9-tolylsulfonyl-4,9-dihydro-3H-β-carboline | 869096-24-2

• 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: 9-tolylsulfonyl-4,9-dihydro-3H-β-carboline
• 英文别名: 9-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole；9-(4-methylphenyl)sulfonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole
• CAS: 869096-24-2
• 化学式: C₁₈H₁₈N₂O₂S
• 分子量: 326.419
• InChiKey: GBFYDRUIMVRLQL-UHFFFAOYSA-N

物化性质

• 沸点：
  549.7±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-tolylsulfonyl-4,9-dihydro-3H-β-carboline 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 2-allyl-1-ethynyl-9-(tolylsulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Enyne and dienyne metathesis reactions in β-carbolines

  摘要：

  New indolic enynes and dienynes, based on the P-carboline system, give metathesis products with ruthenium catalysts. The synthesis of the starting materials is readily achieved from tryptamine. The tuning up of the conditions for the metathesis is discussed. Cascade metathesis gives an oxidized pentacyclic product. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.140
• 作为产物：
  描述：

  N-[2-(1H-吲哚-3-基)乙基]甲酰胺 在 potassium carbonate 、 caesium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 9-tolylsulfonyl-4,9-dihydro-3H-β-carboline
  参考文献：
  名称：

  Enyne and dienyne metathesis reactions in β-carbolines

  摘要：

  New indolic enynes and dienynes, based on the P-carboline system, give metathesis products with ruthenium catalysts. The synthesis of the starting materials is readily achieved from tryptamine. The tuning up of the conditions for the metathesis is discussed. Cascade metathesis gives an oxidized pentacyclic product. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.140

文献信息

• [EN] TETRAHYDROBENZOFURO[2,3-C]PYRIDINE AND BETA-CARBOLINE COMPOUNDS FOR THE TREATMENT, ALLEVIATION OR PREVENTION OF DISORDERS ASSOCIATED WITH TAU AGGREGATES<br/>[FR] COMPOSÉS DE TÉTRAHYDROBENZOFURO[2,3-C]PYRIDINE ET DE BÊTA-CARBOLINE POUR LE TRAITEMENT, LE SOULAGEMENT OU LA PRÉVENTION DE TROUBLES ASSOCIÉS À DES AGRÉGATS DE PROTÉINE TAU
  申请人：AC IMMUNE SA

  公开号：WO2019233883A1

  公开（公告）日：2019-12-12

  The present invention relates to novel compounds of formula (I) that can be employed in the treatment, alleviation or prevention of a group of disorders and abnormalities associated with Tau (Tubulin associated unit) protein aggregates including, but not limited to, Neurofibrillary Tangles (NFTs), such as Alzheimer's disease (AD).

  本发明涉及一种可以用于治疗、缓解或预防与Tau（微管相关单元）蛋白聚集相关的一组疾病和异常的新化合物（I）的公式。这些疾病和异常包括但不限于神经原纤维缠结（NFTs），如阿尔茨海默病（AD）。
• Oxidative Asymmetric Formal Aza-Diels–Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones
  作者：Xiang Wu、Shi-Bao Zhao、Lang-Lang Zheng、You-Gui Li

  DOI：10.3390/molecules23092228

  日期：——

  Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels⁻Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4

  描述了Ru催化的串联胺氧化脱氢/形式的氮杂-Diels⁻Alder反应，用于从四氢-β-咔啉和α，β-不饱和酮的对映体和非对映体选择性合成吲哚并喹喔啉-2-酮。该反应通过叔丁基过氧化氢（TBHP）作为氧化剂和手性硫脲催化的正式氮杂-[4 + 2]环加成反应，通过串联钌催化的胺脱氢进行，为合成这些有价值的杂环化合物提供了分步经济的策略产品。
• Conformationally constrained N1-arylsulfonyltryptamine derivatives as 5-HT6 receptor antagonists
  作者：Derek C. Cole、William J. Lennox、Joseph R. Stock、John W. Ellingboe、Hossein Mazandarani、Deborah L. Smith、Guoming Zhang、Gregory J. Tawa、Lee E. Schechter

  DOI：10.1016/j.bmcl.2005.07.028

  日期：2005.11

  Several series of conformationally constrained N-1-arylsulfonyltryptamine derivatives were prepared and tested for 5-HT6 receptor binding affinity and ability to modulate cAMP production in a cyclase assay. The 3-piperidin-3-yl-, 3-(1-methylpyrrolidin-2-ylmethyl)-, and 3-pyrrolidin-3-yl-1H-indole arrays (8-13) appear to be able to adopt a conformation that allows high affinity 5-HT6 receptor binding, while the beta-carboline array 14 binds with a significantly weaker (10- to 100-fold) affinity. N-1-Benzenesulfonyl-3-piperidin-3-yl-1H-indole 9a is a high affinity full agonist with EC50 = 24 nM. Several of the N-1-arylsulfonyl-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole derivatives behave as very potent antagonists ((S)- 11r, (S)- 11t; IC50 = 0.8, 1.0 nM). (c) 2005 Elsevier Ltd. All rights reserved.
• Enyne and dienyne metathesis reactions in β-carbolines
  作者：Álvaro González-Gómez、Gema Domínguez、Javier Pérez Castells

  DOI：10.1016/j.tetlet.2005.07.140

  日期：2005.10

  New indolic enynes and dienynes, based on the P-carboline system, give metathesis products with ruthenium catalysts. The synthesis of the starting materials is readily achieved from tryptamine. The tuning up of the conditions for the metathesis is discussed. Cascade metathesis gives an oxidized pentacyclic product. (c) 2005 Elsevier Ltd. All rights reserved.