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二氢卟吩化学研究。3. 一种对光动力疗法具有潜在效用的c、d环对称二氢卟吩的实用合成方法。

Studies in chlorin chemistry. 3. A practical synthesis of c,d-ring symmetric chlorins of potential utility in photodynamic therapy.

作者信息

O'Neal William G, Roberts William P, Ghosh Indranath, Wang Hui, Jacobi Peter A

机构信息

Burke Chemical Laboratory, Dartmouth College, Hanover, New Hampshire 03755, USA.

出版信息

J Org Chem. 2006 Apr 28;71(9):3472-80. doi: 10.1021/jo060041z.

DOI:10.1021/jo060041z
PMID:16626128
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2587451/
Abstract

[reaction: see text] C,D-ring symmetric chlorins 8 were prepared in 47-85% yield, on scales up to several hundred milligrams, by condensation of appropriately substituted bis-formyldihydrodipyrrins 6 and dipyrromethane bis-carboxylic acids 7 in 5% TFA/CH2Cl2 (25 examples). Target chlorins were chosen to systematically probe the effect of lipophilic and hydrophilic substituents on tissue partitioning and cellular membrane penetration in photodynamic therapy (PDT).

摘要

[反应：见正文] 通过在5%三氟乙酸/二氯甲烷中使适当取代的双甲酰基二氢二吡咯6和二吡咯甲烷双羧酸7缩合，以47 - 85%的产率制备了C、D环对称的二氢卟吩8，规模可达数百毫克（25个实例）。选择目标二氢卟吩以系统地探究亲脂性和亲水性取代基对光动力疗法（PDT）中组织分配和细胞膜渗透的影响。

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Refined Synthesis of 2,3,4,5-Tetrahydro-1,3,3-trimethyldipyrrin, a Deceptively Simple Precursor to Hydroporphyrins.2,3,4,5-四氢-1,3,3-三甲基二吡咯的精细合成，一种看似简单实则复杂的氢卟啉前体。
Org Process Res Dev. 2005;9(5):651-659. doi: 10.1021/op050087e.
2
Studies in chlorin chemistry. II. A versatile synthesis of dihydrodipyrrins.二氢卟吩化学研究。II. 二氢二吡咯的通用合成方法。
J Org Chem. 2005 Sep 2;70(18):7243-51. doi: 10.1021/jo050907l.
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Simple approach to "locked" chlorins.“锁定”二氢卟吩的简易方法。
Org Lett. 2005 Apr 28;7(9):1749-52. doi: 10.1021/ol050327a.
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