7-(ethoxycarbonyl)dibenzobarrelene | 27649-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 7-(ethoxycarbonyl)dibenzobarrelene
• 英文别名: 9,10-dihydro-9,10-ethenoanthracene-11-ethyl carboxylate；9,10-dihydro-9,10-etheno-anthracene-11-carboxylic acid ethyl ester；9,10-Dihydro-9,10-aetheno-anthracen-11-carbonsaeure-aethylester；Ethyl tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene-15-carboxylate；ethyl tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene-15-carboxylate
• CAS: 27649-95-2
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: AAVOYVVMXYRDJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(ethoxycarbonyl)dibenzobarrelene 在 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 99.0h， 生成 9,10-dihydro-N-methyl-9,10-ethenoanthracene-11-carboxamide
  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
• 作为产物：
  描述：

  蒽 、 丙炔酸乙酯 在 对苯二酚 作用下， 反应 0.75h， 生成 7-(ethoxycarbonyl)dibenzobarrelene
  参考文献：
  名称：

  Synthesis and antiproliferative action of a novel series of maprotiline analogues

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.10.076

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
• ——
  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.
• ——
  作者：J. Karolak-Wojciechowska、H. B. Trzeźwińska、S. Alibert-Franco、C. Santelli-Rouvier、J. Barbe

  DOI：10.1023/a:1022854604046

  日期：——

  As part of our investigation on histamine receptor antagonists, the structures of two 9-10-dihydroanthracene derivatives are reported: 4. C22H28N2; hexagonal, P6(1); a = 10.014(1), c = 34.556(7) Angstrom; V = 3001.0(7)Angstrom(3); and Z = 6; 9: C19H19N: triclinic, P-1; a = 8.427(2), b = 12.806(3), c = 15.292(3) Angstrom, alpha = 70.27(3), beta = 80.83(3), gamma = 72.98(3)degrees; V = 1482.0(6) Angstrom(3); and Z = 4. All non-aromatic rings in both molecules adopt a similar conformation. However, the three six-membered rings in the etheno-anthracene structure adopt a more regular boat form in spite of two sp(2) carbon bridged atoms.
• Photochemical transformations. 34. Some studies on the di-.pi.-methane rearrangement of 7-(ethoxycarbonyl)dibenzobarrelene
  作者：Stanley J. Cristol、James W. Hager

  DOI：10.1021/jo00160a013

  日期：1983.6
• Synthesis and Effects on Chloroquine Susceptibility in <i>Plasmodium </i><i>f</i><i>alciparum </i>of a Series of New Dihydroanthracene Derivatives
  作者：Sandrine Alibert、Christiane Santelli-Rouvier、Bruno Pradines、Carole Houdoin、Daniel Parzy、Janina Karolak-Wojciechowska、Jacques Barbe

  DOI：10.1021/jm011046l

  日期：2002.7.1

  To suggest a mechanism of action for drugs capable to reverse the chloroquine resistance, a new set of 9,10-dihydro-9,10-ethano and ethenoanthracene derivatives was synthesized and compounds were tested with the aim to assess their effect on chloroquine susceptibility in Plasmodium falciparum resistant strains. With respect to this, reversal of resistance and change in drug accumulation were compared

  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。