N-丙酰基-5-甲氧基色胺 | 66012-82-6

• 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
• 中文名称: N-丙酰基-5-甲氧基色胺
• 英文名称: N-Propionyl-5-methoxytryptamine
• 英文别名: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propanamide
• CAS: 66012-82-6
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: VXGNHTKZJOTYNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-丙酰基-5-甲氧基色胺 在 四(三苯基膦)钯 、 potassium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲胺 为溶剂， 反应 19.0h， 生成 N-[2-(11-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepin-13-yl)ethyl]propanamide
  参考文献：
  名称：

  Mapping the Melatonin Receptor. 6. Melatonin Agonists and Antagonists Derived from 6H-Isoindolo[2,1-a]indoles, 5,6-Dihydroindolo[2,1-a]isoquinolines, and 6,7-Dihydro-5H-benzo[c]azepino[2,1-a]indoles

  摘要：

  6H-Isoindolo[2,1-a]indoles (5, 7, 10, 13), 5,6-dihydroindolo[2,1-a]isoquinolines (20, 21), and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]indoles (23, 25, 27, 30) have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human mt(1) and MT2 receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. The 2-methoxyisoindolo[2,1-a]indoles (7a-d) showed much higher binding affinities than the parent isoindoles (5a-e), and whereas 7a-c were agonists in the functional assay, 7d and 5a-e were antagonists. The 2-ethoxyisoindolo[2,1-a]indoles (10a-d) showed reduced binding affinities compared to their methoxy analogues, while the 5-chloro derivative 13 showed a considerable reduction in binding affinity and potency compared to 7a. The 10-methoxy-5,6-dihydroindolo[2,1-a]isoquinolines (21a-c) had higher binding affinities than the corresponding parent indoloisoquinolines (20a-c) in the human receptor subtypes, and the parent compounds were antagonists whereas the 10-methoxy derivatives were agonists in the functional assay. The N-cyclobutanecarbonyl derivatives of both the parent (20d) and 10-methoxyl (21d) series had similar binding affinities and were both antagonists with similar potencies. The 11-methoxy-6,7-5H-benzo[c]azepino[2,1-a]indoles (25a-d) had higher binding affinities than the corresponding parent compounds (23a-d) at the MT2 receptor but similar affinities at the mt(1) site; all of the compounds were antagonists in the functional assay. Changing 11-methoxy for 11-ethoxy decreased the binding affinity slightly, and this was more evident at the MT2 receptor. All of the derivatives investigated had either the same or a greater affinity for the human MT2 receptor compared to the mt(1) receptor (range 1:1-1:132). This suggests that the mt(1) and MT2 receptor pockets differ in their ability to accommodate alkyl groups in the indole nitrogen region of the melatonin molecule. Two compounds (7c and 25c) were tested in functional assays on recombinant mt(1) and MT2 melatonin receptors. Compound 7c is a potent agonist with some selectivity (44-fold) for the MT2 receptor, while 25c is an MT2-preferring antagonist. Increasing the carbon chain length between N-1 of indole and the 2-phenyl group from n = 1 through n = 3 leads to a fairly regular decrease in the binding affinity, but, remarkably, when n = 3, it converts the methoxy compounds from melatonin agonists to antagonists. The Xenopus melatonin receptor thus cannot accommodate an N-n-alkyl chain attached to a 2-phenyl substituent with n > 2 in the required orientation to induce or stabilize the active receptor conformation.

  DOI：

  10.1021/jm980684+
• 作为产物：
  描述：

  '5-Methoxy-β-indoleninideniummethyl-nitronat' 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 N-丙酰基-5-甲氧基色胺
  参考文献：
  名称：

  Ates-Alagoz; Buyukbingol; Buyukbingol, Erdem, Pharmazie, 2005, vol. 60, # 9, p. 643 - 647

  摘要：

  DOI：

文献信息

• Synthesis and study of the influence of certain products of serotonin metabolism, β-carbolines and related compounds, on the voluntary consumption of alcohol in animals
  作者：Yu. V. Burov、V. A. Zagorevskii、V. N. Zhukov、N. N. Novikova、I. D. Silenko

  DOI：10.1007/bf00764690

  日期：1983.8

  metabolite of ethanol [4]. The incorporation of these compounds into the mechanism of formation of alcohol dependence may be determined by their ability to intervene in certain neurochemical processes [4], in particular, the serotoninergic processes. Moreover, the high affinity for the benzodiazepine receptor [5] suggests possible intervention of the compounds under consideration in the emotional processes

  表明某些天然血清素代谢物 [i] 及其环状类似物，代表 8-咔啉类化合物，可能在酒精依赖的形成和表现过程中发挥重要作用，因为它们干预调节酒精消耗量 [2, 3]，是 5-羟色胺及其代谢物与乙醛（乙醇的代谢物）发生~nu~uo 环化的产物 [4]。这些化合物与酒精依赖形成机制的结合可能取决于它们干预某些神经化学过程的能力 [4]，特别是 5-羟色胺能过程。此外，对苯二氮卓受体的高亲和力 [5] 表明考虑中的化合物可能干预与酒精吸引力相关的情绪过程。
• Potential Radioprotective Agents. 1. Homologs of Melatonin
  作者：Robert T. Blickenstaff、Stephan M. Brandstadter、Shailaja Reddy、Robert Witt

  DOI：10.1002/jps.2600830220

  日期：1994.2

  Homologs of melatonin were prepared by acylation of 5-methoxytryptamine with the appropriate acid chloride or anhydride. The products were administered as solutions or suspensions in soybean oil by ip injection to mice 30 min prior to irradiation with 950 cGy of 6 mV photons. Protection was achieved with all compounds, survival rate being maximal for mice treated with the hexanoic amide 5 and the octanoic

  褪黑激素的同系物通过用适当的酰氯或酸酐酰化5-甲氧基色胺来制备。在用950 cGy的6 mV光子照射之前，通过腹腔注射将产物以大豆油中的溶液或悬浮液的形式给予小鼠30分钟。所有化合物均可实现保护，用己酸酰胺5和辛酸酰胺6处理的小鼠的存活率最高。
• SUBSTITUTED INDOLE MCL-1 INHIBITORS
  申请人：VANDERBILT UNIVERSITY

  公开号：US20160214934A1

  公开（公告）日：2016-07-28

  The present application, among other things, provides compounds that are capable of inhibiting the activity of anti-apoptotic Bcl-2 family proteins, for example, myeloid cell leukemia-1 (Mcl-1) protein. The present invention also provides pharmaceutical compositions as well as methods for using provided compounds for treatment of diseases and conditions (e.g., cancer) characterized by the over-expression or dysregulation of Mcl-1 protein. In some embodiments, a provided compound has the structure of formula I. In some embodiments, a provided compound has the structure of formula II.

  本申请提供了一些化合物，其中包括能够抑制抗凋亡Bcl-2家族蛋白（例如髓系细胞白血病-1（Mcl-1）蛋白）活性的化合物。本发明还提供了制药组合物以及使用所提供化合物治疗由Mcl-1蛋白过度表达或调节失常所致的疾病和病况（例如癌症）的方法。在某些实施例中，所提供的化合物具有公式I的结构。在某些实施例中，所提供的化合物具有公式II的结构。
• 2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents
  作者：Swier Copinga、Pieter G. Tepper、Cor J. Grol、Alan S. Horn、Margarita L. Dubocovich

  DOI：10.1021/jm00072a008

  日期：1993.10

  A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to compete for 2-[I-125]iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of [H-3]dopamine from rabbit retina. The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (K(i) = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor. The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows. First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor. We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.
• [EN] MELATONIN DERIVATIVES AND THEIR USE FOR TREATING NEUROLOGICAL DYSFUNCTIONS<br/>[FR] DERIVES DE MELATONINE ET LEUR UTILISATION DANS LE TRAITEMENT DE DYSFONCTIONNEMENTS NEUROLOGIQUES
  申请人：FAUST PHARMACEUTICALS

  公开号：WO2004085395A1

  公开（公告）日：2004-10-07

  The present invention relates to compounds, of the general formula (I), wherein R1 represents -O-R7 in which R7 represents H, or a C1 to C4 alkyl group, R2 and R3, independently from one another, represent H, or a halogen atom, R4 represents H, methyl, or a halogen atom, Ra represents H, or a Cl to C4 alkyl group, Rb represents H, a CL to C4 alkyl group, or a C1 to C4 alkoxy group, for the manufacture of a drug for the treatment and/or prevention of diseases and conditions mediated by the imbalance of acetylcholine and NO, diseases and conditions mediated by the imbalance of acetylcholine and glutamate, or for improving memory capability.