N-(1,2,3,4-四氢-8-甲氧基-2-萘基)乙酰胺 | 80270-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: N-(1,2,3,4-四氢-8-甲氧基-2-萘基)乙酰胺
• 中文别名: N-(1,2,3,4-四氢-8-甲氧基-2-萘)-乙酰胺
• 英文名称: N-(1,2,3,4-tetrahydro,8-methoxy-2-naphthalenyl)-acetamide
• 英文别名: 8-M-ADOT；2-acetamido-8-methoxytetralin；8-methoxy-2-acetamido-tetralin；N-(1,2,3,4-tetrahydro, 8-methoxy-2-naphthalenyl) acetamide；8-Methoxy-2-acetamidotetralin；N-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide
• CAS: 80270-68-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: VDJCYVYVTWEIPD-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.11

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1,2,3,4-四氢-8-甲氧基-2-萘基)乙酰胺 在 吡啶 、 copper(I) oxide 、 五氯化磷 、 碘 、 silver trifluoroacetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 SKF 89748
  参考文献：
  名称：

  .alpha.-Adrenergic agents. 2. Synthesis and .alpha.1-agonist activity of 2-aminotetralins

  摘要：

  Substituted 2-aminotetralins are potent, selective, direct-acting agonists at postjunctional alpha 1 receptors. Within this series, substituent alterations on the ring, as well as on the nitrogen, change the potency of compounds by over three orders of magnitude (EC50 = 12 to greater than 10 000 nM). It has been demonstrated experimentally that substitution at both the 5 and 8 positions of the aromatic ring produces optimum agonist potency. Removal of either substituent results in a loss of potency and efficacy relative to norepinephrine. Substitution at positions 6 and/or 7 is generally detrimental to activity. Methyl, ethyl, or dimethyl substitution on nitrogen is compatible with high agonist potency, while substitution with larger groups is not. The most potent agonist in this series is 5-(thiomethyl)-8-methoxy-2-aminotetralin, which has an EC50 of 12 nM.

  DOI：

  10.1021/jm00344a009
• 作为产物：
  描述：

  8-甲氧基-3,4-二氢-1H-2-萘酮 在 盐酸 、 sodium hydroxide 、 diborane(6) 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.25h， 生成 N-(1,2,3,4-四氢-8-甲氧基-2-萘基)乙酰胺
  参考文献：
  名称：

  .alpha.-Adrenergic agents. 2. Synthesis and .alpha.1-agonist activity of 2-aminotetralins

  摘要：

  Substituted 2-aminotetralins are potent, selective, direct-acting agonists at postjunctional alpha 1 receptors. Within this series, substituent alterations on the ring, as well as on the nitrogen, change the potency of compounds by over three orders of magnitude (EC50 = 12 to greater than 10 000 nM). It has been demonstrated experimentally that substitution at both the 5 and 8 positions of the aromatic ring produces optimum agonist potency. Removal of either substituent results in a loss of potency and efficacy relative to norepinephrine. Substitution at positions 6 and/or 7 is generally detrimental to activity. Methyl, ethyl, or dimethyl substitution on nitrogen is compatible with high agonist potency, while substitution with larger groups is not. The most potent agonist in this series is 5-(thiomethyl)-8-methoxy-2-aminotetralin, which has an EC50 of 12 nM.

  DOI：

  10.1021/jm00344a009

文献信息

• 2-Aminotetralin compounds, pharmaceutical compositions and method of
  申请人：SmithKline Corporation

  公开号：US04320148A1

  公开（公告）日：1982-03-16

  2-Aminotetralin compounds having 5- and 8- substituents are centrally acting alpha.sub.1 agonists.

  具有5-和8-取代基的2-氨基四氢萘化合物是中枢作用的α1激动剂。
• Substituted 2-amidotetralins as melatonin agonists and antagonists
  申请人：Northwestern University

  公开号：US05151446A1

  公开（公告）日：1992-09-29

  The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as therapeutic and diagnostic reagents.

  本发明涉及具有褪黑激素受体活性的化合物，特别是取代的2-氨基四氢萘衍生物；包括含有这种化合物的药物制剂；以及使用这些化合物作为治疗和诊断试剂的方法。
• Substituted 1H,12H-benz-[DE]pyrano[3',4':6,7]
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US05658920A1

  公开（公告）日：1997-08-19

  A novel hexa-cyclic compound, a derivative of camptothecin, of the general formula: ##STR1## The compound is prepared from an aminoketone compound and a pyranoindolizine compound by the condensation-ring closing reaction. It is abundantly water-soluble, and has an excellent antitumor activity and a high degree of safety, and can be applied as an antitumor medicine for curing tumors of various kinds.

  一种新型的六环化合物，是喜树碱的衍生物，其一般式为：##STR1## 该化合物是通过氨基酮化合物和吡喃吲哚啉化合物的缩合-环闭合反应制备而成。它具有丰富的水溶性，具有优异的抗肿瘤活性和高度的安全性，可用作治疗各种类型的肿瘤的抗肿瘤药物。
• Method for treating leukemia with a hexa-cyclic compound
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US05770605A1

  公开（公告）日：1998-06-23

  A novel hexa-cyclic compound, a derivative of camptothecin, of the general formula: ##STR1## The compound is prepared from an aminoketone compound and a pyranoindolizine compound by the condensation-ring closing reaction. It is abundantly water-soluble, and has an excellent antitumor activity and a high degree of safety, and can be applied as an antitumor medicine for curing tumors of various kinds.

  一种新型的六环化合物，是一种喜树碱衍生物，其通式为：##STR1## 该化合物是由氨基酮化合物和吡喃吲哚啉化合物通过缩合-环闭合反应制备而成。它具有丰富的水溶性，优异的抗肿瘤活性和高度的安全性，可作为治疗各种肿瘤的抗肿瘤药物。
• Percutaneous absorption preparation
  申请人：Suzuki Yasuyuki

  公开号：US20090264521A1

  公开（公告）日：2009-10-22

  Percutaneous absorption preparations which make it possible to absorb compounds having a melatonin receptor agonist activity via a convenient administration system, have favorable blood-drug-concentration-time profile and can exert a therapeutic effect on a disease caused by a decrease in secretion of melatonin at night.

  经皮吸收制剂可以通过方便的给药系统吸收具有褪黑素受体激动剂活性的化合物，具有良好的血药浓度时间曲线，并可以对由于夜间褪黑素分泌减少而引起的疾病产生治疗效果。