Synthesis Of Novel N-alkylated3,4-dihydropyrimidinone-Porphyrins

Photosensitizer can generate singlet oxygen under irradiation of aspecificwavelength of light, which can play a role in lesion to achieve the goles of diagnosingdisease and treatment. Currently, it is a central research that focuses onspecific-activation of photosensitizer and how to transport targeted-delivery ofphotosensitizer to lesions, while in the circumstance without specific-activation,photosensitizer can not generate fluorescence and singlet oxygen. Contrarily,photosensitizer can generate fluorescence and singlet oxygen. N1-alkylated3,4-dihydropyrimidine-2(1H)-ones (DHPM) have an pyrimidinyl which can stop thesynthesis and switching of deoxyuridine and deoxycytidine, and have alkyl chainswhich connect with DNA by alkylated reaction to affect DNA’s synthesis. It supplysprerequisites for the influence of photosensitizer that tailed porphyrin substituted byDHPM find the foothold on the lesions through the combination of DHPM and DNA.Therefore, our research majors in the following three parts. Firstly, designed andsynthesized22kinds of N1,N3-dialkyl-3,4-dihydro-pyrimidine-2(1H)-ones (DHPM)having similar structure with the cytotoxic drugs and compared with DHPM andN1-alkyl-DHPM by UV-vis, the compounds’ max peak revealed the redshift. Secondly,we designed and synthesized16kinds of N1-alkyl-DHPM-porphyrin. On this basis,we synthesized9kinds of N1-alkyl-DHPM-metalloporphyrin and found that Zn2+coordinated with nitrogen atoms of porphyrin and DHPM, but Cu2+just coordinatedwith nitrogen atoms of porphyrin. Thirdly, synthesized3kinds of N1,N3-dialkyl-DHPM-bridged porphyrin dimers, the compounds have low productivity, so that weshould improve the reaction conditions. The target product and intermediatecompounds were confirmed by UV-vis, IR,1H NMR,13C NMR, HSQC, HMBC andHR-MS.