3-(indol-3-yl)propan-1-amine hydrochloride | 18237-15-5

• 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-(indol-3-yl)propan-1-amine hydrochloride
• 英文别名: 3-(indol-3-yl)propylamine hydrochloride；1H-indol-3-ylpropanamine hydrochloride；1H-Indole-3-propanamine, monohydrochloride；3-(1H-indol-3-yl)propan-1-amine;hydrochloride
• CAS: 18237-15-5
• 化学式: C₁₁H₁₄N₂*ClH
• 分子量: 210.706
• InChiKey: LQRGNIYFSBEZPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.65
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(indol-3-yl)propan-1-amine hydrochloride 在 盐酸 、 sodium acetate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 2'-phenylspiro[indoline-3,3'-piperidin]-2-one
  参考文献：
  名称：

  Intramolecular Mannich Reaction of 2-Oxotryptamine and Homologues with Oxo Reagents Yielding Spiro Compounds. Part II

  摘要：

  2-氧代色胺及其同系物通过与丙酮和其他酮发生分子内Mannich型环化反应，得到螺[吲哚-3,3'-吡咯啉]-2-酮和螺[吲哚-3,3'-哌啶]-2-酮。对2-氧代色胺的双同系物进行类似反应以获得螺[环庚烷-3,3'-吲哚]-2'-酮的尝试未成功。

  DOI：

  10.1135/cccc20021669

文献信息

• [EN] FUSED BICYCLIC ALKYLENE LINKED IMIDODICARBONIMIDIC DIAMIDES, METHODS FOR SYNTHESIS, AND USES IN THERARY<br/>[FR] DIAMIDES IMIDODICARBONIMIDIQUES LIÉS À UN ALKYLÈNE BICYCLIQUE FUSIONNÉ, PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS DANS UNE THÉRAPIE
  申请人：NOVATARG INC

  公开号：WO2018106907A1

  公开（公告）日：2018-06-14

  The present invention provides novel fused bicyclic alkylene linked imidodicarbonimidic diamides. In particular, described herein are N-[2-(indol-3- yl)alkylene]-linked imidodicarbonimidic diamides and N-[2-(pyrrolopyridin-3- yl)alkylene]-linked imidodicarbonimidic diamides (compound of formula (I) or formula (II)), and uses therefor. The compounds of the present invention are believed to be organic cation transporter selective compounds, useful for the treatment of diseases and conditions caused by reduced activity of 5' adenosine monophosphate-activated protein kinase (AMPK).

  本发明提供了新型的融合的双环烷基亚乙基连接的咪唑二氨基碳亚胺二酰胺。具体来说，本文描述了N-[2-(吲哚-3-基)烷基]-连接的咪唑二氨基碳亚胺二酰胺和N-[2-(吡咯吡啶-3-基)烷基]-连接的咪唑二氨基碳亚胺二酰胺（化合物的结构式（I）或结构式（II）），以及其用途。本发明的化合物被认为是有机阳离子转运体选择性化合物，可用于治疗由于5'腺苷单磷酸活化蛋白激酶（AMPK）活性降低而引起的疾病和症状。
• Fused bicyclic alkylene linked imidodicarbonimidic diamides, methods for synthesis, and uses in therapy
  申请人：NovaTarg, Inc.

  公开号：US11261157B2

  公开（公告）日：2022-03-01

  The present invention provides novel fused bicyclic alkylene linked imidodicarbonimidic diamides. In particular, described herein are N-[2-(indol-3-yl)alkylene]-linked imidodicarbonimidic diamides and N-[2-(pyrrolopyridin-3-yl)alkylene]-linked imidodicarbonimidic diamides (compound of formula (I) or formula (II)), and uses therefor. The compounds of the present invention are believed to be organic cation transporter selective compounds, useful for the treatment of diseases and conditions caused by reduced activity of 5′ adenosine monophosphate-activated protein kinase (AMPK).

  本发明提供了新颖的融合双环烯基连接的咪唑二碳酰亚胺二酰胺。特别是，本发明描述了 N-[2-(吲哚-3-基)亚烷基]连接的咪唑二碳酰亚胺二酰胺和 N-[2-(吡咯并吡啶-3-基)亚烷基]连接的咪唑二碳酰亚胺二酰胺（式 (I) 或式 (II) 的化合物）及其用途。本发明的化合物被认为是有机阳离子转运体选择性化合物，可用于治疗由 5′单磷酸腺苷激活蛋白激酶（AMPK）活性降低引起的疾病和病症。
• Structure Guided Development of Novel Thymidine Mimetics Targeting <i>Pseudomonas aeruginosa</i> Thymidylate Kinase: From Hit to Lead Generation
  作者：Jun Yong Choi、Mark S. Plummer、Jeremy Starr、Charlene R. Desbonnet、Holly Soutter、Jeanne Chang、J. Richard Miller、Keith Dillman、Alita A. Miller、William R. Roush

  DOI：10.1021/jm201349f

  日期：2012.1.26

  Thymidylate kinase (TMK) is a potential chemotherapeutic target because it is directly involved in the synthesis of an essential component, thymidine triphosphate, in DNA replication. All reported TMK inhibitors are thymidine analogues, which might retard their development as potent therapeutics due to cell permeability and off-target activity against human TMK. A small molecule hit (1, IC(50) = 58 μM), which has reasonable inhibition potency against Pseudomonas aeruginosa TMK (PaTMK), was identified by the analysis of the binding mode of thymidine or TP(5)A in a PaTMK homology model. This hit (1) was cocrystallized with PaTMK, and several potent PaTMK inhibitors (leads, 46, 47, 48, and 56, IC(50) = 100-200 nM) were synthesized using computer-aided design approaches including virtual synthesis/screening, which was used to guide the design of inhibitors. The binding mode of the optimized leads in PaTMK overlaps with that of other bacterial TMKs but not with human TMK, which shares few common features with the bacterial enzymes. Therefore, the optimized TMK inhibitors described here should be useful for the development of antibacterial agents targeting TMK without undesired off-target effects. In addition, an inhibition mechanism associated with the LID loop, which mimics the process of phosphate transfer from ATP to dTMP, was proposed based on X-ray cocrystal structures, homology models, and structure-activity relationship results.
• SAITO, ISAO;MURAMATSU, SHIGERU;SUGIYAMA, HIROSHI;YAMAMOTO, AKIHIRO;MATSUU+, TETRAHEDRON LETT., 1985, 26, N 48, 5891-5894
  作者：SAITO, ISAO、MURAMATSU, SHIGERU、SUGIYAMA, HIROSHI、YAMAMOTO, AKIHIRO、MATSUU+

  DOI：——

  日期：——
• FUSED BICYCLIC ALKYLENE LINKED IMIDODICARBONIMIDIC DIAMIDES, METHODS FOR SYNTHESIS, AND USES IN THERAPY
  申请人：NovaTarg, Inc.

  公开号：US20190345103A1

  公开（公告）日：2019-11-14

  The present invention provides novel fused bicyclic alkylene linked imidodicarbonimidic diamides. In particular, described herein are N-[2-(indol-3-yl)alkylene]-linked imidodicarbonimidic diamides and N-[2-(pyrrolopyridin-3-yl)alkylene]-linked imidodicarbonimidic diamides (compound of formula (I) or formula (II)), and uses therefor. The compounds of the present invention are believed to be organic cation transporter selective compounds, useful for the treatment of diseases and conditions caused by reduced activity of 5′ adenosine monophosphate-activated protein kinase (AMPK).