Abstract:
:Enantiomerically pure 1, 2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R, 2S)- and (1S, 2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by (1)H NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K(2)PtCl(4). The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl(2) were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl(2) produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl(2) even in a concentration of 1 microM. The (1S, 2R)- and (1R, 2S)-configurated complexes were far less active (SS > RR > RS = SR) and comparable in this respect with the standard cisplatin.
journal_name
Arch Pharm (Weinheim)journal_title
Archiv der Pharmazieauthors
Dufrasne F,Gelbcke M,Schnurr B,Gust Rdoi
10.1002/1521-4184(200205)335:5<229::AID-ARDP229>3.keywords:
subject
Has Abstractpub_date
2002-05-01 00:00:00pages
229-39issue
5eissn
0365-6233issn
1521-4184journal_volume
335pub_type
杂志文章abstract::Alzheimer's disease (AD) is a neurodegenerative disorder characterized by dementia, memory impairment, cognitive dysfunction, and speech impairment. The utility of cholinergic replacement by acetylcholinesterase (AChE) inhibitors in AD treatment has been well documented so far. Recently, studies have also evidenced th...
journal_title:Archiv der Pharmazie
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abstract::A new series of N,N'-(benzene-1,3-diyldi-1,3,4-oxadiazole-5,2-diyl)bis{2-[(5-benzene-1,3-diyl-1,3,4-oxadiazol-2-yl)amino]acetamide}(macrocycle 1), N,N'-(benzene-1,3-diyldi-1,3,4-thiadiazole-5,2-diyl)bis{2-[(5-benzene-1,3-diyl-1,3,4-thiadiazol-2-yl)amino]acetamide} (macrocycle 2) and S,S'-[benzene-1,3-diylbis(4H-1,2,4-...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201100181
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abstract::Patient-derived cell transplantation is an attractive therapy for regenerative medicine. However, this requires effective strategies to reliably differentiate patient cells into clinically useful cell types. Herein, we report the discovery that 5-nitro-5'hydroxy-indirubin-3'oxime (5'-HNIO) is a novel inducer of cell t...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201400223
更新日期:2014-11-01 00:00:00
abstract::The synthesis of tacrine-thiadiazolidinone hybrids is described. These compounds are designed as dual acetylcholinesterase inhibitors binding simultaneously to the peripheral and catalytic sites of the enzyme. All tested compounds exhibit significant AChE inhibitory activity. Competition assays using propidium as refe...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200400919
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abstract::Synthesis of a new series of 3,4-diarylpyrazole-1-carboxamide derivatives is described. Their antiproliferative activity against A375P human melanoma cell line was tested and the effect of substituents on the diarylpyrazole scaffold was investigated. The biological results indicated that five synthesized compounds (Ig...
journal_title:Archiv der Pharmazie
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doi:10.1002/ardp.201000375
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abstract::A rapid and efficient one-pot condensation reaction of long-chain alkyl and alkenyl acid hydrazides and nitriles was carried out to afford 3,5-disubstituted-1H-1,2,4-triazoles. The compounds 5a-o were screened for in-vitro antibacterial activity against the representative panel of two Gram-positive and two Gram-negati...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200800005
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abstract::A range of novel pyridine-2,4,6-tricarbohydrazide thiourea compounds (4a-i) were synthesized in good to excellent yields (63-92%). The enzyme inhibitory potentials of these compounds were investigated against α- and β-glucosidases because these enzymes play a crucial role in treating type-2 diabetes mellitus (T2DM). A...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201700236
更新日期:2018-01-01 00:00:00
abstract::The stereoisomers of amidinomycin 7 and their intermediates 1-6, which are produced from homochiral 3-oxocyclopentanecarboxylic acids by asymmetric synthesis, are tested for their antimicrobial effects by agar diffusion test and by Bouillon serial dilution assay. Their antibiotic activities against Bacillus subtilis, ...
journal_title:Archiv der Pharmazie
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doi:10.1002/ardp.19973300106
更新日期:1997-01-01 00:00:00
abstract::Fifteen new indazole derivatives have been synthesized. In the Born test, compounds (4f) and (4g) were most active. They inhibited the blood platelet aggregation induced by collagen with an IC(50) = 85 or 90 microM, respectively. After oral administration to rats (60 mg/kg) three of the compounds significantly inhibit...
journal_title:Archiv der Pharmazie
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更新日期:2004-06-01 00:00:00
abstract::1-Substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyl-uracils were synthesized and evaluated in cell-based assays against HIV-1 wild-type and its clinically relevant non-nucleoside reverse transcriptase inhibitor (NNRTI)-resistant mutants. Some of the synthesized compounds showed activity against H...
journal_title:Archiv der Pharmazie
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doi:10.1002/ardp.200900058
更新日期:2009-09-01 00:00:00
abstract::A series of 5-(o-tolyl)-1H-tetrazole derivatives were synthesized and evaluated for their anticonvulsant activities. 1-(2-Methylbenzyl)-5-(o-tolyl)-1H-tetrazole (3h) showed important anticonvulsant activity against the MES-induced seizures, as well as lower neurotoxicity with an ED50 value of 12.7 mg/kg and a TD50 val...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201600389
更新日期:2017-05-01 00:00:00
abstract::Permeability glycoprotein (P-gp) is involved in the pathology of various diseases including cancer and epilepsy, mainly through the translocation of some medicines across the cell membrane. Here, we employed image-based quantitative structure-activity relationship (QSAR) models to predict the P-gp inhibitory activity ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201500333
更新日期:2016-02-01 00:00:00
abstract::The 5-HT1A and 5-HT2 receptor affinity of a set of 44 N-alkylated 1-aryl-piperazines and their analogs has been analyzed: the n-hexyl derivatives were the most potent and the most selective 5-HT1A ligands of all the investigated N-alkyl homologues. The alkyl chain may stabilize the 5-HT1A receptor-ligand complex by hy...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19953280210
更新日期:1995-02-01 00:00:00
abstract::Alzheimer's disease (AD) is the most common type of dementia and related to the degeneration of hippocampal cholinergic neurons, which dramatically affects cognitive ability. Acetylcholinesterase (AChE) inhibitors are employed as drugs for AD therapy. Three series of sulfonylhydrazone compounds were designed, and thei...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201700163
更新日期:2017-11-01 00:00:00
abstract::With the purpose of expanding the structural variety of chemical compounds available as pharmacological tools for the treatment of Alzheimer's disease, we synthesized and evaluated a novel series of indole-benzoxazinones (Family I) and benzoxazine-arylpiperazine derivatives (Family II) for potential human acetylcholin...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201800024
更新日期:2018-05-01 00:00:00
abstract::A series of new indole derivatives 1-18 was synthesized and tested for their cytotoxic activity on a panel of 60 tumor cell lines. Additionally, molecular docking was carried out to study their binding pattern and binding affinity in the VEGFR-2 active site using sorafenib as a reference VEGFR-2 inhibitor. Based on th...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201700299
更新日期:2018-02-01 00:00:00
abstract::Salicylamide amino acid conjugates were prepared utilizing 5-formyl-, 5-dicyanoethenyl-, and 5-nitroethenylsalicylic acid. 5-Substituted salicylanilides were treated with glycine and formaldehyde in a Mannich type reaction affording the corresponding 3-(N-glycino)salicylanilides. The reactions of anilines with pyrans ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19943270402
更新日期:1994-04-01 00:00:00
abstract::Synthesis of some new derivatives of 2-aryl-4-oxo-1-(4-quinazolyl)quinazolines is described. Methyl N-(4-quinazolyl)anthranilate was allowed to react with phenyl iso(thio)cyanate to give 3-phenyl-1-(4-quinazolyl)-1, 2, 3, 4-tetrahydro-2, 4-dioxo- and 4-oxo-2-thioxoquinazolines (3a and 3b respectively) Alternatively, a...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200290009
更新日期:2002-01-01 00:00:00
abstract::A novel approach to the pyridoacridine ring system of the ascididemin-type marine alkaloids is presented. This approach allows for the introduction of the ring A of the alkaloids by using a simple aromatic aldehyde building block. The viability of this approach is demonstrated with the synthesis of AK37, a bioactive d...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201200019
更新日期:2012-10-01 00:00:00
abstract::The aim of this study was to develop a novel nanosize drug candidate for cancer therapy. For this purpose, (S)-methyl 2-[(7-hydroxy-2-oxo-4-phenyl-2H-chromen-8-yl)methyleneamino]-3-(1H-indol-3-yl)propanoate (ND3) was synthesized by the condensation reaction of 8-formyl-7-hydroxy-4-phenylcoumarin with l-tryptophan meth...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.202000137
更新日期:2020-11-01 00:00:00
abstract::This review emphasizes the relationship of breast cancer, estrogen receptor and ligands, especially the centrality of the estrogen receptor, which mediates on one hand the hormone-induced gene transcription and on the other hand the anti-estrogen action against breast cancer. The characterization of the estrogen recep...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章,评审
doi:10.1002/ardp.200800174
更新日期:2009-03-01 00:00:00
abstract::A number of phenylamides of 5-benzamidopyrazole-4-carboxylic acid were prepared in 50-80% yields from 1-phenyl (or methyl)-6-phenylpyrazolo[3,4-d]1,3-oxazin-4(1H)-ones and aniline derivatives. All the compounds were tested for their analgesic and antiinflammatory activities, as well as for their ulcerogenic potential ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/1521-4184(200105)334:5<153::aid-ardp153>3.
更新日期:2001-05-01 00:00:00
abstract::Polyketide-derived macrolactones like zearalenone (1), zearalane (2) or curvularin (3) display a wide range of interesting pharmacological activities. Here, we present a short and efficient approach towards this class of natural products by a combination of the Sonogashira and Mitsunobu reactions. The resulting lacton...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200500132
更新日期:2005-12-01 00:00:00
abstract::Derivatives of the recently described potent neuroprotective 7-O-cinnamoylsilibinin ester were prepared: its hemisuccinate to improve water solubility and the dehydrosilibinin ester that was shown to form in assay media to investigate its role in overall neuroprotective effects. 7-O-Cinnamoyl-2,3-dehydrosilibinin is l...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201800206
更新日期:2018-11-01 00:00:00
abstract::Non-steroidal anti-inflammatory drugs (NSAIDs), which are widely used for the treatment of rheumatic arthritis, pain, and many different types of inflammatory disorders, cause serious gastrointestinal (GI) side effects. The free carboxylic acid group existing on their chemical structure is correlated with GI toxicity ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201700153
更新日期:2017-09-01 00:00:00
abstract::Previously, we demonstrated that certain heterocyclic compounds derived from 3-substituted-1,2,4-triazole-5-thiones had promising analgesic/anti-inflammatory activities together with low ulcerogenic properties. Therefore, we sought to design and synthesize new derivatives of triazol-5-thiones-fused heterocycles. In th...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201700052
更新日期:2017-07-01 00:00:00
abstract::The complex of lanthanum (III) was synthesized reacting the respective inorganic salt with 5-aminoorotic acid in amounts equal to the metal:ligand molar ratio of 1:3. The complex was prepared by adding an aqueous solution of lanthanum (III) nitrate to an aqueous solution of the ligand, subsequently raising the pH of t...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200600077
更新日期:2006-11-01 00:00:00
abstract::3-Ethyl 5-methyl 1,4-dihydro-2-[(2-hydroxyethoxy) methyl]-6-methyl-4-(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate (13), a bioisostere of amlodipine, was prepared by the reaction of ethyl 4-(2-hydroxyethoxy)acetoacetate (11) with methyl 2-(2,3-dichlorobenzylidene)acetoacetate (12) and NH4OAc. Compound 13 was elaborat...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/(sici)1521-4184(199910)332:10<363::aid-ard
更新日期:1999-10-01 00:00:00
abstract::In this study, a number of 2,5-disubstituted 1,3,4-thiadiazoles were synthesized using an appropriate synthetic route, and their anticonvulsant activity was determined by the maximal electroshock seizure (MES) test and their neurotoxicity was evaluated by the rotarod test. Additionally, their hypnotic activity was tes...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.202000066
更新日期:2020-12-01 00:00:00
abstract::The combined effects of amino acid antagonists with proven or potential inhibitory activities on aminoacyl-tRNA synthetases were investigated on the murine leukemic cell line P388 D1. As the best result a summation of the antiproliferative effects was observed. Combinations with established cytostatic agents like plat...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19913240305
更新日期:1991-03-01 00:00:00