methyl 9,10-dihydro-9-oxoacridine-4-carboxylate | 100039-03-0

• 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: methyl 9,10-dihydro-9-oxoacridine-4-carboxylate
• 英文别名: Methyl 9-oxoacridan-4-carboxylate；9-oxo-9,10-dihydro-acridine-4-carboxylic acid methyl ester；9-Oxo-9,10-dihydro-acridin-4-carbonsaeure-methylester；methyl 9-oxo-10H-acridine-4-carboxylate
• CAS: 100039-03-0
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: ACUOXWSHHKOKHJ-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于丙酮、二甲基甲酰胺、二甲基亚砜、四氢呋喃

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 9,10-dihydro-9-oxoacridine-4-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到9-oxo-9,10-dihydroacridine-4-carbohydrazide
  参考文献：
  名称：

  Synthesis and Properties of Novel Biologically Interesting Polycyclic 1,3,4-Oxadiazoles Containing Acridine/Acridone Moieties

  摘要：

  A series of polycyclic 1,3,4-oxadiazoles bearing acridine and acridone pharmacophores were synthesized as potential noncovalent DNA-binding and antitumor agents. The synthesis of oxadiazoles with acridone moiety was performed exploring oxidative cyclization of corresponding aldimines via bromine and the acridine derivatives by cyclization of acylthiosemicarbazides with mercuric oxide. The spectroscopic properties of the compounds in the case of acridonoxadiazoles showed an efficient binding activity to DNA (K = 5.3-9.2 x 10(4) M-1), whereas the acridine analogues are suitable as biomarkers. The structure of compounds were characterized by spectral methods (UV-vis, IR, H-1, C-13, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO).

  DOI：

  10.3987/com-08-s(f)80
• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 在 copper diacetate polyphosphoric ethyl ester 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 methyl 9,10-dihydro-9-oxoacridine-4-carboxylate
  参考文献：
  名称：

  The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 3. The Reaction of Methyl Anthranilates with Diphenyliodonium-2-carboxylates

  摘要：

  DOI：

  10.1055/s-1985-31165

文献信息

• 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。
• Thermal stabilisation of the short DNA duplexes by acridine-4-carboxamide derivatives
  作者：Filip Kostelansky、Miroslav Miletin、Zuzana Havlinova、Barbora Szotakova、Antonin Libra、Radim Kucera、Veronika Novakova、Petr Zimcik

  DOI：10.1093/nar/gkac777

  日期：2022.10.14

  combination. The acridines interact with both single- and double-stranded DNAs with substantially preferred interaction for the latter. The study of interaction suggested higher affinity of the acridines toward the GC- than AT-rich sequences. Good discrimination of two point mutations was shown in practical application with HFE gene (wild type, H63D C > G and S65C A > C mutations). Acridine itself can also

  短寡脱氧核苷酸 (ODN) 探针适用于点突变的良好区分。然而，这些探针的熔化温度较低。在这项工作中，研究了使用吖啶-4-甲酰胺嵌入剂来提高热稳定性的策略。大量吖啶的研究表明，在通过双碳连接基团进行空间上不要求基本功能的仲甲酰胺修饰吖啶后，可实现最佳稳定性。通过点击化学进入位置 7 和/或 13，将两个高活性嵌入剂连接到短探针（13 或 18 个碱基；设计为 HFE 基因的一部分），并证明将双链体的熔化温度 (Tm) 提高近 8° C 为最佳组合。吖啶与单链和双链 DNA 相互作用，后者具有实质上优选的相互作用。相互作用的研究表明吖啶对 GC 序列的亲和力高于富含 AT 的序列。在 HFE 基因（野生型、H63D C > G 和 S65C A > C 突变）的实际应用中，显示了对两个点突变的良好区分。吖啶本身也可以用作荧光团，并且还允许在仅用吖啶标记的探针中将完全匹配的序列与具有点突变的序列区分开来。
• 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.
• Ullmann, Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 355
  作者：Ullmann

  DOI：——

  日期：——