5-甲氧基-1-(4-甲氧基苯磺酰基)-1H-吲哚-3-甲醛 | 651331-50-9

• 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: 5-甲氧基-1-(4-甲氧基苯磺酰基)-1H-吲哚-3-甲醛
• 英文名称: 5-methoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde
• 英文别名: 1-(4-methoxybenzenesulfonyl)-5-methoxy-1H-indole-3-carboxaldehyde；1-(4-Methoxy benzenesulfonyl)-5-methoxy-1H-indole-3-carbaldehyde；1-(4-methoxy-benzenesulfonyl)-5-methoxy-1H-indole-3-carbaldehyde；5-methoxy-1-(4-methoxybenzsulfonyl)-1H-indole-3-carbaldehyde；5-methoxy-1-(4-methoxyphenyl)sulfonylindole-3-carbaldehyde
• CAS: 651331-50-9
• 化学式: C₁₇H₁₅NO₅S
• 分子量: 345.376
• InChiKey: SDBROVTUPVJMEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-甲氧基-1-(4-甲氧基苯磺酰基)-1H-吲哚-3-甲醛 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 生成 18-[5-methoxy-1-(4-methoxybenzsulfonyl)-1H-indole-3-yl]-octadecane-1-ol
  参考文献：
  名称：

  Effects of Indole Fatty Alcohols on the Differentiation of Neural Stem Cell Derived Neurospheres

  摘要：

  In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared. 13C (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.

  DOI：

  10.1021/jm0493616
• 作为产物：
  描述：

  5-甲氧基吲哚-2-羧酸甲酯 在 喹啉 、 sodium hydroxide 、 铜 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 5-甲氧基-1-(4-甲氧基苯磺酰基)-1H-吲哚-3-甲醛
  参考文献：
  名称：

  Effects of Indole Fatty Alcohols on the Differentiation of Neural Stem Cell Derived Neurospheres

  摘要：

  In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared. 13C (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.

  DOI：

  10.1021/jm0493616

文献信息

• [EN] PPAR ACTIVE COMPOUNDS<br/>[FR] COMPOSES AYANT UNE ACTIVITE SUR DES PPAR
  申请人：PLEXXIKON INC

  公开号：WO2005009958A1

  公开（公告）日：2005-02-03

  Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

  描述了对PPARs具有活性的化合物，包括全活性化合物。还描述了开发或识别具有所需选择性配置文件的化合物的方法。
• PPAR active compounds
  申请人：Arnold James

  公开号：US20050288354A1

  公开（公告）日：2005-12-29

  Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

  描述了对PPARs活性的化合物，包括全活性化合物。还描述了开发或识别具有所需选择性配置文件的化合物的方法。
• Indole derivatives and drugs containing the same
  申请人：Luu Bang

  公开号：US20050261357A1

  公开（公告）日：2005-11-24

  An indole derivative represented by the following general formula (1): wherein at least one of R 1 , R 2 , R 3 , and R 4 represents an alkoxy group containing 1 to 20 carbon atoms, and other groups of the R 1 , R 2 , R 3 , and R 4 represent hydrogen, an alkyl group containing 1 to 6 carbon atoms, acetyl group, or hydroxyl group; and either one of X and Y represents —(CH 2 ) n OH wherein n is an integer of 0 to 30, and the other one of the X and Y represents hydrogen atom; or a salt thereof; and a drug and an agent for promoting differentiation of a stem cell containing such indole derivative or its salt as an effective component. The indole derivative (1) of the present invention has action of inducing differentiation of neural stem cell specifically into a neuron, and this indole derivative is useful as a prophylactic or therapeutic drug for brain dysfunction or neuropathy caused by loss or degeneration of the neuron.

  以下是一种由下述通式（1）表示的吲哚衍生物: 其中，R1、R2、R3和R4中至少有一个表示含有1到20个碳原子的烷氧基，而R1、R2、R3和R4的其他基团则表示氢、含有1到6个碳原子的烷基、乙酰基或羟基；X和Y中的一个表示—（CH2）nOH，其中n为0到30的整数，而X和Y的另一个表示氢原子；或其盐；以及包含这种吲哚衍生物或其盐作为有效成分的药物和促进干细胞分化的药剂。本发明的吲哚衍生物（1）具有特异性诱导神经干细胞分化为神经元的作用，因此这种吲哚衍生物可用作预防或治疗因神经元丧失或退化引起的脑功能障碍或神经病变的药物。
• PPAR ACTIVE COMPOUNDS
  申请人：Arnold James

  公开号：US20080045581A1

  公开（公告）日：2008-02-21

  Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

  描述了对PPARs活性的化合物，包括全面活性的化合物。还描述了开发或识别具有所需选择性配置文件的化合物的方法。
• Design, synthesis, and biological evaluation of deuterated indolepropionic acid derivatives as novel long-acting pan PPARα/γ/δ agonists
  作者：Lianru Chen、Ya Chen、Bin Wang、Zhongcheng Yang、Zongyu Cai、Xuekun Wang、Lidan Sun、Zheng Li、Guangji Wang

  DOI：10.1016/j.bmc.2023.117533

  日期：2023.12

  at Indeglitazar. To overcome this metabolic instability, two deuterium atoms were introduced to the α-position of indolepropionic acid to block the β-oxidation. In this study, several deuterated derivatives were found to sustain PPARs activity and extend the half-life of liver microsomes. In oral glucose tolerance tests, I-1 exhibited the strongest glucose-lowering effect on ob/ob mice in this series

  代谢综合征是一种具有多种症状的复杂疾病，但目前的药物干预效果有限。 Indeglitazar 是一种针对三过氧化物酶体增殖物激活受体 (PPAR) 的全激动剂，对糖尿病和脂肪肝动物模型均具有显着的治疗效果。然而，其半衰期短限制了体内功效，这可能归因于 Indeglitazar 中吲哚丙酸的 β-氧化。为了克服这种代谢不稳定性，将两个氘原子引入吲哚丙酸的 α 位以阻止 β 氧化。在这项研究中，发现几种氘代衍生物可以维持 PPAR 活性并延长肝微粒体的半衰期。在口服葡萄糖耐量试验中， I-1对该系列中的ob/ob小鼠表现出最强的降糖作用。在db/db小鼠中， I-1降低了脂质水平、肝脏脂肪变性并促进白色脂肪组织中 UCP1 的表达。机制研究进一步表明， I-1对脂质代谢、线粒体功能和氧化应激相关基因的调节作用比 Indeglitazar 更强。此外， I-1显着减轻HFD+CCl 4诱导的NA