acetyl‐5‐nitrotryptophan methyl ester (3), N‐acetyl‐6‐nitrotryptophan methyl ester (4) and N‐acetyl‐7‐nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF3‐methanol. Assignments of the 1H and 13C NMR chemical shifts were made using a combination of 1H–1H COSY, 1H–13C HETCOR and 1H–13C selective INEPT experiments. Copyright © 2008 Crown in the right of Canada. Published by John Wiley & Sons, Ltd 相似文献
13.
Hassan A. H. El‐Sherief Galal M. El‐Naggar Zeinab A. Hozien Suliman M. El‐Sawaisi 《Journal of heterocyclic chemistry》2008,45(2):467-473
14.
Khaled R. A. Abdellatif Morshed A. Chowdhury Edward E. Knaus 《Journal of heterocyclic chemistry》2008,45(6):1707-1710
15.
Quinolone Analogs 14: Synthesis of Antimalarial 1‐Aryl‐3‐(4‐quinolon‐2‐yl)ureas and Related Compounds
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Yoshihisa Kurasawa Kiminari Yoshida Naoki Yamazaki Kenji Sasaki Yoshito Zamami Zhao Min Atsumi Togi Hideyuki Ito Eisuke Kaji Haruhiko Fukaya 《Journal of heterocyclic chemistry》2014,51(Z1):E241-E248
The 4‐quinolone‐2‐carbohydrazide 6a was converted into 1‐aryl‐3‐(4‐quinolon‐2‐yl)ureas 5a , 5b , 5c , 5d , 5e , 1‐aryl‐3‐(4‐quinolon‐2‐yl)imidazolidine‐2,4‐diones 9a , 9b , and N‐(4‐quinolon‐2‐yl)carbamates 10a , 10b via 4‐quinolone‐2‐carbonylazide 7a . The 4‐methoxyquinoline‐2‐carbohydrazide 6b was also transformed into 1‐aryl‐3‐(4‐methoxyquinolin‐2‐yl)ureas 11a , 11b , 11c , 11d , 1‐aryl‐3‐(4‐methoxyquinolin‐2‐yl)imidazolidine‐2,4‐diones 12a , 12b , and N‐(4‐methoxyquinolin‐2‐yl)carbamates 13a , 13b via 4‐methoxyquinoline‐2‐carbonylazide 7b . Some of the 1‐aryl‐3‐(4‐quinolon‐2‐yl)ureas 5a , 5b , 5c , 5d , 5e showed the in vitro antimalarial activity to chloroquine‐resistant Plasmodium falciparum, wherein IC50 was 0.93 to 4.00 μM. 相似文献
16.
《Journal of heterocyclic chemistry》2017,54(1):325-330
A series of novel 1‐(3‐chloropyridin‐2‐yl)‐N‐substituted‐5‐(trifluoromethyl)‐pyrazole carboxamide derivatives TC1 , TC2 , TC3 , TC4 , TC5 , TC6 , TC7 , TC8 , TC9 , TC10 , TC11 were synthesized and characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis. All the target compounds were tested in vitro for their antibacterial activities and antifungal activities. The preliminary bioassays indicated that compound TC6 exhibited excellent activity against Xanthomonas oryzae (94.9% and 84.9%) at different concentrations (200 µg/mL and 100 µg/mL), which was higher than that of Bismerthiazol (94.6% and 64.0%), respectively. At the same time, most of the compounds exhibited moderate antifungal activities against four kinds of phytopathogenic fungi 相似文献
17.
Fuyi Zhang Bruno Bernet Véronique Bonnet Olivier Dangles Francisco Sarabia Andrea Vasella 《Helvetica chimica acta》2008,91(4):608-617
Chitosan ( 1 ) was prepared by basic hydrolysis of chitin of an average molecular weight of 70000 Da, 1H‐NMR spectra indicating almost complete deacetylation. N‐Phthaloylation of 1 yielded the known N‐phthaloylchitosan ( 2 ), which was tritylated to provide 3a and methoxytritylated to 3b . Dephthaloylation of 3a with NH2NH2?H2O gave the 6‐O‐tritylated chitosan 4a . Similarly, 3b gave the 6‐O‐methoxytritylated 4b . CuSO4‐Catalyzed diazo transfer to 4a yielded 95% of the azide 5a , and uncatalyzed diazo transfer to 4b gave 82% of azide 5b . Further treatment of 5a with CuSO4 produced 2‐azido‐2‐deoxycellulose ( 7 ). Demethoxytritylation of 5b in HCOOH gave 2‐azido‐2‐deoxy‐3,6‐di‐O‐formylcellulose ( 6 ), which was deformylated to 7 . The 1,3‐dipolar cycloaddition of 7 to a range of phenyl‐, (phenyl)alkyl‐, and alkyl‐monosubstituted alkynes in DMSO in the presence of CuI gave the 1,2,3‐triazoles 8 – 15 in high yields. 相似文献
18.
Elena I. Klimova Tatiana Klimova Marcos Flores Alamo José M. Méndez Stivalet Lena Ruíz Ramírez Leon V. Backinowsky Marcos Martínez García 《Journal of heterocyclic chemistry》2011,48(2):441-448
The reactions of α‐ferrocenylmethylidene‐β‐oxocarboxylates ( 1 , 2 , 3a , and 3b ) with N‐methyl‐ and N‐(2‐hydroxyethyl)hydrazines ( 5a , 5b ) afford ethyl 1‐alkyl‐5‐aryl(methyl)‐3‐ferrocenylpyrazole‐4‐carboxylates ( 6a , 6b , 6c , 6d , 6e ) (~50%) and N‐alkylhydrazine insertion products, viz., ethyl (N′‐acyl‐N′‐alkylhydrazino)‐3‐ferrocenylpropanoates ( 7a , 7b , 7c , 7d , 7e ) (~20%) and 1‐acyl‐2‐(N′‐alkyl‐N′‐ethoxycarbonylhydrazino)‐2‐ferrocenylethanes ( 8a , 8b , 8c , 8d , 8e ) (~10%). The structures of the compounds obtained were established based on the spectroscopic data and X‐ray diffraction analysis (for pyrazoles 6a and 6b ). J. Heterocyclic Chem., (2011). 相似文献
19.
Some new N-alkoxycarbonyl-N″-benzoyl-benzamidrazones (p-toluamidrazones) 3a-3d, and 1,3,5-trisubstituted 1,2,4-triazole 4a-4h derivatives by starting from N-benzoylbenzimidates or N-benzoyl-p-toluimidates. The structures of compounds 3 and 4 were established on the basis of elemental analyses, IR, ^1H NMR, ^13C NMR and UV data. Antimicrobial experiments of the compounds performed by using agar-well diffusion and broth microdilution methods revealed that only compounds 3a-3d, 4a and 4b showed inhibitory effect only on Candida albicans ATCC 60193. However, compound 4b had also specific antibacterial activity against Staphylococcus aureus ATCC 25923. The other compounds showed neither antifungal nor antibacterial activities. Compounds 3a, 4a and 4b have been screened on three human tumor cell lines, breast cancer (MCF7), non small cell lung cancer (NCI-H460), and CNS cancer (SF-268) at the National Cancer Institute (NCI), USA, which were found to exhibit low antiproliferative activity. 相似文献
20.
Synthesis of 1‐silacyclopent‐2‐ene derivatives using 1,2‐hydroboration, 1,1‐organoboration and protodeborylation
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The reaction of di(alkyn‐1‐yl)vinylsilanes R1(H2C═CH)Si(C≡C―R)2 (R1 = Me ( 1 ), Ph ( 2 ); R = Bu (a), Ph (b), Me2HSi (c)) at 25°C with 1 equiv. of 9‐borabicyclo[3.3.1]nonane (9‐BBN) affords 1‐silacyclopent‐2‐ene derivatives ( 3a , 3b , 3c , 4a , 4b ), bearing one Si―C≡C―R function readily available for further transformations. These compounds are formed by consecutive 1,2‐hydroboration followed by intramolecular 1,1‐carboboration. Treated with a further equivalent of 9‐BBN in benzene they are converted at relatively high temperature (80–100°C) into 1‐alkenyl‐1‐silacyclopent‐2‐ene derivatives ( 5a , 5b 6a , 6b ) as a result of 1,2‐hydroboration of the Si―C≡C―R function. Protodeborylation of the 9‐BBN‐substituted 1‐silacyclopent‐2‐ene derivatives 3 , 4 , 5 , 6 , using acetic acid in excess, proceeds smoothly to give the novel 1‐silacyclopent‐2‐ene ( 7 , 8 , 9 , 10 ). The solution‐state structural assignment of all new compounds, i.e. di(alkyn‐1‐yl)vinylsilanes and 1‐silacyclopent‐2‐ene derivatives, was carried out using multinuclear magnetic resonance techniques (1H, 13C, 11B, 29Si NMR). The gas phase structures of some examples were calculated and optimized by density functional theory methods (B3LYP/6‐311+G/(d,p) level of theory), and 29Si NMR parameters were calculated (chemical shifts δ29Si and coupling constants nJ(29Si,13C)). Copyright © 2014 John Wiley & Sons, Ltd. 相似文献