1-(3-dimethylamino-propyl)-1-phenyl-1,3-dihydro-isobenzofuran-5-carbonitrile | 1026009-77-7

• 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-(3-dimethylamino-propyl)-1-phenyl-1,3-dihydro-isobenzofuran-5-carbonitrile
• 英文别名: 1-{3-(dimethylamino)propyl}-1-phenyl-1,3-dihydro-5-isobenzofurancarbonitrile；Desfluorocitalopram；1-[3-(dimethylamino)propyl]-1-phenyl-3H-2-benzofuran-5-carbonitrile
• CAS: 1026009-77-7
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: DCABXDIJRCWHAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-dimethylamino-propyl)-1-phenyl-1,3-dihydro-isobenzofuran-5-carbonitrile 在 1-氯乙基氯甲酸酯 、 乙醇 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.5h， 生成 1-(3-methylamino-propyl)-1-phenyl-1,3-dihydro-isobenzofuran-5-carbonitrile
  参考文献：
  名称：

  From the Selective Serotonin Transporter Inhibitor Citalopram to the Selective Norepinephrine Transporter Inhibitor Talopram: Synthesis and Structure−Activity Relationship Studies

  摘要：

  Citalopram and talopram are structurally closely related, but they have very distinct pharmacological profiles as selective inhibitors of the serotonin and norepinephrine transporters, respectively. A systematic structure-activity relationship study was performed, in which each of the four positions distinguishing the two compounds were varied. The inhibitory potencies of the resulting 16 compounds were tested at both serotonin and norepinephrine transporters. This showed that particularly two of the four positions are determinants for the biological activity.

  DOI：

  10.1021/jm701602g
• 作为产物：
  描述：

  sodium cyanide 、 {3-[5-溴-1-苯基-1,3-二氢-异苯并呋喃-1-基]-丙基}-二甲基-胺 在 nickel dibromide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.5h， 生成 1-(3-dimethylamino-propyl)-1-phenyl-1,3-dihydro-isobenzofuran-5-carbonitrile
  参考文献：
  名称：

  From the Selective Serotonin Transporter Inhibitor Citalopram to the Selective Norepinephrine Transporter Inhibitor Talopram: Synthesis and Structure−Activity Relationship Studies

  摘要：

  Citalopram and talopram are structurally closely related, but they have very distinct pharmacological profiles as selective inhibitors of the serotonin and norepinephrine transporters, respectively. A systematic structure-activity relationship study was performed, in which each of the four positions distinguishing the two compounds were varied. The inhibitory potencies of the resulting 16 compounds were tested at both serotonin and norepinephrine transporters. This showed that particularly two of the four positions are determinants for the biological activity.

  DOI：

  10.1021/jm701602g

文献信息

• NOVEL 1,3-DIHYDRO-5-ISOBENZOFURANCARBONITRILE DERIVATIVES AND PHARMACEUTICAL COMPOSITION THEREOF FOR THE TREATMENT OF PREMATURE EJACULATION
  申请人：Lee Yeong Geon

  公开号：US20100240725A1

  公开（公告）日：2010-09-23

  Disclosed herein are novel 1,3-dihydro-5-isobenzofurancarbonitrile derivatives represented by Formula 1, or pharmaceutically acceptable salts thereof. Also disclosed is a pharmaceutical composition for treating or preventing premature ejaculation including the compound. The 1,3-dihydro-5-isobenzofurancarbonitrile derivatives have a short half-life and inhibit the ejaculation process by selectively inhibiting serotonin reuptake via a serotonin reuptake transporter present in a presynaptic neuron. Thus, the compounds are useful in the treatment and prevention of premature ejaculation.

  本文披露了一种新颖的由式1表示的1,3-二氢-5-异苯并呋喃腈衍生物，或其药学上可接受的盐。还披露了一种治疗或预防早泄的药物组合物，包括该化合物。1,3-二氢-5-异苯并呋喃腈衍生物具有短半衰期，并通过选择性地通过存在于突触前神经元中的5-羟色胺再摄取转运体抑制5-羟色胺再摄取来抑制射精过程。因此，这些化合物在早泄的治疗和预防中是有用的。
• NOVEL CHIRAL METAL COMPLEX AND USE THEREOF FOR ANALYZING CHIRALITY OF CHARGED COMPOUND BY 1H NMR SPECTROSCOPY
  申请人：KOREA ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20170052131A1

  公开（公告）日：2017-02-23

  Provided are novel ligand, a chiral metal complex including the same, and a use of the chiral metal complex for analyzing the chirality of a charged compound by 1 H NMR spectroscopy. The chiral metal complex of the present invention may be used as the chiral solvating agent to conveniently analyze the optical purity of charged compounds such as various amine derivatives, carboxylic acid derivatives, cyanohydrin derivatives and charged metal complexes by 1 H NMR spectroscopy.

  本发明提供了一种新型配体，包括该配体的手性金属配合物，以及利用该手性金属配合物通过1H NMR光谱分析带电化合物的手性的用途。本发明的手性金属配合物可用作手性溶剂化剂，方便地通过1H NMR光谱分析各种胺衍生物、羧酸衍生物、氰醇衍生物和带电金属配合物等带电化合物的光学纯度。
• US8242159B2
  申请人：——

  公开号：US8242159B2

  公开（公告）日：2012-08-14
• US9851314B2
  申请人：——

  公开号：US9851314B2

  公开（公告）日：2017-12-26
• [EN] NOVEL 1,3-DIHYDRO-5-ISOBENZOFURANCARBONITRILE DERIVATIVES AND PHARMACEUTICAL COMPOSITION THEREOF FOR THE TREATMENT OF PREMATURE EJACULATION<br/>[FR] NOUVEAUX DÉRIVÉS DE 1,3-DIHYDRO-5-ISOBENZOFURANCARBONITRILE ET COMPOSITION PHARMACEUTIQUES LES RENFERMANT POUR LE TRAITEMENT DE L'ÉJACULATION PRÉCOCE
  申请人：DONG A PHARM CO LTD

  公开号：WO2009057974A2

  公开（公告）日：2009-05-07

  Disclosed herein are novel l,3-dihydro-5-isobenzofurancarbonitrile derivatives represented by Formula 1, or pharmaceutically acceptable salts thereof. Also disclosed is a pharmaceutical composition for treating or preventing premature ejaculation including the compound. The l,3-dihydro-5-isobenzofurancarbonitrile derivatives have a short half- life and inhibit the ejaculation process by selectively inhibiting serotonin reuptake via a serotonin reuptake transporter present in a presynaptic neuron. Thus, the compounds are useful in the treatment and prevention of premature ejaculation.