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1.
J. Epsztajn J. Z. Brzeziński K. Czech 《Monatshefte für Chemie / Chemical Monthly》1993,124(5):549-558
Summary The preparation of the pyridazinones10a,10b,11a,11b, and12a,12b from the ketoamides7,8, and9 and hydrazine hydrate is described. It was found that from ketoamides8b and9b in addition to the expected pyridopyridazinones11b and12b also aminopyridopyridazines14 and15 were formed and that ketoamide7b gave exclusively aminopyridopyridazine13. The pyridopyridazinones10b,11b, and12b were alkylated with alkyl iodides.
Anwendungen von Organolithium und verwandten Reagenzien in organischen Synthesen, Teil XII. Synthese von Phenyl- und Pyridylpyridopyridazinonen und ihren Derivaten
Zusammenfassung Die Darstellung der Pyridazinone10a,10b,11a,11b und12a,12b aus Ketoamiden7,8 und9 und Hydrazinhydrat wird beschrieben. Es wurde festgestellt, daß aus Ketoamiden8b und9b außer den erwarteten Pyridopyridazinonen11b und12b auch Aminopyridopyridazine14 und15 enstanden und daß das Ketoamid7b ausschließlich ins Aminopyridopyridazin13 überführt wurde. Die Pyridopyridazinone10b,11b und12b wurden mit Alkyljodiden alkyliert.相似文献
2.
Alessandro Venditti Claudio Frezza Fabio Sciubba Sebastiano Foddai Mauro Serafini Marcello Nicoletti 《Natural product research》2016,30(15):1698-1705
We compared the respective metabolite patterns of two Pedicularis species from Dolomites. Seven phenylethanoid glycosides, i.e., verbascoside (1), echinacoside (2), angoroside A (3), cistantubuloside B1 (4), wiedemannioside C (5), campneoside II (11) and cistantubuloside C1 (12), together with several iridoid glucosides as aucubin (6), euphroside (7), monomelittoside (8), mussaenosidic acid (9) and 8-epiloganic acid (13) were identified. Pedicularis verticillata showed also the presence of greatly unexpected secoiridoids, ligustroside (14) and excelside B (15), very rare compounds in Lamiales. Both PhGs and iridoids are considered of taxonomical relevance in the Asteridae and their occurrence in Pedicularis was discussed. In particular, the exclusive presence of several compounds such as 8-epiloganic acid (13), campneoside II (11), cistantubuloside C1 (12), ligustroside (14) and excelside B (15) in Pedicularis rostratocapitata, and angoroside A (3), cistantubuloside B1 (4) and wiedemannioside C (5) in P. verticillata could be considered specific markers for the two botanical entities. 相似文献
3.
Joung Heo 《Journal of Coordination Chemistry》2017,70(23):3837-3858
The reaction of [ZnCl2] with N-cyclopentyl-1-(quinolin-2-yl)methanimine (LA), N-cyclohexyl-1-(quinolin-2-yl)methanimine (LB), N-cyclohexyl-1-(pyridin-2-yl)methanimine (LC), 2,6-diethyl-N-(pyridin-2-ylmethylene)aniline (LD), N-cyclopentyl-1-(pyridin-2-yl)methanimine (LE), and N-phenyl-(pyridin-2-yl)methanimine (LF) in ethanol produced the bidentate [(NN′)ZnCl2] complexes, [LAZnCl2], [LBZnCl2], [LCZnCl2], [LDZnCl2], [LEZnCl2] and [LFZnCl2], respectively. The molecular structures revealed that the zinc in [LnZnCl2] (Ln = LA ? LD) showed a distorted tetrahedral geometry involving two nitrogens of N,N’-bidentate ligands and two chloride ligands. Most of these initiators were effective for polymerization of methyl methacrylate (MMA) and polymerization of rac-lactide (rac-LA). [LCZnCl2] (with N-cyclohexyl substituted at imine-pyridine moiety) exhibited the highest catalytic activity for MMA polymerization in the presence of modified methylaluminoxane (MMAO) with an activity of 3.33 × 104 g PMMA/mol·Zn·h at 60 °C, giving moderate syndiotactic poly methyl methacrylate (PMMA) with high molecular weight (9.62 × 105 g/mol). The dimethyl derivatives [LnZnMe2] (Ln = LA ? LF), generated in situ, polymerized rac-LA with moderate activity and yielded a polylactide (PLA) with good number-average molecular weights and narrower polydispersity indices (PDIs). [LAZnMe2] effectively initiates the ring-opening polymerization (ROP) of rac-LA to attain heterotactic PLA (Pr = 0.91). 相似文献
4.
Abdulmumeen A. Hamid Olapeju O. Aiyelaagbe Arvind S. Negi Fatima Kaneez Suaib Luqman Stephen O. Oguntoye 《Natural product research》2019,33(2):296-301
Chloroform extract from the leaves of Turraea vogelii Hook f. ex Benth demonstrated cytotoxic activity against a chronic myelogenous leukemia cell, K-562 with IC50 of 14.27 μg/mL, while chloroform, ethyl acetate and methanol extracts from the stem of the plant inhibited K-562 cells growth with IC50 of 19.50, 24.10 and 85.40 μg/mL respectively. Bioactive chloroform extract of Turraea vogelii leaves affords two triterpenoids: oleana-12,15,20-trien-3β-ol (1), and oleana-11,13-dien-3β,16α,28-triol (2), with six fatty esters, ethyl hexaeicos-5-enoate (3), 3-hydroxy-1,2,3-propanetriyltris(tetadecanoate) (4), 1,2,3-propanetriyl(7Z,7′Z,7′′Z)tris(-7-hexadecenoate) (5), 1,2,3-propanetriyl(5Z,5′Z,5′′Z)tris(-5-hexadecenoate) (6), 1,2,3-propanetriyltris(octadecanoate) (7), and 2β-hydroxymethyl tetraeicosanoate (8). Tetradecane (9), four fatty acids: hexadecanoic acid (10), tetradecanoic acid (11), (Z)-9-eicosenoic acid (12), and ethyl tetradec-7-enoate (13) were isolated from chloroform extract of Turraea vogelii stem. 1,2,3-propanetriyltris(heptadecanoate) (14), (Z)-9-octadecenoic acid (15) and (Z)-7-tetradecenoic acid (16) were isolated from ethyl acetate extract while (Z)-5-pentadecenoic acid (17) was obtained from methanol extract of the plant stem. Compounds 1, 2, 5, 6, 11, 12, 15, 16 and 17 exhibited pronounced antiproliferative activity against K-562 cell lines. 相似文献
5.
R. M. Shaker A. F. Mahmoud F. F. Abdel-Latif 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):397-406
Abstract The terephthalic acid hydrazide(1) reacted with phenyl/benzyl isothiocyanate2a,bto yield the corresponding bis-thiosemicarbazides4a,b,viaacid hydrolysis of the intermediate 3whereas cyclization of4gave the bis-1,2,4-triazoles 5,6and bis-1,3,4-thiadiazoles7,8. Similarly, compound 1reacted with phenyl isocyanate9to give the bis-semicarbazide10, which was cyclized to the bis-oxadiazole 11and/or bis-1,2,4-triazole12in POClti3and NaOH respectively. 相似文献
6.
Julia E. Morozova Ella Kh. Kazakova Eduard Ph. Gubanov Nelly A. Makarova Victor P. Archipov Tatjana V. Timoshina Zaymil Sh. Idijatullin Wolf D. Habicher Alexander I. Konovalov 《Journal of inclusion phenomena and macrocyclic chemistry》2006,55(1-2):173-183
Present paper reports on tensiometric studies of tetramethylsulfonatoresorcinarenes 1 and 2 with nonionogenic guests 3 and 4, pyrimidin derivative and O,O-dymethyl-1,1-dimethyl-3-oxobutylphosphonate, respectively. Association of resorcinarenes with these guests leads to dramatic change of adsorption characteristics of their solutions. CCMs1 of associates (1&3, 1&4, 2&3, and 2&4) are lower and the estimated surface activity, as well as the height of adsorption layers are higher than for individual substances. Aggregation of compounds 1–4 and association of 1 with 3 and 4 in solution were confirmed by 1H NMR spectra and studied by diffusion NMR with impulse magnetic field gradient. 相似文献
7.
Virayu Suthiphasilp Wisanu Maneerat Raymond J. Andersen Stephen G. Pyne Chatchai Muanprasat Sawinee Seemakhan 《Natural product research》2019,33(20):2945-2950
A phytochemical investigation of the fruit and root extracts of Micromelum integerrimum resulted in the isolation and identification of a new compound, integerravone (1), together with 23 known compounds (2–24). Their structures were characterized by spectroscopic methods as well as comparisons made from the literature. Compounds 2, 3–15, 17–18 and 20–23 were evaluated for their cytotoxicities against the colon cancer cell line, HCT116. All of them were inactive at 50?µM. Most of the phenolic compounds were evaluated for their antioxidant activity using the DPPH assay. Compounds 14 and 22–24 showed antioxidant activity with IC50 values ranging from 24.83-135.05?µM. 相似文献
8.
Hassan M. Faidallah Khalid A. Khan Abdullah M. Asiri 《Journal of fluorine chemistry》2011,132(11):870-877
Fluorinated 1,2,4-triazoles 3 and benzenesulfonyl urea and thiourea derivatives as well as their cyclic sulfonylthioureas 4–10 were prepared as antimicrobial agents. The chemistry involves the condensation of sulfanilamide derivatives 1 with trifluoroacetic anhydride to give N-di(trifluoroacetyl)sulfonamides 2 which upon reaction with hydrazine hydrate afforded the corresponding triazole derivatives 3. Reaction of triazole derivative 3a with isocyanates and isothiocyanates gave the corresponding ureas 4 and thioureas 5. Cyclization of thiourea derivatives with ethyl bromoacetate, 1,2-diiodoethane, diethyl oxalate and α-bromoacetophenone derivatives yielded the corresponding 4-oxothiazolidines 7, thiazolidines 8, 4,5-dioxothiazolidines 9 and thiazolines 10. Preliminary biological screening of the prepared compounds revealed significant antimicrobial and mild antidiabetic activities. 相似文献
9.
Tetramic acid derivatives and polyphenols from sponge-derived fungus and their biological evaluation
Jun-Feng Wang Xiaochu Qin Fu-Quan Xu Tianyu Zhang Shengrong Liao Xiuping Lin 《Natural product research》2015,29(18):1761-1765
Fifteen compounds, including two tetramic acid derivatives, penicillenol A1 (1) and penicillenol A2 (2), six polyphenols containing both phenolic bisabolane sesquiterpenoid and diphenyl ether units, expansols A–F (3–8), together with six phenolic bisabolane sesquiterpenoids (9–14) and diorcinol (15), were isolated from the fermentation broth of the marine-derived fungus ZSDS1-F11 isolated from the sponge Phakellia fusca Thiele collected in the Yongxing island of Xisha. Their structures were elucidated mainly by using extensive NMR spectroscopic and mass spectrometric analyses. Compounds 3–5, 7 and 8 showed potent COX-1 inhibitory activity with IC50 values of 5.3, 16.2, 30.2, 41.0 and 56.8 μM, respectively. Meanwhile, compounds 3–8 showed potent COX-2 inhibitory activity with IC50 values of 3.1, 5.6, 3.0, 5.1, 3.2 and 3.7 μM, respectively. In addition, compound 1 exhibited antituberculosis activity with 96.1% inhibition at concentration of 10 μM. 相似文献
10.
Asha Chilwal A. K. Narula 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):1369-1381
Abstract Six diorganotin(IV) derivatives of α-aminoacids with general formulae [(CH3)2 SnAACl]2 and [(CH3CH2CH2CH2)2SnAACl]2, where AA = L-alaninate, L-phenylalaninate, and L-isoleucinate, have been synthesized by reacting dimethyltin(IV) dichloride (M) and dibutyltin(IV) dichloride (B) with L-alanine (A) or L-phenylalanine (PA) or L-isoleucine (I) using acetonitrile as the solvent and designated as MA, MPA, MI, BA, BPA, and BI. These complexes have been characterized by elemental analysis, infrared (IR), 1H NMR, 13C NMR, and 119Sn NMR spectroscopy. Thermal studies of all of the synthesized complexes were also carried out using thermogravimetric (TG) and differential scanning calorimetry (DSC) techniques. The thermal decomposition mechanisms were similar for MA, BA, MI, and BI and occurred in one step, while in compounds MPA and BPA, it occurred in two consecutive steps. The TG curves of MPA and BPA suggest the loss of the ligand (AA) in the first step, with probable formation of a tin oxide R2SnO as an intermediate, and in the second step, free tin is obtained, similar to MA, BA, MI, and BI, in accordance with the stoichiometry of the related derivatives. The diorganotin(IV) complexes have also been screened for their antibacterial activity against Escherichia coli, Staphylococcus aureus, Staphylococcus epidermidis, and Pseudomonas aeruginosa. The minimum inhibitory concentration values of these complexes show enhanced activity. 相似文献
11.
Min Hu Ling-Yu Yue E. Carolina Sañudo Shao-Ming Fang 《Journal of Coordination Chemistry》2016,69(14):2164-2173
Three new lanthanide complexes incorporating salicylate (HSA or SA) and 1,10-phenanthroline (phen), Ln3(HSA)5(SA)2(phen)3 [Ln = Ho (1) and Er (2)], and Sm2(HSA)2(SA)2(phen)3 (3), have been synthesized. X-ray structural analysis reveals that 1 and 2 are isostructural with a trinuclear pattern, and 3 exhibits a binuclear structure. Comparison of the structural differences between 1/2 and 3 suggests that the identity of metal plays an important role in construction of such complexes. The magnetic properties of 1 are discussed. Moreover, 2 and 3 are both photoluminescent materials, and their emission properties are closely related to their corresponding LnIII centers. 相似文献
12.
《Journal of Coordination Chemistry》2012,65(17):1891-1904
The triethylammonium dicarboxylatotriorganostannates, [(C2H5)3NH][R3Sn(3,5-pdc)]?·?mH2O (3,5-pdc?=?3,5-pyridinedicarboxylate) (m?=?1, R?=?Me 1; m?=?0, R?=?Ph 2, PhCH2 3, n-Bu 4), [(C2H5)3NH][R3Sn(5-nip)] (5-nip?=?5-nitroisophthalate) (R?=?Me 5, Ph 6, PhCH2 7, n-Bu 8) have been prepared from triethylamine, 3,5-pyridinedicarboxylic acid, 5-nitroisophthalic acid and triorganotin chloride. Complexes 1–8 have been characterized by elemental, IR, 1H, 13C and 119Sn NMR analyses. Complexes 1, 2, 5 and 6 are also determined by single crystal X-ray diffraction. For 1, 2, 5 and 6, each carboxylate moiety is involved in coordination to a tin center via only one O atom showing that the Sn atoms are five-coordinate and exist in trigonal bipyramidal geometries. Moreover, for 2, 5 and 6, the nitrogen atoms of ammonium are hydrogen bonded to the pendant carboxyl oxygen. In 1, adjacent polymeric chains and triethylammonium are linked by hydrogen bonds through the co-crystallized water molecule, thus a 2D network is formed. 相似文献
13.
Abd El-Badih A. G. Ghattas Hassan M. Moustafa Elsayed A. A. Hassanein Bahgat R. M. Hussein 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):1469-1481
Abstract Alkylation of 4-anilino-5-phenyl-4H-1,2,4-triazole-3-thiol (1) with some halo compounds yielded the corresponding sulfides 2a–f. Some sulfides 2e,f were cyclized to give triazolothiadiazines 3 and 4. Triazolothiadiazoles 5 and 6 were prepared through the reaction of compound 1 with carbon disulfide or ethyl orthoformate, respectively. Treatment of compound 1 with ethyl chloroformate or phenyl isothiocyanate yielded triazolo-thiadiazole and triazole 9 and 10, respectively. Reaction of compound 1 with Lawesson's reagent gave triazolothiadiazaphosphole derivative 11. Also, compound 1 underwent cyclocondensation reactions with some bidentate reagents to give triazolothiazines 4, 12, and 13. Triazolo-thiazepines and triaziepine 14–16 were synthesized via the reaction of compound 1 with β-ketoesters or ethyl cyanoacetate. Tricyclic systems 19 and 20 were prepared through the reaction of compound 4 with the appropriate reagent. Some synthesized compounds were tested for antibacterial activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. 相似文献
14.
《Journal of Coordination Chemistry》2012,65(14):2358-2366
Three new coordination polymers [Zn(btp)(NCS)2] n (1), {[Zn(btp)2(dca)2] n (2), and {[Zn(btp)3](BF4)2} n (3) (btp = 1,3-bis(1,2,4-triazol-1-yl)propane, dca = dicyanamide) were synthesized and characterized. In 1, 2, and 3, one-, double-, triple-btp ligands link two Zn(II) atoms and extend to form a 1-D zigzag chain for 1, 1-D double chain for 2, and 1-D triple chain for 3. The conformations of the btp ligands in 1, 2, and 3 are analyzed. 1, 2, and 3 have emission maxima at approximately 405, 407, and 409 nm, respectively, in the solid state at room temperature. 相似文献
15.
Davood Nori-Shargh Daryoush Tahmassebi Mahboobeh Poukalhor Mostafa Mohammadpour Amini Saeed Jameh-Bozorghi Farzad Deyhimi 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2419-2434
Ab initio molecular orbital and density functional theory were used to investigate energetic and structural properties of the various conformations of hexa-tertbutylbenzene (1), hexakis(trimethylsilyl)benzene (2), hexakis (trimethylgermyl)benzene (3), and hexakis(trimethylstannyl)benzene (4). HF/3-21G//HF/3-21G and B3LYP/3-21G//HF/3-21G results revealed that the Twist-Boat (TB) conformer of compound 1 is more stable than the 1-Chair (C), 1-Boat (B), and 1-Planar (P) conformers. B3LYP/3-21G//HF/3-21G results show that the 1- TB conformer is more stable than 1- C, 1- B, and 1- P conformers of about 1.13, 4.34, and 99.94 kcal mol?1 , respectively. Contrary to the stability order of compound 1 conformers, the C conformer of compounds 2–4 is more stable than TB, B, and P conformations, as calculated by B3LYP/3-21G//HF/3-21G and HF/3-21G//HF/3-21G levels of theory. The energy gap between the C and P conformers in compounds 1–4 is decreased in the following order: ΔE(4: C, P) < ΔE (3: C, P) < ΔE(2: C, P) < ΔE (1: C, P). This fact can be explained in terms of the increase of C aromatic -M (M═C, Si, Ge, and Sn) bond lengths and the decrease of steric (van der Waals) repulsions in the previously discussed compounds. For compounds 1–3, the calculations were also performed at the B3LYP/ 6-31G*//HF/3-21G level of theory. However, the comparison showed that the results at B3LYP/3-21G//HF/3-21G methods correlated well with those obtained at the B3LYP/6-31G*// HF/6-31G method. Further, NBO analysis revealed that in compounds 1–4, the resonance energy associated with the σM-C1 to σ*C2-C3 delocalization is 5.20, 9.68, 11.15, and 12.27 kcal mol?1, respectively. These resonance energy values could explain the easiness of the ring flipping processes of C, B, and TB conformers of compounds 4 to 1. Also, the NBO results showed that by an increase of the σM-C1 → σ *C2-C3 resonance energies in compounds 1–4, the σM-C1 bonding orbital occupancies decrease. This fact could fairly explain the increase of the Caryl-M bond length from compound 1 to 4. The NBO results are also in good agreement with the calculated energy barriers for the ring flipping of the chair conformations in compounds 1–4, as calculated by B3LYP and HF methods. 相似文献
16.
Youssef L. Aly Ashraf A. El-Shehawy Adel M. Attia Mohmed E. Sobh 《Phosphorus, sulfur, and silicon and the related elements》2013,188(7):1572-1584
Abstract 5-Anthracenylidene- and 5-(4-benzyloxy-3-methoxy)benzylidene-hydantoin and 2-thiohydantoin derivatives 3a-g were prepared by condensation of anthracene-9-carboxaldehyde and 4-benzyloxy-3-methoxybenzylaldehyde with hydantoin and 2-thiohydantoin derivatives. Compounds 3a, b, f undergo Mannich reaction with formaldehyde and morpholine to give the corresponding Mannich products 4a–c. For the synthesis of alkylmercaptohydantoin 5a–o, the potassium salt of compounds 3a, b, e, f were reacted with an alkylhalide, either methyl iodide, phenacyl bromide, ethyl bromo acetate, allyl bromide, or methallyl bromide, under stirring at room temperature to afford the alkylmercaptohydantoins 5a–o. Acid hydrolysis of compounds 5a–c afforded the corresponding arylidene-hydantoin derivatives 3c, d, g. 2-Methylmercapto-hydantoin derivatives 5a, c were reacted with some secondary amines such as morpholine or piperidine to afford 5-(4-benzyloxy-3-methoxy)benzylidene-2-morpholino- or piperidino glycocyamidine derivatives 7a, 5-anthracenylidene-2-morpholin-, or piperidino glycocyamidine derivatives 7b, c. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT 相似文献
17.
18.
Watchara Sangsopha Kwanjai Kanokmedhakul Somdej Kanokmedhakul 《Natural product research》2018,32(10):1176-1179
Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1–6), five steroids (7–11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1–15 have been isolated for the first time from this plant. 相似文献
19.
The synthesis and liquid crystalline properties of novel achiral amides (Ia–g, IIa–g and IVa,b), achiral Schiff's bases (IIIa–g and Va–g), chiral amides (VI, VII) and chiral Schiff's bases (VIII–XI) incorporating a 1,3,4-oxadiazole ring are reported. All amides of the series I and II display an enantiotropic smectic A phase. The amide IVa,b did not show mesomorphic properties. Amides of the series Ia–g and IIa–g contain a flexible n-tetradecylthio chain, the other terminal substituent is an n-alkoxy chain and n-alkyl chain, respectively (n?=?4–10) and the 1,3,4-oxadiazole is in the terminal rigid core. Amides Ia–g have broader mesomorphic range and higher thermal stability than the corresponding amides IIa–g. Amides IVa,d contain the 1,3,4-oxadiazole ring in the centre of the rigid core and two flexible alkoxy chains as flexible terminal substituents. Thus, the mesomorphic properties are favoured if 1,3,4-oxadiazole is shifted to a terminal position of the rigid core. Schiff's bases IIIa–g display an enantiotropic dimorphism smectic C–smectic A. Schiff's bases IIIa–g have a broader mesomorphic range than the analogous amides Ia–g. Schiff's bases Va–g exhibit a dimorphism smectic A–nematic, and in contrast to this the analogous amide IVa,b did not show mesomorphism. The chiral amides VI and VII and chiral Schiff's bases X and XI did not show mesomorphic properties and only the chiral Schiff's bases VIII and IX display a chiral smectic C phase in a short mesomorphic range. A density functional theory theoretical study at the B3LYP/6–311++G(d,p) level was performed in order to analyse the structural features that must be related with the mesomorphic behaviour of the reported compounds. 相似文献
20.
Phytochemical investigation of the ethanol extract from the whole plant of Agrimonia pilosa led to the isolation of 31 compounds, including 16 flavonoids (1–16), 5 triterpenes (17–21), 1 isocoumarin (22), 5 phenolic acids (23–27), 1 ceramide (28), 2 agrimols (29–30) and 1 fatty acid (31). Their structures were determined by various spectroscopic analyses. Compounds 5, 7 and 20 were firstly isolated from the genus Agrimonia, and compounds 6, 10–11, 15, 26, 28 and 31 were isolated from the family Rosaceae for the first time. Moreover, the chemotaxonomic significance of these compounds was summarised. 相似文献