d'acide dihydro-9,10 etheno-9,10 anthracenecarboxylique | 27649-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: d'acide dihydro-9,10 etheno-9,10 anthracenecarboxylique
• 英文别名: 9,10-dihydro-9,10-ethenoanthracene-11-carboxylic acid；9,10-dihydro-9,10-etheno-anthracene-11-carboxylic acid；9,10-Dihydro-9,10-aetheno-anthracen-11-carbonsaeure；tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene-15-carboxylic acid
• CAS: 27649-96-3
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: SLBPFXSUYSLDCM-UHFFFAOYSA-N

物化性质

• 沸点：
  441.4±45.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  d'acide dihydro-9,10 etheno-9,10 anthracenecarboxylique 在 氢溴酸 、 甲苯 作用下， 生成 (+-)-trans-12-bromo-9,10-dihydro-9,10-ethano-anthracene-11-carboxylic acid
  参考文献：
  名称：

  Reactions of Hindered α-Substituted Acids. V. The Effect of a β-Methyl Group on the Acid-Catalyzed Rearrangement^1,2

  摘要：

  DOI：

  10.1021/ja01578a050
• 作为产物：
  描述：

  7-(ethoxycarbonyl)dibenzobarrelene 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 d'acide dihydro-9,10 etheno-9,10 anthracenecarboxylique
  参考文献：
  名称：

  一系列新的二氢蒽衍生物的合成及其对恶性疟原虫中氯喹敏感性的影响。

  摘要：

  为了提出一种能够逆转氯喹耐药性的药物的作用机理，合成了一组新的9,10-二氢-9,10-乙醇和乙炔蒽衍生物，并对其进行了测试，目的是评估其对氯喹敏感性的影响。恶性疟原虫抗性菌株。对此，比较了耐药性的逆转和药物积累的变化。结构-活性关系和分子建模研究使得为逆转剂定义药效基团和提出与某些选定氨基酸相互作用的推定模型成为可能。

  DOI：

  10.1021/jm011046l

文献信息

• Reactions of Hindered α-Bromo- and Hydroxysuccinic Acids^1a,b
  作者：Wyman R. Vaughan、Kirby M. Milton

  DOI：10.1021/ja01142a026

  日期：1952.11
• Lasne, Marie-Claire; Ripoll, Jean-Louis, Bulletin de la Societe Chimique de France, 1986, # 5, p. 766 - 770
  作者：Lasne, Marie-Claire、Ripoll, Jean-Louis

  DOI：——

  日期：——
• Reactions of Hindered α-and β-Substituted Acids. VI. Monocarboxylic Bromoacids^1,2
  作者：Wyman R. Vaughan、A. Charles Schoenthaler

  DOI：10.1021/ja01541a045

  日期：1958.4
• Synthesis and antiproliferative action of a novel series of maprotiline analogues
  作者：Y.M. McNamara、S.A. Bright、A.J. Byrne、S.M. Cloonan、T. McCabe、D.C. Williams、M.J. Meegan

  DOI：10.1016/j.ejmech.2013.10.076

  日期：2014.1

  The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymphoma (BL) cell lines is reported. A series of 9,10-dihydro-9,10-ethanoanthracenes were synthesised with modifications to the bridge of the dihydroethanoanthracene structure and with alterations to the basic side chain. A number of compounds were found to reduce cell viability to a greater extent than maprotiline in BL cell lines. In addition a related series of novel 9-substituted anthracene compounds were investigated as intermediates in the synthesis of 9,10-dihydro-9,10-ethanoanthracenes. These compounds proved the most active from the screen and were found to exert a potent caspase-dependant apoptotic effect in the BL cell lines, while having minimal effect on the viability of peripheral blood mononuclear cells (PBMCs). Compounds also displayed activity in multi-drug resistant (MDR) cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• ——
  作者：Andrzej Fruziński、Janina Karolak-Wojciechowska、Sandrine Alibert-Franco、Christiane Santelli-Rouvier、Jacques Barbe

  DOI：10.1023/a:1009507701327

  日期：——

  As a part of studies on MDR reversing agents, the structure of a benzylamido-9,10-dihydro-9,10-ethenoanthracene is reported: C-24 H-19 N O; orthorhombic; space group: Pca2(1); a = 9.214(2), b = 18.624(4), c = 10.170(2) Angstrom; 1745.2(6) Angstrom(3); Z = 4. The three nonplanar rings from the 9,10-dihydro-9,10-ethenoanthracene skeleton of the molecule adopt a boat conformation. The benzamide side-chain is extended (conformation, trans-trans-gauche). The molecules in the crystal are joined by infinite chains of H-bonds N14-H14 ... O13.