Study on Synthesis and Biological Activities of Novel Water-Soluble Metalloporphyrins

The synthesis and characterization of a series of metal porphyrins, MII(Por), {Por=dianionic of 5, 10, 15, 20-tetrakis [4-(4′-bromobutyloxy) phenyl]porphyrinato and 5, 10, 15, 20-tetrakis [4-(4′-butyloxypyridine bromide)phenyl]porphyrinato, M=Zn, Cu, Mn, Co, Ni, Ru-CO} were described. The complexes 3a-3e were prepared from the reactions of compound 2 with metal acetates in chloroform, and the treatment of 3a-3f with excess of pyridine gave corresponding complexes 4a-4f. These new compounds were identified by absorption spectroscopies,1H-NMR and elemental analyses. The results of biological activity testing for 4a-4f revealed that 4a and 4c had stronger inhibiting action on the growth metabolism ofEsche richia coli.

Synthesis, Characterization and Biological Activities of Novel Water-soluble Metalloporphyrins

The synthesis, characterization, and biological activities of a series of metal porphyrins were described. The complexes 3a similar to 3e were prepared from the reaction of compound 2 with M(OAc)(2) in CHCl3, and the treatment of 3a similar to 3f with pyridine gave corresponding complexes 4a similar to 4f. These new compounds were identified by absorption spectroscopies, H-1 NMR and elemental analysis. The results of biological activity,testing revealed that 4a and 4c had stronger inhibiting action for Escherichia coli (CCTCC AB91115).

Study on the synthesis and antimicrobial activity of novel cationic porphyrins

A novel series of quaternary ammonium cationic derivatives based on tetrapyridyl-porphyrin was synthesized. All the compounds were evaluated for their in vitro antibacterial activities against S. aureus, E. coli and P. aeruginosa, and antifungal activities against C. albicans, where microorganisms were exposed and unexposed to the irradiation. The results revealed that some of these compounds, especially, 3a and 4a displayed satisfactory antibacterial activity against Gram-positive bacteria S. aureus and moderate antifungal activity against C. albicans. Unfortunately, Gram-negative bacteria P aeruginasa was resistant to all compounds. The antimicrobial activity was found to be sensitive to the functional groups attached on the aromatic ring and the complex metal in the porphyrin ring, and decreased with the increase of electron-withdrawing capability of the functional groups. These preliminary results suggested that the remarkable antibacterial efficiency against S. aureus makes these substances promising antimicrobial agents.

Study on Synthesis and Deplete Harmful Radical of Cobalt Porphyrins as the Mimic of Enzyme

The four cobalt porphyrins [Co (3, 4, 5 MeO TPP) (1) ; Co (TTP) (2) ; Co (4 CI TPP) (3);Co (4 HSO 3 TPP) (4)] were synthesized and considered as two mimic of superoxide dismutaes (SOD) and catalase (CAT). The catalytic efficiency of them on deplete the harmful radical have been proved using riboflavin methionine photoreduction method in the concentration range of 10 6 ～10 5 mol/L. The catalytic efficiency of them at decomposing H 2O 2 has been performed by spectrophotometer. The percentage of decomposing H 2O 2 while the increasing the concentration of the imitating compounds. The lipid peroxidationproduced in liver homogenatcd of mice was determined by spectrophotometer detecting the content of MDA.

Synthesis of Metal Porphyrins Tailed with Salicylic Acid and their Interaction with Bovine Serum Albumin

A synthetic method of porphyrins tailed with salicylic substituents is described. Reaction of bromoalkoxyphenyl porphyrin 1 with salicylic acid gave porphyrins 2~5. These new compounds were confirmed by 1H NMR, IR, UV-vis, MS and elemental analysis, and observed their interaction with bovine serum albumin (BSA) in fluorescence spectrum.

Synthesis of β-Cyclodextrin Bonded Metal Porphyrins

6-Deoxy- 6-iodo-β-cyclodextrin (1) reacted with 5-(p-aminophenyl)-10, 15,20-triphenyl porphyrin(2), 5-(p-aminophenyl)-10,15,20-triphenyl nickel(Ⅱ) porphyrin [NiⅡTPPNH2P](3),5-(p-aminophenyl)-10,15,20-triphenyl manganese(Ⅲ) porphyrin [MnⅢTPPNH2P] (4) and 5-(p-aminophenyl)-10,l5,20-triphenyl carbonyl ruthenium porphyrin [RuⅡ (CO)TPPNH2P] (5) to generate the compounds 6-9, respectively. Those new compound 5-9 have been identified by 1H NMR, IR, MS and UV-visible spectra and elemental analysis.

Synthesis of Novel Tailed Porphyrins with Covalently Linked Saccharide

The reaction of 5-(p-hydroxyphenyl)-10, 15, 20- (p-methoxy phenyl) porphyrin with Br(CH2)4 Br produced monobromo substituted porphyrin 1. The tailed porphyrins 2–4 were synthesized by the reactions of 1 with small molecular offering biological activities such as D-glucose, D-glucuronic acid. These new compounds were confirmed by1H NMR, IR, UV-vis and element analyses.

Synthesis of Glucoside Bonded Metal Porphyrins

The reactions of 5,10,15,20-tetrakis(p-hydroxyphenyl) porphyrin 1 and 5-(p-hydroxyphenyl)-10,15,20-tris(p-methoxyphenyl) porphyrin 2 with 1-bromo-2,3,4,6-O-acetyl-alpha -D- glucoside 3 respectively afforded 5,10,15,20-tetrakis[p-(2,3,4,6-O-acetyl-glucoside)-1-O-phenyl]porphyrin 4 and 5,10,15-tris(p-methoxyphenyl)-20-[p-(2,3,4,6-O-acetyl-glucoside)-1-O-phenyl] porphyrin 5. Their metal complexes Co-II(4), Mn-II (4) and Co-II(5), Mn-II'(5) also have been prepared. These new compounds have been identified by IR, UV-visible,H-1 NMR spectra and elemental analysis.

Synthesis of Polymer-Bonded Carbonyl Ruthenium (Ⅱ) and Osmium (Ⅱ) Porphyrins

The reactions of 5- (p-hydroxyphenyl)-10, 15, 20-tris (p-methoxyphenyl) porphyrin(H2Por) 1 respectively with triruthenium dodecacarbonyl [Ru3 (CO)12] and triosmiumdodecacarbonyl [Os3 (CO)12] under N2 gave complexes 2 and 3. Treatment of 2 (and 3) withMerrifield' peptide resin gave 4 (and 5) respectively.

Synthesis of Novel Polymer-Bonded Water-Soluble Metal Porphyrins

The reaction of 5, 10, 15, 20-tetra-(4-pyridyl) porphyrin 1 with triruthenium dodecacarbonyl [Ru3(CO)12], zinc(II) acetate, copper(II) acetate, cobalt(II) acetate afforded complexes 2a?2d respectively. Treatment of 2a?2d with Merrifield’s peptide resin obtained 3a?3d. The compounds 3a?3d reacted with methyl iodide respectively gave 4a?4d. New complexes 4a?4d have been identified by IR, UV-visible spectra, and AES.

Synthesis of Novel Diporphyrins

The novel diporphyrin ligands in which the two porphyrin ring units attached via a rigid aromatic linker were prepared. Their structures have been identified by IR, UV visible, 1 H NMR spectra and elemental analysis.

Synthesis and characterization of a novel series of unsymmetrical porphyrins

A novel series of unsymmetrical porphyrins with aldehyde group at the terminal of the linkage which connected to meso-phenyl through acylamide bond have been synthesized and structurally characterized by IR, (1)H NMR, MS, UV–vis, fluorescence.

Synthesis and Characterization of Novel Bridged Porphyrins

The reaction of 5-(4-hydroxyphenyl)-10,15,20-triphenyl porphyrin with 2,6-dibromomethylpyridine and 4,4′-dicarboxyl-2,2′-bipyridine respectively gave 2,6-bis-[5,10,15-triphenyl-20-(4-phenoxymethyl)-porphyrin-yl]-pyridine(3) and 4,4′-di-[5,10,15-triphenyl-20-(p-phenoxycarbonyl)-porphyrin-yl]-2,2′-bipyridine (4). 5-[4-(4′- Bromobutoxy) phenyl]-10,15,20-triphenyl porphyrin reacted with 2,6-dihydroxymethylpyridine to give 2,6-bis-[5,10,15-triphenyl-20-(4-(p-phenoxy)-butoxymethyl)-porphyrin-yl]-pyridine(5). Those new compounds have been identified by1H NMR, IR, MS and UV-visible spectra, and elemental analysis. Key words bridged porphyrin - synthesis - structure characterization CLC number O 626.13 Foundation item: Supported by the National Natural Science Foundation of China (29972035)Biography: FU Shi-tao (1979-), male, Ph. D candidate, research direction: porphyrin chemistry.

Synthesis of Polymer-Bonded Quaternary Ammonium Type Metal Porphyrins

The reaction of pyrrole with 4-hydroxybenzaldehyde and 4-pyridinecarboxaldehyde afforded new porphyrin ligand 1. Treatment of 1 with copper( II ) acetate, cobalt ( II ) acetate gave complexes 2-3 respectively. 2 and 3 reacted with Merrifield's peptide resin produced 4 and 5. Complexes 4 and 5 reacted with methyl iodide respectively gave 6-7. The new compounds 1-7 have been identified by H-1 NMR, IR, MS and UV-visible spectra, elemental analysis and AES.

Meso-substituted cationic 3-and 4-N-Pyridylporphyrins and their Zn(II)derivatives for antibacterial photodynamic therapy

Photodynamic inactivation of microorganisms known as antibacterial photodynamic therapy(APDT)is one of the most promising and innovative approaches for the destruction of pathogenic microorganisms.Among the photosensitizers(PSs),compounds based on cationic porphyrins/metalloporphyrins are most successfully used to inactivate microorganisms.Series of meso-substituted cationic pyridylporphyrins and metalloporphyrins with various peripheral groups in the third and fourth positions of the pyrrole ring have been synthesized in Armenia.The aim of this work was to determine and test the most e®ective cationic porphyrins and metalloporphyrins with high photoactivity against Gram negative and Gram positive microorganisms.It was shown that the synthesized cationic pyridylporphyrins/metalloporphyrins exhibit a high degree of phototoxicity towards both types of bacteria,including the methicillinresistant S.aureus strain.Zinc complexes of porphyrins are more phototoxic than metal-free porphyrin analogs.The e®ectiveness of these Zn–metalloporphyrins on bacteria is consistent with the level of singlet oxygen generation.It was found that the high antibacterial activity of the studied cationic porphyrins/metalloporphyrins depends on four factors:the presence in the porphyrin macrocycle of a positive charge(+4),a central metal atom(Zn2þÞand hydrophobic peripheral functional groups as well as high values of quantum yields of singlet oxygen.The results indicate that meso-substituted cationic pyridylporphyrins/metalloporphyrins cannd wider application in photoinactivation of bacteria than anionic or neutral PSs usually used in APDT.

The synthesis of fluorine-containing porphyrins

The synthesis of polyfluoroalkoxyl substituted tetrakisphenylporphyrin is reported.The reaction is carrying out using Lewis acid BF_3·OEt_2 as catalyst and p-chloranil as oxidant.The yields of the porphyrins are about 30—40%.

Further study on the synthesis of F-containing porphyrins and their catalytic activity on oxidation of cyclohexene

Reaction of tetrakis(p-allyloxyphenyl)porphyrin and perfluoroalkanesulfonyl bromides gives tetrakis(p-polyfluoroalkoxylphenyl)substituted porphyrins.The yields are over 90%.The synthesis of the metal ion complexes of these F-containing porphyrins is also reported.Preliminary results on the study of the catalytic activity of the manganese(Ⅲ)complexes of various fluorinated porphyrins on oxidation of cyclohexene indicate that the introduction of R_F group into porphyrin contributes to the stability of the catalysts.

ZnTPP Axially Coordinated with a Novel Dipyridylamine Ligand:Hydrothermal Synthesis and Crystal Structure

A novel complex ZnTPPL1·3DMF 1（TPP = tetraphenylporphyrin,L1 = N-（4-（9-carbazolyl） phenyl）-N,N-di（4-pyridyl）amine） was prepared by a hydrothermal method and characterized by elemental analysis,IR,and single-crystal X-ray diffraction analysis.Compound 1 crystallizes in triclinic,space group P1 with a = 13.3082（2）,b = 14.3276（2）,c = 18.6120（3） ,α = 109.853（1）,β = 95.054（1）,γ = 98.832（1）°,V = 3260.57（9） 3,Z = 2,Dc = 1.334 g/cm3,C81H69N11O3Zn,Mr = 1309.84,μ（MoKα） = 0.438 mm-1,F（000） = 1372,GOF = 1.159,the final R = 0.0482 and wR = 0.1479 for 12091 observed reflections（Ⅰ 〉 2σ（Ⅰ））.Crystal structure analyses revealed that L1 utilizes one pyridyl N atom to bind Zn via axial coordination,affording a 1：1 complex.The binding constant was estimated to be 1.74（7） × 10^4 M^-1 from electronic spectra measurements.

A Facile Synthesis of Manganese Porphyrin Thiolates

The attractive and impertan complexes, manganese porphyrin aromatic thiolates, are prepared directly by the reaction of chloro(5, 10, 15, 20-tetraphenylporphyrinato) manganese Mn(TPP)Cl with PhSNa and (p-NO2)PhSNa under extremely simple and mild reaction