N-methoxytryptamine | 148586-24-7

• 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: N-methoxytryptamine
• 英文别名: methoxy-tryptamine；1H-Indole-3-ethanamine, N-methoxy-；2-(1H-indol-3-yl)-N-methoxyethanamine
• CAS: 148586-24-7
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: IPDWWXSORFZFOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methoxytryptamine 在 三甲基氯硅烷 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 1-(2-Methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-2-methylsulfanyl-ethylamine
  参考文献：
  名称：

  Antiviral and tumor cell antiproliferative SAR studies on tetracyclic eudistomins—II

  摘要：

  In a search for the minimum pharmacophore of the naturally occurring tetracyclic eudistomins, five structural analogues (4-8) were evaluated for their in vitro antiviral and tumor cell antiproliferative activities. For the synthesis of these derivatives both intra- and intermolecular Pictet-Spengler reactions have been used. Opening of the beta-carboline annulated 7-membered D-ring in 6 and 7 resulted in a complete loss of activity. On the other rand, replacement of either the oxygen atom or the sulfur atom in the 7-membered ring by a methylene group in 5 and 8, respectively, is allowed. These results combined with previous SAR data underline the crucial importance of the D-ring in eudistomins as a scaffold for the correct positioning of both basic nitrogen atoms. Also bioisosteric replacement of the bicyclic indole system with a dimethoxyphenyl group, to give the isoquinoline skeleton, is allowed. The tricyclic isoquinoline derivative 4 is, so far, the most promising antiviral analogue; it combines a high potency (MIG at 100 ng/mL (340 nM)) with high MCC/MIC ratios (ranging from 1000 to 5000 against HSV-1, HSV-2, vaccinia virus, and vesicular stomatitis virus). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00034-5
• 作为产物：
  描述：

  芦竹碱 在 aluminum amalgam 、 四丁基氟化铵 、 水 、 sodium methylate 、 sodium hydride 、 硫酸二甲酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 34.0h， 生成 N-methoxytryptamine
  参考文献：
  名称：

  N-羟色胺衍生物对5-羟色胺和色胺受体的合成及受体亲和力 分子模型研究

  摘要：

  报道了一系列色胺的N-氧基衍生物（6-8、13-14）的血清素和色胺受体的合成及其亲和力。发现N-羟基色胺（6）是5-HT 1C受体的相对选择性的配体。受体结合数据通过分子建模研究解释，其中比较了5-HT 1A和5-HT 1C受体的结合位点。在5-HT 1A的螺旋7中存在但在5-HT 1C中不存在的天冬酰胺残基起关键作用。基于5-HT 1A七个跨膜区域的三维模型受体在这种天冬酰胺残基和螺旋3上的天冬氨酸残基的氧之一之间预计存在氢键相互作用，仅留下一个氧原子用于配体相互作用。在5-HT 1C中，螺旋3上天冬氨酸残基的两个氧自由地通过双氢键结合的配合物与6的N-羟基相互作用。N-甲氧基衍生物13缺乏这种额外的氢键可能性并且缺乏结合亲和力，大概是由于静电排斥的结果。

  DOI：

  10.1002/recl.19931120210

文献信息

• [EN] COMPOUNDS USEFUL FOR THE TREATMENT AND/OR CARE OF THE SKIN, HAIR, NAILS AND/OR MUCOUS MEMBRANES<br/>[FR] COMPOSÉS UTILES DANS LE TRAITEMENT ET/OU LE SOIN DE LA PEAU, DES CHEVEUX, DES ONGLES ET/OU DES MUQUEUSES
  申请人：LUBRIZOL ADVANCED MAT INC

  公开号：WO2018102508A1

  公开（公告）日：2018-06-07

  A compound of formula (I) R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-(AA7)a-(AA8)b-Yp-Zq-R2 effective in maintaining and/or improving the physical and immunological barrier functions of the skin and useful in the treatment and/or care of the skin, hair, nails and/or mucous membranes.

  化合物的化学式（I）为R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-(AA7)a-(AA8)b-Yp-Zq-R2，有效地维护和/或改善皮肤的物理和免疫屏障功能，并且在皮肤、头发、指甲和/或粘膜的治疗和/或护理中有用。
• Substituted Aryl-Indole Compounds and Their Kynurenine/Kynuramine-Like Metabolites As Therapeutic Agents
  申请人：Peleg-Shulman Tal

  公开号：US20080132559A1

  公开（公告）日：2008-06-05

  This invention is directed to substituted aryl compounds, which are linked to a substituted indole moiety by various linkers, and the kynurenine/kynuramine-like metabolites of these agents, their preparation and pharmaceutical compositions containing these compounds. This invention further is directed to the pharmaceutical use of the compounds for inhibiting GSK3β kinase and/or modulating N-methyl-D-aspartate (NMDA) channel activities for the treatment of neurodegenerative and other disorders.

  本发明涉及取代芳基化合物，其通过各种连接剂与取代吲哚基团相连，并且这些药剂的酮尿氨酸/酮尿胺类似物以及它们的制备和含有这些化合物的药物组合物。本发明进一步涉及这些化合物用于抑制GSK3β激酶和/或调节N-甲基-D-天冬氨酸(NMDA)通道活性，用于治疗神经退行性和其他疾病的药物用途。
• COSMETIC COMPOSITION FOR STIMULATING THE CELLULAR ANTI-AGING FUNCTIONS OF THE SKIN
  申请人：SYNTIVIA

  公开号：US20150031740A1

  公开（公告）日：2015-01-29

  The use of a compound of general formula (I), where: R 1 , R 2 , R 3 , R 4 , R 5 are identical or different and each represent a hydrogen atom, a halogen atom, a hydroxyl group or an —OR′ radical in which R′ is a straight or branched, saturated or unsaturated C1-C16 hydrocarbon radical, wherein at least one group from among R 1 , R 2 , R 3 , R 4 , and R 5 does not represent a hydrogen atom or a halogen atom; X is a halogen atom, a hydroxyl group, a nitro group, a straight or branched, saturated or unsaturated optionally substituted C1-C14 hydrocarbon radical, or an —OR″ radical in which R″ is a straight or branched, saturated or unsaturated optionally substituted C1-C14 hydrocarbon radical; and Z is a covalent bond or a spacer arm, or of one of the salts thereof, in a cosmetic composition for stimulating the cellular anti-aging functions of the skin.

  使用通式（I）的化合物，其中：R1、R2、R3、R4、R5相同或不同，每个代表氢原子、卤素原子、羟基或—OR′基团，其中R′是直链或支链、饱和或不饱和的C1-C16烃基基团，其中至少一个来自于R1、R2、R3、R4和R5的基团不代表氢原子或卤素原子；X是卤素原子、羟基、硝基、直链或支链、饱和或不饱和的可选取代的C1-C14烃基基团，或—OR″基团，其中R″是直链或支链、饱和或不饱和的可选取代的C1-C14烃基基团；Z是共价键或间隔臂，或其盐之一，在化妆品配方中用于刺激皮肤的细胞抗衰老功能。
• [EN] N-(2-ARYLETHYL)BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR<br/>[FR] N-(2-ARYLETHYL)BENZYLAMINES UTILISEES EN TANT QU'ANTAGONISTES DU RECEPTEUR 5-HT6
  申请人：LILLY CO ELI

  公开号：WO2002078693A2

  公开（公告）日：2002-10-10

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT6 receptor.

  本发明提供了式（I）的化合物，它们是5-HT6受体的拮抗剂。
• NEUROGENESIS BY MUSCARINIC RECEPTOR MODULATION
  申请人：Barlow Carrolee

  公开号：US20070049576A1

  公开（公告）日：2007-03-01

  The instant disclosure describes methods for treating diseases and conditions of the central and peripheral nervous system by stimulating or increasing neurogenesis. The disclosure includes compositions and methods based on muscarinic receptor modulation, such as via inhibition of acetylcholine esterase (AChE) activity, alone or in combination with another neurogenic agent to stimulate or activate the formation of new nerve cells.

  该即时披露描述了通过刺激或增加神经发生来治疗中枢神经系统和外周神经系统的疾病和病症的方法。该披露包括基于毒蕈碱受体调节的组合物和方法，例如通过抑制乙酰胆碱酯酶（AChE）活性，单独或与另一种神经生成剂结合以刺激或激活新神经细胞的形成。