4,5-(methylenedioxy)-1-indanone | 19843-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4,5-(methylenedioxy)-1-indanone
• 英文别名: 7,8-Dihydrocyclopenta[g][1,3]benzodioxol-6-one
• CAS: 19843-01-7
• 化学式: C₁₀H₈O₃
• mdl: MFCD18647751
• 分子量: 176.172
• InChiKey: IGECQYWWTCKFMT-UHFFFAOYSA-N

物化性质

• 熔点：
  161 °C
• 沸点：
  338.4±42.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  4,5-(methylenedioxy)-1-indanone 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 亚硝酸异戊酯 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 1.25h， 生成 4,5-(methylenedioxy)-2-aminoindan
  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 哌啶 、 吡啶 、 光气 、 palladium on activated charcoal 、 氢气 、 四氯化钛 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 4,5-(methylenedioxy)-1-indanone
  参考文献：
  名称：

  通过 Aza-Heck 环化全合成 (±)-Impatien A

  摘要：

  描述了天然产物凤仙花 A 的首次全合成。这种简洁的合成以 aza-Heck 环化为特征，以构建复杂的螺环系统，并为在复杂分子合成中使用 aza-Heck 环化提供了一个罕见的例子。为了实现亲电子氮原子与四取代烯烃的关键环化，我们利用高通量实验来鉴定新的配体，并最终通过已知化合物的七个步骤提供凤仙花 A。

  DOI：

  10.1021/acs.orglett.1c02767

文献信息

• SUBSTITUTED TRICYCLICS AND METHOD OF USE
  申请人：AbbVie S.à.r.l.

  公开号：US20170015675A1

  公开（公告）日：2017-01-19

  The present invention provides for compounds of formula (I) wherein X, Y, and R 1 have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions mediated and modulated by CFTR, including cystic fibrosis, Sjögren's syndrome, pancreatic insufficiency, chronic obstructive lung disease, and chronic obstructive airway disease. Also provided are pharmaceutical compositions comprised of one or more compounds of formula (I).

  本发明提供了一种具有以下结构的化合物（I），其中X、Y和R1具有规范中定义的任何值，以及其药学上可接受的盐，这些化合物在治疗由CFTR介导和调节的疾病和症状中是有用的，包括囊性纤维化、Sjögren综合征、胰腺功能不全、慢性阻塞性肺病和慢性阻塞性气道疾病。还提供了由一个或多个具有结构（I）的化合物组成的药物组合物。
• [EN] PYRIDINONE ANTAGONISTS OF ALPHA-4 INTEGRINS<br/>[FR] ANTAGONISTES À BASE DE PYRIDINONE D'INTÉGRINES ALPHA-4
  申请人：ELAN PHARM INC

  公开号：WO2010126914A1

  公开（公告）日：2010-11-04

  The present invention provides compounds that are alpha4 integrin antagonists having a structure according to the following formula (I) or a tautomer, mixture of tautomers, salt or solvate thereof, wherein Cy, ring A, m, n, p, R1, R2, R3, R4, R5 and R6 are defined in the specification. The invention further provides pharmaceutical compositions including the compounds of the invention as well as methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various conditions and disorders, such as Crohn's disease and ulcerative colitis.

  本发明提供具有以下结构的α4整合素拮抗剂化合物（I）或其互变异构体、互异构体混合物、盐或溶剂化合物，其中Cy、环A、m、n、p、R1、R2、R3、R4、R5和R6在规范中定义。该发明还提供包括本发明化合物的药物组合物，以及制备和使用本发明化合物和组合物的方法，例如在治疗和预防各种疾病和疾病，如克罗恩病和溃疡性结肠炎中的应用。
• Conformationally defined adrenergic agents. 1. Design and synthesis of novel .alpha.2-selective adrenergic agents: electrostatic repulsion based conformational prototypes
  作者：John F. DeBernardis、Daniel J. Kerkman、Martin Winn、Eugene N. Bush、David L. Arendsen、William J. McClellan、John J. Kyncl、Fatima Z. Basha

  DOI：10.1021/jm00148a005

  日期：1985.10

  determined, it was found that the overall pattern of binding affinity results supported the electrostatic repulsion hypothesis. The radioligand binding assay also revealed several highly alpha 2 selective adrenergic agents among these compounds, with the binding selectivity maximizing for compounds having nitrogen substituted with a group no larger than methyl and having a five-membered carbocyclic ring (i.e

  先前关于2-和6-氟去甲肾上腺素的肾上腺素选择性的报道促使我们提出一个假设，该假设基于由芳族氟原子和侧链羟基之间的静电排斥引起的构象偏爱来解释这种选择性。制备了一系列氮取代的邻苯二酚（氨基甲基）苯并环丁烯，茚满，四氢化萘和苯并环庚烯，并确定了它们的放射性配体结合亲和力时，发现结合亲和力结果的整体模式支持静电排斥假设。放射性配体结合测定还揭示了这些化合物中几种高度α2选择性肾上腺素能药物，
• Aryl-radical cyclization onto an enamide double bond. A route to benz[d]indeno[l2-b]azepines
  作者：Jesús Fidalgo、Luis Castedo、Domingo Domínguez

  DOI：10.1016/s0040-4039(00)79318-x

  日期：1993.11

  A novel synthesis of benz[d]indeno[1,2-b]azepines from bromoaryl enamides 1a-d has been achieved by way of regioselective 7-endo-trig radical cyclization with tri-n-butylin hydride

  苯并[d]茚并[1,2-B]从溴代烯酰胺氮杂的新型的合成1A-d已经通过区域选择性的方式实现的7 -内trig的自由基环化与三Ñ -butylin氢化
• PYRIDINONE ANTAGONISTS OF ALPHA-4 INTEGRINS
  申请人：ELAN PHARMACEUTICALS, INC.

  公开号：US20130252957A1

  公开（公告）日：2013-09-26

  The present invention provides compounds that are alpha4 integrin antagonists having a structure according to the following formula: or a tautomer, mixture of tautomers, salt or solvate thereof, wherein Cy, ring A, m, n, p, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are defined in the specification. The invention further provides pharmaceutical compositions including the compounds of the invention as well as methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various conditions and disorders, such as Crohn's disease and ulcerative colitis.

  本发明提供具有以下结构的α4整合素拮抗剂化合物：或其互变异构体，互变异构体混合物，盐或溶剂化物，其中Cy，环A，m，n，p，R1，R2，R3，R4，R5和R6在说明书中定义。本发明还提供包括本发明化合物的制药组合物，以及使用本发明化合物和组合物的方法，例如在治疗和预防各种疾病和障碍，如克罗恩病和溃疡性结肠炎中。