7-ethyl-18-(2-methoxycarbonyl-ethyl)-20-methoxycarbonylmethyl-3,8,13,17-tetramethyl-12-vinyl-17,18-dihydro-21H,23H-porphine-2-carboxylic acid methyl ester | 15592-17-3

• 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: 7-ethyl-18-(2-methoxycarbonyl-ethyl)-20-methoxycarbonylmethyl-3,8,13,17-tetramethyl-12-vinyl-17,18-dihydro-21H,23H-porphine-2-carboxylic acid methyl ester
• 英文别名: chlorin e6 trimethyl ester；methyl (2S,3S)-8-ethenyl-13-ethyl-2,3-dihydro-18-methoxycarbonyl-20-methoxycarbonylmethyl-3,7,12,17-tetramethylporphyrin-2-propionate；18-methyl formate-20-(methyl acetate)-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-8-vinyl-21H,23H-porphine-2-methyl propionate；chlorin e₆ trimethyl ester；chlorin-e₆ trimethyl ester；chlorin e6 trimethylester；methyl 17S,18S-[8-ethyl-17-(2-methoxycarbonylethyl)-15-methoxycarbonylmethyl-2,7,12,18-tetramethyl-3-vinyl-17,18-dihydro-21H,23H-porphyrin-13-yl]carboxylate；chlorin e₆ trimethyl ester；chlorin e₈ trimethyl ester；chlorin e6-trimethyl ester
• CAS: 15592-17-3；55721-87-4
• 化学式: C₃₇H₄₂N₄O₆
• 分子量: 638.764
• InChiKey: LXSAEOQFNKQCFM-MIUGAMJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  47.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  7-ethyl-18-(2-methoxycarbonyl-ethyl)-20-methoxycarbonylmethyl-3,8,13,17-tetramethyl-12-vinyl-17,18-dihydro-21H,23H-porphine-2-carboxylic acid methyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以0.66 g的产率得到chloroporphyrin e₆ trimethyl ester
  参考文献：
  名称：

  Design, synthesis, and in vitro photodynamic activities of benzochloroporphyrin derivatives as tumor photosensitizers

  摘要：

  Novel benzochloroporphyrin derivatives (BCPDs) were designed, synthesized, and characterized. In vitro dark cytotoxicity and photodynamic efficacy of BCPDs were evaluated by MTT assay on human hepatoma BEL-7402 cells. The experimental results showed that BCPDs 15, 16, 17, and 18 have strong long wavelength absorptions around 670 nm and exhibit significantly lower dark cytotoxicity than BPDMA and possess potent photocytotoxicity, IC50 values 1.32 mu g/mL for 15, 0.26 mu g/mL for 16, 0.47 mu g/mL for 17 of 0.27 mu g/mL for 18, and 0.23 mu g/mL for BPDMA. Among them, BCPDs 16 and 18 are more effective and promising PDT photosensitizers based on the studies with BEL-7402 cells and show nearly the same photodynamic efficacy as BPDMA. MG-P staining qualitative analysis also indicated that PDT with BCPDs 16 can induce apoptosis in BEL7402 cells. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.10.086
• 作为产物：
  描述：

  chlorin e₆ nitrile 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以26%的产率得到7-ethyl-18-(2-methoxycarbonyl-ethyl)-20-methoxycarbonylmethyl-3,8,13,17-tetramethyl-12-vinyl-17,18-dihydro-21H,23H-porphine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  叶绿素a的全合成

  摘要：

  详细描述了从克诺尔吡咯（1）开始的叶绿素a的总合成。涉及到达到目标分子的四阶段是二氢卟酚e 6三甲基酯（46），从中已经描述了叶绿素a的制备。

  DOI：

  10.1016/0040-4020(90)80003-z

文献信息

• 二氢卟吩衍生物及其相应的制备方法和用途
  申请人：广州易斯生物科技发展有限公司

  公开号：CN111943954B

  公开（公告）日：2021-08-13

  本发明涉及一种二氢卟吩衍生物及其制备方法，以及包含所述二氢卟吩衍生物的光声敏感剂，包含所述二氢卟吩衍生物的抗肿瘤药物，及所述二氢卟吩衍生物在制备抗肿瘤药物中的用途。本发明的二氢卟吩衍生物可以用于光动力治疗和声动力治疗，从而有效地抑制和治疗癌症。
• [EN] METHODS FOR MAKING BACTERIOCHLORIN MACROCYCLES COMPRISING AN ANNULATED ISOCYCLIC RING AND RELATED COMPOUNDS<br/>[FR] PROCÉDÉS DE FABRICATION DE MACROCYCLES BACTÉRIOCHLORINES COMPRENANT UN NOYAU ISOCYCLIQUE ANNELÉ ET DES COMPOSÉS APPARENTÉS
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2018102252A1

  公开（公告）日：2018-06-07

  Described herein are bacteriochlorins comprising an annulated isocyclic ring. Also described are methods and intermediates for the synthesis of bacteriochlorins comprising an annulated isocyclic ring, and methods of using such bacteriochlorins for, among other things, diagnostic and therapeutic purposes such as, e.g., luminescent compounds in flow cytometry, and/or as active agents in photodynamic therapy (PDT).

  本文描述了包含环接合异环戊二烯环的细菌叶绿素。还描述了合成包含环接合异环戊二烯环的细菌叶绿素的方法和中间体，以及利用这种细菌叶绿素进行诊断和治疗等用途的方法，例如，在流式细胞术中用作发光化合物，和/或作为光动力疗法（PDT）中的活性剂。
• 具有光、声敏活性的二氢卟吩e6二茂铁结合物、制备方法与应用
  申请人：大连理工大学

  公开号：CN111454302B

  公开（公告）日：2022-07-05

  本发明提供了一种具有光、声敏活性的二氢卟吩e6二茂铁结合物、制备方法与应用，属于化学医药技术领域。本发明所述的二氢卟吩e6二茂铁结合物在体外抗肿瘤活性评价中对Hela细胞具有不同程度的抑制作用。二茂铁基团的引入显著提高了化合物对肿瘤细胞的增殖抑制活性，二氢卟吩e6二茂铁结合物对肿瘤细胞的增殖抑制活性远高于作为对照的二氢卟吩e6。可用于肿瘤治疗的光动力学治疗、声动力学治疗方法中光敏剂和声敏剂的制备。
• Protonation-deprotonation equilibria in tetrapyrroles Part 3: Mono- and diprotonations of the trimethyl esters of chlorin e₆ and the 7¹-acetal of rhodin g₇ in methanolic hydrochloric acid
  作者：Paavo H. Hynninen

  DOI：10.1142/s1088424612501167

  日期：2012.11

  Spectrophotometric protonation titrations were performed for the trimethyl esters (TME) of chlorin e₆ (3¹,3²-didehydrorhodochlorin-15-acetic acid) and the 7¹-acetal of rhodin g₇ (3¹,3²-didehydrorhodochlorin-7¹-oxo-15-acetic acid) using HCl as the acid and methanol as the solvent. For rhodin g₇ TME, the 7¹-acetal formation could be clearly detected as the first step in the titration. Only two spectroscopically different protonated species were observed for each chlorin derivative in addition to the neutral forms. The two protonated species were assigned to the monocation and dication of each chlorin derivative. The following p K _a values were obtained: p K₃ = 4.63 and p K₄ = 0.62 for chlorin e₆ TME and p K₃ = 4.40 and p K₄ = 0.60 for the acetal of rhodin g₇ TME. The protonation titration for chlorin e₆ TME with HCl in acetic acid afforded UV-vis spectra similar to those obtained with HCl in methanol. The UV-vis spectrometric parameters are given for the neutral forms of chlorin e₆ TME, rhodin g₇ TME and its 7¹-acetal, as well as for the mono- and diprotonated species of chlorin e₆ TME and rhodin g₇ TME acetal. The protonation titration results of the chlorin e₆ derivatives are compared with those previously obtained for phytyl/methyl pyropheophorbide a.

  以盐酸为酸，甲醇为溶剂，对氯素 e6（31,32-二脱氢二氯-15-乙酸）的三甲基酯（TME）和罗丹 g7（31,32-二脱氢二氯-71-氧代-15-乙酸）的 71-缩醛进行了分光光度质子滴定。对于罗丹 g7 三甲基甲烷，71-乙醛的形成可以作为滴定的第一步被清楚地检测到。除了中性形式外，每种氯素衍生物只观察到两种光谱不同的质子化物种。这两种质子化物质分别属于每种氯素衍生物的一元化和二元化。得出的 p K a 值如下：氯素 e6 三甲基甲烷的 p K3 = 4.63，p K4 = 0.62；罗丹 g7 三甲基甲烷缩醛的 p K3 = 4.40，p K4 = 0.60。用乙酸中的盐酸对氯素 e6 三甲基甲烷进行质子化滴定，得到的紫外-可见光谱与用甲醇中的盐酸滴定得到的光谱相似。给出了中性形式的氯素 e6 TME、罗丹 g7 TME 及其 71-缩醛，以及单质子化和双质子化形式的氯素 e6 TME 和罗丹 g7 TME 缩醛的紫外-可见光谱参数。氯素 e6 衍生物的质子化滴定结果与之前获得的phytyl/methyl pyropheophorbide a 的质子化滴定结果进行了比较。
• Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins
  作者：Ravindra K. Pandey、Fuu-Yau Shiau、Meden Isaac、S. Ramaprasad、Thomas J. Dougherty、Kevin M. Smith

  DOI：10.1016/s0040-4039(00)74751-4

  日期：1992.12

  presence of electron-withdrawing groups on the macrocycle, the oxidation taking place at the subunit in the quadrant opposite to the electronegative group. Migratory aptitudes in subsequent pinacol-pinacolone rearrangements of porphyrin and pheophorbide vic-dihydroxy systems are likewise dependent upon the presence of electron-withdrawing functionalities.

  卟啉中吡咯亚基OsO 4氧化的区域专一性受到大环上吸电子基团的显着影响，氧化发生在与负电基团相反的象限中的亚基上。在卟啉和脱镁叶绿的后续频哪醇-频哪酮重排洄游性向VIC -二羟基系统同样是依赖于吸电子官能团的存在。