3-(2-aminoethyl)-1H-indole-5-carbonitrile | 46276-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(2-aminoethyl)-1H-indole-5-carbonitrile
• 英文别名: 5-cyanotryptamine；2-[5-Cyano-1H-indol-3-yl]ethylamine；3-(2-aminoethyl)-5-cyanoindole；3-(2-amino-ethyl)-indole-5-carbonitrile；2-(5-cyano-1H-indol-3-yl)ethylamine；5-Cyan-tryptamin
• CAS: 46276-24-8
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: NYEZIGVQPDFDQF-UHFFFAOYSA-N

物化性质

• 沸点：
  423.6±30.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-aminoethyl)-1H-indole-5-carbonitrile 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 生成 N-tert-Butyloxycarbonyl-2-[5-aminomethyl-1H-indol-3-yl]ethylamine
  参考文献：
  名称：

  Methiodide approach to the synthesis of 3-[2-(dimethylamino)ethyl]-5-[(1,1-dioxo-5-methyl-1,2,5-thiadiazolidin-2-yl)methyl]-1H-indole and analogues

  摘要：

  Tryptamines 1, 2 and 3 have been synthesised in a convergent and efficient manner by reaction of a novel methiodide 4c with the anions of the cyclic sulphamides 5, 6 and 7 as the key step.

  DOI：

  10.1016/s0040-4039(00)60662-7
• 作为产物：
  描述：

  5-氰基吲哚-3-甲醛 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 ammonium acetate 、 锌 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 3-(2-aminoethyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  新型 1,3,5-三嗪的设计、合成和生物学评价：芳香环装饰对 5-HT7 受体亲和力的影响

  摘要：

  考虑到 5-HT 7受体的关键功能，特别是在精神病学中，以及有效和选择性的 5-HT 7受体配体尚未可用的事实，在这项工作中，我们设计并合成了新的 1,3,5-三嗪衍生物特别是基于评估芳环上的取代基对生物活性的影响。测试的化合物对 5-HT 7受体，尤其是配体 N 2 -(2-(5-fluoro-1H-indol-3-yl)ethyl)-N 4 -phenethyl-1,3,5-triazine表现出高亲和力-2,4,6-三胺2 ( K i = 8 nM) 和 N 2 -(2-(1H-indol-3-yl)ethyl)-N 4-(2-((4-氟苯基)氨基)乙基)-1,3,5-三嗪-2,4,6-三胺12 ( K i = 18 nM) 表现出适度的代谢稳定性和对 CYP3A4 同工酶的亲和力. 至于肝毒性评估，受试化合物仅在浓度高于 50 µM 时显示出中等的细胞毒性。化合物12在斑马鱼体内模型中表现出比2更小的心脏毒性作用。

  DOI：

  10.3390/ijms232113308

文献信息

• NOVEL COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：Griffioen Gerard

  公开号：US20130289033A1

  公开（公告）日：2013-10-31

  This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds. The compounds have the formula (A1), wherein R 1 , R 2 , R 4 , R 5 , R 6 , E, n, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , B, R 8 , and m are as defined in the claims.

  本发明提供了新型化合物，以及这些新型化合物作为药物的使用，特别是用于预防或治疗神经退行性疾病，更具体地是一些神经系统疾病，例如统称为tauopathies的疾病，以及以细胞毒性α-突触核蛋白淀粉样生成特征的疾病。本发明还涉及将所述新型化合物用于制造用于治疗此类神经退行性疾病的药物。本发明进一步涉及包括所述新型化合物的药物组合物以及制备所述新型化合物的方法。这些化合物的公式为(A1)，其中R1、R2、R4、R5、R6、E、n、Y1、Y2、Y3、Y4、Y5、B、R8和m如权利要求中所定义。
• [EN] NOVEL COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：UNIV LEUVEN KATH

  公开号：WO2012080220A1

  公开（公告）日：2012-06-21

  This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds. The compounds have the formula (A1), wherein R1, R2, R4, R5, R6, E, n, Y1, Y2, Y3, Y4, Y5, B, R8, and m are as defined in the claims.

  这项发明提供了新颖的化合物，以及这些新颖的化合物用作药物，更具体地用于预防或治疗神经退行性疾病，更具体地说是某些神经系统疾病，例如被统称为tau病变的疾病，以及以细胞毒性α-突触核蛋白淀粉样生成为特征的疾病。本发明还涉及利用这些新颖的化合物制备对治疗这种神经退行性疾病有用的药物。本发明还涉及包括这些新颖化合物的药物组合物，以及这些新颖化合物的制备方法。这些化合物的化学式为(A1)，其中R1、R2、R4、R5、R6、E、n、Y1、Y2、Y3、Y4、Y5、B、R8和m的定义如索赔中所述。
• [EN] SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN<br/>[FR] INHIBITEURS DE SÉPIAPTÉRINE RÉDUCTASE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：HERCULES TECHNOLOGY MAN CO V INC

  公开号：WO2011047156A1

  公开（公告）日：2011-04-21

  Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and prodrugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain).

  本文介绍的是对丝氨酸脱氢酶（SPR）的小分子杂环抑制剂，以及它们的前药和药用盐。还包括这些化合物的药物组合物以及这些化合物用于治疗或预防疼痛（如炎症性疼痛、伤害性疼痛、功能性疼痛和神经病理性疼痛）的用途。
• Indole compounds and use thereof
  申请人：Glaxo Group Limited

  公开号：US04252803A1

  公开（公告）日：1981-02-24

  Compounds are disclosed of general formula (I): ##STR1## wherein R.sub.1 and R.sub.2 each independently represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl, fluoroalkyl or alkyl group, which alkyl group is optionally substituted by an alkenyl group or by a group -OR.sub.7 or by ##STR2## where R.sub.7 and R.sub.8 each independently represents a hydrogen atom, an alkyl, aryl or aralkyl group; or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz--O--, --NH or ##STR3## R.sub.3 and R.sub.4 have the same meanings as R.sub.1 and R.sub.2 and may together form an aralkylidene group; R.sub.5 represents a hydrogen atom or an alkyl or aralkyl group; R.sub.6 represents a hydrogen atom or an aryl or C.sub.1 -C.sub.3 alkyl group; Alk represents an C.sub.1 -C.sub.4 alkylene group optionally substituted at one or more of its carbon atoms by one to three C.sub.1 -C.sub.3 alkyl groups; and X represents an oxygen or sulphur atom, and its physiologically acceptable salts, hydrates and bioprecursors. The indoles (I) may be prepared by combinations of reactions to introduce the desired substituents into suitable intermediates either before or after cyclization to form the indole nucleus. The compounds have selective actions on blood vessels and, in particular exhibit antihypertensive properties. They may be formulated in conventional manner as pharmaceutical compositions.

  化合物的通用结构式（I）已披露如下：##STR1## 其中，R.sub.1和R.sub.2各自独立地代表氢原子，或芳基、芳基烷基、环烷基、氟烷基或烷基基团，该烷基基团可选择地被烯基基团或基团-OR.sub.7或##STR2##所取代，其中R.sub.7和R.sub.8各自独立地代表氢原子、烷基、芳基或芳基烷基；或者R.sub.1和R.sub.2与它们连接的氮原子一起形成饱和的单环5到7成员环，该环可能包含进一步的杂原子功能（即-O-，-NH或##STR3## R.sub.3和R.sub.4的含义与R.sub.1和R.sub.2相同，它们可以一起形成芳基烷基亚甲基基团；R.sub.5代表氢原子或烷基或芳基烷基基团；R.sub.6代表氢原子或芳基或C.sub.1 -C.sub.3烷基基团；Alk代表一个C.sub.1 -C.sub.4烷基基团，该烷基基团在其一个或多个碳原子上可以被一个到三个C.sub.1 -C.sub.3烷基基团取代；X代表氧原子或硫原子，以及其生理上可接受的盐、水合物和生物前体。这些吲哚（I）可以通过反应的组合制备，将所需的取代基引入适当的中间体，无论是在环化形成吲哚核之前还是之后。这些化合物对血管具有选择性作用，特别表现出降压性能。它们可以按照传统方式制备成药物组合物。
• Fused imidazole and triazole derivatives as 5-HT1 receptor agonists
  申请人：Merck Sharp & Dohme Limited

  公开号：US05514682A1

  公开（公告）日：1996-05-07

  Compounds of formula (I) wherein F represents a Group of the formula (a) ; E represents a bond or a straight or branched alkylene chain containing from 1 to 4 carbon atoms; and the rest of the variables are defined in the specification are selective agonists of 5HT.sub.1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.

  式(I)的化合物中，其中F表示公式(a)的一组；E表示键合或直链或支链烷基链，含有1至4个碳原子；其余变量在说明书中定义，是5HT.sub.1-类受体的选择性激动剂，因此在治疗临床情况，特别是偏头痛和相关疾病方面非常有用，因为这些情况需要这些受体的选择性激动剂。