1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine | 135882-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine
• 英文别名: 4-amino-1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinoline；AH-357/02177012；1-Benzyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-amine
• CAS: 135882-37-0
• 化学式: C₁₈H₁₇N₃
• 分子量: 275.353
• InChiKey: ZCZQCKJQIGWLFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-piperidinyl)acetyl chloride 、 1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 以49%的产率得到N-(1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-yl)-2-piperidin-1-yl-acetamide
  参考文献：
  名称：

  Synthesis and Evaluation of Dihydropyrroloquinolines That Selectively Antagonize P-Glycoprotein

  摘要：

  In a search for improved multiple drug resistance (MDR) modulators, we identified a novel series of substituted pyrroloquinolines that selectively inhibits the function of P-glycoprotein (Pgp) without modulating multidrug resistance-related protein 1 (MRP1). These compounds were evaluated for their toxicity toward drug-sensitive tumor cells (i.e. MCF-7, T24) and for their ability to antagonize Pgp-mediated drug-resistant cells (i.e. NCI/ADR) and MRP1-mediated resistant cells (i.e. MCF-7NP). Cytotoxicity and drug accumulation assays demonstrated that the dihydropyrroloquinolines inhibit Pgp to varying degrees, without any significant inhibition of MRP1. The compound termed PGP-4008 was the most effective at inhibiting Pgp in vitro and was further evaluated in vivo. PGP-4008 inhibited tumor growth in a murine syngeneic Pgp-mediated MDR solid tumor model when given in combination with doxorubicin. PGP4008 was rapidly absorbed after intraperitoneal administration, with its plasma concentrations exceeding the in vitro effective dose for more than 2 h. PGP-4008 did not alter the plasma distribution of concomitantly administered anticancer drugs and did not cause systemic toxicity as was observed for cyclosporin A. Because of their enhanced selectivity toward Pgp, these substituted dihydropyrroloquinolines may be effective MDR modulators in a clinical setting.

  DOI：

  10.1021/jm0303204
• 作为产物：
  描述：

  2-(1-benzyl-pyrrolidin-2-ylideneamino)benzonitrile 以 四氢呋喃 、 ice-water 、 乙醇 、 正己烷 为溶剂， 以14.6 g (39%)的产率得到1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine
  参考文献：
  名称：

  Novel compounds for enhancing chemotherapy

  摘要：

  本发明提供了化学化合物、药物组合物和方法，用于增强药物的治疗效果。具体地，本发明提供了抑制药物转运蛋白的化合物和组合物，这些蛋白从细胞中排出治疗剂量的药物，并提供使用这些化合物和药物组合物的方法，以增加被这些药物转运蛋白排出的治疗剂量的药物的疗效。

  公开号：

  US20020013322A1
• 作为试剂：
  描述：

  2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile 、 四氢呋喃 、 在 1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine 、 氩 、 Lithium diisopropylamine mono(tetrahydrofuran) 、 氯仿 、 Sodium sulfate-III 、 乙醇 作用下， 以 正己烷 为溶剂， 以to yield 14.6 g (39%) of Compound 25 as needles的产率得到1-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine
  参考文献：
  名称：

  Compounds for enhancing chemotherapy

  摘要：

  本发明提供了1H-喹喔啉酮，其化学式如下：或其药学上可接受的盐，其中R1，R2，R3和n如本文所定义。本发明还揭示了包含这种化合物的药物组合物，并使用这些化合物来增强药物的治疗功效的方法。

  公开号：

  US06537993B2

文献信息

• Small molecule toll-like receptor (TLR) antagonists
  申请人：Lipford B. Grayson

  公开号：US20050119273A1

  公开（公告）日：2005-06-02

  The invention provides methods and compositions useful for modulating signaling through Toll-like receptors. The methods involve contacting a TLR-expressing cell with a small molecule having a core structure including at least two rings. Certain of the compounds are 4-primary amino quinolines. Many of the compounds and methods are useful specifically for inhibiting immune stimulation involving at least one of TLR9, TLR8, TLR7, and TLR3. The methods may have use in the treatment of autoimmunity, inflammation, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer, and immunodeficiency.

  本发明提供了用于调节通过Toll样受体信号传导的方法和组合物。该方法涉及使用含有至少两个环的核心结构的小分子与表达TLR的细胞接触。其中某些化合物是4-主氨基喹啉。许多化合物和方法特别适用于抑制涉及至少一个TLR9、TLR8、TLR7和TLR3的免疫刺激。该方法可用于治疗自身免疫、炎症、过敏、哮喘、移植排斥、移植物抗宿主病、感染、败血症、癌症和免疫缺陷。
• Quinoxalinones for enhancing chemotherapy
  申请人：The Penn State Research Foundation

  公开号：US06815442B2

  公开（公告）日：2004-11-09

  The present invention provides 1H-quinoxalinones, of the formula: or pharmaceutically acceptable salts thereof, wherein R1, R2, and n are as defined herein. Also disclosed are pharmaceutical compositions comprising such compounds, and methods for using the compounds to increase the therapeutic efficacy of drugs.

  本发明提供了1H-喹喔啉酮，其化学式为：或其药学上可接受的盐，其中R1，R2和n如本文所定义。还揭示了包含这种化合物的药物组成物，以及使用这些化合物来增加药物的治疗功效的方法。
• COMPOUNDS AND METHODS FOR 18F LABELED AGENTS
  申请人：Lehmann Lutz

  公开号：US20080292548A1

  公开（公告）日：2008-11-27

  The present invention relates to novel compounds suitable for or already radiolabeled with 18 F, methods of making such compounds and use of such compounds for diagnostic imaging. Such labeled compounds are characterized by Formula II, wherein the substituents G, Q, L, Y and U have the meaning as defined in the specification and claims.

  本发明涉及适用于或已经标记有18F的新化合物，制备这种化合物的方法以及将这种化合物用于诊断成像的用途。这些标记化合物的特征由公式II表示，其中取代基G、Q、L、Y和U的含义如规范和要求所定义。
• Quinoline compound
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0430485A2

  公开（公告）日：1991-06-05

  There is disclosed a quinoline compound represented by the following formula (I): wherein R¹ and R² each represent a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a hydroxyl group, a lower alkoxy group, a lower alkanoyloxy group, a nitro group, an amino group or a lower alkanoylamino group; R³ represents a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group, an aralkyl group having 7 to 15 carbon atoms which may be substituted by a halogen atom, a lower alkyl group or a lower alkoxy group, an alkanoyl group having 2 to 15 carbon atoms, or a benzoyl group which may be substituted by a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a hydroxy group or an amino group; and n represents an integer of 2 to 5, and an acid addition salt thereof.

  本发明公开了由下式（I）代表的喹啉化合物： 其中 R¹ 和 R² 各自代表氢原子、卤素原子、低级烷基、三氟甲基、羟基、低级烷氧基、低级烷酰氧基、硝基、氨基或低级烷酰氨基；R³ 代表氢原子、具有 1 至 15 个碳原子的烷基、环烷基、具有 7 至 15 个碳原子且可被卤素原子、低级烷基或低级烷氧基取代的芳烷基、具有 2 至 15 个碳原子的烷酰基或可被卤素原子、低级烷基、低级烷氧基、硝基、羟基或氨基取代的苯甲酰基；以及 n 代表 2 至 5 的整数、 及其酸加成盐。
• Compounds and methods for 18F labeled agents
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2279759A2

  公开（公告）日：2011-02-02

  The present invention relates to novel compounds suitable for or already radiolabeled with 18F, methods of making such compounds and use of such compounds for diagnostic imaging. Such labeled compounds are characterized by Formula II, wherein the substituents G, Q, L, Y and U have the meaning as defined in the specification and claims.

  本发明涉及适用于或已经用 18F 进行放射性标记的新型化合物、制造此类化合物的方法以及将此类化合物用于诊断成像的用途。此类标记化合物的特征为式 II，其中取代基 G、Q、L、Y 和 U 的含义如说明书和权利要求书中所定义。