共查询到20条相似文献,搜索用时 62 毫秒
1.
Zhang L Liu G Zhang SD Yang HZ Li L Wu XH Yu J Kou BB Xu S Li J Sun GC Ji YF Cheng GF 《Journal of combinatorial chemistry》2004,6(3):431-436
A parallel solution-phase synthesis of 2-quinoxalinol analogues is described. The key step-simultaneous reductions of m-Ar(NO(2))(2) to m-Ar(NH(2))(2) was investigated extensively. We obtained preliminary pharmacological activity of those analogues for the inhibition of LPS-induced TNF-alpha release on mouse macrophage in vitro. Two compounds revealed inhibitory activity, with IC(50) values of 0.40 microM (7-amino-6-[(3-methoxypropyl)amino]-3-methyl-2-quinoxalinol) and 2.2 microM (7-amino-6-[(3-butoxypropyl)amino]-3-methyl-2-quinoxalinol), respectively. 相似文献
2.
A new stilbene, 4-[(2"E)-7"-hydroxy-3",7"-dimethyloct-2"-enyl]-2',3,4',5-tetrahydroxy-trans-stilbene (1), and the known compound chlorophorin (2) were isolated from the heartwood of Chlorophora excelsa. Both 1 and 2 showed tyrosinase inhibitory activity with IC(50) values of 96 and 1.3 microM, respectively. 相似文献
3.
Csatayová K Davies SG Lee JA Roberts PM Russell AJ Thomson JE Wilson DL 《Organic letters》2011,13(10):2606-2609
Aminohydroxylation of tert-butyl sorbate [tert-butyl (E,E)-hexa-2,4-dienoate] using enantiopure lithium (R)-N-benzyl-N-(α-methylbenzyl)amide and (-)-camphorsulfonyloxaziridine gives tert-butyl (R,R,R,E)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate in >99:1 dr. Subsequent dihydroxylation under Upjohn conditions (OsO(4)/NMO) gives tert-butyl (2R,3R,4S,5S,αR)-2,4,5-trihydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]hexanoate (in 95:5 dr) while dihydroxylation under Donohoe conditions (OsO(4)/TMEDA) proceeds with antipodal diastereofacial selectivity to give the (R,R,R,R,R)-diastereoisomer (in 95:5 dr). The amino triols resulting from these dihydroxylation reactions are useful for further elaboration, as demonstrated by the asymmetric synthesis of 3,6-dideoxy-3-amino-L-talose. 相似文献
4.
John S. Fossey Mark L. Russell Christopher J. Richards 《Journal of organometallic chemistry》2007,692(22):4843-4848
(S,S)-2,6-bis[(N-α-methylbenzyl)imino]phenylpalladium bromide was synthesised by oxidative addition of palladium(0) to (S,S)-1-bromo-2,6-bis[(N-α-methylbenzyl)imino]benzene. In contrast, (S,S)-2,6-bis[(N-α-methylbenzyl)imino]phenylplatinum chloride was synthesised by direct C-H activation from the reaction of potassium tetrachloroplatinate with (S,S)-1,3-bis[(N-α-methylbenzyl)imino]benzene. The X-ray crystal structures of both pincer complexes were obtained. Treatment of both complexes with silver hexafluoroanimonate gave effective but not stereoselective catalysts for a Michael reaction between methyl vinyl ketone and methyl 2-cyanopropanoate. 相似文献
5.
Biotransformation study was conducted on the marine dipyrroloquinone, terreusinone (1) isolated from the marine-derived fungus Aspergillus terreus. Preparative-scale fermentation of terreusinone with Streptomyces sp. has resulted in the isolation of a new oxidized metabolite, terreusinol (2). The structure was elucidated as 2-[(1R)-1-hydroxyisobutyl]-6-[(1R)-1,2-dihydroxyisobutyl]-1H,5H-pyrrolo[2,3-b]indole-4,8-dione (2) on the basis of physicochemical evidence. Terreusinol (2) showed an ultraviolet-A (UV-A) (320-390 nm) protecting activity with ED(50) values of 150 microM, which is more active than oxybenzone (ED(50), 350 microM) currently being used as sunscreen. 相似文献
6.
N. N. Romanova T. G. Tallo A. A. Borisenko Yu. G. Bundel' 《Chemistry of Heterocyclic Compounds》1990,26(7):761-767
The methylation of the lithium derivatives of the (11S,4S) and (11S,4R) diastereomers of 4-methyl-1-(-methylbenzyl)azetidin-2-one proceeds stereospecifically with the formation of only trans-(3S,4S)- and trans-(3R,4R)-dimethyl-1-[(S)--methylbenzyl] azetidin-2-one, respectively. The process is accompanied by epimerization at the asymmetric center of the N--methylbenzyl substituent.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 914–920, July, 1990. 相似文献
7.
Synthesis and total 1H- and 13C-NMR assignment of cephem derivatives for use in ADEPT approaches 总被引:1,自引:0,他引:1
Blau L Menegon RF Ferreira EI Ferreira AG Boffo EF Tavares LA Heleno VC Chung MC 《Molecules (Basel, Switzerland)》2008,13(4):841-854
We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4'-nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product, 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (6), as well as the synthesis of the antimalarial primaquine prodrug 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid-3-[methyl 4-(6-methoxyquinolin-8-ylamino)pentylcarbamate]-8-oxo-7-[(2-thienyloxoacetyl)amino]- 5-dioxide (7) are also described, together with their total (1)H- and (13)C-NMR assignments. 相似文献
8.
Leslie M. Werbel Ann Curry Edward F. Elslager Carolyn Hess 《Journal of heterocyclic chemistry》1973,10(3):363-382
A group of fifty-five 2-[(4-11[(dialkylamino)alkyI]amino11-6-methyl-2-pyrimidinyl)amino]-benzimidazoles (VII) was synthesized in 3-88% yield by the condensation of the requisite 2-[(2-benzimidazolyl)amino]-4-chloro-6-methylpyrimidine (VI) with the appropriate polyamine in ethanol-hydrochloric acid or neat with excess amine containing potassium iodide. The 2-[(2-benzimidazolyl)amino]-6-methyl-4-pyrirnidinol precursors (V), obtained in 11-51% yield by cyclization of 2-(cyanoamino)-4-hydroxy-6-methylpyrimidine with a suitably substituted o-phenylenediamine, were chlorinated with phosphorus oxychloride to give the intermediate 2-[(2-benzimidazolyl)amino]-4-chloro-6-rnethylpyrimidines (VI) (27-99%). Oxidation of 5,6-dichloro-2-[(4-11[4-(diethylamino)-l-methylbutyl] amino 11-6-methyl-2-pyrimidinyl) amino ]benzimidazole ( 29 ) with m-chloroperbenzoic acid gave the distal N4'-oxide ( 31 ) (19%). Fusion of 2,3-uiaminopyridine with 2-(cyanoamino)-4-hydroxy-6-methylpyrimidine provided 2-[(4-hydroxy-6-tnethyl-2-pyrimidinyl)amino]-lH-imitlazo[4,5-b]pyrimidine (VIII) (30%), which upon chlori-nation with phosphorus oxychloride (63%) followed by amination with i N, N-diethylethylene-diamine afforded 2-(4-11[2-(diethylamino)ethyl] amino 11-6-methyl-2-pyrimidinyl)-lH-imidazo [4,5-b]pyridine (X) (8%). Thirty-eight of the novel 2-[(4-amino-6-methyl-2-pyrimidinyl)amino]-benzimidazoles possessed “curative” activity against Plasmodium berghei at single subcutaneous doses ranging from 20.640 mg./kg. Orally, thirty-one compounds exhibited suppressive activity against P. berghei comparable with or superior to the reference drugs 1-(p-chlorophenyl)-3-(4-11[2-(diethylarnino)ethyl]amino 11-6-methyl-2-pyrimidinyl)guanidine (I) and quinine hydrochloride, while twelve of them were 5 to 28 times as potent as I and quinine hydrochloride. Eight compounds also displayed strong suppressive activity against P. gallinaceum in chicks. 5,6-Dichloro-2-[(4-112-(diethylamino)ethyl]amino11-6-methyl-2-pyrimidinyl] benzimidazole (18) showed marked activity against a cycloguanil-resistant line of P. berghei, and the most promising member of the series, namely 5,6-dichloro-2-[(4-11[4-(diethylamino)-l-methylbutyl]amino11-6-methyl-2-pyrimidinyl)amino]benzimidazole ( 29 ) (Q = 28), was designated for preclinical toxico-logical studies and clinical trial. Structure-activity relationships are discussed. 相似文献
9.
Ingrida Tumosien? Ilona Jonu?kien? Kristina Kantminien? Zigmuntas Jonas Beresnevi?ius 《Monatshefte für Chemie / Chemical Monthly》2012,43(9):1441-1450
Abstract
5-[2-[(4-Methylphenyl)amino]ethyl]-1,3,4-oxadiazol-2(3H)-thione, 5-[2-[(4-methylphenyl)amino]ethyl]-1,3,4-oxadiazol-2(3H)-one, N-(2,5-dimethyl-1H-pyrrol-1-yl)-3-[(4-methylphenyl)amino]propanamide, and a series of N-[(phenylcarbamoyl)amino]-3-[(4-methylphenyl)amino]propanamides and 3-[(4-methylphenyl)(phenylcarbamoyl)amino]-N-[(phenylcarbamoyl)amino]propanamides, and their thio analogues were synthesized from 3-[(4-methylphenyl)amino]propanehydrazide. 1,3,4-Oxadiazole-2(3H)-thione was converted to 4-amino-2,4-dihydro-5-[2-[(4-methylphenyl)amino]ethyl]-3H-1,2,4-triazole-3-thione, whereas cyclization of N′-phenylcarbamoyl derivatives provided thiazole, oxadiazoles, and thiadiazole, as well as triazole derivatives. Two of the synthesized compounds exhibited good antibacterial activity against Rhizobium radiobacter. 相似文献10.
Imamura S Ishihara Y Hattori T Kurasawa O Matsushita Y Sugihara Y Kanzaki N Iizawa Y Baba M Hashiguchi S 《Chemical & pharmaceutical bulletin》2004,52(1):63-73
A novel lead compound, N-(3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide (1), was identified as a CCR5 antagonist by high-throughput screening using [(125)I]RANTES and CCR5-expressing CHO cells. The IC(50) value of 1 was 1.9 microM. In an effort to improve the binding affinity of 1, a series of 5-oxopyrrolidine-3-carboxamides was synthesized. Introduction of 3,4-dichloro substituents to the central phenyl ring (10i, IC(50)=0.057 microM; 11b, IC(50)=0.050 microM) or replacing the 1-methyl group of the 5-oxopyrrolidine moiety with a 1-benzyl group (12e, IC(50)=0.038 microM) was found to be effective for improving CCR5 affinity. Compound 10i, 11b, and 12e also inhibited CCR5-using HIV-1 envelope-mediated membrane fusion with IC(50) values of 0.44, 0.19, and 0.49 microM, respectively. 相似文献
11.
Carroll J Jonsson EN Ebel R Hartman MS Holman TR Crews P 《The Journal of organic chemistry》2001,66(21):6847-6851
A human 15-lipoxygenase (15-HLO) assay has been employed to discover new marine-sponge-derived bioactive compounds. Extracts from two different sponges, Jaspis splendens (order Choristida, family Jaspidae) and Suberea sp. (order Verongida, family Aplysinellidae), exhibited potent IC(50) values of 0.4 and 0.1 microg/mL, respectively. Both are sources of terpenoids, and the former is a known source of (+)-jasplakinolide (7), which is inactive as a 15-HLO inhibitor. The terpenoids included (+)-(5S,6S)-subersin (1, IC(50) > 100 microM), (-)-(5R,10R)-subersic acid (2, IC(50) = 15 microM), jaspaquinol (3, IC(50) = 0.3 microM), and (-)-jaspic acid (4, IC(50) = 1.4 microM). Structure elucidations and lipoxygenase activity studies of these compounds are reported. 相似文献
12.
The metabolism of 1-(2-methyl-4-methoxyphenyl)-4-[(3-hydroxypropyl)amino]-6-methyl-2,3-dihydropyrrolo[3,2c]quinoline (DBM-819), a new H(+)/K(+) ATPase inhibitor, has been studied by HPLC with spectrometric detection and on-line LC-electrospray mass spectrometry. In vitro incubation of DBM-819 with rat liver microsomes in the presence of NADPH resulted in the production of four metabolites (M1-4), whereas DBM-819 was oxidized to two metabolites, M2 and M4, by human liver microsomes. M2, M3 and M4 were identified as O-demethyl-DBM-819, 8-hydroxy-DBM-819 and N-dehydroxypropyl-DBM-819, respectively, based on LC/MS/MS analysis with authentic standards. M1 was tentatively identified as 1-(hydroxy-2-methyl-4-methoxyphenyl)-4-[(3-hydroxypropyl)amino]-6-methyl-2,3-dihydropyrrolo[3,2c]quinoline. Rat liver CYP1A1/2 catalyzed the oxidation of DBM-819 to 8-hydroxy-DBM-819 and N-dehydroxypropyl-DBM-819. Human CYP3A4 was a major isozyme for the formation of O-demethyl-DBM-819 as well as N-dehydroxypropyl-DBM-819. 相似文献
13.
Thymidine and uridine were modified at the C2' and C5' ribose positions to form amine analogues of the nucleosides (1 and 4). Direct amination with NaBH(OAc)3 in DCE with the appropriate aldehydes yielded 1-{5-[(bis(pyridin-2-ylmethyl)amino)methyl]-4-hydroxytetrahydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (L1), 1-{5-[(bis(quinolin-2-ylmethyl)amino)methyl]-4-hydroxytetrahydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (L2), and 1-[3-(bis(pyridin-2-ylmethyl)amino)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione (L5), while standard coupling procedures of 1 and 4 with 5-(bis(pyridin-2-ylmethyl)amino)pentanoic acid (2) and 5-(bis(quinolin-2-ylmethyl)amino)pentanoic acid (3) in the presence of HOBT-EDCI in DMF provided a second novel series of bifunctional chelators: 5-(bis(pyridin-2-ylmethyl)amino)pentanoic acid [(3-hydroxy-5-(5-methyl-4-oxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-yl)methyl] amide (L3), 5-(bis(quinolin-2-ylmethyl)amino)pentanoic acid [(3-hydroxy-5-(5-methyl-4-oxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-yl)methyl] amide (L4), 5-(bis(pyridin-2-ylmethyl)amino)pentanoic acid [2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] amide (L6), and 5-(bis(quinolin-2-ylmethyl)amino)pentanoic acid [2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] amide (L7). The rhenium tricarbonyl complexes of L1-L4, L6, and L7, [Re(CO)3(LX)]Br (X=1-4, 6, 7: compounds 5-10, respectively), have been prepared by reacting the appropriate ligand with [NEt4][Re(CO)3Br3] in methanol. The ligands and their rhenium complexes were obtained in good yields and characterized by common spectroscopic techniques including 1D and 2D NMR, HRMS, IR, cyclic voltammetry, UV, and luminescence spectroscopy and X-ray crystallography. The crystal structure of complex 6.0.5NaPF6 displays a facial geometry of the carbonyl ligands. The nitrogen donors of the tridentate ligand complete the distorted octahedral spheres of the complex. Crystal data: monoclinic, C2, a = 24.618(3) A, b = 11.4787(11) A, c = 15.5902(15) A, beta = 112.422(4) degrees , Z = 4, D(calc) = 1.562 g/cm3. 相似文献
14.
《Tetrahedron: Asymmetry》2003,14(15):2153-2160
Mono-O-acylation of (R)-2-(α-methylbenzyl)amino-1,3-propanediol 1 with 4-nitrobenzoyl chloride and DMAP in dichloromethane at room temperature gave crystals of optically active (2S,αR)-3-hydroxy-2-(α-methylbenzyl)aminopropyl 4-nitrobenzoate hydrochloride [(2S)-2a·HCl] in 33% yield by fractional crystallization. Optically active oxazolidinones, aziridines, and serinol derivatives were synthesized from the benzoate (2S)-2a. 相似文献
15.
Hua DH Tamura M Huang X Stephany HA Helfrich BA Perchellet EM Sperfslage BJ Perchellet JP Jiang S Kyle DE Chiang PK 《The Journal of organic chemistry》2002,67(9):2907-2912
A number of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones have been synthesized and their anticancer and antimalarial activities evaluated. A one-pot synthesis of 2,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione (4) was achieved by heating a mixture of 1,4-dimethoxyanthracene, methoxyhydroquinone, silver oxide, and zinc iodide in toluene. Regioselective bromination of 4 and 2-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (7) with N-bromosuccinimide provided 2-bromo-3,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione and 2-bromo-3-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (1), respectively. The reactions of 1 with aliphatic primary amines and secondary amines, respectively, produced different products, a result most likely attributed to the different basicities (or nucleophilicities) and steric effects of the two kinds of amines. The structure of the displacement product, 2-bromo-3-[2-(tert-butoxycarbonyl)ethylamino]-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone, from the reaction of 1 with tert-butyl 3-aminopropanoate was unequivocally determined by a single-crystal X-ray analysis. IC(50) values of triptycene bisquinones for the inhibition of L1210 leukemia cell viability are in the 0.11-0.27 microM range and for the inhibition of Plasmodium falciparum 3D7 are in the 4.7-8.0 microM range. 相似文献
16.
以7-羟甲基-1-四氢萘酮和1-溴-4-氯-苯甲醛为起始原料,经14步反应合成了抗丙肝新药维拉帕维--甲基(2S)-1-【(2S,5S)-2-【9{2[(2S,4S)-1-(2R)-2-[(甲氧基羰基)氨基]-2-苯乙酰基-4-(甲氧基甲基)吡咯烷-2-基]-1H-咪唑 5 基} 1,11-二氢异色烯[4′,3′ :6,7]萘并[1,2-d]咪唑-2-基-5-甲基吡咯烷-1-基】-3-甲基-1-氧丁烷-2-基】氨基甲酸酯,总产率10.14%,其结构经1H NMR和ESI-MS确证。 相似文献
17.
Peacock AF Habtemariam A Moggach SA Prescimone A Parsons S Sadler PJ 《Inorganic chemistry》2007,46(10):4049-4059
Relatively little is known about the kinetics or the pharmacological potential of organometallic complexes of osmium compared to its lighter congeners, iron and ruthenium. We report the synthesis of seven new complexes, [(eta6-arene)Os(NN)Cl]+, containing different bidentate nitrogen (N,N) chelators, and a dichlorido complex, [(eta6-arene)Os(N)Cl2]. The X-ray crystal structures of seven complexes are reported: [(eta6-bip)Os(en)Cl]PF6 (1PF6), [(eta6-THA)Os(en)Cl]BF4 (2BF4), [(eta6-p-cym)Os(phen)Cl]PF6 (5PF6), [(eta6-bip)Os(dppz)Cl]PF6 (6PF6), [(eta6-bip)Os(azpy-NMe2)Cl]PF6 (7PF6), [(eta6-p-cym)Os(azpy-NMe2)Cl]PF6 (8PF6), and [(eta6-bip)Os(NCCH3-N)Cl2] (9), where THA = tetrahydroanthracene, en = ethylenediamine, p-cym = p-cymene, phen = phenanthroline, bip = biphenyl, dppz = [3,2-a: 2',3'-c]phenazine and azpy-NMe2 = 4-(2-pyridylazo)-N,N-dimethylaniline. The chelating ligand was found to play a crucial role in enhancing aqueous stability. The rates of hydrolysis at acidic pH* decreased when the primary amine N-donors (NN = en, t1/2 = 0.6 h at 318 K) are replaced with pi-accepting pyridine groups (e.g., NN = phen, t1/2 = 9.5 h at 318 K). The OsII complexes hydrolyze up to 100 times more slowly than their RuII analogues. The pK*a of the aqua adducts decreased with a similar trend (pK*a = 6.3 and 5.8 for en and phen adducts, respectively). [(eta6-bip)Os(en)Cl]PF6/BF4 (1PF6/BF4) and [(eta6-THA)Os(en)Cl]BF4 (2BF4) were cytotoxic toward both the human A549 lung and A2780 ovarian cancer cell lines, with IC50 values of 6-10 microM, comparable to the anticancer drug carboplatin. 1BF4 binds to both the N7 and phosphate of 5'-GMP (ratio of 2:1). The formation constant for the 9-ethylguanine (9EtG) adduct [(eta6-bip)M(en)(9EtG)]2+ was lower for OsII (log K = 3.13) than RuII (log K = 4.78), although the OsII adduct showed some kinetic stability. DNA intercalation of the dppz ligand in 6PF6 may play a role in its cytotoxicity. This work demonstrates that the nature of the chelating ligand can play a crucial role in tuning the chemical and biological properties of [(eta6-arene)Os(NN)Cl]+ complexes. 相似文献
18.
The first syntheses of (-)-funebrine [(-)-1] and (-)-funebral [(-)-2] are described. The syntheses feature sequential formation of nitrone VI from methyl glyoxylate (5) with oxime 6, transesterification of nitrone VI with (E)-crotyl alcohol (4), and intramolecular cycloaddition of the resulting nitrone VII bearing crotyl ester to afford cycloadduct 7 as a major product. The adduct 7 was readily elaborated to amino lactone (-)-3, the key synthetic intermediate of (-)-1 and (-)-2. 相似文献
19.
The BF(3).Et(2)O-promoted Diels-Alder addition of 1-acetylvinyl RADO(Et)-ate (RADO(Et)-ate = 3-ethyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate) to 1-(dimethoxymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane led to one major monoadduct that added to 1,2-didehydrobenzene and was converted into (-)-4-demethoxy-7-deoxydaunomycinone and (2R)-12-acetoxy-2-acetyl-5-(bromomethyl)-1,2,3,4-tetrahydronaphthacen-2-yl RADO(Et)-ate. The latter compound was used to construct (8R)-8-acetyl-6,8-dihydroxy-11-[[(3'-[(aminopropyl)oxy]-, -4'-[(aminobutyl)oxy], and -5'-[(aminopentyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrochloride (-)-8, (-)-9, (-)-10, respectively, as well as (8R)-8-acetyl-6,8-dihydroxy-11- [[[2'-[(3"-aminopropyl)amino]ethyl]oxy]- ((-)-11) and -[[3'-[(3"-aminopropyl)amino]propyl]oxy]methyl]-7,8,9, 10-tetrahydronaphthacene-5,12-dione hydrochloride ((-)-12). (8R)-8-Acetyl-6,8-dihydroxy-11-[[(alpha-L-daunosaminyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrochloride ((-)-13), a mimic of idarubicin, was also prepared. Absorbance and fluorescence titration experiments showed (-)-8, (-)-9, and (-)-10 to intercalate calf thymus DNA whereas (-)-11, (-)-12, and (-)-13 did not. The best intercalator was (-)-9 (K(b) = (1.1 +/- 0.1) x 10(5) M(-)(1)) with the [(4'-aminobutyl)oxy]methyl chain. Inhibition of topoisomerase II-induced DNA strand religation was observed for (-)-8 at a concentration of 50 &mgr;M. 相似文献
20.
Kusano G Orihara S Tsukamoto D Shibano M Coskun M Guvenc A Erdurak CS 《Chemical & pharmaceutical bulletin》2002,50(2):185-192
Investigation of the constituents of the fruits of Morus alba LINNE (Moraceae) afforded five new nortropane alkaloids (1-5) along with nor-psi-tropine (6) and six new amino acids, morusimic acids A-F (7-12). The structures of the new compounds were determined to be 2alpha,3beta-dihydroxynortropane (1), 2beta,3beta-dihydroxynortropane (2), 2alpha,3beta,6exo-trihydroxynortropane (3), 2alpha,3beta,4alpha-rihydroxynortropane (4), 3beta,6exo-dihydroxynortropane (5), (3R)-3-hydroxy-12-[(1S,4S)-4-[(1S)-1-hydroxyethyl]-pyrrolidin-1-yll-dodecanoic acid-3-O-beta-D-glucopyranoside (7), (3R)-3-hydroxy-12-[(1S,4S)-4-[(1S)-1-hydroxyethyl]-pyrrolidin-1-yll-dodecanoic acid (8), (3R)-3-hydroxy-12-1(1R,4R,5S)-4-hydroxy-5-methyl-piperidin-1-yll-dodecanoic acid-3-O-beta-D-glucopyranoside (9), (3R)-3-hydroxy-12-[(1R,4R,5S)-4-hydroxy-5-methyl-piperidin-1-yll-dodecanoic acid (10), (3R)-3-hydroxy-12-[(1R,4R,5S)-4-hydroxy-5-hydroxymethyl-piperidin-1-yl]-dodecanoic acid-3-O-beta-D-glucopyranoside (11), and (3R)-3-hydroxy-12-[(1R,4S,5S)-4-hydroxy-5-methyl-piperidin-1-yl]-dodecanoic acid (12) on the basis of spectral and chemical data. 相似文献