1-(2-chlorophenyl)-N-hexylamino-3-isoquinoline carboxamide | 419535-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(2-chlorophenyl)-N-hexylamino-3-isoquinoline carboxamide
• 英文别名: N-(6-aminohexyl)-1-(2-chlorophenyl)isoquinoline-3-carboxamide
• CAS: 419535-36-7
• 化学式: C₂₂H₂₄ClN₃O
• 分子量: 381.905
• InChiKey: HANJVTJDGCUCCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)-N-hexylamino-3-isoquinoline carboxamide 、 1-(2-methylene-6-methylquinoline)-4,10-bis(methylene-phosphonic acid)-7-(acetic acid)-1,4,7,10-tetraazacyclododecane 在 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以46%的产率得到1-(2-methylene-6-methylquinoline)-4-10-bis(methylene-phosphonic acid)-7-(methylene-1-(2-chlorophenyl)-N-hexyl-3-isoquinoline carboxamide)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Facile, Efficient Conjugation of a Trifunctional Lanthanide Chelate to a Peripheral Benzodiazepine Receptor Ligand

  摘要：

  [GRAPHICS]Receptor-mediated imaging and therapy of diseased tissue is rapidly gaining favor in the medical community. The synthesis and facile aqueous/organic coupling of a peripheral-type benzodiazepine receptor ligand to a cyclen-based fluorophore is described herein. The contrast agent QM-CTMC-PK11195, when chelated with lanthanides, produces bright luminescence and good MRI contrast and can potentially serve as an imaging and demarcation agent for certain types of cancers.

  DOI：

  10.1021/ol017155b
• 作为产物：
  描述：

  2-氨基-1-苯基-1-丙醇盐酸盐 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 phosphorus pentoxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 silver nitrate 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 15.0h， 生成 1-(2-chlorophenyl)-N-hexylamino-3-isoquinoline carboxamide
  参考文献：
  名称：

  Facile, Efficient Conjugation of a Trifunctional Lanthanide Chelate to a Peripheral Benzodiazepine Receptor Ligand

  摘要：

  [GRAPHICS]Receptor-mediated imaging and therapy of diseased tissue is rapidly gaining favor in the medical community. The synthesis and facile aqueous/organic coupling of a peripheral-type benzodiazepine receptor ligand to a cyclen-based fluorophore is described herein. The contrast agent QM-CTMC-PK11195, when chelated with lanthanides, produces bright luminescence and good MRI contrast and can potentially serve as an imaging and demarcation agent for certain types of cancers.

  DOI：

  10.1021/ol017155b

文献信息

• AGENTS FOR THERAPY EFFICACY MONITORING AND DEEP TISSUE IMAGING
  申请人：Bornhop J. Darryl

  公开号：US20080031823A1

  公开（公告）日：2008-02-07

  Compounds and methods related to NIR molecular imaging, in-vitro and in-vivo functional imaging, therapy/efficacy monitoring, and cancer and metastatic activity imaging. Compounds and methods demonstrated pertain to the field of peripheral benzodiazepine receptor imaging, metabolic imaging, cellular respiration imaging, cellular proliferation imaging as targeted agents that incorporate signaling agents.

  与近红外分子成像、体外和体内功能成像、治疗/疗效监测以及癌症和转移活动成像相关的化合物和方法。展示的化合物和方法涉及外周苯二氮平受体成像、代谢成像、细胞呼吸成像、细胞增殖成像作为包含信号剂的靶向剂。
• MULTI-USE MULTIMODAL IMAGING CHELATES
  申请人：Bornhop Darryl J.

  公开号：US20080241873A1

  公开（公告）日：2008-10-02

  Cyclen-based chelates can be used as contrast agents for multi-modal imaging of tissue cells. The cyclen-based chelates are preferably polyazamacrocyclic molecules formed from 1,4,7,10 tetraazacyclododecane (“cyclen”) having varying chelating ions, phosphoester chains, and light harvesting moieties. By changing the chelating ion, phosphoester chain length and/or the light harvesting moiety different imaging techniques, such as MRI, CT, fluorescence and absorption, x-ray and NIR, may be employed to image the tissue cells. Additionally, the cyclen-based chelates may be conjugated to provide for site-specific delivery of the cyclen-based chelate to the desired tissue cells. The cyclen-based chelates may also be delivered to the tissue cells by attaching the cyclen-based to a polymeric delivery vehicle. Although these cyclen-based chelates have a wide variety of application, the preferred use is for imaging of cancer cells, such as brain cancer, for improving resection of a cancerous tissue.

  基于环丙氮（Cyclen）的螯合剂可用作多模态组织细胞成像的对比剂。这些基于环丙氮的螯合剂最好是由1,4,7,10-四氮杂环十二烷（“Cyclen”）形成的多氮杂大环分子，具有不同的螯合离子、磷酸酯链和光收集基团。通过改变螯合离子、磷酸酯链长度和/或光收集基团，可以使用不同的成像技术，如MRI、CT、荧光和吸收、X射线和近红外线来成像组织细胞。此外，可以将基于环丙氮的螯合剂共价结合，以实现对所需组织细胞的位点特异性递送。也可以通过将基于环丙氮的螯合剂连接到聚合物递送载体上来将其递送到组织细胞中。尽管这些基于环丙氮的螯合剂有广泛的应用，但首选用途是用于癌细胞成像，如脑癌，以改善癌组织切除。
• TARGETED, NIR IMAGING AGENTS FOR THERAPY EFFICACY MONITORING, DEEP TISSUE DISEASE DEMARCATION AND DEEP TISSUE IMAGING
  申请人：Bornhop Darryl J.

  公开号：US20100278739A1

  公开（公告）日：2010-11-04

  Compounds and methods related to NIR molecular imaging, in-vitro and in-vivo functional imaging, therapy/efficacy monitoring, and cancer and metastatic activity imaging. Compounds and methods demonstrated pertain to the field of peripheral benzodiazepine receptor imaging, metabolic imaging, cellular respiration imaging, cellular proliferation imaging as targeted agents that incorporate signaling agents.
• US7338651B2
  申请人：——

  公开号：US7338651B2

  公开（公告）日：2008-03-04
• US7754884B2
  申请人：——

  公开号：US7754884B2

  公开（公告）日：2010-07-13