Abstract:
:A group of racemic 3-[2-nitrooxyethyl (1,3-dinitrooxy-2-propyl or 4-nitrophenylethyl)] 5-isopropyl 1,4-dihydro-2,6-dimethyl-4-[2- trifluoromethylphenyl (2-nitrophenyl or 3-nitrophenyl)]-3,5-pyridinedicarboxylates 13-15 were prepared using the Hantzsch reaction that involved the condensation of 2-nitrooxyethyl 9a, 1,3-dinitrooxy-2-propyl 9b or 4-nitrophenylethyl 9c acetoacetate with isopropyl 3-aminocrotonate 11 and 2-trifluoromethyl 12a, 2-nitro 12b or 3-nitro 12c benzaldehyde. In vitro calcium channel antagonist activities were determined using a guinea pig ileum longitudinal smooth muscle assay. Compounds 13-15 exhibited superior, or equipotent, calcium channel antagonist activity (10(-8) to 10(-10) M range) relative to the reference drug nifedipine (IC50 = 1.43 x 10(-8) M). The R1 C-3 ester substituent was a determinant of calcium channel antagonist activity where the potency order was CH2CH2ONO2 > CH2CH2-C6H4-4-NO2 > or = CH(CH2ONO2)2. In contrast, the C-4 R2-aryl substituent (2-CF3-C6H4-, 2-O2N-C6H4- or 3-O2N-C6H4-) was not a major determinant of activity. Compounds 13a-15a, which possess a 3-(2-nitrooxyethyl) ester substituent exhibit superior calcium channel antagonist smooth muscle relaxant activity (IC50 = 10(-10) M range) relative to nifedipine, could serve as potential probes to investigate the in vivo release of nitric oxide (NO) which induces vascular muscle relaxation.
journal_name
Arch Pharm (Weinheim)journal_title
Archiv der Pharmazieauthors
Iqbal N,Knaus EEdoi
10.1002/ardp.19963290105subject
Has Abstractpub_date
1996-01-01 00:00:00pages
23-6issue
1eissn
0365-6233issn
1521-4184journal_volume
329pub_type
杂志文章abstract::Twelve ethoxycarbonyl or phenylsulfonyl derivatives as prodrugs of hydroxylamine or phenylhydroxylamine were prepared and tested for antiplatelet (in vitro, Born test) antithrombotic (in vivo thrombosis model), and antihypertensive (in vivo, SHR rats) effects. In the Born test N,N-bisphenylsulfonylhydroxylamine (10) w...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/(sici)1521-4184(199811)331:11<365::aid-ard
更新日期:1998-11-01 00:00:00
abstract::The 2-(2-Bromophenyl)-acetaldehyde acetals 8 are treated with n-BuLi and the aldehydes 7 and 11 to form the hydroxyacetales 9 and 12, respectively. 9 is cyclized under acidic conditions to the epoxybenzoxocine 2; analogously 12 yields the epoxydibenzoxocine 14. ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19903231111
更新日期:1990-11-01 00:00:00
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 new chemical entities febuxostat and topiroxostat have been approved by the US Food and Drug Administration, opening new avenues for exploiting different heterocycles other than purines as xanthine oxidase (XO) inhibitors. A different series of substituted 2-benzamido-4-methylthiazole-5-carboxylic acid derivatives...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201600313
更新日期:2017-02-01 00:00:00
abstract::Furfurylidenemalononitriles and thienylidenemalononitriles were treated with 1,3-cyclohexanediones to afford 2-amino-4-hetaryl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives. The molluscicidal activity of these compounds was investigated. ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200400881
更新日期:2004-09-01 00:00:00
abstract::(2S,3R)-3,7-Diamino-2-hydroxy-heptanoyl-Leu-Pro-OH [(2S,3R)-DAHHA-Leu-Pro-OH, 4], analogue of the N-terminal tripeptide of probestin, has been synthesized, and tested as inhibitor of AP-B, Leu-AP, AP-M, and enkephalin-degrading APs, and as analgesic. In order to establish structure-activity relationships the dipeptide...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19923250812
更新日期:1992-08-01 00:00:00
abstract::Numerous novel N,N-disubstituted 5-alkyliden- or 5-aralkyliden-3-aminorhodanines 2 have been prepared by condensation of carbonyl compounds with 1. The effectiveness of some derivatives in an "akanthose test" with hairless mice was shown. ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19933260609
更新日期:1993-06-01 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::Three series of imidazolidinium ligands (NHC precursors) substituted with 4-vinylbenzyl, 2-methyl-1,4-benzodioxane, and N-propylphthalimide were synthesized. N-Heterocyclic carbene (NHC) precursors were prepared from N-alkylimidazoline and alkyl halides. The novel NHC precursors were characterized by 1 H NMR, 13 C NMR...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201700045
更新日期:2017-06-01 00:00:00
abstract::The activity of 72 1,4-dihydropyridines as calcium channel antagonists was examined. The simplified molecular input-line entry system (SMILES) was used as representation of the molecular structure of the calcium channel antagonists. Quantitative structure-activity relationships (QSARs) were developed using CORAL softw...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201200373
更新日期:2013-02-01 00:00:00
abstract::A series of new benzofuran/oxadiazole hybrids (8a-n) was synthesized from 2H-chromene-3-carbonitriles (3a-c) through the multistep synthetic methodology, and these hybrids are known to exhibit anticancer activities. All the compounds were evaluated for their in vitro cytotoxicity against the HCT116 and MIA PaCa2 cell ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.202000006
更新日期:2020-06-01 00:00:00
abstract::N-Methoxyquinolinium salts 3 are prepared as potential cardiotonic agents by alkylation of the corresponding N-oxides 2 synthesized by two different methods. 1. Oxidation of some quinoline derivatives 1 using 30% H2O2 or 3-chloroperbenzoic acid. 2. Nitration of the quinoline-N-oxides 2a, 2c, and 2m. Preparation of 2h ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19933260410
更新日期:1993-04-01 00:00:00
abstract::Platensimycin is a natural product isolated from various strains of Streptomyces platensis which exhibits antimicrobial activity against Gram positive bacteria, including vancomycin- and linezolide-resistant species. Analogues of platensimycin were synthesized from 3-aminobenzoic acid or other aniline derivatives and ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200700177
更新日期:2008-06-01 00:00:00
abstract::A series of 4β-[(4-substituted)-1,2,3-triazol-1-yl]podophyllotoxin congeners were synthesized by employing click chemistry and further evaluated for their antitumor activity by MTT assay. Among them, six congeners (10, 11, 12, 13, 22, and 24) exhibited approximately 100-fold more potent inhibitory activity against fou...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201100438
更新日期:2012-12-01 00:00:00
abstract::Several 5-alkoxy-tetrazolo[1,5-a]quinazoline derivatives have been synthesized by reacting 2,4-dichloroquinazoline with various phenols or aliphatic alcohol and then with sodium azide. The structures of these compounds have been confirmed by IR, MS,( 1)H-NMR, and elementary analysis. Anticonvulsant activities were eva...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200900119
更新日期:2009-11-01 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::The syntheses, conformational studies, and investigations on the estrogen receptor binding of [R/S-1-(2,6-dichloro-4-hydroxyphenyl)ethylenediamine]platinum(II) complexes (1-PtL2, 2L = leaving groups) are described. A Strecker synthesis using the 2,6-dichloro-4-methoxybenzaldehyde, NaCN, and NH4Cl afforded the cyanoami...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/1521-4184(200103)334:3<93::aid-ardp93>3.0.
更新日期:2001-03-01 00:00:00
abstract::The preparation and detailed composition of an oil newly extracted from pure soy germ (not less than 96 % hypocotyle) are presented. Experiments in vivo showed that soybean-germ oil (SGO) possesses a remarkable protective activity against UVB-induced skin inflammation, exceeding that of tocopherol acetate by a factor ...
journal_title:Archiv der Pharmazie
pub_type: 临床试验,杂志文章
doi:10.1002/ardp.200500159
更新日期:2005-12-01 00:00:00
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
pub_type: 杂志文章
doi:10.1002/ardp.201000375
更新日期:2011-11-01 00:00:00
abstract::Both 2-nitrooxymethyl-4-phenyl- (2) and 4-nitrooxymethylphenyl-1,4-dihydropyridines (3) represent new combinations of two different vasodilating structures. 2 could not be isolated due to its spontaneous lactonization. Derivatives of 3 were obtained via Hantzsch synthesis using nitrooxymethylated benzaldehydes. The in...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.19973300804
更新日期:1997-08-01 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 accordance with the significant impetus of the discovery of potent vascular endothelial growth factor receptor 2 (VEGFR-2) inhibitors, herein, we report the design, synthesis, and anticancer evaluation of 12 new N-substituted-4-phenylphthalazin-1-amine derivatives against HepG2, HCT-116, and MCF-7 cells as VEGFR-2 ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.202000219
更新日期:2020-11-16 00:00:00
abstract::1-Acetylcarbazoles are readily converted to 3-desazacanthin-4-ones upon treatment with Bredereck's reagent, but in contrast to canthin-4-ones, these do not undergo ring transformation reactions with guanidine. Only after N-protection (methyl or 2-(trimethylsilyl)ethoxymethyl group), 2-desaza analogues of the alkaloid ...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201400328
更新日期:2015-02-01 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::A synthesis of two new active substances, DOMCl (1-(4-chloromethyl-2, 5-dimethoxyphenyl)-2-propanamine; 2) and DOMOM (1-(2, 5-dimethoxy-4-methoxymethylphenyl)-2-propanamine; 3), was developed. Unexpectedly, the Blanc reaction permitted successful synthesis of 2, 5-dimethoxyphenylpropylamine derivatives having a substi...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200390014
更新日期:2003-06-01 00:00:00
abstract::2-Acetyl-(6-picolyl)-4N-substituted thiosemicarbazones and their copper(II) complexes were shown to be potent antineoplastic and cytotoxic agents against murine and human cultured cells. Numerous derivatives were as active against solid tumor growth as clinically useful agents. The agents inhibited L1210 DNA and RNA s...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/(sici)1521-4184(199804)331:4<121::aid-ardp
更新日期:1998-04-01 00:00:00
abstract::Styrylquinazoline derivatives were prepared by Perkin condensation and evaluated for inhibitory activity against HIV-1 integrase. Among them, compound 5c containing a free catechol ring was the most potent (IC(50)=0.8 +/- 1.9 microM)and showed 6-fold more potency than the corresponding styrylquinoline compound (IC(50)...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/1521-4184(200208)335:6<277::AID-ARDP277>3.
更新日期:2002-06-01 00:00:00
abstract::Syntheses of a new series of biologically potent α-aminophosphonates were accomplished by one-pot Kabachnik-Fields reaction using TiO2-SiO2 as solid supported catalyst under microwave irradiation conditions. The chemical structures of all the newly synthesized compounds were confirmed by analytical and spectral (IR, 1...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.201300214
更新日期:2013-09-01 00:00:00
abstract::The ongoing interest in very efficient systems for the imitation of cytochrome P-450-dependent monooxygenase reactions, consisting of metalloporphyrin and oxygen donor, prompted us to develop a method to compare the catalytic activity of soluble metalloporphyrins with those which have been immobilised on different sil...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/ardp.200600064
更新日期:2006-12-01 00:00:00
abstract::The photochemical stability of 2, 6, 6-trimethyl-3-carbmethoxy-4-phenyl-5-oxo-1, 4, 5, 6, 7, 8-hexahydroquinoline (HHQ) derivatives with different substituents on the phenyl ring (-Cl, -NO(2), -CF(3), -CH(3), -OCH(3)) has been studied.The process of photodegradation was studied by UV spectrophotometry. The rate of pho...
journal_title:Archiv der Pharmazie
pub_type: 杂志文章
doi:10.1002/1521-4184(200205)335:2<77::AID-ARDP77>3.0.
更新日期:2002-05-01 00:00:00