10-(12-bromododecyl)-10H-phenothiazine | 80548-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 10-(12-bromododecyl)-10H-phenothiazine
• 英文别名: 12-(10'-phenothiazinyl)dodecyl-1-bromide；10-(12-bromododecyl)phenothiazine
• CAS: 80548-36-3
• 化学式: C₂₄H₃₂BrNS
• 分子量: 446.495
• InChiKey: MZOPYJSKKJPOMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.59
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  10-(12-bromododecyl)-10H-phenothiazine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以78.2%的产率得到
  参考文献：
  名称：

  一种具有(D-D-π-A)3结构的吩噻嗪染料及其 制备方法和应用

  摘要：

  本发明涉及一种具有(D‑D‑π‑A) 3 结构的吩噻嗪染料及其制备方法和应用，所述(D‑D‑π‑A) 3 结构的吩噻嗪染料具有式(VII)所示结构，其中R 1 、R 2 、R 3 、R 4 、P、D和L的定义见说明书。本发明还提供所述具有(D‑D‑π‑A) 3 结构的噻吩嗪染料的制备方法；本发明所述(D‑D‑π‑A) 3 结构的吩噻嗪染料能显著拓宽染料的光谱响应范围并增强染料的吸光强度。相比单D‑D‑π‑A结构的有机光敏染料，本发明提供的染料具有更大的摩尔吸光系数，将本发明所述的具有(D‑D‑π‑A) 3 结构的噻吩嗪染料用于制备染料敏化太阳能电池，可得到更大的短路电流密度(Jsc)。

  公开号：

  CN107698999B
• 作为产物：
  描述：

  吩噻嗪 、 1,12-二溴十二烷 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以50%的产率得到10-(12-bromododecyl)-10H-phenothiazine
  参考文献：
  名称：

  水溶液中吩噻嗪磺酸烷基酯胶束组装的研究

  摘要：

  已经对9-烷基吩噻嗪磺酸钠和ω-咔唑-9-烷基链烷磺酸钠（其中烷基= C 10 H 21和C 12 H 25）的胶束性质和光化学行为进行了研究，以用于胶束组件中光电离的基础研究。

  DOI：

  10.1039/f19868202615

文献信息

• Synthesis and Biochemical Characterization of New Phenothiazines and Related Drugs as MDR Reversal Agents
  作者：Matthias Schmidt、Marlen Teitge、Marianela E. Castillo、Tobias Brandt、Bodo Dobner、Andreas Langner

  DOI：10.1002/ardp.200800115

  日期：2008.10

  for pharmacophor structures is a promising strategy to increase the efficacy of those drugs still influencing multidrug resistance. In this study a range of phenothiazine derivatives was synthesizied with systematical variation of three molecule domains. The biochemical determination of multidrug resistance reversal activity was achieved with the crystalviolet assay on LLC‐PK1/MDR1 cells. The results

  化疗是治疗癌症最重要的方法之一。然而，化疗期间耐药性的发展是癌症患者治疗失败和生存率下降的主要原因。多药耐药 (MDR) 是 30 多年来广泛研究的耐药形式之一。ATP 结合盒蛋白家族的成员负责以 P-糖蛋白作为最具代表性的转运蛋白的多药耐药性。为了克服多药耐药性，外排泵抑制剂对转运蛋白的药理学调节似乎是首选，但临床前研究并未导致临床应用。因此，对药效基团结构进行系统研究是提高那些仍影响多药耐药性的药物疗效的有前途的策略。在这项研究中，一系列吩噻嗪衍生物合成了三个分子结构域的系统变异。多药耐药逆转活性的生化测定是通过对 LLC-PK1/MDR1 细胞的结晶紫测定实现的。将考虑文献中关于新的结构-活性关系以克服未来耐药性的假设来讨论结果。
• Effect of Self-Assembly of Amphiphilic Redox-Chromophores on Photoionization Processes
  作者：Robin Humphry-Baker、André M. Braun、Michael Grätzel

  DOI：10.1002/hlca.19810640708

  日期：1981.11.4

  solution. Concomitantly with micellization, strong changes in the photochemical behaviour occur. In particular, monophotonic photoionization is only observed above the critical micelle concentration (CMC.). Cooperative effects associated with self-assembly of this amphiphilic redox chromophore leading to local electrostatic barriers are evoked to explain these effects.

  合成了吩噻嗪的表面活性剂衍生物，其能够在水溶液中形成胶束。与胶束化同时，发生光化学行为的强烈变化。特别是，仅在临界胶束浓度（CMC。）以上才能观察到单光子光电离。引起与这种两亲性氧化还原生色团的自组装相关联的协同作用导致局部静电屏障，被认为是解释这些作用的原因。
• Nakagaki, Ryoichi; Mutai, Kiyoshi; Hiramatsu, Mitsuo, Canadian Journal of Chemistry, 1988, vol. 66, p. 1989 - 1996
  作者：Nakagaki, Ryoichi、Mutai, Kiyoshi、Hiramatsu, Mitsuo、Tukada, Hideyuki、Nakakura, Saburo

  DOI：——

  日期：——
• Comparative electron spin resonance and electron spin echo modulation studies of the photoionization of positively and negatively charged and neutral alkylphenothiazines in cationic dioctadecyldimethylammonium chloride, neutral dipalmitoylphosphatidylcholine, and anionic dihexadecyl phosphate vesicles at 77 K
  作者：Young Soo Kang、Hugh J. D. McManus、Larry Kevan

  DOI：10.1021/j100111a049

  日期：1993.3

  Positively charged phenothiazine N-alkyltrimethylammonium bromides (PC(n)TAB) and negatively charged sodium phenothiazine-N-alkanesulfonates (PC(n)S) were synthesized and photoionized in cationic dioctadecyldimethylammonium chloride (DODAC), neutral dipalmitoylphosphatidylcholine (DPPC), and anionic dihexadecyl phosphate (DHP) vesicles. The photoproduced radicals were identified and quantitated with electron spin resonance. The microenvironments of the various photoproduced PC(n)S and PC(n)TAB cation radicals in frozen D2O solutions were investigated with electron spin echo modulation (ESEM). These results are compared with those of neutral N-alkylphenothiazines (PC(n)) in the same vesicles. The effects of the pendent alkyl chain length on the photoyields of PC(n)S and PC(n)TAB are similar. For short alkyl chains (n = 2 or 3), a large deuteron modulation depth is observed, which correlates with a high photoyield. The large deuteron modulation depth indicates a short interaction distance between the phenothiazine radical and water at the interface. As the alkyl chain length of the anionic and cationic types of phenothiazines increases, the photoyield decreases reaching a minimum near six carbons. The decreased deuteron modulation depth indicates that the increased hydrophobic interaction of the phenothiazine alkyl chain with the vesicle surfactant alkyl chains pulls the phenothiazine group toward the interior of the vesicles, which results in a decrease of the photoyield. At still longer alkyl chain lengths (n = 12), the photoyield increases. This is explained by alkyl chain bending so that the phenothiazine moiety moves toward the vesicle interface region, which results in an increased photoyield. The effects of the pendent alkyl chain length of PC(n)TAB and PC(n)S contrast with those of PC(n) in the same vesicles. As the alkyl chain length of PC(n) increases, the photoyield decreases monotonically in DHP and DPPC vesicles with no evidence of alkyl chain bending. These photoyields are well supported by the ESEM results. In DODAC vesicles the photoyields and deuteron modulation depths decrease up to twelve carbons and then increase which is consistent with some alkyl chain bending. Overall, the photoionization yields and deuteron modulation depths show good self-consistency for all systems studied. For the same vesicle system the photoyields decrease in the order PC(n)S > PC(n)TAB > PC(n). This is explained by the greater hydrophilicity of the sulfonate group of PC(n)S relative to the trimethylammonium group in PC(n)TAB relative to the methyl group of PC(n). This difference locates the phenothiazine moiety closer to the interface region of the vesicles for greater hydrophilicity. These distance differences are verified by the ESE deuteron modulation depths. The photoyields for a given alkylphenothiazine series in the three different vesicles decrease as DODAC > DPPC > DHP. This constrasts with ESE deuteron modulation depths which decrease as DHP > DPPC > DODAC. This indicates that the photoyield for the same alkylphenothiazines in different vesicles is determined primarily by the energy barrier of the vesicle interface charge.