1-(3-carboxypropyl)indole | 1884-59-9

• 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: 1-(3-carboxypropyl)indole
• 英文别名: 4-(1H-indol-1-yl)butanoic acid；4-(Indol-1-yl)butyric acid；indolyl butyric acid；4-indol-1-yl-butyric acid；4-Indol-1-yl-buttersaeure；4-indol-1-ylbutanoic acid
• CAS: 1884-59-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: MQLJZFAKVWTELE-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  180 °C(Press: 2 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-carboxypropyl)indole 在 ammonium acetate 、 肼 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 1-[3-(5,6-Dimethyl-1,2,4-triazin-3-yl)propyl]indole
  参考文献：
  名称：

  Indole as a dienophile in inverse electron demand Diels-Alder reactions. 3. Intramolecular reactions with 1,2,4-triazines to access the canthine skeleton

  摘要：

  The intramolecular inverse electron demand cycloaddition of indole with 1,2,4-triazines connected by a tri- or tetramethylene tether linking the indole N-1 position with the triazinyl 3-position successfully produces the canthine skeleton and the homologous system with a seven-membered D-ring.

  DOI：

  10.1021/jo00046a005
• 作为产物：
  描述：

  γ-丁内酯 、 吲哚 在 potassium hydride 作用下， 生成 1-(3-carboxypropyl)indole
  参考文献：
  名称：

  Indole as a dienophile in inverse electron demand Diels-Alder reactions. 3. Intramolecular reactions with 1,2,4-triazines to access the canthine skeleton

  摘要：

  The intramolecular inverse electron demand cycloaddition of indole with 1,2,4-triazines connected by a tri- or tetramethylene tether linking the indole N-1 position with the triazinyl 3-position successfully produces the canthine skeleton and the homologous system with a seven-membered D-ring.

  DOI：

  10.1021/jo00046a005

文献信息

• [EN] NOVEL OXADIAZOLE COMPOUNDS<br/>[FR] COMPOSÉS INÉDITS D'OXADIAZOLE
  申请人：ABBOTT LAB

  公开号：WO2011071570A1

  公开（公告）日：2011-06-16

  Novel oxadiazole compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions as agonists or antagonists of the S1P family of G protein-coupled receptors for treating diseases associated with modulation of S1P family receptor activity, in particular by affording a beneficial immunosuppressive effect are disclosed.

  新型噁二唑化合物，含有这种化合物的药物组合物以及将这些化合物或组合物用作治疗与调节S1P家族G蛋白偶联受体活性相关的疾病的激动剂或拮抗剂的用途被披露，特别是通过提供有益的免疫抑制作用。
• [EN] AZA-OXO-INDOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION<br/>[FR] AZA-OXO-INDOLES POUR LE TRAITEMENT ET LA PROPHYLAXIE DE L'INFECTION À VIRUS RESPIRATOIRE SYNCYTIAL
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014184163A1

  公开（公告）日：2014-11-20

  The invention provides compounds having the general formula: wherein R1, R2, R3, R4, R5, R6, W1, W2, W3, A and X are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有以下一般式的化合物：其中R1、R2、R3、R4、R5、R6、W1、W2、W3、A和X如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。
• Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole
  作者：Robert Coyle、Patrick McArdle、Fawaz Aldabbagh

  DOI：10.1021/jo5008543

  日期：2014.6.20

  A one-pot initiator-free Barton ester decomposition with tandem radical addition onto alkyl propiolates or phenylacetylene with aromatic substitution of the resultant vinyl radical allows convenient access to new 9-substituted 6,7-dihydropyrido[1,2-a]indoles. Propyl radical cyclizations compete when forming the expanded 7,8-dihydro-6H-azepino[1,2-a]indole system. 2-Thiopyridinyl S-radical is incorporated

  一锅式无引发剂的Barton酯分解反应，将自由基串联添加到丙炔酸烷基酯或苯乙炔上，并用芳香族取代所得的乙烯基，可以方便地获得新的9-取代的6,7-二氢吡啶并[1,2- a ]吲哚。丙基自由基环化在形成扩展的7,8-二氢-6 H-氮杂环庚烷[1,2- a ]吲哚体系时竞争。当使用未取代的吲哚-1-链烷酸前体时，将2-硫代吡啶基S-自由基结合到芳族加合物中。取代产物的X射线晶体学分析可以确定将自由基加成到反应性较低的内部炔烃上的选择性。
• The first synthesis of the benzo[b]indolo[1,2-h][1,7]naphthyridine ring system
  作者：Olga V. Baranova、Maxim E. Zhidkov、Sergey V. Dubovitskii

  DOI：10.1016/j.tetlet.2011.02.106

  日期：2011.5

  The first syntheses of representatives of the benzo[b]indolo[1,2-h][1,7]naphthyridine ring system have been accomplished using the Friedländer reaction.

  苯并[ b ]吲哚并[1,2- h ] [1,7]萘啶环系统代表的第一批合成反应已使用弗里德兰德反应完成。
• Inhibition of thromboxane synthetase by 3-(1-Imidazolylalkyl) indoles
  申请人：Pfizer Inc.

  公开号：US04273782A1

  公开（公告）日：1981-06-16

  Novel 3-(1-Imidazolylalkyl)indoles and the pharmaceutically acceptable acid addition salts thereof are disclosed. The novel compounds are useful in selectively inhibiting the action of the thromboxane synthetase enzyme without significantly inhibiting the action of the prostacycline synthetase or cyclooxygenase enzymes and are thus of value as therapeutic agents for the treatment of ischaemic heart disease, stroke, transient ischaemic attack, thrombosis, migraine and the vascular complications of diabetes.

  本文披露了新型3-(1-咪唑基烷基)吲哚化合物及其药用酸盐。这些新型化合物可用于选择性抑制血栓素合酶酶的作用，而不显著抑制前列环素合酶或环氧合酶的作用，因此对于治疗缺血性心脏病、中风、短暂性缺血性发作、血栓形成、偏头痛和糖尿病的血管并发症具有治疗价值。