2,3,8,8,12,13,17,18-octaethylbenzochlorin | 114586-23-1

• 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: 2,3,8,8,12,13,17,18-octaethylbenzochlorin
• 英文别名: 1,2,3,4,5,6,7,7-Octaethylbenzochlorin；Octaethylbenzochlorin
• CAS: 114586-23-1
• 化学式: C₃₉H₄₈N₄
• 分子量: 572.837
• InChiKey: KSWVPTSGNPIFJG-PCYMNQLUSA-N

物化性质

• 熔点：
  241-243 °C
• 沸点：
  822.9±60.0 °C(predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.55
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.36
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3,8,8,12,13,17,18-octaethylbenzochlorin 在 二溴亚砜 作用下， 反应 2.0h， 以64%的产率得到5²-bromo-2,3,8,8,12,13,17,18-octaethyl-benzochlorin
  参考文献：
  名称：

  Involvement of both endoplasmic reticulum and mitochondria in photokilling of nasopharyngeal carcinoma cells by the photosensitizer Zn–BC–AM

  摘要：

  Photodynamic therapy (PDT) is recently developed as an effective treatment for malignant disease. In PDT, the photosensitizer eradicates tumour by induction of apoptosis. In this study, we investigated the mechanistic actions of a recently developed second generation photo sensitizer, Zn-BC-AM, on nasopharyngeal carcinoma (NPC) cells. Zn-BC-AM was found to localize in the mitochondria, endoplasmic reticulum (ER), and golgi body. Photoactivation of Zn-BC-AM loaded NPC cells resulted in a rapid collapse of mitochondrial membrane potential (Deltapsi(m)) (15 min), followed by the release of cytochrome c (I h), and activation of caspases-9 and -3 (4 h). Expression of ER chaperones Bip/Grp78 and Grp94, and ER resident lectin-like chaperone calnexin (CNX) was also enhanced in PDT-stressed NPC cells. Caspase-12, an important caspase involved in ER stress-induced apoptosis, was also activated. Inhibition of Ca2+ uptake into mitochondria by ruthenium red (RR) or loading the cells with EGTA-AM, an agent that buffers intracellular Ca2+ released from ER, resulted in a significant reduction of Zn-BC-AM PDT-induced cell death. These observations suggest that both ER and mitochondria are the subcellular targets of Zn-BC-AM. Effective activation of ER- and mitochondria-mediated apoptotic pathways is responsible for Zn-BC-AM PDT-induced NPC cell death. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2004.08.024
• 作为产物：
  描述：

  Copper(II) meso-(2-formylvinyl)octaethylporphyrin 在 硫酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.25h， 以70%的产率得到2,3,8,8,12,13,17,18-octaethylbenzochlorin
  参考文献：
  名称：

  Vilsmeier reactions of porphyrins and chlorins with 3-(dimethylamino)acrolein to give meso-(2-formylvinyl)porphyrins: new syntheses of benzochlorins, benzoisobacteriochlorins, and benzobacteriochlorins and reductive coupling of porphyrins and chlorins using low-valent titanium complexes

  摘要：

  Vilsmeier reactions between nickel(II) or copper(II) porphyrins or chlorins and 3-(dimethylamino)-acrolein/phosphoryl chloride (3-DMA/POCl3) are described. For example, copper(II) octaethylporphyrin 5 affords the meso-(2-formylvinyl) derivative 7, which cyclizes in strong acid to give the benzochlorin 10. Treatment of the nickel(II) benzochlorin 9 with 3-DMA/POCl3 gives the meso-(2-formylvinyl) derivative 14, which is cyclized in acid to give the dibenzoisobacteriochlorin 16. Prolonged treatment of nickel(II) octaethylporphyrin (4) with 3-DMA/POCl3 gives the disubstituted compound 17 in which the acrolein substituents are on adjacent rather than opposite meso positions. Acid-promoted cyclization of 17 afforded the monocyclized product 15 as well as the dibenzobacteriochlorin 18. The reaction is extended to obtain spiro benzochlorins (37, 38) from (tetrabutano- and -pentanoporphyrinato)nickel(II) complexes, as well as benzoisobacteriochlorins (e.g., 28, 29) from nickel(II) mesochlorin e6 trimethyl ester (19) and nickel(II) octaethylchlorin (26), respectively. Nickel(II) deuteroporphyrin IX dimethyl ester (11) also affords benzochlorins (12, 13) resulting from the corresponding meso-(2-formylvinyl)porphyrin. A centrally chelated metal is shown to be essential in order to accomplish cyclization of the 2-formylvinyl substituents to afford benzo derivatives. Porphyrin and chlorin dimers joined by one or three carbon-carbon double bond linkages are formed in good yields via reductive coupling by low valent titanium complexes of nickel(II) or copper(II) porphyrins or chlorins containing a formyl or an acrolein side chain. For example, nickel(II) alpha-(formylvinyl)octaethylporphyrin (6) reacts with the active titanium reagent to produce dimer 48 in 96% yield. When two different porphyrins or chlorins are cross-reacted under the same conditions, a mixture of products is obtained. The acrolein group seems to be more reactive in reductive coupling reactions than does the corresponding formyl substituent.

  DOI：

  10.1021/jo00014a016

文献信息

• Synthesis of benzopurpurins isobacteriobenzopurpurins and bacteriobenzopurpurins
  作者：Alan R. Morgan、Sapna Gupta

  DOI：10.1016/s0040-4039(00)73336-3

  日期：1994.6

  Cyclization of porphyrins substituted at the meso position(s) with acrylate or acrolein groups leads to the formation of benzopurpurin derivatives at the oxidation state of a chlorin, bacteriochlorin or isobacteriochlorin, depending upon reaction conditions.
• Efficient new syntheses of benzochlorins, benzoisobacteriochlorins, and benzobacteriochlorins
  作者：M. Graça、H. Vicente、Irene N. Rezzano、Kevin M. Smith

  DOI：10.1016/s0040-4039(00)88807-3

  日期：1990.1
• Method of Preparing Porphyrin Derivatives, Porphyrin Derivatives, Uses Thereof and Pharmaceutical Compositions
  申请人：Lugtenburg Johannis

  公开号：US20080280934A1

  公开（公告）日：2008-11-13

  Method of preparing a porphyrin derivative starting from a meso-substituted porphyrin compound. According to the invention, the meso-substituted porphyrin compound used is a meso-(2′-cyanovinyl)-substituted porphyrin compound, wherein said meso-(2′-cyanovinyl)-substituted porphyrin compound, in a form in which its porphyrin ring is complexed with a bivalent metal ion is converted, in the present of an acid for which 0