3-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol | 103796-16-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol
• 英文别名: 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol
• CAS: 103796-16-3
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: VWVQGAZGJUMWLL-UHFFFAOYSA-N

物化性质

• 熔点：
  116.0-116.7 °C
• 沸点：
  362.9±37.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 以91%的产率得到3-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol
  参考文献：
  名称：

  强效GluN2B选择性NMDA受体拮抗剂的苯并咪唑酮生物甾酮。

  摘要：

  如在阿尔茨海默氏病，帕芬森氏病，霍里亚·亨廷顿舞蹈症和癫痫病的发展过程中所观察到的，NMDA受体的过度活化与导致神经变性过程的兴奋性毒性事件有关。负变构调节剂选择性解决包含NMDA受体的GluN2B亚基的艾芬地尔结合位点是主要关注的问题，因为它们具有潜在的神经保护作用，且几乎没有副作用。效GluN2B拮抗剂的苯并咪唑酮本文生物电子等排1 - 5设计并合成。七个步骤的顺序提供了中心中间体19，产率为28％。消除水，甲基化，环氧化，环氧化物重排，最后进行还原胺化，得到了[7]环烯基苯并咪唑酮30具有在6-位的3-苯基丙基氨基取代基。虽然30个能装进有力GluN2B拮抗剂的药效，的gluN2B结合亲和性30仅中度（ķ我 = 697纳米）。此外，30显示了在σ低选择性2受体（ķ我 = 549纳米）。中等的GluN2B亲和力由[7] annulenobenzizimidazolone 30的刚性三环结构解释。

  DOI：

  10.1016/j.ejmech.2016.03.065
• 作为产物：
  描述：

  6,7,8,9-四氢-3-硝基-5H-苯并庚烯酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以80%的产率得到3-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol
  参考文献：
  名称：

  迈向 Waltheriones C 和 D：氧杂双环核心的合成

  摘要：

  描述了 HIV 细胞保护喹诺酮生物碱、waltheriones C 和 D 的氧双环核心的途径。该方法依赖于立体特异性跨环溴醚化，然后进行还原脱溴。该路线还可以通过关键中间体的酶促还原（> 99:1 er）实现对映选择性。

  DOI：

  10.1055/s-0036-1588150

文献信息

• [EN] COMPOUNDS HAVING SEROTONIN 5-HT17 RECEPTOR ANTAGONIST ACTIVITY AND MUSCARINIC M4 RECEPTOR AGONIST ACTIVITY AND THEIR USE IN THE TREATMENT OF PSYCHOTIC DISORDERS<br/>[FR] COMPOSES PRESENTANT UNE ACTIVITE ANTAGONISTE DU RECEPTEUR DE LA SEROTONINE 5-HT17 ET UNE ACTIVITE AGONISTE DU RECEPTEUR MUSCARINIQUE M4 ET UTILISATION DE CES COMPOSES POUR LE TRAITEMENT DES TROUBLES PSYCHOTIQUES
  申请人：MITSUBISHI PHARMA CORP

  公开号：WO2004087124A1

  公开（公告）日：2004-10-14

  The present invention relates to novel treatments for schizophrenia, based on the concept of identifying agents capable of selectively binding to the serotonin 5-HT7 and muscarinic M4 receptors and the use of such compounds in treating schizophrenia. The present invention also relates to novel amidine compounds for treating schizophrenia, a method of manufacturing such compounds, pharmaceutical formulations comprising said compounds, as well as medical uses and methods of treatment using said compounds.

  本发明涉及基于识别能够选择性结合到5-羟色胺5-HT7和肌碱M4受体的药剂，并将这类化合物用于治疗精神分裂症的新型治疗方法。本发明还涉及用于治疗精神分裂症的新型胺基化合物，一种制造这类化合物的方法，包含该化合物的药物配方，以及使用该化合物进行治疗的医疗用途和治疗方法。
• Ethanolamine derivatives having sympathomimetic and anti-pollakiuria
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05387710A1

  公开（公告）日：1995-02-07

  This invention relates to new ethanolamine derivatives having gut selective sympathomimetic and anti-pollakiuria activities and represented by the general formula [I]: ##STR1## wherein R.sup.1 is aryl or a heterocyclic group, each of which may be substituted with halogen, etc., R.sup.2 is hydrogen, halogen, nitro, hydroxy, lower alkyl optionally substituted with acyl, lower alkenyl optionally substituted with acyl, lower alkoxy optionally substituted with acyl, or amino optionally substituted with acyl(lower)alkyl, R.sup.3 is hydrogen, an N-protective group, or lower alkyl optionally substituted with lower alkylthio, n is an integer of 0 to 3, and a heavy solid line means a single bond or a double bond, provided that when n is 1, then 1) R.sup.1 is a condensed aromatic hydrocarbon group or a heterocyclic group, each of which may be substituted with halogen, etc., and the like, and pharmaceutically acceptable salts thereof to processes for the preparation thereof and to a pharmaceutical composition comprising the same.

  这项发明涉及具有肠道选择性交感兴奋作用和抗多尿活性的新乙醇胺衍生物，其通式为[I]：其中R.sup.1是芳基或杂环基，每个都可以用卤素等取代，R.sup.2是氢、卤素、硝基、羟基、可选择用酰基取代的较低烷基、可选择用酰基取代的较低烯基、可选择用酰基取代的较低烷氧基、或者可选择用酰基（较低）烷基取代的氨基，R.sup.3是氢、N-保护基，或者可选择用较低烷基硫代取代的较低烷基，n是0到3的整数，重实线表示单键或双键，但当n为1时，则1）R.sup.1是缩合芳香烃基或杂环基，每个都可以用卤素等取代，等等，以及其药学上可接受的盐，以及制备它们的方法和包含相同的药物组合。
• Sulfonamide-substituted fused 7-membered ring compounds, their use as a medicament, and pharmaceutical preparations comprising them
  申请人：Hoechst Aktiengesellschaft

  公开号：US20020072514A1

  公开（公告）日：2002-06-13

  The present invention relates to compounds of formula I, 1 in which X1, X2, X3, X4, Y1, Y2, Y3, Y4, R(3), R(4) and R(5) have the meanings mentioned in the specification, their preparation and their use, in particular in pharmaceuticals. The compounds effect the potassium channel or the I Ks channel opened by cyclic adenosine monophosphate (cAMP) and are outstandingly suitable as pharmaceutical active compounds, for example for the prophylaxis and therapy of cardiovascular disorders, in particular arrhythmias, for the treatment of ulcers of the gastrointestinal region or for the treatment of diarrheal disorders.

  本发明涉及式I的化合物，其中X1、X2、X3、X4、Y1、Y2、Y3、Y4、R（3）、R（4）和R（5）具有规范中提到的意义，它们的制备和应用，特别是在制药方面。该化合物影响钾通道或由环磷酸腺苷（cAMP）打开的IKs通道，并且非常适用于作为制药活性化合物，例如用于心血管疾病的预防和治疗，特别是心律失常，用于治疗胃肠区溃疡或腹泻性疾病的治疗。
• M4 agonists/5HT7 antagonists with potential as antischizophrenic drugs: Serominic compounds
  作者：Colin J. Suckling、John A. Murphy、Abedawn I. Khalaf、Sheng-ze Zhou、Dimitris E. Lizos、Albert Nguyen van Nhien、Hiroshi Yasumatsu、Allan McVie、Louise C. Young、Corinna McCraw、Peter G. Waterman、Brian J. Morris、Judith A. Pratt、Alan L. Harvey

  DOI：10.1016/j.bmcl.2007.01.093

  日期：2007.5

  Chronic low-dose treatment of rats with the psychomimetic drug, phencyclidine, induces regionally specific metabolic and neurochemical changes in the CNS that mirror those observed in the brains of schizophrenic patients. Recent evidence suggests that drugs targeting serotoninergic and muscarinic receptors, and in particular 5-HT7 antagonists and M-4 agonists, exert beneficial effects in this model of schizophrenia. Compounds that display this combined pattern of activity we refer to as serominic compounds. Based upon leads from natural product screening, we have designed and synthesised such serominic compounds, which are principally arylamidine derivatives of tetrahydroisoquinolines, and shown that they have the required serominic profile in ligand binding assays and show potential antipsychotic activity in functional assays. (c) 2007 Elsevier Ltd. All rights reserved.
• Aryl sulfonamido indane inhibitors of the Kv1.5 ion channel
  作者：Michael F. Gross、Serge Beaudoin、Grant McNaughton-Smith、George S. Amato、Neil A. Castle、Christine Huang、Anruo Zou、Weifeng Yu

  DOI：10.1016/j.bmcl.2007.02.052

  日期：2007.5

  A collection of aryl sulfonamido indanes based on the lead compound I was synthesized and evaluated for Kv1.5 inhibitory activity. Kv1.5 inhibitors have the potential to be atrium-selective agents for treatment of atrial fibrillation. (1R,2R)-1 has an IC50 of 0.033 mu M against Kv1.5 and is selective against other cardiac ion channels, including hERG. (c) 2007 Elsevier Ltd. All rights reserved.