2-(1-benzyl-pyrrolidin-2-ylideneamino)benzonitrile

• 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: 2-(1-benzyl-pyrrolidin-2-ylideneamino)benzonitrile
• 英文别名: 2-(1-benzylpyrrolidin-2-ylideneamino)benzonitrile；2-[(1-benzyl-2-pyrrolidinyliden)amino]benzonitrile
• 化学式: C₁₈H₁₇N₃
• 分子量: 275.353
• InChiKey: MDJXKNLPTDVNJN-CZIZESTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  39.39
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-苄基-2-吡咯烷酮 、 2-氨基苯甲腈 在 四氯化锡 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 6.5h， 以91%的产率得到2-(1-benzyl-pyrrolidin-2-ylideneamino)benzonitrile
  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

文献信息

• Novel compounds for enhancing chemotherapy
  申请人：——

  公开号：US20020013322A1

  公开（公告）日：2002-01-31

  The present invention provides chemical compounds, pharmaceutical compositions, and methods for increasing the therapeutic efficacy of drugs. Specifically, the invention provides compounds and compositions for inhibiting drug transport proteins that efflux therapeutic agents from cells, and to methods for using these compounds and pharmaceutical compositions to increase the efficacy of the therapeutic agents that are effluxed by these drug transport proteins.

  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。
• Compounds for enhancing chemotherapy
  申请人：The Penn State Research Foundation.

  公开号：US20030105122A1

  公开（公告）日：2003-06-05

  The present invention provides 2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamines, of the formula: 1 or pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , and R 7 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2,3-二氢-1H-吡咯并[2,3-b]喹啉-4-胺，化学式为：1或其药学上可接受的盐，其中R1、R2、R3和R7如本文所定义。还披露了包含这些化合物的药物组合物，以及使用这些化合物来增强药物的治疗效果的方法。
• 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。
• NOVEL COMPOUNDS FOR ENHANCING CHEMOTHERAPY
  申请人：THE PENN STATE RESEARCH FOUNDATION

  公开号：EP1272479A2

  公开（公告）日：2003-01-08
• US6537993B2
  申请人：——

  公开号：US6537993B2

  公开（公告）日：2003-03-25