3,6-二溴-9-(环氧乙烷-2-基甲基)-9H-咔唑 | 85446-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,6-二溴-9-(环氧乙烷-2-基甲基)-9H-咔唑
• 英文名称: 3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole
• 英文别名: 3,6-dibromo-9-(oxiran-2-ylmethyl)carbazole
• CAS: 85446-05-5
• 化学式: C₁₅H₁₁Br₂NO
• mdl: MFCD00218277
• 分子量: 381.066
• InChiKey: DGMRGIDWASSLGY-UHFFFAOYSA-N

物化性质

• 沸点：
  503.8±43.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  17.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 储存条件：
  室温、密闭保存，并保持干燥。

反应信息

• 作为反应物：
  描述：

  3,6-二溴-9-(环氧乙烷-2-基甲基)-9H-咔唑 在 indium 、 lithium amide 作用下， 以 1,4-二氧六环 、 正己烷 、 乙腈 为溶剂， 生成 methyl (3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)(3-methoxyphenyl)carbamate
  参考文献：
  名称：

  Development of a scalable synthesis of P7C3-A20, a potent neuroprotective agent

  摘要：

  A scalable synthesis of the neuroprotective agent P7C3-A20 is described. The synthesis has provided hundred-gram batches of the final compound for biological evaluation in rodents and primates. The synthesis can be performed without chromatographic purification of intermediates or the final product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.024
• 作为产物：
  描述：

  9-(环氧-2-甲基)-9H-咔唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50.7%的产率得到3,6-二溴-9-(环氧乙烷-2-基甲基)-9H-咔唑
  参考文献：
  名称：

  Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of Enterococcus faecalis

  摘要：

  A series of isopropanol-bridged carbazole azoles as potential antimicrobial agents were designed and synthesized from commercial carbazoles. Bioassay revealed that 3,6-dichlorocarbazolyl triazole 3f could effectively inhibit the growth of E. faecalis with minimal inhibitory concentration of 2 mu g/mL. The active molecule 3f showed lower propensity to trigger the development of resistance in bacteria than norfloxacin and exerted rapidly bactericidal ability. Compound 3f also exhibited low cytotoxicity to normal mammalian RAW264.7 cells. Further mechanism exploration indicated that conjugate 3f was membrane active against E. faecalis and could form 3f-DNA complex by intercalating into DNA of resistant E. faecalis, which might be responsible for its antimicrobial action. Molecular docking showed an efficient binding of triazole derivative 3f with DNA gyrase enzyme through noncovalent interactions.

  DOI：

  10.1021/acsmedchemlett.7b00514

文献信息

• Pro-neurogenic compounds
  申请人：Board of Regents of the University of Texas System

  公开号：US09095571B2

  公开（公告）日：2015-08-04

  This invention relates generally to stimulating neurogenesis (e.g., post-natal neurogenesis, e.g., post-natal hippocampal neurogenesis) and protecting from neuron cell death.

  这项发明通常涉及刺激神经发生（例如，后生神经发生，例如，后生海马神经发生）并保护免受神经细胞死亡的影响。
• Synthesis and biological evaluation of novel 1,2,4-triazine derivatives bearing carbazole moiety as potent α-glucosidase inhibitors
  作者：Guangcheng Wang、Jing Wang、Dianxiong He、Xin Li、Juan Li、Zhiyun Peng

  DOI：10.1016/j.bmcl.2016.04.071

  日期：2016.6

  A new series of 1,2,4-triazine derivatives bearing carbazole moiety 7a-7p were designed, synthesized, and evaluated for their α-glucosidase inhibitory activity. The majority of the screened compounds displayed potent α-glucosidase inhibitory activity, with IC50 values in the range of 4.27±0.07-47.75±0.25μM as compared to the standard drug acarbose. Among the series, compound 7k represented the most

  设计，合成了一系列新的带有咔唑部分7a-7p的1,2,4-三嗪衍生物，并评估了其对α-葡萄糖苷酶的抑制活性。与标准药物阿卡波糖相比，大多数被筛选的化合物显示出有效的α-葡萄糖苷酶抑制活性，IC50值在4.27±0.07-47.75±0.25μM范围内。在该系列中，化合物7k表现出最强的α-葡萄糖苷酶抑制活性，IC50值为4.27±0.07μM。动力学分析表明，化合物7k是一种非竞争性抑制剂，Ki为4.43μM。此外，通过分子对接证实了化合物7k与α-葡糖苷酶的结合相互作用。这项研究表明，这些带有咔唑部分的1,2,4-三嗪衍生物是一类新型的α-葡萄糖苷酶抑制剂。
• Molecular construction of multitarget neuroprotectors 4.* Synthesis and biological activity of conjugates of carbazoles and tetrahydrocarbazoles
  作者：V. B. Sokolov、A. Yu. Aksinenko、T. V. Goreva、T. A. Epishina、L. G. Dubova、E. S. Dubrovskaya、S. G. Klochkov、P. N. Shevtsov、E. F. Shevtsova、S. O. Bachurin

  DOI：10.1007/s11172-016-1582-x

  日期：2016.9

  Unknown conjugates of carbazoles and tetrahydrocarbazoles were obtained by the alkylation of carbazoles and tetrahydrocarbazoles with 3,6-substituted 9-oxiranylmethylcarbazoles. The influence of synthesized 1-(9Н-carbazol-9-yl)-3-(1,2,3,4-tetrahydro-5Н-pyrido[4,3-b]-indol-5-yl)propan-2-ones on functional characteristics of brain mitochondria has been studied. The potential neuroprotective activity

  咔唑和四氢咔唑的未知共轭物是通过咔唑和四氢咔唑与 3,6-取代的 9-环氧乙烷基甲基咔唑的烷基化获得的。合成1-(9Н-咔唑-9-基)-3-(1,2,3,4-四氢-5Н-吡啶并[4,3-b]-吲哚-5-基)丙-2-的影响对脑线粒体功能特性的研究。已使用谷氨酸毒性模型证明了几种代表性缀合物的潜在神经保护活性。
• Pro-Neurogenic Compounds
  申请人：Board of Regents of The University of Texas System

  公开号：US20140057900A1

  公开（公告）日：2014-02-27

  Compounds and methods for stimulating neurogenesis (e.g., post-natal neurogenesis, including post-natal hippocampal and hypothalamic neurogenesis) and/or protecting neuronal cell from cell death are disclosed herein. In vivo activity tests suggest that these compounds may have therapeutic benefits in neuropsychiatric and/or neurodegenerative diseases such as schizophrenia, major depression, bipolar disorder, normal aging, epilepsy, traumatic brain injury, post-traumatic stress disorder, Parkinson's disease, Alzheimer's disease, Down syndrome, spinocerebellar ataxia, amyotrophic lateral sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of a neuro-active drug, retinal degeneration, spinal cord injury, peripheral nerve injury, physiological weight loss associated with various conditions, as well as cognitive decline associated with normal aging, chemotherapy, and the like.

  本发明公开了刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生）和/或保护神经细胞免于细胞死亡的化合物和方法。体内活性测试表明，这些化合物可能在精神神经疾病和/或神经退行性疾病中具有治疗益处，例如精神分裂症、重度抑郁症、双相情感障碍、正常衰老、癫痫、创伤性脑损伤、创伤后应激障碍、帕金森病、阿尔茨海默病、唐氏综合症、脊髓小脑共济失调、肌萎缩侧索硬化症、亨廷顿病、中风、放射治疗、慢性压力、滥用神经活性药物、视网膜退化、脊髓损伤、周围神经损伤、与各种情况相关的生理体重减轻，以及与正常衰老、化疗等相关的认知衰退。
• Branched Methoxydiphenylamine-Substituted Carbazole Derivatives for Efficient Perovskite Solar Cells: Bigger Is Not Always Better
  作者：Povilas Luizys、Jianxing Xia、Maryte Daskeviciene、Kristina Kantminiene、Ernestas Kasparavicius、Hiroyuki Kanda、Yi Zhang、Vygintas Jankauskas、Kasparas Rakstys、Vytautas Getautis、Mohammad Khaja Nazeeruddin

  DOI：10.1021/acs.chemmater.1c02114

  日期：2021.9.14

  A set of novel branched molecules bearing a different number of 3,6-bis(4,4′-dimethoxydiphenylamino)carbazole-based (Cz-OMeDPA) periphery arms linked together by aliphatic chains have been developed, and their performance has been tested in perovskite solar cells (PSCs). Electrical and photovoltaic properties have been evaluated with respect to the number of Cz-OMeDPA moieties and the nature of the

  已经开发了一组带有不同数量的 3,6-双（4,4'-二甲氧基二苯基氨基）咔唑基（Cz-OMeDPA）外围臂的新型支链分子，这些外围臂通过脂肪链连接在一起，并且它们的性能已在钙钛矿太阳能电池（PSC）。已经根据 Cz-OMeDPA 部分的数量和连接脂肪链的性质评估了电气和光伏特性。分离的化合物具有足够的热稳定性，并且是无定形的，具有高玻璃化转变温度 (>120 °C)，最大限度地降低了直接层结晶的风险。μ 0 = 3.1 × 10 –5 cm 2 V –1 s –1的最高空穴漂移迁移率在相同条件下与参考标准 spiro-OMeTAD (4.1 × 10 –5 cm 2 V –1 s –1 )相当。最后，PSC 采用两种新的 HTM（2Cz-OMeDPA和3Cz-OMeDPA-OH），带有两个和三个取代咔唑发色团，通过脂肪链连接，表现出约 20% 的性能，与使用 spiro-OMeTAD 的设备相当并展示了略微增强的设备稳定性。