6,7,7-trimethyl-7H-[1,3]dioxolo[4,5-f]indole | 129014-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6,7,7-trimethyl-7H-[1,3]dioxolo[4,5-f]indole
• 英文别名: 6,7,7-Trimethyl-[1,3]dioxolo[4,5-f]indole
• CAS: 129014-14-8
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: DMFUIUMRWSPCGR-UHFFFAOYSA-N

物化性质

• 沸点：
  306.2±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7,7-trimethyl-7H-[1,3]dioxolo[4,5-f]indole 在 sodium acetate 、 乙酸酐 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 6-((1E,5E)-3-bromo-5-(5,7,7-trimethyl-5,7-dihydro-6H-[1,3]-dioxolo[4,5-f ]indol-6-ylidene)penta-1,3-dien-1-yl)-5,7,7-trimethyl-7H-[1,3]dioxolo[4,5-f ]indol-5-ium iodide
  参考文献：
  名称：

  Near-Infrared Illumination of Native Tissues for Image-Guided Surgery

  摘要：

  Our initial efforts to prepare tissue-specific near infrared (NIR) fluorescent compounds generated successful correlation between physicochemical, properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.

  DOI：

  10.1021/acs.jmedchem.6b00038
• 作为产物：
  描述：

  3-溴-3-甲基-2-丁酮 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 6,7,7-trimethyl-7H-[1,3]dioxolo[4,5-f]indole
  参考文献：
  名称：

  Near-Infrared Illumination of Native Tissues for Image-Guided Surgery

  摘要：

  Our initial efforts to prepare tissue-specific near infrared (NIR) fluorescent compounds generated successful correlation between physicochemical, properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.

  DOI：

  10.1021/acs.jmedchem.6b00038

文献信息

• A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes
  作者：Eric A. Owens、Nicholas Bruschi、Joseph G. Tawney、Maged Henary

  DOI：10.1016/j.dyepig.2014.07.035

  日期：2015.2

  pentamethine cyanine dyes and their corresponding precursors. The synthesis outlined herein drastically reduced the reaction pathway for pentamethine carbocyanine dye syntheses from days to min, as well as producing increased yields (89–98%) to the conventional heating method (18–64%). Twelve examples of pentamethine cyanine dyes were synthesized by means of microwave-assisted organic synthesis which provided

  开发了一种省时，环保的微波方法，并将其用于合成五甲胺花青染料及其相应前体的系统库。本文概述的合成从几天到几分钟极大地减少了五甲胺碳菁染料合成的反应途径，并且与常规加热方法（18-64％）相比，产率提高（89-98％）。通过微波辅助有机合成方法合成了十二个五次甲基花青染料实例，该化合物在快速的反应时间内提供了优异的收率，并使用简便的分离方法获得了该实例。此外，制备了三种具有新的亚甲基二氧基杂环结构的花青，与未取代的对应物相比，它们具有约40 nm的红移。
• Second Generation G-Quadruplex Stabilizing Trimethine Cyanines
  作者：Eric A. Owens、Hang T. Huynh、Ekaterina M. Stroeva、Arghya Barman、Kostiantyn Ziabrev、Ananya Paul、Sarah V. Nguyen、Matthew Laramie、Donald Hamelberg、Markus W. Germann、W. David Wilson、Maged Henary

  DOI：10.1021/acs.bioconjchem.9b00571

  日期：2019.10.16

  G-Quadruplex DNA has been recognized as a highly appealing target for the development of new selective chemotherapeutics, which could result in markedly reduced toxicity toward normal cells. In particular, the cyanine dyes that bind selectively to G-quadruplex structures without targeting duplex DNA have attracted attention due to their high amenability to structural modifications that allows fine-tuning of their biomolecular interactions. We have previously reported pentamethine and symmetric trimethine cyanines designed to effectively bind G-quadruplexes through end stacking interactions. Herein, we are reporting a second generation of drug candidates, the asymmetric trimethine cyanines. These have been synthesized and evaluated for their quadruplex binding properties. Incorporating a benz[c,d]indolenine heterocyclic unit increased overall quadruplex binding, and elongating the alkyl length increases the quadruplex-to-duplex binding specificity.

  G-四链 DNA 被认为是开发新型选择性化疗药物的一个非常吸引人的靶点，这可能显著减少对正常细胞的毒性。特别是，选择性结合 G-四链结构而不针对双链 DNA 的氰染料因其高度适应结构改造而受到关注，这使得对其生物分子相互作用进行微调成为可能。我们之前报道了设计用于通过末端堆叠相互作用有效结合 G-四链的五甲基和对称三甲基氰染料。在这里，我们报告了一种第二代药物候选物，即不对称三甲基氰染料。这些化合物已经合成并评估了它们的四链结合属性。引入苯[c,d]吲哚啉杂环单元提高了整体四链结合能力，而延长烷基链的长度则增加了四链与双链的结合特异性。
• Indolenine derivative
  申请人：Asahi Chemical Co., Ltd.

  公开号：US05055589A1

  公开（公告）日：1991-10-08

  The present invention provides an indolenine derivative represented by the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, X and Y are the same or different and each represent a methylene group or an oxygen atom. This indolenine derivative is useful as an intermediate for synthesizing a cyanine compound suitable for use as an organic near infrared light-absorbing dye useful as an optical disc recording medium adapted for semiconductor laser recording.

  本发明提供了一种由下式表示的吲哚啉衍生物##STR1##其中R.sup.1是氢原子或较低的烷基，X和Y相同或不同，每个代表一个亚甲基或一个氧原子。该吲哚啉衍生物可用作合成适用于作为有机近红外光吸收染料的青菁化合物的中间体，该染料适用于作为半导体激光记录的光盘记录介质。
• INDOLENINE DERIVATIVES
  申请人：ASAHI CHEMICAL CO., LTD.

  公开号：EP0387357A1

  公开（公告）日：1990-09-19

  Indolenine derivatives represented by general formula (I), wherein R' represents a hydrogen atom or a lower alkyl group, and X and Y may be the same or different from each other and each represents a methylene group or an oxygen atom are disclosed. They are useful compounds as intermediates for synthesizing cyanine compounds to be favorably used as organic near-infrared absorbing dyes for use in an optical disc recording medium using a semiconductor laser.

  本发明公开了通式 (I) 所代表的吲哚啉衍生物，其中 R' 代表氢原子或低级烷基，X 和 Y 可以彼此相同或不同，并且各自代表亚甲基或氧原子。这些化合物是合成氰基化合物的有用中间体，可用作有机近红外吸收染料，用于使用半导体激光器的光盘记录介质。
• CYANINE COMPOUNDS
  申请人：ASAHI CHEMICAL CO., LTD.

  公开号：EP0387360B1

  公开（公告）日：1994-01-12