methyl 4-((3,5-dimethyl-1H-pyrrol-2-yl)(3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)benzoate | 1202222-31-8

• 分子结构分类: 有机化合物
• 英文名称: methyl 4-((3,5-dimethyl-1H-pyrrol-2-yl)(3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)benzoate
• CAS: 1202222-31-8
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: UWWKRZRPBSQMNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54.45
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 4-((3,5-dimethyl-1H-pyrrol-2-yl)(3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)benzoate 在 碘酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.5h， 生成 4,4-difluoro-2,6-di-iodo-8-(4-(methoxycarbonyl)phenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs

  摘要：

  A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalization of the BODIPY framework via iodination at the 2,6-pyrrolic positions was explored in order to determine the effect of these heavy atoms on the photophysical and cytotoxicity of the meso-aryl-BODIPYs. BODIPYs bearing meso-thienyl substituents showed the largest red-shifted absorptions and emissions and reduced fluorescence quantum yields. The phototoxicity of the BODIPYs in human carcinoma HEp2 cells depends on both the presence of iodines and the nature of the meso-aryl groups. Six of the eleven 2,6-diiodo-BODIPYs investigated showed at least a sevenfold enhancement in phototoxicity (IC50 = 3.5-28 mu M at 1.5 J/cm(2)) compared with the non-iodinated BODIPYs, while the others showed no cytotoxicity, while their singlet oxygen quantum yields ranged from 0.02 to 0.76. Among the series investigated, BODIPYs 2a and 4a bearing electron-donating meso-dimethoxyphenyl substituents showed the highest phototoxicity and dark/phototoxicity ratio, and are therefore the most promising for application in PDT. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.017
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 methyl 4-((3,5-dimethyl-1H-pyrrol-2-yl)(3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)benzoate
  参考文献：
  名称：

  用于一步生产可溶性和靶向荧光染料的双功能蛋白。

  摘要：

  低水溶性和差的选择性是损害近红外（NIR）荧光探针应用的两个基本限制。方法：在这里，使用疏水蛋白HFBI和精氨酸-甘氨酸-天冬氨酸（RGD）肽融合产生的新型杂交蛋白RGD-HFBI，开发了一种可以同时解决这些问题的简单策略。这种独特的杂合蛋白分别继承了HFBI和RGD肽的自组装和靶向功能。结果：通过简单混合和超声处理30分钟，可以将用作模型NIR染料的硼二吡咯甲烷（BODIPY）有效地分散在RGD-HFBI溶液中。数据表明，使用BODIPY作为组装模板，自组装的RGD-HFBI形成蛋白质纳米笼。细胞摄取分析证明RGD-HFBI / BODIPY可以有效地染色αvβ3整联蛋白阳性癌细胞。最后，体内亲和力测试充分证明，由于RGD肽的高选择性，可溶性RGD-HFBI / BODIPY复合物选择性靶向并标记了荷瘤小鼠的肿瘤部位。结论：我们使用双功能RGD-HFBI的一步策略为以可简单且有效的方式生

  DOI：

  10.7150/thno.24613

文献信息

• Novel Fluorescent Probe for Analysis of Hydroperoxides Based on Boron Dipyrromethane Fluorophore
  作者：Naoko INOUE、Yoshio SUZUKI、Kenji YOKOYAMA、Isao KARUBE

  DOI：10.1271/bbb.80899

  日期：2009.5.23

  A new reagent, N-[2-(diphenylphosphino)ethyl]-4-(1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-yl)benzamide (DPPEA-BODIPY), was designed and synthesized for analysis of hydroperoxides. DPPEA-BODIPY fluoresces at low levels in the visible range (λex⁄λem = 502 nm/515 nm) and reacts with hydroperoxides to produce DPPEA-BODIPY oxide, which fluoresces at high levels. The fluorescence intensity of the reaction mixture was observed to be linearly related to the methyl linoleate hydroperoxide (MeLOOH) concentration.

  一种新的试剂，N-[2-(二苯基磷基)乙基]-4-(1,3,5,7-四甲基-4,4-二氟-4-硼-3a,4a-二氮杂-印达烯-8-基)苯酰胺（DPPEA-BODIPY），被设计和合成用于过氧化氢化合物的分析。DPPEA-BODIPY在可见光范围内（λex⁄λem = 502 nm/515 nm）低强度荧光，并与过氧化氢化合物反应生成DPPEA-BODIPY氧化物，该氧化物具有高强度荧光。反应混合物的荧光强度与亚油酸甲酯过氧化物（MeLOOH）浓度呈线性相关。
• Photodynamic antimicrobial activities of a series of <i>meso</i>-substituted 2,6-dibrominated 1,3,5,7-tetramethylBODIPY dyes
  作者：Aviwe K. May、Bokolombe P. Ngoy、John Mack、Tebello Nyokong

  DOI：10.1142/s1088424623501316

  日期：2024.2

  The photodynamic antimicrobial chemotherapy (PACT) activities of seven 1,3,5,7-tetramethyl-2,6-dibromoBODIPY dyes with 4-acetamidophenyl (2a), 2-iodophenyl (2b), 3-iodophenyl (2c), 4-iodophenyl (2d), 2-bromophenyl (2e), 5-bromothien-2-yl (2f), and methylphenyl ester (2g) meso-substituents were studied against Staphylococcus aureus through irradiation with a 530 nm Thorlabs M530L3 light emitting diode (LED) (110 mW.cm[Formula: see text] to identify structure-property relationships related to modifying the meso-substituent. Significant differences are observed in the log[Formula: see text] reduction values obtained with 1 [Formula: see text]M of 2a exhibiting the highest PACT activity with a value of 9.60 after 15 min of photoirradiation. In contrast, log[Formula: see text] reduction values < 1.20 were obtained after 60 min of photoirradiation for iodophenyl dyes 2b-2d. The data demonstrate that the singlet oxygen quantum yield of the dye is not the most important factor determining the PACT activity properties.

  研究了含有 4-乙酰氨基苯基（2a）、2-碘苯基（2b）、3-碘苯基（2c）、4-碘苯基（2d）、2-溴苯基（2e）、5-溴噻吩-2-基（2f）和甲基苯基酯（2g）的七种 1,3,5,7-四甲基-2,6-二溴 BODIPY 染料的光动力抗菌化疗（PACT）活性、2-溴苯基（2e）、5-溴噻吩-2-基（2f）和甲基苯基酯（2g）中取代基，通过 530 nm Thorlabs M530L3 发光二极管（LED）（110 mW）照射，研究了它们对金黄色葡萄球菌的作用。cm[计算公式：见正文]，以确定与改变中间取代基有关的结构-性质关系。光照射 15 分钟后，1 [式：见正文] M 的 2a 显示出最高的 PACT 活性，其对数值为 9.60。相比之下，碘苯基染料 2b-2d 在光照 60 分钟后的对数[式：见正文]还原值为 1.20。这些数据表明，染料的单线态氧量子产率并不是决定 PACT 活性特性的最重要因素。