methyl 3-[8,13-bis(1-hydroxyethyl)-18-(3-methoxy-3-oxopropyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoate | 32562-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: methyl 3-[8,13-bis(1-hydroxyethyl)-18-(3-methoxy-3-oxopropyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoate
• 英文别名: hematoporphyrine IX dimethylester；hematoporphyrin(IX)dimethylester；hematoporphyrin-dimethyl ester；hematoporphyrin IX dimethyl ester；dimethyl ester of hematoporphyrin-IX；haematoporphyrin dimethyl ester；hematoporphyrin dimethyl ester；3,3'-[7,12-bis-(1-hydroxy-ethyl)-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-diyl]-bis-propionic acid dimethyl ester；hematoporphyrin-IX dimethyl ester；hematoporphyrin dimethylester
• CAS: 32562-61-1；119366-88-0；119366-89-1；131070-54-7；131070-74-1
• 化学式: C₃₆H₄₂N₄O₆
• 分子量: 626.753
• InChiKey: BIONBQTVWKNFKA-HRBATZQVSA-N

物化性质

• 密度：
  1.250

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  150.42
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 3-[8,13-bis(1-hydroxyethyl)-18-(3-methoxy-3-oxopropyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoate 在 manganese(IV) oxide 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 bis[1-(2-acetyldeuteroporphyrin IX 13,17-dimethyl ester-8-yl)]-3-methylpropene
  参考文献：
  名称：

  Synthesis of ether- and carbon-linked polycarboranyl porphyrin dimers for cancer therapies

  摘要：

  Porphyrin dimers bearing multiple carborane cages for potential use as sensitizers in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) were synthesized from protoporphyrin dimethyl ester and characterized. Diastereomeric ether-linked dimers bearing four closo carborane cages (40 boron atoms) were found to be unstable to the acidic conditions necessary for conversion into water-soluble salts. In contrast, the carbon-carbon-linked dimers bearing six icosahedral carboranes (60 boron atoms) were stable to acid and could be isolated as water-soluble sodium salts. In vitro and in vivo studies of these novel molecules are currently under investigation. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00391-7
• 作为产物：
  描述：

  2,4-diacetyl-6,7-bis<2-(methoxycarbonyl)ethyl>-1,3,5,8-tetramethylporphyrin 在 sodium tetrahydroborate 、 盐酸 、 水 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 以95%的产率得到methyl 3-[8,13-bis(1-hydroxyethyl)-18-(3-methoxy-3-oxopropyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoate
  参考文献：
  名称：

  Process For Preparing Porphyrin Derivatives, Such As Protoporphyrin (IX) And Synthesis Intermediates

  摘要：

  本发明涉及一种制备公式（I）的卟啉的方法，可选地以碱金属的盐形式和/或金属配合物的形式存在： 其中： R和R′如权利要求1中定义的那样， 包括： 在酸性介质中，通过公式（II）的二吡咯甲烷和公式（III）的二吡咯甲烷之间的缩合步骤： 其中R′b如上述（I）中定义的那样， 以及公式（III）的化合物。

  公开号：

  US20080242857A1

文献信息

• Porphyrin dimers as photosensitizers in photodynamic therapy
  作者：Ravindra K. Pandey、Kevin M. Smith、Thomas J. Dougherty

  DOI：10.1021/jm00169a038

  日期：1990.7

  (1-hydroxyethyl)vinyldeuteroporphyrin IX dimethyl esters (Hvd). The pure Hvd isomers 2-(1-hydroxyethyl)-4-vinyldeuteroporphyrin IX dimethyl ester (7) and 4-(1-hydroxyethyl)-2-vinyldeuteroporphyrin IX dimethyl ester (8) were obtained from 2-acetyl-4-(1-hydroxyethyl) deuteroporphyrin IX dimethyl ester (3) and 4-acetyl-2-(1-hydroxyethyl)deuteroporphyrin IX dimethyl ester (4). Porphyrins 3 and 4 were prepared

  由2-乙酰基-4-（1）得到纯的Hvd异构体2-（1-羟乙基）-4-乙烯基氘卟啉IX二甲酯（7）和4-（1-羟乙基）-2-乙烯基氘卟啉IX二甲酯（8）。 （3-羟乙基）氘卟啉IX二甲酯（3）和4-乙酰基-2-（1-羟乙基）氘卟啉IX二甲酯（4）。卟啉3和4可以通过部分还原2,4-二乙酰基氘卟啉IX二甲酯（2）或通过使用四正丙基过钌酸铵（Prn4N）（RuO4）和N-氧化血卟啉IX二甲酯（1）来制备。甲基吗啉N-氧化物作为氧化剂。比较了DBA / 2 Ha小鼠皮下生长的SMT-F肿瘤中二聚体9-12与Photofrin II的体内光敏能力和治疗比率。
• Regioselective syntheses of ether-linked porphyrin dimers and trimers related to photofrin-II®
  作者：Ravindra K. Pandey、Fuu-Yau Shiau、Thomas J. Dougherty、Kevin M. Smiths

  DOI：10.1016/s0040-4020(01)91025-7

  日期：1991.11

  Using isomerically pure 4-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 10, 2-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 11, 2-acetyl-4-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 12 and 4-acetyl-2-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 13 as starting materials, a series of regiochemically pure ether-linked porphyrin dimers 25–41 and trimers 42–47 related to an anticancer

  使用异构体纯的4-（1-羟乙基）次卟-IX二甲酯10，2-（1-羟乙基）次卟-IX二甲酯11 2-乙酰基-4-（1-羟乙基）次卟-IX二甲酯12和4 -乙酰基-2-（1-羟乙基）氘卟啉-IX二甲酯13作为起始原料，一系列区域化学纯的醚连接卟啉二聚体25-41和三聚体42-47合成了与一种称为Photofrin-II®的抗癌药物有关的药物。质子NMR核Overhauser增强实验和可变温度质子NMR光谱用于表征异构体。测试了其中某些化合物相对于Photofrin-II的体内光敏能力，并简要描述了初步结果。
• Derivatives of Natural Tetrapyrroles for Photodynamic Therapy, 4. Oxidative Degradation Studies: Direct Analysis and Determination of Ether and Ester Linkages in Porphyrin Dimers and Oligomers of Hematoporphyrin Derivative (HPD),
  作者：Nikolaus Risch、Ulrike Hesse、Andrea Josephs、Rainer Gauler

  DOI：10.1002/jlac.199619961122

  日期：1996.11

  Oxidative degradation studies of dimeric porphyrins provide valuable information about the individual linkages between the porphyrin units. MS and NMR data of the degradation products of hematoporphyrin derivative furnish unambiguous evidence of ester and ether linkages in the di- and oligomeric compounds of HPD.

  二聚卟啉的氧化降解研究提供了有关卟啉单元之间各个键的有价值的信息。血卟啉衍生物降解产物的MS和NMR数据提供了HPD二聚和低聚化合物中酯键和醚键的明确证据。
• Method and apparatus for performing novel high-performance liquid chromatography
  申请人：SATO PHARMACEUTICAL RESEARCH INSTITUTE LIMITED

  公开号：EP0211411A2

  公开（公告）日：1987-02-25

  This invention relates to an apparatus and a method of high performance liquid chromatography comprising irradiating a high performance liquid chromatography column (4) and detecting separation conditions and separation patterns of a material charged onto said column by measuring the intensity of transmitted light, reflected light or fluorescent light from the column by means of a line sensor (8).

  本发明涉及一种高效液相色谱设备和方法，包括照射高效液相色谱柱 (4)，并通过线传感器 (8) 测量来自色谱柱的透射光、反射光或荧光的强度，从而检测加载到所述色谱柱上的材料的分离条件和分离模式。
• Pyropheophorbides and their use in photodynamic therapy
  申请人：HEALTH RESEARCH, INC.

  公开号：EP1146046A2

  公开（公告）日：2001-10-17

  Pyropheophorbides compounds are injected into a host and accumulate in tumor tissue to a higher degree than surrounding normal tissues. When the pyropheophorbide compounds are exposed to a particular wavelenght of light the compounds become cytotoxic and destroy the tumor or diseased tissue without causing irreversible normal tissues damage. The phyropheophorbide compounds have shown improved results as compared to drugs currently used in photodynamic therapy. Further, they absorb light further in the red, optimizing tissue penetration and are retained in the skin for short time periods relative to other drugs used in photodynamic therapy.

  将焦酚酰胺化合物注射到宿主体内，其在肿瘤组织中的蓄积程度高于周围的正常组织。当焦佛得角化合物暴露在特定波长的光线下时，化合物就会产生细胞毒性，破坏肿瘤或病变组织，而不会对正常组织造成不可逆的损伤。与目前用于光动力疗法的药物相比，植物鞘氨醇化合物的效果更好。此外，与光动力疗法中使用的其他药物相比，它们对红色光的吸收更强，组织穿透性更好，在皮肤中保留的时间更短。