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1.
Reaction of readily available 2-methyl-4-formylthiazole ( 1 ) with glyoxal and ammonia gave 2-(2-methyl-4-thiazolyl)imidazole ( 2 ). Nitration of 2 with a mixture of nitric acid-sulfuric acid at 100° yielded 2-(2-methyl-4-thiazolyl)-4,5-dinitroimidazole ( 3 ) as the sole reaction product, while nitration at 65° afforded 2-(2-methyl-4-thiazolyl)-4-(or 5)-nitroimidazole ( 4 ). N-Methylation of compound 4 in the presence of base gave 1-methyl-2-(2-methyl-4-thiazolyl)4-nitroimidazole ( 6 ), whereas N-methylation with diazomethane afforded 1-methyl-2-(2-methyl-4-thiazolyl)-5-nitroimidazole ( 5 ). N-Methylation of compound 3 yielded 1-methyl-2-(2-methyl-4-thiazolyl)-3,5-dinitroimidazole ( 7 ) in high yield. 相似文献
2.
Photolysis of N-benzyl-N-phenylearbamoylazide (IVc) afforded 1-benzy 1-2-benzimidazolinone (Ic), 2-benzimidazolinone (IIe), 4-benzy 1-2-benzimidazolinone (IIe), and 5-benzy1-2-benzimidazo-linone (IIf)- The same reaction of N-benzyl-N-(4-chlorophenyl) carbamoyl azide (IVd) gave 3-benzyl-1-(phenylhydrazocarbonyl)-2-benzimidazolinone (VIb) besides the above four products. In the case of N-benzyl-4-(4-butoxyphenyl)carbamoyl azide (IVe), 1-benzy1-5-butoxy-2-benz-imidazolinone (1e), 5-butoxy-2-benzimidazolinone (IId), 5-benzy1-2-benzimidazolinone (IIf), and 4-benzy1-6-butoxy-2-benzimidazolinone (IIg). 相似文献
3.
Six new alkaloids, broussonetines W, X, M1, U1, J3, and J2 (1-6) were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae) as minor constituents. They were formulated as (2R,3R,4R,5R)-2-hydroxy-methyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyllpyrrolidine (1), (2R,3S,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyl]pyrrolidine-4-O-beta-D-glucopyranoside (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(9R)-9,13-dihydroxytridecyl]- pyrrolidine (3), (2S,3S,4S)-2-hydroxymethyl-3,4-dihydroxy-5-(10-oxo-13-hydroxytridecyl)-5- pyrroline (4), (2R)-2-[(IS,2S)-1,2-dihydroxy-8-1(2R,3R,4R,5R)-5-(2-hydroxymethyl-3,4-dihydroxy-1-acetylpyrrolidinyl)loctyl]piperidine (5), (2R)-2-[(1S,2S)-1,2-dihydroxy-8-[(2R,3R, 4R,5R)-5-(2-hydroxymethy]-3,4-dihydroxypyrrolidinyl)]octyl]piperidine (6). 相似文献
4.
Bruno Danieli Monica Luisetti Manfred Schubert-Zsilavecz Werner Likussar Sabine Steurer Sergio Riva Daniela Monti Josef Reiner 《Helvetica chimica acta》1997,80(4):1153-1160
Bovine β-1,4-galactosyltransierase is an efficient catalyst for the regioselective transfer of galactose from UPD-galactose, generated in situ with the UDP-glucose/UDP-glucose-4-epimerase system, to the kaurane glycosides stevioside ( 1 ) and Steviolbioside ( 2 ), affording the corresponding galactosyl derivatives 3 and 4 in high yields. By a combination of 2D NMR techniques (COSY, TOCSY, ROESY, HMQC, and HMBC), the structure of the products is established as 13-[(β -D -galactopyranosyl-(1 → 4)-β-D -glucopyranosyl-(1 → 2)- β -D -glucopyranosyl)oxy]kaur-16-en-19-oic acid β -D -glucopyranosyl ester ( 3 ) and 13-[(β-D -galactopyranosyl-(1 → 4)- β-D -glu-copyranosyl-(1 → 2)- β-D -glucopyranosyl)oxy]kaur-16-en-19-oic acid ( 4 ). 相似文献
5.
Tetsuji Kametani Kazuo Kigasawa Mineharu Hiiragi Nagatoshi Wagatsuma Tuneo Uryu Hideo Sugi 《Journal of heterocyclic chemistry》1973,10(1):27-29
Treatment of 1,2,5,6-tetrahydro-2-(4-hydroxy- and/or 4-methoxybenzyl)-3,4-dimethyl-I-(3-methyl-2-butenyl)pyridines (IV and V) and 2-(4-methoxybenzyl)-3,4-dimethyl-1-(3-methyl-2-butenyl)-4-piperidinol (X) with acid afforded 9-(4-hydroxy- and/or 4-methoxybenzyl)-4,4,5,6-tetramethyl-1-azabicyelo[3,3,1]non-6-ene (XIII and XIV). In contrast, the corresponding 1-allyl-substituted derivatives VI, VII, and XI were converted into the expected 3-allyl-1,2,3,4,5,6-hexahydro-8-hydroxy- and/or 8-methoxy-6,11-dimethyl-2,6-methano-3-benzazocine (II and III). 相似文献
6.
J. W. Mcfarland T. H. Kozel K. R. Stuhlmacher T. S. Chevalier 《Journal of heterocyclic chemistry》1980,17(2):273-276
4-Toluenesulfonyl isocyanate (I) reacted with 2-aminoethanol and 3-amino-l-propanol to give 2:1 isocyanate/amino alcohol addition products. 1-Amino-2-propanol and I gave 1:1 and 2:1 adducts while 2-amino-2-methyl-l-propanol afforded only a 1:1 adduct. 4-Toluenesulfonyl isothio-cyanate (III) gave 1:1 adducts with 2-aminoethanol, l-amino-2-propanol and 3-amino-l-propanol, the first two of which were cyclized by concentrated sulfuric acid to 1-(4-toluenesulfonyl)-imidazoline-2-thiones and the third to 1-(4-toluenesulfonyl)hexahydropyrimidine-2-thione. A 1:2 adduct was obtained from III and 2-amino-2-methyl-l-propanol. Amino acids reacted with I and with 4-chlorobenzenesulfonyl isocyanate (II) to give N-(arylsulfonyl)-N1-(carboxylic acid)-ureas. N-(4-Toluenesulfonyl)-N1-(acetic acid)-urea (XVI) was converted to the methyl ester (XIX) by concentrated sulfuric acid and methanol and to water-soluble unrecoverable products by sulfuric acid alone. Glycine and III gave N-(4-toluenesulfonyl)-N1-(acetic acid)-thiourea (XX) which was converted to the methyl ester (XXII) by concentrated sulfuric acid/methanol and to the cyclic 1-(4-toluenesulfonyl)imidazolin-5-one-2-thione (XXI) by sulfuric acid alone. 相似文献
7.
J. W. Mcfarland C. E. Hayes E. B. Blair K. R. Stuhlmacher 《Journal of heterocyclic chemistry》1980,17(2):271-272
4-Chlorobenzenesulfonyl isocyanate (I) reacted with 2-chloroethanol and 1-chloro-2-propanol to give, respectively, 2-chloroethyl 4-chlorobenzenesulfonyl carbamate (III) and 1-chloro-2-propyl 4-chlorobenzenesulfonyl carbamate (VI). The carbamates III and VI cyclized under the influence of pyridine to afford, respectively, 3-(4-chlorobenzenesulfonyl)oxazolidin-2-one (IV) and 3-(4-chlorobenzenesulfonyl)-5-methyloxazolidin-2-one (VII). The oxazolidin-2-ones were stable toward hydrochloric acid but hydrolyzed in 2M sodium hydroxide solution to N-(2-hydroxyethyl)-4-chlorobenzenesulfonamide (V) and N-(2-hydroxy-1-propyl)-4-chlorobenzene-sulfonamide (VIII), respectively. 4-Toluenesulfonyl isothiocyanate (II) reacted with 2-chloroethanol to give 2-chloroethyl 4-chlorobenzenesulfonyl thiocarbamate (IX), which was converted by pyridine to 3-(4-toluenesulfonyl)oxazolidine-2-thione (X). 相似文献
8.
Gerhard W. Fischer 《Journal of heterocyclic chemistry》1994,31(6):1529-1534
The acid-catalyzed reaction of 1-aryl-5-(2-dimethylaminovinyl)-1H-tetrazoles 2 with arylamines suitably functionalized in the ortho-position resulted in Z-configurated transamination products which were cyclized to novel 3-tetrazolylquinolines by the action of sodium ethoxide. Thus, on reacting 2 with 2-aminoacetophenone or 2-aminobenzophenone, respectively, the 2-[2-(1-aryl-1H-tetrazol-5-yl)vinyl-amino]aryl ketones 3a-g were obtained, the cyclization of which gave 4-substituted 3-(1-aryl-1H-tetrazol-5-yl)quinolines 4 . In the case of the transamination products 3h-1 , prepared from 2 and methyl anthranilate, the ring closure afforded 3-(1-aryl-1H-tetrazol-5-yl)-1H-quinolin-4-ones 5 . Starting from 2 and anthranilonitrile 4-amino-3-(1-aryl-1H-tetrazol-5-yl)quinolines 10 were obtained via the corresponding intermediates 9 . 相似文献
9.
The reactions of 3-phenylsydnonyllithium with a variety of ketones to afford tertiary carbinols 4a-4i and their subsequent dehydration to 4-(3-phenylsydnonyl) alkenes 5a-5i are discussed. Among the alkenes, 2-[4-(3-phenylsydnonyl)]propene ( 5b ) and 1-[4-(3-phenylsydnonyl)]-1-cyclohexene ( 5i ) were photochromic. A Wittig reaction between ethyl-4-(3-phenylsydnonyl)-ketone and methylenetriphenylphosphorane afforded the photochromic 2-[4-(3-phenylsydnon-yl)]-1-butene(5j). 相似文献
10.
Phosphorus-containing dendrimers 1-[G'(1)]-1-[G'(4)] (generation 1 to generation 4) possessing terminal aldehyde groups reacted with a variety of hydrazino compounds. Addition of hydrazine itself to 1-[G'(1)]-1-[G'(4)] afforded the corresponding dendrimers 2-[G(1)]-2-[G(4)] with hydrazono groups at the periphery. Addition of methylhydrazine to 1-[G'(1)], 1-[G'(4)] gave the dendrimers 3-[G(1)], 3-[G(4)]. A Schiff reaction between 1-[G'(1)]-1-[G'(4)] and 1-amino-4-(2-hydroxyethyl)piperazine led to dendrimers 5-[G(1)]-5-[G(4)] possessing up to 48 alcohol chain ends. Treatment of 1-[G'(1)], 1-[G'(3)] with fluorenone hydrazone gave rise to macromolecules 7-[G(1)], 7-[G(3)] while the reaction of 1-[G'(1)], 1-[G'(2)], 1-[G'(4)] with 4-aminobenzo-15-crown-5 afforded the macromolecules 9-[G(1)], 9-[G(2)], 9-[G(4)] in which up to 48 crown ether units are anchored on the surface. Wittig reactions between 1-[G'(1)]-1-[G'(4)] with (acetylmethylene)triphenylphosphorane (10) or (cyanomethylene)triphenylphosphorane (12) allowed the formation of dendrimers 11-[G(1)]-11-[G(4)] or 13-[G(1)], 13-[G(4)] with alpha,beta unsaturated ketones or cinnamonitrile units, respectively, on the surface. Disubstitution of terminal P(S)Cl(2) groups of dendrimers 1-[G(1)]-1-[G(7)] with allylamine, propargylamine, or N-(trimethylsilyl)imidazole easily occurred to give macromolecules 14-[G(1)]-14-[G(7)], 15-[G(1)], 15-[G(4)], 16-[G(1)], 16-[G(4)]. 相似文献
11.
Seiichi Nishizawa Tomoyuki Kamaishi Tomoyuki Yokobori Ryo Kato Ying-Yu Cui Takeshi Shioya Norio Teramae 《Analytical sciences》2004,20(11):1559-1565
Facilitated SO4(2-) transfers by hydrogen bond-forming ionophores are investigated across the nitrobenzene (NB)-water interface by using polarography with a dropping electrolyte electrode. Bis-thiourea 1, alpha,alpha'-bis(N'-p-nitrophenylthioureylene)-m-xylene, is found to significantly facilitate the transfer of the highly hydrophilic SO4(2-) whereas its counterpart, N-(p-nitrophenyl)-N'-propylthiourea (ionophore 2), cannot. In contrast to the predominant formation of a 1:1 complex with SO4(2-) in the bulk NB phase, the SO4(2-) transfer assisted by 1 is indeed based on the formation of a 1:2 complex between SO4(2-) and ionophore, even under the condition of [SO4(2-)]aq > [1]org. Such an exclusive formation of the 1:2 (SO4(2-) to ionophore) complex at the NB-water interface is not observed with structurally similar bis-thiourea 3, alpha,alpha'-bis(N'-phenylthioureylene)-m-xylene, where p-nitrophenyl moietes of bis-thiourea 1 are simply replaced by phenyl groups. The facilitated transfer of SO4(2-) with bis-thiourea 1 is further compared to that of HPO4(2-) and H2PO4- across the NB-water interface, which was previously shown to be assisted by 1 through the formation of the 1:1 and 2:1 (anion to ionophore) complexes, respectively. On the basis of these examinations, unique binding behaviors of hydrogen bond-forming ionophores at the NB-water interface are discussed, with a view towards development of ionophore-based anion-selective chemical sensors. 相似文献
12.
A Sasaki H Matsumura T Yano S Takata M Sunagawa 《Chemical & pharmaceutical bulletin》1992,40(5):1098-1104
We synthesized useful intermediates 5 and 6 for 1 beta- and 1 alpha-methylcarbapenems from 4-carboxy-3-[(R)-1-hydroxyethyl]-2-azetidinone 4 as a starting material by using stereoselective hydrogenation and hydroboration, respectively. A practical synthetic route from 4 to the (3S,4S)-4-[(R)-1-carboxyethyl]-3-[(R)-1-hydroxyethyl]-2-azetidinone derivative 1, a useful intermediate for the synthesis of 1 beta-methylcarbapenem antibiotics, was established. 相似文献
13.
Imoto H Matsumoto M Odaka H Sakamoto J Kimura H Nonaka M Kiyota Y Momose Y 《Chemical & pharmaceutical bulletin》2004,52(1):120-124
Preparation and biological activity of the metabolites of the potent antihyperglycemic and antihyperlipidemic agent, (E)-4-(4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyloxyimino)-4-phenylbutyric acid (TAK-559) (1), were investigated. Metabolites M-I (2), M-II (3), M-III (4) and M-IV (5) were synthesized and their biological activities were evaluated by in vitro and in vivo experiments. Compounds 2-4 activate human peroxisome proliferator-activated receptor gamma one (hPPARgamma1) and hPPARalpha, but their activities are weaker than those of TAK-559 (1). Compound 5 only activates hPPARgamma1 weakly. TAK-559 (1) showed potent in vivo plasma glucose and triglyceride lowering activities in Wistar fatty rats after intraperitoneal administration, while its metabolites (2-5) showed comparatively weak activities. 相似文献
14.
Komala I Rahmani M Sukari MA Mohd Ismail HB Cheng Lian GE Rahmat A 《Natural product research》2006,20(4):355-360
Investigation on the leaves of Melicope bonwickii (F.Muell.) T.Hartley (Rutaceae) afforded a new 7-(2'-hydroxy-3'-chloroprenyloxy)-4-methoxyfuroquinoline (1) together with the known 7-(2',3'-epoxyprenyloxy)-4-methoxyfuroquinoline (2), evellerine (3) kokusaginine (4) and an amide aurantiamide acetate (5). Compounds 1 and 2 showed significant activity against cervical cell lines (Hela). 相似文献
15.
The synthesis of 3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-ones 2 and of 2-(1H-imidazol-1-yl)-4H-1-benzopyr-an-4-ones 11 are described. The former proceeds through chroman ring closure from 2-(1H-imidazol-1-yl)-2′-hydroxyacetophenones, the latter occurs reacting 3-bromo-4H-1-benzopyran-4-ones with imidazole and represents an example of a new synthesis of 2-heteroarylchromones. Compounds 2 can be easily reduced to the corresponding chromanones and chromanols previously described in Part 1. 相似文献
16.
Sheng Yang HUANG Jian Gong SHI* Yong Chun YANG Shi Lin HU Institute of Materia Medica Chinese Academy of Medical Sciences Peking Union Medical College Bejing Institute of Chinese Materia Medica Chinese Academy of Traditional Chine 《中国化学快报》2002,13(6)
Coeloglossum viride (L.) Hartm. var. bracteatum (Willd.) Richter is a plant of the Orchidaceae family, distributed in the Xinjiang, Inner Mongolia, Gansu and Qinghai provinces of China1. Its dried rhizomes have been used as a tonic in chinese folk medicine2. No chemical constituent is reported from this plant. The present paper deals with the isolation and structural elucidation of two new isobutyltartrate monoesters, named coelovirin A 1 and B 2. The ethanolic extract of the air-drie… 相似文献
17.
A Ashimori T Ono Y Inoue S Morimoto M Eda T Uchida Y Ohtaki Y Fujino H Kido Y Ogura 《Chemical & pharmaceutical bulletin》1991,39(1):91-99
Novel 1,4-dihydropyridine derivatives bearing 3-[4-(substituted amino)phenylalkyl]ester side chains were prepared and tested for their antihypertensive activity in spontaneously hypertensive rats. Most compounds showed a more potent antihypertensive effect and a longer duration of action than nicardipine. The derivatives with a benzhydrylpiperazinyl and a benzhydrylpiperidinyl group were distinctive. 2-[4-(4-Benzhydryl-1-piperazinyl)phenyl]ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (4e), its 4-(4-cyano-2-pyridyl) analogue (4f), its 3-[4-(4-benzhydryl-1-piperazinyl)phenyl]propyl ester analogue (4h), its 2-[4-(4-benzhydryl-1-piperidinyl)phenyl]ethyl ester analogue (4j), and its 2-[4-(1-benzhydryl-4-piperidinyl)phenyl]ethyl ester analogue (4k) were selected as candidates for further pharmacological investigations. 相似文献
18.
Yamada K Harada Y Miyamoto T Isobe R Higuchi R 《Chemical & pharmaceutical bulletin》2000,48(1):157-159
A new ganglioside molecular species, HPG-7 (1) was obtained from the polar fraction of the chloroform/methanol extract of the sea cucumber, Holothuria pervicax. On the basis of chemical and spectroscopic evidence, the structure of 1 was determined, and the major component was 1-O-[alpha-L-fucopyranosyl-(1-->4)-(N-acetyl-alpha-D-neuraminosyl) - (2-->11)-(N-glycolyl-alpha-D-neuraminosyl)-(2-->4)-(N-acetyl -alpha-D- neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-(2S,3S,4R)-2-[(2R)-2- hydroxytetracosanoylamino]-14-methyl-hexadecane-1,3,4-triol. This is the first report on the isolation and structure elucidation of trisialo-ganglioside from sea cucumber. 1 showed neuritogenic activity toward the rat pheochromocytoma cell line, PC-12 cell. 相似文献
19.
J. S. Amato V. J. Grenda T. M. H. Liu E. J. J. Grabowski 《Journal of heterocyclic chemistry》1979,16(6):1153-1155
Reactions of 2-(4′-fluorophenyl)imidazole ( 1 ) and related compounds under various nitrating conditions are discussed. With 90% nitric acid in 20% oleum at ?10°, 1 affords 2-(4′fluorophenyl)-4(5)-nitroimidazole ( 2 ) in 80% yield. Reaction of 2 with the same reagents at 25° affords 2-(4′-fluoro-3′-nitrophenyl)-4(5)-nitroimidazole ( 4 ) in 90% yield, whereas with 90% nitric acid in acetic acid at 95°, 2 affords 4,5-dinitro-2-(4′-fluorophenyl)imidazole ( 5 ) in 80% yield. Reaction of 1 with 70% nitric acid in concentrated sulfuric acid at 25° affords 2-(4′-fluorophenyl)-5-hyroximinoimidazolin-4-one ( 6 ), which rearranges and hydrolyzes to 5-(4′-fluorophenyl)-1,2,4-oxadiazole-3-carboxylic acid. A discussion of these reactions is presented. 相似文献
20.
P. Cabildo R. M. Claramunt D. Sanz M. C. Foces-Foces F. Hernndez Cano J. P. Fayet M. C. Vertut J. Elguero 《Journal of heterocyclic chemistry》1986,23(4):1045-1050
The crystal structures of 1-(1-adamantyl)-3,5-dimethylpyrazole 1 and 1-(1-adamantyl)-3,4,5-trimethylpyrazole 2 were studied by X-ray analysis. The space groups and cell parameters are: 1 , Cc, 13.4452(4), 14.9407(4), 7.1119(2) Å, 90, 111.944(2), 90°, with Z = 4. 2, P21/c, 6.7466(1), 21.2565(7), 10.1462(2) Å, 90, 106.368(2), 90°, with Z = 4. The final disagreement factors were 0.069 and 0.061, for 721 [2σ(I)] and 1950 [2σ(I)] observed reflexions, respectively. Compound 1 presents the adamantyl residue disordered between the two usual conformations. The experimental dipole moments and the carbon-13 chemical shifts (both in hexadeuteriodi-methylsulfoxide and in the solid state) were measured and discussed in connection with the structure of these compounds. 相似文献