9,10-dihydro-9,10-ethano-anthracen-11-ylamine | 6372-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dihydro-9,10-ethano-anthracen-11-ylamine
• 英文别名: 9,10-Dihydro-9,10-aethano-anthracen-11-ylamin；7-Amino-dibenzobicyclo<2.2.2>octadien；7-Aminodibenzobicyclo<2.2.2>octadien；9.10-(11-Aminoethano)-9.10-dihydroanthracen；9,10-Dihydro-9,10-ethanoanthracen-11-amine；tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-amine
• CAS: 6372-65-2
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: URRYLKCWJQMOQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-9,10-ethano-anthracen-11-ylamine 以 苯 为溶剂， 反应 72.0h， 生成 蒽
  参考文献：
  名称：

  Malecot, Yves-Michel; Ripoll, Jean-Louis; Thuillier, Andre, Journal of Chemical Research, Miniprint, 1983, # 4, p. 959 - 993

  摘要：

  DOI：
• 作为产物：
  描述：

  (9,10-dihydro-9,10-ethano-anthracen-11-yl)-carbamic acid ethyl ester 在 溶剂黄146 作用下， 生成 9,10-dihydro-9,10-ethano-anthracen-11-ylamine
  参考文献：
  名称：

  THE SYNTHESIS OF 9,10-DIHYDRO-9,10-(11-AMINOETHANO)ANTHRACENES

  摘要：

  DOI：

  10.1021/jo01131a009

文献信息

• New triazine derivatives as potent modulators of multidrug resistance
  作者：Alain Dhainaut、Gilbert Regnier、Ghanem Atassi、Alain Pierre、Stephane Leonce、Laurence Kraus-Berthier、Jean Francois Prost

  DOI：10.1021/jm00091a017

  日期：1992.6

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.
• Geometry−Affinity Relationships of the Selective Serotonin Receptor Ligand 9-(Aminomethyl)-9,10-dihydroanthracene
  作者：Scott P. Runyon、Srinivas Peddi、Jason E. Savage、Bryan L. Roth、Richard A. Glennon、Richard B. Westkaemper

  DOI：10.1021/jm010354g

  日期：2002.4.1

  With the exception of its two aromatic rings and basic nitrogen atom, 9-(aminomethyl)-9,10-dihydroanthracene (AMDA; 1) is remarkably devoid of the pharmacophore features usually associated with high-affinity receptor ligands such as the heteroatom hydrogen bonding features of the endogenous ligand serotonin. AMDA does contain a phenylethylamine skeleton within a tricyclic ring system, and the presence of the second aromatic group is necessary for optimal receptor affinity. The structural requirements for the binding of AMDA at 5-HT2A receptors were investigated with respect to the geometric relationship between the two aromatic rings. It appears that the geometry of the AMDA parent is in the optimal range for fold angle between aromatic moieties. Evaluation of conformationally constrained derivatives of AMDA suggests that a chain extended trans, gauche form is most likely responsible for high affinity.
• The Diels-Alder Reaction of Anthracene with Nitroölefins. A New Route to 11-Nitro- and 11-Amino-9,10-dihydro-9,10-ethanoanthracenes¹
  作者：Wayland E. Noland、Howard I. Freeman、M. Scott Baker

  DOI：10.1021/ja01582a053

  日期：1956.1
• RIPOLL J. L.; LEBRUN H.; THUILLIER A., TETRAHEDRON, 1980, 36, NO 17, 2497-2503
  作者：RIPOLL J. L.、 LEBRUN H.、 THUILLIER A.

  DOI：——

  日期：——
• CHUNG, YONGSEOG;DUERR, BROOK F.;MCKELVEY, TIMOTHY A.;NANJAPPAN, P.;CZARNI+, J. ORG. CHEM., 54,(1989) N, C. 1018-1032
  作者：CHUNG, YONGSEOG、DUERR, BROOK F.、MCKELVEY, TIMOTHY A.、NANJAPPAN, P.、CZARNI+

  DOI：——

  日期：——