6-amino-5-methoxy-3,4-dihydronaphthalen-1(2H)-one | 192576-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-amino-5-methoxy-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 6-amino-5-methoxy-1-tetralone；6-amino-5-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 192576-55-9
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: RMWHXKOXIYKSJY-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C
• 沸点：
  405.9±45.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-amino-5-methoxy-3,4-dihydronaphthalen-1(2H)-one 在 碳酸氢钠 platinum(IV) oxide 、 palladium on activated charcoal 、 硫酸 、 氢气 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 21.33h， 生成
  参考文献：
  名称：

  通过抗体催化和在水性缓冲液中将烯二炔转化为醌：对另一种烯二炔治疗机制的意义。

  摘要：

  DOI：

  10.1021/ja005864z
• 作为产物：
  描述：

  4-{3-[(tert-butoxycarbonyl)amino]-2-methoxyphenyl}-butanoic acid 在 磷酸酐 、 磷酸 作用下， 反应 2.0h， 以46%的产率得到6-amino-5-methoxy-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Design, synthesis, and pharmacological evaluation of N-bicyclo-5-chloro-1H-indole-2-carboxamide derivatives as potent glycogen phosphorylase inhibitors

  摘要：

  As a result of the various N-bicyclo-5-chloro-1H-indole-2-carboxamide derivatives with a hydroxy moiety synthesized in an effort to discover novel glycogen phosphorylase (GP) inhibitors, 5-chloro-N-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide (5b) was found to have potent inhibitory activity. The introduction of fluorine atoms both at a position adjacent to the hydroxy group and in the central benzene moiety lead to the optically active derivative 5-chloro-N-[(5R)-1,3,6,6-tetrafluoro-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl]-1H-indole-2-carboxamide(25e alpha, which was the most potent compound in this series (IC(50) = 0.020 mu M). This compound inhibited glucagon-induced glucose output in cultured primary hepatocytes with an IC(50) value of 0.69 mu M, and showed oral hypoglycemic activity in diabetic db/db mice at 10 mg/kg. Compound 25e alpha also had an excellent pharmacokinetic profile, with high oral bioavailability and a long plasma half-life, in male SD rats. The binding mode of 25e alpha to this molecule and the role of fluorine atoms in that binding were speculated in an enzyme docking study. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.021

文献信息

• Synthesis and Antitumor Activity of Ring A- and F-Modified Hexacyclic Camptothecin Analogues
  作者：Masamichi Sugimori、Akio Ejima、Satoru Ohsuki、Kouichi Uoto、Ikuo Mitsui、Yasuyoshi Kawato、Yasuhide Hirota、Keiki Sato、Hirofumi Terasawa

  DOI：10.1021/jm970765q

  日期：1998.6.1

  and F-modified hexacyclic analogues of camptothecin were synthesized by Friedlander condensation of appropriately substituted bicyclic amino ketones with tricyclic ketone and were evaluated for cytotoxicity and topoisomerase I inhibitory activity. Seventeen of the compounds showed cytotoxic effects comparable or superior to those of 7-ethyl-10-hydroxycamptothecin (SN-38) against mouse leukemia P388 and

  通过适当取代的双环氨基酮与三环酮的弗里德兰德缩合合成喜树碱的19个A和F环修饰的六环类似物，并评价其细胞毒性和拓扑异构酶I抑制活性。17种化合物对小鼠白血病P388和人肿瘤细胞系HOC-21和QG-56的细胞毒性作用与7-乙基-10-羟基喜树碱（SN-38）相当或更好。在六环化合物的A环的5位上引入致密且感应吸电子的取代基，例如羟基，甲氧基，氯或氟基，显着提高了抗肿瘤活性。拓扑异构酶I抑制这些化合物的效力与其细胞毒性显示出良好的相关性。他们之中，
• Conformationally constrained analogues of N′-(4-tert-butylbenzyl)-N-(4-methylsulfonylaminobenzyl)thiourea as TRPV1 antagonists
  作者：Ju-Ok Lim、Mi-Kyoung Jin、HyungChul Ryu、Dong Wook Kang、Jeewoo Lee、Larry V. Pearce、Richard Tran、Attila Toth、Peter M. Blumberg

  DOI：10.1016/j.ejmech.2008.02.026

  日期：2009.1

  A series of bicyclic analogues having indan and tetrahydronaphthalene templates in the A-region were designed as conformationally constrained analogues of our previously reported potent TRPV1 antagonists (1, 3). The activities for rat TRPV1 of the conformationally restricted analogues were moderately or markedly diminished, particularly in the case of the tetrahydronaphthalene analogues. The analysis indicated that steric constraints at the benzylic position in the bicyclic analogues may be an important factor for their unfavorable interaction with the receptor. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Pinna; Loriga; Curzu, Il Farmaco, 1997, vol. 52, # 1, p. 25 - 28
  作者：Pinna、Loriga、Curzu、D'Amico

  DOI：——

  日期：——