2-(methoxycarbonyl)canthin-6-one | 84133-31-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 英文名称: 2-(methoxycarbonyl)canthin-6-one
• 英文别名: methyl 6-oxo-6H-indolo[3,2,1-de][1,5]naphthyridine-2-carboxylate；methyl 2-oxo-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaene-7-carboxylate
• CAS: 84133-31-3
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: XQXQAMBHZZKHOL-UHFFFAOYSA-N

物化性质

• 熔点：
  247-249 °C
• 沸点：
  439.1±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(methoxycarbonyl)canthin-6-one 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-morpholinocarbonylcanthin-6-one
  参考文献：
  名称：

  铁屎米-6-酮衍生物及其制备方法和用途

  摘要：

  本发明公开了一种铁屎米‑6‑酮衍生物或其在药学上可接受的盐、水合物，所述的铁屎米‑6‑酮衍生物如结构式I所示，其中：R1选自‑OR2、‑NHR3、‑NR4R5、含一个或多个N的杂环基团；R2选自除甲基外的烷基、取代烷基、苯环取代的烷基、环烷基、苯基、取代苯基；R3、R4、R5分别独立地选自烷基、苯环取代的烷基、苯基、取代苯基。本发明还公开了铁屎米‑6‑酮衍生物或其在药学上可接受的盐、水合物在制备抗肿瘤药物中的用途。本发明首先通过6步反应合成2‑羧基铁屎米‑6‑酮原料，再对2‑羧基铁屎米‑6‑酮进行结构修饰制得铁屎米‑6‑酮衍生物，铁屎米‑6‑酮衍生物对A549、HepG2具有显著的抑制活性。

  公开号：

  CN105693718B
• 作为产物：
  描述：

  3-benzyl-6-oxo-2,3,3a,4,5,6-hexahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-2-carboxylic acid methyl ester 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以66%的产率得到2-(methoxycarbonyl)canthin-6-one
  参考文献：
  名称：

  Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids

  摘要：

  DOI：

  10.1021/ja00342a045

文献信息

• Reactivity ofβ-Carbolines and Cyclopenta[b]indolones Prepared from the Intramolecular Cyclization of 5(4H)-Oxazolones Derived fromL-Tryptophan
  作者：Glenn C. Condie、Jan Bergman

  DOI：10.1002/ejoc.200300673

  日期：2004.3

  omethyl-1,3-oxazol-5(4H)-one (4) was shown to undergo an intramolecular reaction in the presence of TFA, to afford a β-carboline 5 and a cyclopenta[b]indolone 6 by nucleophilic addition at C-2 and C-5, respectively. The distribution of these two products was found to be dependent on the reaction temperature, with lower temperatures favouring the formation of the β-carboline 5. Subsequent reactions

  4-(1H-Indol-3-ylmethyl)-2-trichloromethyl-1,3-oxazol-5(4H)-one (4) 显示在 TFA 存在下进行分子内反应，得到 β-咔啉5 和环戊二烯 [b] 吲哚酮 6 分别在 C-2 和 C-5 处亲核加成。发现这两种产物的分布取决于反应温度，较低的温度有利于 β-咔啉 5 的形成。随后对 β-咔啉 5 进行的反应导致形成 canthine 和 canthin-6-one衍生品。这些合成均涉及 1-甲酰基-β-咔啉-3-羧酸甲酯 (20)，这是一种有用的前体，通过四步程序从容易获得的 L-色氨酸中以 54% 的产率制备。环戊二烯 [b] 吲哚酮 6 很容易进行氧化脱酰胺，得到环戊二烯 [b] 吲哚-2,3-二酮 (37)，
• Biomimetic approach to potential benzodiazepine receptor agonists and antagonists
  作者：Filadelfo Guzman、Michael Cain、Paul Larscheid、Tim Hagen、James M. Cook、Margaret Schweri、Phil Skolnick、Steven M. Paul

  DOI：10.1021/jm00371a002

  日期：1984.5

  Several beta-carbolines, isoquinolines, imidazopyridines , and canthin -6-ones prepared in biomimetic fashion were tested for their ability to bind to the benzodiazepine receptor. Methyl isoquinoline-3-carboxylate, methyl 6,7- dimethoxyisoquinoline -3-carboxylate (3b) 1-phenyl-3- carbomethoxyimidazopyridine , (6B,) and canthin -6- one ( 13a ) bound with moderate affinities, while 2- carbomethoxycanthin -6- one ( 13b ) bound to benzodiazepine receptors with an affinity comparable to several pharmacologically active benzodiazepines. The potency of 13b suggests that the benzodiazepine receptor(s) can tolerate substitution at positions 1 and 9 of a beta-carboline without loss of activity if the substituents are trigonal and maintain a planar topography. Moreover, displacement of the carbonyl group by two atoms from the aromatic ring (C) of the beta-carboline skeleton caused a marked decrease in binding to the benzodiazepine receptor. This observation supports the hypothesis that maximum binding affinity of beta-carbolines is achieved when the carbonyl group at position 3 is attached directly to the aromatic pyridine ring.
• Synthesis and evaluation of β-carboline derivatives as inhibitors of human immunodeficiency virus
  作者：Keyur G. Brahmbhatt、Nafees Ahmed、Sudeep Sabde、Debashis Mitra、Inder Pal Singh、Kamlesh K. Bhutani

  DOI：10.1016/j.bmcl.2010.06.052

  日期：2010.8

  A series of beta-carboline derivatives were synthesized by utilizing aromatization and chemoselective alkylation method recently reported from our laboratory. Synthesized derivatives were evaluated for anti-HIV activity in human CD4+ T cell line (CEM-GFP) infected with HIV-1 NL4.3 virus. 1-Formyl-beta-carboline-3-carbxylic acid methyl ester (15) showed inhibition of human immunodeficiency virus at IC50 = 2.9 mu M. (C) 2010 Elsevier Ltd. All rights reserved.
• Giudice, Maria Rosaria Del; Gatta, Franco; Settimj, Guido, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 4, p. 967 - 973
  作者：Giudice, Maria Rosaria Del、Gatta, Franco、Settimj, Guido

  DOI：——

  日期：——
• DEL, GUIDICE MARIA ROSARIA;GATTA, FRANCO;SETTIMJ, GUIDO, J. HETEROCYCL. CHEM., 27,(1990) N, C. 967-973
  作者：DEL, GUIDICE MARIA ROSARIA、GATTA, FRANCO、SETTIMJ, GUIDO

  DOI：——

  日期：——