3-[(5Z,10Z,14Z,19Z)-8-Hydroxy-7-[2-hydroxy-eth-(E)-ylidene]-18-(2-methoxycarbonyl-ethyl)-3,8,13,17-tetramethyl-12-vinyl-7,8,21,23-tetrahydro-porphin-2-yl]-propionic acid methyl ester | 78422-39-6

• 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: 3-[(5Z,10Z,14Z,19Z)-8-Hydroxy-7-[2-hydroxy-eth-(E)-ylidene]-18-(2-methoxycarbonyl-ethyl)-3,8,13,17-tetramethyl-12-vinyl-7,8,21,23-tetrahydro-porphin-2-yl]-propionic acid methyl ester
• CAS: 78422-39-6
• 化学式: C₃₆H₄₀N₄O₆
• 分子量: 624.737
• InChiKey: OJCBMWHXIONVRX-VUNVUHQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 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：
  0.33
• 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：

  3-[(5Z,10Z,14Z,19Z)-8-Hydroxy-7-[2-hydroxy-eth-(E)-ylidene]-18-(2-methoxycarbonyl-ethyl)-3,8,13,17-tetramethyl-12-vinyl-7,8,21,23-tetrahydro-porphin-2-yl]-propionic acid methyl ester 在 氢气 作用下， 以81%的产率得到3,3'-[7-(1,2-dihydroxy-ethyl)-3,8,13,17-tetramethyl-12-vinyl-21H,23H-porphine-2,18-diyl]-bis-propionic acid dimethyl ester
  参考文献：
  名称：

  原卟啉氟类似物的合成

  摘要：

  为了获得可用于癌症的诊断和治疗的卟啉衍生物，通过甲酰基卟啉与氯二氟乙酸钠的氯仿反应，合成了原卟啉的氟类似物，其中乙烯基被二氟乙烯基取代。三苯基膦的存在。

  DOI：

  10.1016/s0022-1139(00)82758-x
• 作为产物：
  描述：

  3-[8-hydroxy-3,8,13,17-tetramethyl-7-(2-oxo-ethylidene)-12-vinyl-7,8-dihydro-21H,23H-porphine-2,18-diyl]-bis-propionic acid dimethyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-[(5Z,10Z,14Z,19Z)-8-Hydroxy-7-[2-hydroxy-eth-(E)-ylidene]-18-(2-methoxycarbonyl-ethyl)-3,8,13,17-tetramethyl-12-vinyl-7,8,21,23-tetrahydro-porphin-2-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of fluorine analogues of protoporphyrin potentially useful for diagnosis and therapy of tumors.

  摘要：

  为了获得一种可用于诊断和治疗癌症的卟啉衍生物，我们在三苯基膦存在下，通过甲酰卟啉与二氟氯乙酸钠的反应，合成了原卟啉的氟类似物，其中乙烯基被二氟乙烯基取代。此外，还介绍了已报道的甲酰基卟啉合成程序的一些改进。对产品进行生物测试的初步结果表明，82, 82-二氟卟啉比其他氟类似物更有选择性地累积到胃癌中，32, 32, 82, 82-四氟卟啉比其他氟类似物更容易被大鼠肝癌细胞吸收。

  DOI：

  10.1248/cpb.38.2175

文献信息

• Synthesis and biological evaluation of new chlorin derivatives as potential photosensitizers for photodynamic therapy
  作者：Ryuji Asano、Amon Nagami、Yuki Fukumoto、Futoshi Yazama、Hideyuki Ito、Isao Sakata、Akihiro Tai

  DOI：10.1016/j.bmc.2013.02.005

  日期：2013.4

  Three new water-soluble chlorin derivatives 3, 5 and 8 for potential use as photosensitizers in photodynamic therapy (PDT) for cancer were synthesized from photoprotoporphyrin IX dimethyl ester (1). The in vivo biodistribution and clearance of chlorin derivatives 3, 5 and 8 were investigated in tumor-bearing mice. Iminodiacetic acid derivative 8 showed the greatest tumor-selective accumulation among the new chlorin derivatives with maximum accumulation in tumor tissue at 3 h after intravenous injection and rapid clearance from normal tissues within 24 h after injection. The in vivo therapeutic efficacy of PDT using 8 was evaluated by measuring tumor growth rates in tumor-bearing mice with 660 nm light-emitting diode irradiation at 3 h after injection of 8. Tumor growth was significantly inhibited by PDT using 8. These results indicate that iminodiacetic acid derivative 8 is useful as a new photosensitizer to overcome the disadvantages of photosensitizers that are currently in clinical use. (C) 2013 Elsevier Ltd. All rights reserved.