3-bromo-6-methyl-9H-carbazole

• 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: 3-bromo-6-methyl-9H-carbazole
• 化学式: C₁₃H₁₀BrN
• 分子量: 260.133
• InChiKey: ILXXEUBYYTUTNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-bromo-6-methyl-9H-carbazole 在 bismuth(III) chloride 、 potassium hydroxide 作用下， 以 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1-(3-bromo-6-methyl-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-propan-2-ol
  参考文献：
  名称：

  Development of Proneurogenic, Neuroprotective Small Molecules

  摘要：

  Degeneration of the hippocampus is associated with Alzheimer's disease and occurs very early in the progression of the disease. Current options for treating the cognitive symptoms associated with Alzheimer's are inadequate, giving urgency to the search for novel therapeutic strategies. Pharmacologic agents that safely enhance hippocampal neurogenesis may provide new therapeutic approaches. We discovered the first synthetic molecule, named P7C3, which protects newborn neurons from apopotic cell death, and thus promotes neurogenesis in mice and rats in the subgranular zone of the hippocampal dentate gyrus, the site of normal neurogenesis in adult mammals. We describe the results of a medicinal chemistry campaign to optimize the potency, toxicity profile, and stability of P7C3. Systematic variation of nearly every position of the lead compound revealed elements conducive toward increases in activity and regions subject to modification. We have discovered compounds that are orally available, nontoxic, stable in mice, rats, and cell culture, and capable of penetrating the blood brain barrier. The most potent compounds are active at nanomolar concentrations. Finally, we have identified derivatives that may facilitate mode-of-action studies through affinity chromatography or photo-cross-linking.

  DOI：

  10.1021/ja108211m
• 作为产物：
  描述：

  N-(4-溴-2-甲酰基苯基)-4-甲基苯磺酰胺 在 正丁基锂 、 四丁基氟化铵 、 silver(I) acetate 、 三乙胺 、 palladium dichloride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 19.08h， 生成 3-bromo-6-methyl-9H-carbazole
  参考文献：
  名称：

  取代指导的钯-烯反应合成咔唑和环戊[ b ]吲哚

  摘要：

  开发了一种有效的钯催化的分子内Trost-Oppolzer型Alder-ene策​​略，用于从易于获得的（3-烯丙基-1 H-吲哚-2-基）乙酸甲酯合成咔唑和环戊[ b ]吲哚。该策略也扩展到了萘和二苯并呋喃的合成中。另外，还实现了抗菌和抗真菌天然产物糖唑啉及其类似物的短合成。

  DOI：

  10.1021/acs.orglett.9b00410

文献信息

• Predictable site-selective functionalization: Promoter group assisted <i>para</i>-halogenation of <i>N</i>-substituted <b>(</b>hetero<b>)</b>aromatics under metal-free condition
  作者：Shiv Shankar Gupta、Manisha、Rakesh Kumar、Ankit Kumar Dhiman、Upendra Sharma

  DOI：10.1039/d1ob02000e

  日期：——

  SEAr (electrophilic aromatic substitution) type reaction is disclosed. SEAr type reaction has been utilized for the C5-bromination of indolines (para-selective) with N-bromosuccinimide under metal and additive-free conditions in good to excellent yields. The developed methodology is also applicable for iodination and challenging chlorination. The pyrimidyl group is identified as a reactivity tuner

  本文公开了通过 S E Ar（亲电芳族取代）型反应对N-嘧啶基（杂）芳烃进行区域选择性对-C-H 卤化。S E Ar 型反应已用于二氢吲哚的 C5-溴化（对位选择性）与N-溴代琥珀酰亚胺在无金属和无添加剂的条件下具有良好至极好的收率。所开发的方法也适用于碘化和具有挑战性的氯化。嘧啶基被确定为反应性调节剂，它也控制区域选择性。本方法也适用于苯胺、吡啶、吲哚、羟吲哚、吡唑、四氢喹啉、异喹啉和咔唑的选择性卤化。Fukui 亲核性和自然电荷图等 DFT 研究也支持观察到的p-选择性。标题化合物后官能化为相应的芳基化、烯化和二卤化产物是通过一锅两步的方式实现的。还对药物/天然分子（哈明、依托考昔、可乐定和氯唑沙宗）进行了后期 C-H 溴化，以证明所开发方案的适用性。
• 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。
• Short synthesis of carbazole alkaloids: Ekeberginine, murrayaquinone A, and glycozoline
  作者：Aadil A. Momin、Tukaram D. Urmode、Shrikar M. Bhosale、Radhika S. Kusurkar

  DOI：10.1080/00397911.2016.1192652

  日期：2016.8.2

  short and simple routes. The prenyl group was selectively introduced at the C4 position using a Stille coupling reaction in the synthesis of ekeberginine. Murrayaquinone A was synthesized using Raney nickel–mediated desulfurization of dithiane as a key step. Synthesis of glycozoline was achieved in two steps from 3-methyl carbazole via an intermediate 3-bromo-6-methyl carbazole. GRAPHICAL ABSTRACT

  摘要 三种不同取代的、天然存在的、具有生物活性的咔唑衍生物（即 ekeberginine、murrayaquinone A 和 glycozoline）使用短而简单的路线以良好的收率合成。在 ekeberginine 的合成中，使用 Stille 偶联反应在 C4 位置选择性地引入异戊二烯基。Murrayaquinone A 是使用雷尼镍介导的二噻烷脱硫作为关键步骤合成的。从 3-甲基咔唑到中间体 3-溴-6-甲基咔唑，分两步合成糖唑啉。图形概要
• 以氮杂苯为核心的化合物及其在有机电致发 光器件上的应用
  申请人：中节能万润股份有限公司

  公开号：CN108148048B

  公开（公告）日：2021-03-30

  本发明公开了一种以氮杂苯为核心的化合物及其在有机电致发光器件上的应用，该化合物以氮杂苯为核心，具有分子间不易结晶、不易聚集、具有良好成膜性的特点。本发明化合物作为有机电致发光器件的发光层材料使用时，器件的电流效率，功率效率和外量子效率均得到很大改善；同时，对于器件寿命提升非常明显。
• Neuroprotective Chemicals and Methods for Identifying and Using Same
  申请人：Board of Regents of The University of Texas System

  公开号：US20150132783A1

  公开（公告）日：2015-05-14

  Provided herein are methods for identifying a compound having cell-protective (e.g., neuroprotective) activity. Compounds identified therefrom are also provided. These compounds can be used to treat various diseases, disorders, or conditions associated with, for example, unwanted cell death.

  本文提供了一种鉴定具有细胞保护（例如神经保护）活性的化合物的方法。同时也提供了从中鉴定出的化合物。这些化合物可用于治疗与不必要的细胞死亡相关的各种疾病、障碍或状况。