5,6-亚甲二氧基-2-氨基茚满 | 132741-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 5,6-亚甲二氧基-2-氨基茚满
• 中文别名: 6,7-二氢-5H-茚并[5,6-d]-1,3-二氧戊环-6-胺；5.6-亚甲二氧基-2-氨基茚满盐酸盐
• 英文名称: 6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
• 英文别名: 2-amino-5,6-(methylenedioxy)indane；5,6-(methylenedioxy)-2-aminoindan；5,6-methylenedioxy-2-amino-indan；5,6-methylenedioxy-2-aminoindane；MDAI
• CAS: 132741-81-2
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: FQDRMHHCWZAXJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯酐 、 5,6-亚甲二氧基-2-氨基茚满 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到N-<5,6-(methylenedioxy)indan-2-yl>phthalimide
  参考文献：
  名称：

  N-（2-芳基乙基）邻苯二甲酰亚胺的光环合成4-芳基-2-苯并ze庚因-1,5-二酮

  摘要：

  描述了N-（2-芳基乙基）邻苯二甲酰亚胺向4-芳基-2-苯并ze庚因-1,5-二酮的光环化。我们发现芳基环上的供电子取代基的存在（如10a和b所示）对于环化过程的发生是必要的。该方法还允许合成在C 3（11c和d）具有羧酸根基团的2-苯并ze庚二酮，其以非对映异构体的1：1混合物获得。照射邻苯二甲酰亚胺12的结果取决于在取代基的性质，该邻苯二甲酰亚胺在苄基的位置带有一个氧化的取代基。尝试光环化N-（茚满-2-基）邻苯二甲酰亚胺16富电子的邻苯二甲酰亚胺23失效。

  DOI：

  10.1016/s0040-4020(01)87039-3
• 作为产物：
  描述：

  3-[3,4-(亚甲二氧基)苯基]丙酸 在 palladium on activated charcoal 盐酸 、 氯化亚砜 、 硫酸 、 氢气 、 四氯化锡 、 亚硝酸异戊酯 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 22.92h， 生成 5,6-亚甲二氧基-2-氨基茚满
  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

文献信息

• [EN] NOVEL PSILOCIN DERIVATIVES HAVING PRODRUG PROPERTIES<br/>[FR] NOUVEAUX DÉRIVÉS DE PSILOCINE AYANT DES PROPRIÉTÉS DE PROMÉDICAMENT
  申请人：COMPASS PATHFINDER LTD

  公开号：WO2022038299A1

  公开（公告）日：2022-02-24

  The present invention provides a novel group of active compounds based on the psychoactive compound psilocin. The psilocin derivatives provided herein exhibit improved pharmacokinetic properties during uptake as compared to psilocin, as well as reduced side effects resulting from the metabolites thus formed. Due to the affinity of the novel psilocin derivatives for the 5-HT2A-receptor, these derivatives are particularly advantageous for use in therapy, e.g., in the treatment of depression or drug addiction.

  本发明提供了一种基于精神活性化合物psilocin的新型活性化合物组。本文提供的psilocin衍生物在吸收过程中表现出比psilocin更好的药代动力学性能，并且由此形成的代谢产物副作用减少。由于新型psilocin衍生物对5-HT2A受体的亲和力，这些衍生物在治疗中特别有优势，例如在治疗抑郁症或药物成瘾方面。
• [EN] COMPLEXING AGENT SALT FORMULATIONS OF PHARMACEUTICAL COMPOUNDS<br/>[FR] FORMULATIONS SALINES DE COMPOSÉS PHARMACEUTIQUES À BASE D'AGENTS COMPLEXANTS
  申请人：BEXSON BIOMEDICAL INC

  公开号：WO2022109050A1

  公开（公告）日：2022-05-27

  Provided herein are pharmaceutical formulations and pharmaceutical compound salts which utilize complexing agents as counterions. Such formulations and salts are useful for treating a variety of disease and disorders.

  本文提供了药物制剂和药物化合物盐，其使用络合剂作为反离子。这些制剂和盐对治疗各种疾病和障碍有用。
• Methods and compositions for treating cancer using P2RX2 inhibitors
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US10457740B1

  公开（公告）日：2019-10-29

  The present invention provides methods for treating cancer using P2RX2 inhibitors, such as P2RX2 inhibitory antibodies, among others. The invention also features compositions containing P2RX2 inhibitors, methods of diagnosing patients with P2RX2-associated cancer, and methods of predicting the response of cancer in a subject to treatment with P2RX2 inhibitors.

  本发明提供了使用 P2RX2 抑制剂（如 P2RX2 抑制抗体等）治疗癌症的方法。本发明还包括含有 P2RX2 抑制剂的组合物、诊断 P2RX2 相关癌症患者的方法以及预测癌症对 P2RX2 抑制剂治疗的反应的方法。
• Indole AHR inhibitors and uses thereof
  申请人：Kyn Therapeutics

  公开号：US10570138B2

  公开（公告）日：2020-02-25

  The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

  本发明提供了可用作 AHR 抑制剂的化合物、其组合物及其使用方法。
• Methods of treating food allergy conditions
  申请人：Palo Alto Investors LP

  公开号：US11045454B2

  公开（公告）日：2021-06-29

  Methods for treating a subject for a food allergy condition are provided. Aspects of the methods include administering to a subject in need thereof a psychedelic agent in a manner effective to treat the subject for a food allergy condition. Effective administration of a psychedelic agent may include administering the psychedelic agent in an amount effective to treat the subject for the food allergy condition. In some instances, the subject is known to have a food allergy condition.

  本文提供了治疗食物过敏症的方法。这些方法的各个方面包括以有效治疗食物过敏症的方式向有需要的受试者施用迷幻剂。有效施用迷幻剂可包括以有效治疗受试者食物过敏症的量施用迷幻剂。在某些情况下，受试者已知患有食物过敏症。