2,3-dichloro-6H-indolo[2,3-b]quinoxaline | 34712-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-dichloro-6H-indolo[2,3-b]quinoxaline
• 英文别名: 2,3-dichloro-6H-indolo[2,3-b]quinoxaline；2,3-Dichloro-indophenazin；6H-Indolo(2,3-b)quinoxaline, 2,3-dichloro-；2,3-dichloro-6H-indolo[3,2-b]quinoxaline
• CAS: 34712-15-7
• 化学式: C₁₄H₇Cl₂N₃
• mdl: MFCD15081310
• 分子量: 288.136
• InChiKey: NMCOVSLCEMGHKK-UHFFFAOYSA-N

物化性质

• 沸点：
  495.5±55.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-6H-indolo[2,3-b]quinoxaline 在 吡啶 、 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 (S)-1-(4,4'-dimethoxytriphenylmethyloxy)-3-(2,3-dichloro-indolo[2,3-b]quinoxalin-6-yl)-propan-2-ol
  参考文献：
  名称：

  Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

  摘要：

  6H-Indolo[2,3-b]quinoxaline was studied as a covalently bound heteroaromatic intercalator. Six monomers were synthesized and incorporated into DNA oligonucleotides. Through a study of linker length dependence it was concluded that the linker between the oligo and the intercalator must consist of at least five C atoms in order to stabilize a DNA duplex. An intercalator with a 2 '-deoxy-D-riboside linker to the oligo could also stabilize a DNA/RNA duplex, while (S)-4-(6-methylindolo[2,3-b]quinoxalin-3-ylmethoxy)-butane-1,2-diol was able to stabilize both DNA/DNA, DNA/RNA and a DNA/LNA duplex. Mismatch studies revealed a huge sensitivity to the C-C mismatch at the 5'-site of the intercalator. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.017
• 作为产物：
  描述：

  4,5-二氯邻苯二胺 、 靛红 在 溶剂黄146 作用下， 反应 1.0h， 生成 2,3-dichloro-6H-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  <I>P</I>-Glycoprotein Targeted Nanoscale Drug Carriers

  摘要：

  多重耐药性（MDR）是指暴露于一种细胞毒性药物的肿瘤细胞对一系列结构和功能上无关的化合物产生交叉耐药性的趋势。P-糖蛋白（P-gp）外排泵是最 extensively 研究的药物转运过程之一，它负责将药物排出肿瘤细胞。因此，P-gp 抑制剂引起了广泛关注，因为它们可以阻止癌症药物被排出靶细胞，同时消耗 ATP。通过量化结构活性关系（QSAR），我们成功合成了一系列新型 P-gp 抑制剂。所获得的二氢吡咯并喹啉系列化合物经过全面表征，并在 P-gp 表达过表达的细菌和肿瘤实验中进行了测试。所有化合物均具有生物活性，特别是化合物 1c 具有增强的抗菌活性。此外，这些化合物被用作靶向载体，将药物递送载体如二氧化硅纳米颗粒（SNPs）靶向输送到 P-gp 表达过高的癌症 Hela 细胞。细胞摄取研究显示，与未修饰的 SNPs 相比，这些修饰的 SNPs 成功地在肿瘤细胞中积累。获得的结果表明，二氢吡咯并喹啉构成了针对具有 MDR 的癌症的有希望的药物候选者。

  DOI：

  10.1166/jnn.2013.6084

文献信息

• PSEUDONUCLEOTIDE COMPRISING AN INTERCALATOR
  申请人：Christensen Ulf Bech

  公开号：US20100121056A1

  公开（公告）日：2010-05-13

  The present invention relates to intercalator pseudonucleotides. Intercalator pseudonucleotides according to the invention are capable of being incorporated into the backbone of a nucleic acid or nucleic acid analogue and they comprise an intercalator comprising a flat conjugated system capable of co-stacking with nucleobases of DNA. The invention also relates to oligonucleotides or oligonucleotide analogues comprising at least one intercalator pseudo nucleotide. The invention furthermore relates to methods of synthesising intercalator pseudo nucleotides and methods of synthesising oligonucleotides or oligonucleotide analogues comprising at least one intercalator pseudonucleotide. In addition, the invention describes methods of separating sequence specific DNA(s) from a mixture comprising nucleic acids, methods of detecting a sequence specific DNA (target DNA) in a mixture comprising nucleic acids and/or nucleic acid analogues and methods of detecting a sequence specific RNA in a mixture comprising nucleic acids and/or nucleic acid analogues. In particular said methods may involve the use of oligonucleotides comprising intercalator pseudo nucleotides. The invention furthermore relates to pairs of oligonucleotides or oligonucleotide analogues capable of hybridising to one another, wherein said pairs comprise at least one intercalator pseudonucleotide. Methods for inhibiting a DNAse and/or a RNAse and methods of modulating transcription of one or more specific genes are also described.

  本发明涉及插入剂伪核苷酸。本发明的插入剂伪核苷酸能够被合并到核酸或核酸类似物的骨架中，并且它们包括一个插入剂，该插入剂包含一个平面共轭系统，能够与DNA的碱基共堆叠。本发明还涉及至少包括一个插入剂伪核苷酸的寡核苷酸或寡核苷酸类似物。此外，本发明还涉及合成插入剂伪核苷酸的方法以及合成至少包括一个插入剂伪核苷酸的寡核苷酸或寡核苷酸类似物的方法。此外，本发明还描述了从包括核酸的混合物中分离序列特异性DNA的方法，检测包括核酸和/或核酸类似物的混合物中的序列特异性DNA（目标DNA）的方法，以及检测包括核酸和/或核酸类似物的混合物中的序列特异性RNA的方法。特别是所述方法可能涉及使用包括插入剂伪核苷酸的寡核苷酸。本发明还涉及能够杂交到一起的寡核苷酸或寡核苷酸类似物的配对，其中所述配对包括至少一个插入剂伪核苷酸。还描述了抑制DNA酶和/或RNA酶的方法以及调节一个或多个特定基因的转录的方法。
• Methods and materials for detection of mutations
  申请人：PentaBase ApS

  公开号：US10988810B2

  公开（公告）日：2021-04-27

  Provided herein are specially modified blocking nucleotides allowing for the sensitive detection of low copies of variant sequences, while significantly reducing signals from non-variant sequences that are similar but not identical to the variant sequence. These nucleotides can be used to detect rare variants in a sample mixture, as described in the present methods.

  本文提供的是经过特殊修饰的阻遏核苷酸，可以灵敏地检测低拷贝的变异序列，同时显著降低与变异序列相似但不相同的非变异序列的信号。如本方法所述，这些核苷酸可用于检测样本混合物中的稀有变异体。
• OLIGONUCLEOTIDES COMPRISING SIGNALLING PAIRS AND HYDROPHOBIC NUCLEOTIDES, STEMLESS BEACONS, FOR DETECTION OF NUCLEIC ACIDS, METHYLATION STATUS AND MUTANTS OF NUCLEIC ACIDS
  申请人：Christensen Ulf Bech

  公开号：US20100068704A1

  公开（公告）日：2010-03-18

  The invention relates to novel oligonucleotides comprising a signalling pair and at least hydrophobic nucleotide. The oligonucleotide analogues are useful for detecting the status of nucleic acid sequences, such as presence, expression, methylation and/or mutation, in particular single point mutations and other sequences where the variation between the correct target and other targets may vary in as little as one nucleotide. The invention also relates to new ways of detecting sequence differences and optimizing conditions by using oligonucleotide analogues and readily available instruments. In particular the invention relates to specifically detecting quantity of a target nucleic acids or detecting one sequence over others that may vary in as little as one nucleotide using oligonucleotides or oligonucleotide analogues comprising a signalling pair and at least one hydrophobic nucleotide, such as a nucleotide analogue comprising an intercalator.
• METHODS AND MATERIALS FOR DETECTION OF MUTATIONS
  申请人：PentaBase ApS

  公开号：US20190085400A1

  公开（公告）日：2019-03-21

  Provided herein are specially modified blocking nucleotides allowing for the sensitive detection of low copies of variant sequences, while significantly reducing signals from non-variant sequences that are similar but not identical to the variant sequence. These nucleotides can be used to detect rare variants in a sample mixture, as described in the present methods.
• US8133984B2
  申请人：——

  公开号：US8133984B2

  公开（公告）日：2012-03-13