N-(2-(diethylamino)ethyl)-2,7-diiodoacridine-9-carboxamide | 1005030-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(2-(diethylamino)ethyl)-2,7-diiodoacridine-9-carboxamide
• 英文别名: N-(2-diethylaminoethyl)-2,7-diiodoacridine-9-carboxamide；N-[2-(diethylamino)ethyl]-2,7-diiodoacridine-9-carboxamide
• CAS: 1005030-50-1
• 化学式: C₂₀H₂₁I₂N₃O
• 分子量: 573.215
• InChiKey: AMCYANBCZPCWKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-diethylaminoethyl)-6-iodo-2-naphthamide hydrochloride 、 N-(2-(diethylamino)ethyl)-2,7-diiodoacridine-9-carboxamide 、 溴化钾 生成 N-(2-diethylaminoethyl)-2,7-diiodoacridine-9-carboxamide dihydrochloride
  参考文献：
  名称：

  LABELLED ANALOGUES OF HALOBENZAMIDES AS RADIOPHARMACEUTICALS

  摘要：

  本发明涉及使用式（I）化合物：其中R1代表放射性核素，Ar代表芳香环，m为2到4的整数，R2和R3代表独立的氢原子，（C1-C6）烷基，（C1-C6）烯基或苯基，所述苯基选择自苯基，苄基，咪唑基，吡啶基，嘧啶基，吡嗪基，吲哚基，吲唑基，呋喃基和噻吩基，并且它们与药学上可接受的酸的加成盐，用于制备放射性药物组合物，用于诊断和/或治疗黑色素瘤。

  公开号：

  US20100061928A1
• 作为产物：
  描述：

  methyl 2,7-diiodoacridine-9-carboxylate 、 N,N-二乙基乙二胺 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以57%的产率得到N-(2-(diethylamino)ethyl)-2,7-diiodoacridine-9-carboxamide
  参考文献：
  名称：

  Design, synthesis and preliminary biological evaluation of acridine compounds as potential agents for a combined targeted chemo-radionuclide therapy approach to melanoma

  摘要：

  Various iodo-acridone and acridine carboxamides have been prepared and evaluated as agents for targeted radionuclide and/or chemotherapy for melanoma, due to their structural similarity to benzamides which are known to possess specific affinity for melanin. Three of these carboxamides selected for their in vitro cytotoxic properties were radioiodinated with [I-125] NaI at high specific activity. Biodistribution studies carried out in B16F0 murine melanoma tumour-bearing mice highlighted that acridone 8f and acridine 9d, presented high, long-lasting tumour concentrations together with an in vivo kinetic pro. le favourable to application in targeted radionuclide therapy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.015

文献信息

• Labelled analogues of halobenzamides as radiopharmaceuticals
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP2363399A1

  公开（公告）日：2011-09-07

  The present invention relates to the use of a compound of formula (I): in which R1 represents a radionuclide, Ar represents an aromatic nucleus, m is an integer varying from 2 to 4, R2 and R3 represent, independently of one another, a hydrogen atom, a (C1-C6)alkyl group, a (C1-C6)alkenyl group or an aryl group chosen from a phenyl, benzyl, imidazolyl, pyridyl, pyrimidinyl, pyrazinyl, indolyl, indazolyl, furyl and thienyl group, and their addition salts with pharmaceutically acceptable acids, in the preparation of a radiopharmaceutical composition intended for the diagnosis and/or treatment of melanoma.

  本发明涉及式（I）化合物的用途： 其中 R1 代表放射性核素 Ar 代表芳香核 m 是 2 至 4 之间的整数、 R2和R3相互独立地代表氢原子、(C1-C6)烷基、(C1-C6)烯基或选自苯基、苄基、咪唑基、吡啶基、嘧啶基、吡嗪基、吲哚基、吲唑基、呋喃基和噻吩基的芳基，以及它们与药学上可接受的酸的加成盐，用于制备诊断和/或治疗黑色素瘤的放射性药物组合物。
• Design, synthesis and preliminary biological evaluation of acridine compounds as potential agents for a combined targeted chemo-radionuclide therapy approach to melanoma
  作者：Nicolas Desbois、Maryline Gardette、Janine Papon、Pierre Labarre、Aurélie Maisonial、Philippe Auzeloux、Claire Lartigue、Bernadette Bouchon、Eric Debiton、Yves Blache、Olivier Chavignon、Jean-Claude Teulade、Jean Maublant、Jean-Claude Madelmont、Nicole Moins、Jean-Michel Chezal

  DOI：10.1016/j.bmc.2008.07.015

  日期：2008.8

  Various iodo-acridone and acridine carboxamides have been prepared and evaluated as agents for targeted radionuclide and/or chemotherapy for melanoma, due to their structural similarity to benzamides which are known to possess specific affinity for melanin. Three of these carboxamides selected for their in vitro cytotoxic properties were radioiodinated with [I-125] NaI at high specific activity. Biodistribution studies carried out in B16F0 murine melanoma tumour-bearing mice highlighted that acridone 8f and acridine 9d, presented high, long-lasting tumour concentrations together with an in vivo kinetic pro. le favourable to application in targeted radionuclide therapy. (C) 2008 Elsevier Ltd. All rights reserved.
• LABELLED ANALOGUES OF HALOBENZAMIDES AS RADIOPHARMACEUTICALS
  申请人：Madelmont Jean-Claude

  公开号：US20100061928A1

  公开（公告）日：2010-03-11

  The present invention relates to the use of a compound of formula (I): in which R 1 represents a radionuclide, Ar represents an aromatic nucleus, m is an integer varying from 2 to 4, R 2 and R 3 represent, independently of one another, a hydrogen atom, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkenyl group or an aryl group chosen from a phenyl, benzyl, imidazolyl, pyridyl, pyrimidinyl, pyrazinyl, indolyl, indazolyl, furyl and thienyl group, and their addition salts with pharmaceutically acceptable acids, in the preparation of a radiopharmaceutical composition intended for the diagnosis and/or treatment of melanoma.

  本发明涉及使用式（I）化合物：其中R1代表放射性核素，Ar代表芳香环，m为2到4的整数，R2和R3代表独立的氢原子，（C1-C6）烷基，（C1-C6）烯基或苯基，所述苯基选择自苯基，苄基，咪唑基，吡啶基，嘧啶基，吡嗪基，吲哚基，吲唑基，呋喃基和噻吩基，并且它们与药学上可接受的酸的加成盐，用于制备放射性药物组合物，用于诊断和/或治疗黑色素瘤。