N-acetyl-2,6-dibromo-5-methoxytryptamine | 155443-53-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-2,6-dibromo-5-methoxytryptamine
• 英文别名: 2,6-dibromomelatonin；N-[2-(2,6-dibromo-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• CAS: 155443-53-1
• 化学式: C₁₃H₁₄Br₂N₂O₂
• 分子量: 390.074
• InChiKey: AEPQBPVSJSMGAD-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  593.0±50.0 °C(Predicted)
• 密度：
  1.695±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-bromomelatonine 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 4.0h， 以25%的产率得到N-acetyl-2,6-dibromo-5-methoxytryptamine
  参考文献：
  名称：

  Melatonin Receptor Ligands:  Synthesis of New Melatonin Derivatives and Comprehensive Comparative Molecular Field Analysis (CoMFA) Study

  摘要：

  The CoMFA methodology was applied to melatonin receptor ligands in order to establish quantitative structure-affinity relationships. One hundred thirty-three compounds were considered: they were either collected from literature or newly synthesized in order to gain information about the less explored positions. To this end, various melatonin derivatives were prepared and their affinity for quail optic tecta melatonin receptor was tested. Compounds were aligned on the putative active conformation of melatonin proposed by our previously reported pharmacophore search, and their relative affinities were calculated from the displacement of 2-[I-125]-iodomelatonin on different tissues expressing aMT receptors. Compounds were grouped into three sets according to their topology. Subset A: melatonin-like compounds; subset B: N-acyl-2-amino-8-methoxytetralins and related compounds; subset C: N-acyl-phenylalkylamines and related compounds. CoMFA models were derived for each set, using the steric, electrostatic, and lipophilic fields as structural descriptors; the PLS analyses were characterized by good statistical parameters, taking into account the heterogeneity of the binding data, obtained with different experimental protocols. From the CoMFA model for the melatonin-like compounds, besides the well-known positive effect of 2-substitution, a low steric tolerance for substituents in 1, 6, and 7, and a negative effect of electron-rich 4-substituents were observed; the information provided by the newly synthesized compounds was essential for these results. Moreover, a comprehensive model for the 133 compounds, accounting for a common alignment and a common mode of interaction at the melatonin receptor, was derived (Q(2) = 0.769, R-2 = 0.905). This model validates our previously reported pharmacophore search and offers a clear depiction of the structure-affinity relationships for the melatonin receptor ligands.

  DOI：

  10.1021/jm9810093

文献信息

• Syntheses of Melatonin and Its Derivatives
  作者：Masanori Somei、Yoshikazu Fukui、Masakazu Hasegawa、Naoki Oshikiri、Toshikatsu Hayashi

  DOI：10.3987/com-00-8930

  日期：——

  Two simple synthetic methods for melatonin are newly developed from tryptamine through intermediates, which are promising lead compounds for drug developing research. Novel chemical reactivities of melatonin in its bromination, lithiation, and acylation are also reported.
• NOUVEAUX DERIVES DE SPIRO[INDOLE-PYRROLIDINE] AGONISTES MELATONINERGIQUES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION A TITRE DE MEDICAMENT
  申请人：CEMAF

  公开号：EP0754183A1

  公开（公告）日：1997-01-22
• Receptor Blocker and Vasodilator Comprising Indole Derivative as Active Ingredient
  申请人：Somei Masanori

  公开号：US20090005430A1

  公开（公告）日：2009-01-01

  It is intended to find a compound that is structurally simpler than yohimbine, a pentacyclic condensed heterocyclic compound, and has an effect similar to that of yohimbine. The present invention relates to a pharmaceutical or food composition for α 2 receptor blockage comprising a compound represented by the formula (I) or a pharmaceutically acceptable salt thereof: (wherein R 1 represents a hydrogen, alkyl group, alkenyl group, alkynyl group, aromatic group, aralkyl group, acyl group, arylsulfonyl group, alkylsulfonyl group, or hydroxyl group; R 2 represents a hydrocarbon group; R 3 , R 4 , R 5 , R 6 , and R 7 are the same or different and represent a hydrogen, halogen, alkyl group, or alkoxy group; R 8 represents a hydrogen or acyl group; n represents an integer of 1 to 6; and a and b are the same or different and represent 1 or 0).
• US5552428A
  申请人：——

  公开号：US5552428A

  公开（公告）日：1996-09-03
• US5763471A
  申请人：——

  公开号：US5763471A

  公开（公告）日：1998-06-09