1-(benzylamino)-3-(9H-carbazolyl)-2-hydroxypropanol | 119091-27-9

• 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: 1-(benzylamino)-3-(9H-carbazolyl)-2-hydroxypropanol
• 英文别名: 1-(benzylamino)-3-(9H-carbazol-9-yl)propan-2-ol；MB1_C_000839A-4；SJ000128054-2；1-(Benzylamino)-3-carbazol-9-ylpropan-2-ol
• CAS: 119091-27-9
• 化学式: C₂₂H₂₂N₂O
• 分子量: 330.429
• InChiKey: CDKKRSGGFNLVQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzylamino)-3-(9H-carbazolyl)-2-hydroxypropanol 、 4-氯苯磺酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-N-benzyl-4-chloro-benzenesulfonamide
  参考文献：
  名称：

  Sulfonamido-derivatives of unsubstituted carbazoles as BACE1 inhibitors

  摘要：

  A novel series of variously substituted N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-arylsulfonamides has been synthesized and assayed for beta-Secretase (BACE1) inhibitory activity. BACE1 is a widely recognized drug target for the prevention and treatment of Alzheimer's Disease (AD). The introduction of benzyl sub-stituents on the nitrogen atom of the arylsulfonamide moiety has so far led to the best results, with three derivatives showing IC50 values ranging from 1.6 to 1.9 mu M. Therefore, a significant improvement over the previously reported series of N-carboxamides (displaying IC50's >= 2.5 mu M) has been achieved, thus suggesting an active role of the sulfonamido-portion in the inhibition process. Preliminary molecular modeling studies have been carried out to rationalize the observed structure-activity relationships. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.058
• 作为产物：
  描述：

  咔唑 在 caesium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 1-(benzylamino)-3-(9H-carbazolyl)-2-hydroxypropanol
  参考文献：
  名称：

  Wiskostatin 和其他咔唑支架作为 dynamin I GTPase 活性和内吞作用的脱靶抑制剂

  摘要：

  Wiskostatin (1-(3,6-dibromo-9 H -carbazol-9-yl)-3-(dimethylamino)propan-2-ol) ( 1 ) 是一种基于咔唑的化合物，被报道为特异性且相对有效的抑制剂N-WASP 肌动蛋白重塑复合物（S-异构体 EC 50  = 4.35 μM；R-异构体 EC 50 = 3.44 μM）。NMR 溶液结构显示 wiskostatin 与 N-WASP 的调节 GTPase 结合域中的裂缝相互作用。然而，许多研究报告了 wiskostatin 对独立于 N-WASP-Arp2/3 复合通路的膜转运和胞质分裂的作用，但提供的替代解释有限。大型 GTP 酶、动力蛋白已在这些途径中发挥功能作用。这项研究表明，wiskostatin 及其类似物以及其他基于咔唑的化合物是螺旋动力蛋白 GTP 酶活性和内吞作用的抑制剂。我们描述了 wiskostatin

  DOI：

  10.1016/j.ejmech.2022.115001

文献信息

• 一类咔唑基异丙醇胺衍生物的制备方法及其 应用
  申请人：贵州大学

  公开号：CN109627205B

  公开（公告）日：2022-04-12

  本发明涉及一类咔唑基异丙醇胺衍生物的制备方法及其应用。该化合物具有如通式(I)所示的结构：该化合物对如水稻白叶枯病菌、烟草青枯病菌、黄瓜白叶枯病菌、魔芋白叶枯病菌、柑桔溃疡病菌、葡萄溃疡病菌、番茄溃疡病菌、猕猴桃溃疡病菌、苹果溃疡病菌、黄瓜灰霉病菌、辣椒枯萎病原菌、油菜菌核病菌、小麦赤霉病菌、马铃薯晚疫病菌、蓝莓根腐病菌等均具有较好的抑制效果。
• PRO-NEUROGENIC COMPOUNDS
  申请人：McKnight Steven L.

  公开号：US20120022096A1

  公开（公告）日：2012-01-26

  This technology relates generally to 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. Various compounds 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.

  该技术通常涉及化合物和方法，用于刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生），和/或保护神经细胞免受细胞死亡的影响。本文披露了各种化合物。体内活性测试表明，这些化合物可能在神经精神疾病和/或神经退行性疾病（如精神分裂症、重度抑郁症、躁郁症、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、脊髓小脑性共济失调、肌萎缩侧索硬化症、亨廷顿病、中风、放射治疗、慢性应激、神经活性药物滥用、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性体重减轻，以及与正常衰老、化疗等相关的认知衰退方面具有治疗益处。
• Pro-Neurogenic Compounds
  申请人：McKnight Steven L.

  公开号：US20130040977A1

  公开（公告）日：2013-02-14

  This technology relates generally to 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. Various compounds 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.

  该技术通常涉及化合物和方法，用于刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生）和/或保护神经细胞免受细胞死亡的影响。本文披露了各种化合物。体内活性测试表明，这些化合物可能在神经精神疾病和/或神经退行性疾病的治疗方面具有治疗益处，例如精神分裂症、重度抑郁症、躁狂症、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、脊髓小脑性共济失调、肌萎缩性侧索硬化症、亨廷顿病、中风、放射治疗、慢性应激、神经活性药物滥用、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性减重，以及与正常衰老、化疗等相关的认知衰退。
• Methods for Treating Parkinson's Disease Using Pro-Neurogenic Compounds
  申请人：UNIVERSITY OF TEXAS SYSTEM BOARD OF REGENTS OF THE

  公开号：US20130184271A1

  公开（公告）日：2013-07-18

  This technology relates generally to 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. Various compounds 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.

  本技术通常涉及化合物和方法，用于刺激神经发生新生（例如，出生后神经发生新生，包括出生后海马和下丘脑神经发生新生）和/或保护神经细胞免受细胞死亡。本文介绍了各种化合物。体内活性测试表明，这些化合物可能在神经精神疾病和/或神经退行性疾病（如精神分裂症、重度抑郁症、躁郁症、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、脊髓小脑性共济失调、肌萎缩性侧索硬化症、亨廷顿病、中风、放射治疗、慢性应激、神经活性药物滥用、视网膜退化、脊髓损伤、外周神经损伤、与各种疾病相关的生理性体重下降以及与正常衰老、化疗等相关的认知衰退中具有治疗益处。
• Methods of Treating Traumatic Brain Injury Using Pro-Neurogenic Compounds
  申请人：Board of Regents of the University of Texas System

  公开号：US20130184300A1

  公开（公告）日：2013-07-18

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

  本发明通常涉及刺激神经发生（例如，产后神经发生，例如，产后海马神经发生）和保护神经细胞免受死亡的影响。