5,6-(methylenedioxy)-2(1H)-naphthalenone | 124399-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,6-(methylenedioxy)-2(1H)-naphthalenone
• 英文别名: 5,6-methylenedioxy-2-tetralone；5,6-Methylendioxy-2-tetralone；8,9-dihydro-6H-benzo[g][1,3]benzodioxol-7-one
• CAS: 124399-96-8
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: VZBMGTVIJSAFPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-(methylenedioxy)-2(1H)-naphthalenone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 25.5h， 生成 2-(N-benzylamino)-5,6-(methylenedioxy)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA)

  摘要：

  Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA.HCl (1.75 mg/kg) from saline. In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4- methylphenyl)-2-aminopropane (DOM) were also evaluated. None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats. Compounds 4a and 4b did not substitute in MDMA-trained rats. Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc. Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for [3H]paroxetine. By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity. These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.

  DOI：

  10.1021/jm00164a037
• 作为产物：
  描述：

  2,3-(亚甲二氧基)苯甲醛 在 palladium on activated charcoal 吡啶 、 三甲基氯硅烷 、 氢气 、 sodium hydride 、 三氟乙酸 作用下， 以 乙醇 、 溶剂黄146 、 苯 为溶剂， 20.0~85.0 ℃ 、413.68 kPa 条件下， 反应 64.75h， 生成 5,6-(methylenedioxy)-2(1H)-naphthalenone
  参考文献：
  名称：

  替代苯并[a] ac啶和苯并[c] ac啶为哺乳动物拓扑异构酶毒物。

  摘要：

  与原小ber碱生物碱有关的Coralyne和其他几种合成的苯并[a，g]喹啉鎓衍生物已显示出作为拓扑异构酶毒物的活性。这些化合物的特征是存在带正电的亚胺基，据推测与它们的药理特性有关。本研究的目的是设计出这些化合物的稳定的不带电生物等排体。合成了几种相似取代的苯并[a] ac啶和苯并[c] ac啶衍生物，并确定了它们作为拓扑异构酶毒物的相对活性。虽然作为这项研究的一部分评估的苯并[c] void啶衍生物没有拓扑异构酶中毒活性，但在存在topo I的情况下，几种二氢苯并[a] ac啶能够增强DNA裂解。与某些确实表现出作为topo II毒物活性的原小ber碱衍生物相反，在topo II存在的情况下，苯并[a] s啶衍生物均不能增强DNA裂解。在所研究的苯并[a] ac啶中，5e-6-二氢-3,4-亚甲二氧基-9,10-二甲氧基苯并[a] r啶13e是最有效的topo I毒物，其功效与珊瑚烯相

  DOI：

  10.1016/s0968-0896(00)00048-1

文献信息

• Substituted heterocycles as anti-tumor agents
  申请人：Rutgers, The State University of New Jersey

  公开号：US05981541A1

  公开（公告）日：1999-11-09

  The present invention provides compounds of formula (I): ##STR1## wherein R.sub.1 -R.sub.7, W, X, Y, and Z have any of the values defined in the specification, and pharmaceutically acceptable salt thereof, that are are useful as anticancer agents. Also disclosed are pharmaceutical compositions comprising one or more compounds of formula I, processes for preparing compounds of formula I, and intermediates useful for preparing compounds of formula I.

  本发明提供了式(I)的化合物：##STR1##其中R.sub.1 -R.sub.7、W、X、Y和Z具有规范中定义的任何值，及其药用盐，这些化合物可用作抗癌剂。还公开了包含一个或多个式I化合物的药物组合物，制备式I化合物的方法，以及制备式I化合物的有用中间体。
• SUBSTITUTED HETEROCYCLES AS ANTI-TUMOR AGENTS
  申请人：RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：EP0950054A1

  公开（公告）日：1999-10-20
• US4267178A
  申请人：——

  公开号：US4267178A

  公开（公告）日：1981-05-12
• US5981541A
  申请人：——

  公开号：US5981541A

  公开（公告）日：1999-11-09
• [EN] SUBSTITUTED HETEROCYCLES AS ANTI-TUMOR AGENTS<br/>[FR] COMPOSES HETEROCYCLIQUES DE SUBSTITUTION S'UTILISANT COMME AGENTS ANTI-TUMORAUX
  申请人：RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY

  公开号：WO1998012181A1

  公开（公告）日：1998-03-26

  (EN) The present invention provides compounds of formula (I) wherein R1-R7, W, X, Y, and Z have any of the values defined in the specification, and pharmaceutically acceptable salt thereof, that are useful as anticancer agents. Also disclosed are pharmaceutical compositions comprising one or more compounds of formula (I), processes for preparing compounds of formula (I), and intermediates useful for preparing compounds of formula (I).(FR) La présente invention concerne des composés de la formule (I) dans laquelle R1-R7, W, X, Y, et Z présentent n'importe laquelle des valeurs définies dans la spécification, et un sel de ces composés acceptable du point de vue pharmaceutique, ces composés s'utilisant comme agents anticancéreux. L'invention concerne également des compositions pharmaceutiques comprenant un ou plusieurs composés de la formule (I), des procédés de préparation de composés de la formule (I), et des produits intermédiaires utiles dans la préparation de composés de la formule (I).