Synthesis and pharmacological screening of novel meso-substituted porphyrin analogs.
نویسندگان
چکیده
A novel series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 2a-j was synthesized from the condensation of aldehyde derivatives 1a-j with pyrrole in the presence of p-toluenesulfonic acid. The synthesized porphyrins were considered as a model to study the free radical-induced damage of biological membranes and the protective effects of these porphyrins. It was found that these compounds effectively inhibit the free radical-induced oxidative hemolysis of red blood cells. Compounds 2c and 2d which bear a sulfur atom, a nitro group, and a chlorine atom exhibited markedly higher antihemolysis activity than the other analogous. Compounds 2a, 2c, 2d, and 2j showed the highest protection activity against DNA damage induced by the bleomycin-iron complex. Compounds 2d, 2f, 2i, and 2j were proved to exhibit antioxidative activity.
منابع مشابه
One-Flask Synthesis of Meso-Substituted Dipyrromethanes and Their Application in the Synthesis of Trans-Substituted Porphyrin Building Blocks
The reaction at room temperature of an aldehyde with excess pyrrole in the absence of solvent affords the meso-substituted dipyrromethane. The reaction is catalyzed with trifluoroacetic acid or with BF9,0(Et)2. The dipyrromethaue is purified by crystallixation or by flash chromatography on silica with eluants containing 1% triethylamine. The reaction is compatible with aliphatic or aromatic ald...
متن کاملSynthesis and Pharmacological Evaluation of Some Novel Isatin Derivatives for Antimicrobial Activity
In the present work, a series of new 5-substituted-3-(4-arylimino)-1-[5-mercapto(1,3,4-oxadiazolyl)]-methyl-indol-2-one (4a-g) have been synthesized by heterocyclization of 5-substituted-3-(4-arylimino)-2-oxo-1-indole acetylhyrazide (3a-g) on treatment with CS2 in ethanolic KOH. The compound 4a was characterized by its elemental analysis, IR, 1HNMR and Mass Spectroscopy. The synthesized compoun...
متن کاملSynthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds
The preparation of β-meso directly linked porphyrin-corrole hybrids was realized for the first time via an InCl3-catalyzed condensation reaction of 2-formyl-5,10,15,20-tetraphenylporphyrins with meso-substituted dipyrromethanes. Hybrid compounds have been characterized by 1H NMR, 13C NMR, 2D NMR, UV-vis absorption and fluorescence spectroscopy.
متن کاملSynthesis and Screening of Some New Isatin Containing Thiazole Derivatives for Antimicrobial Activity
In the present work, a series of new N’-[{5-(4-aryl) 1,3-thiazol-2yl}carbohydrazide-methyl]- 3(4-arylimino) indol-2-one analogs (5a-g) had heen synthesized from 3-(4-arylimino)-2-oxo- 1-indole-acetylthiosemicarbazide (4a-g) in ethanol, in the presence of phenacyl bromide or substituted phenacyl bromides. The compound 5e was characterized by its elemental analysis, IR, 1 HNMR and Mass Spectrosco...
متن کاملFirst synthesis of meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins
A synthetic protocol for the construction of new meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins is described starting from 5-(4-amino-3-nitrophenyl)-10,15,20-triphenylporphyrin. The reaction of this porphyrin with 2,5-dimethoxytetrahydrofuran, followed by the reduction of the nitro group in the presence of NiCl2/NaBH4 afforded 5-(3-amino-4-(pyrrol-1-yl)phenyl)-10,15,20-triphenylporphyrin....
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Archiv der Pharmazie
دوره 346 1 شماره
صفحات -
تاریخ انتشار 2013