2-ethoxy-4,5-dihydro-3H-benzazepine | 53687-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2-ethoxy-4,5-dihydro-3H-benzazepine
• 英文别名: 2-Ethoxy-4,5-dihydro-3H-1-benzazepine
• CAS: 53687-78-8
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: KZXJHQYIGRFGJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethoxy-4,5-dihydro-3H-benzazepine 在 氨 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以72%的产率得到Cambridge id 5219834
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1023918911369
• 作为产物：
  描述：

  1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮 、 triethyloxonium fluoroborate 以 二氯甲烷 为溶剂， 生成 2-ethoxy-4,5-dihydro-3H-benzazepine
  参考文献：
  名称：

  Targeting the Polyamine Transport System with Benzazepine- and Azepine-Polyamine Conjugates

  摘要：

  The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.

  DOI：

  10.1021/jm1007648

文献信息

• New synthesis of benzo[b][1,6]naphthyridines and pyrido[4,3-b]benz[f]azepines from lactim ethers of 3,4-dihydrocarbostyril and 1H-2,3,4,5-tetrahydrobenz[b]azepin-2-one
  作者：T. V. Golovko、O. B. Smirnova、N. P. Solov’eva、O. S. Anisimova、V. G. Granik

  DOI：10.1007/s11172-007-0155-4

  日期：2007.5

  Condensation of lactim ethers of 3,4-dihydrocarbostyril and 1H-2,3,4,5-tetrahydrobenz[b]azepin-2-one with malonodinitrile, cyanoacetamide, and ethyl cyanoacetate gave the corresponding 2-methylidene derivatives. Their reactions with dimethylformamide diethyl acetal followed by cyclization into benzo[b][1,6]naphthyridines and pyrido[4,3-b]benz[f ]azepines were studied.

  3,4-二氢羰基苯乙炔和1H-2,3,4,5-四氢苯并[b]氮杂卓-2-酮与丙二腈、氰乙酰胺和氰乙酸乙酯的缩合反应产生了相应的2-亚甲基衍生物。研究了它们与二甲基甲酰胺二乙基缩醛的反应，随后发生环化反应生成苯并[b][1,6]萘啶和吡啶并[4,3-b]苯并[f ]氮杂卓。
• Synthesis and Antimicrobial Evaluation of Some New 2-(5,6-Dihydro-4H-1,2,4- triazolo[4,3-a]benz[F]azepin-1-yl)methyl)-4-substituted Phthalazin-1(2H)-ones
  作者：Ibrahim E. El-Shamy、A.M. Abdel-Mohsen、Moustafa M.G. Fouda、Salem S. Al-Deyab、Ahmed Abdel-Megeed、Maher A. El-Hashash

  DOI：10.14233/ajchem.2014.17984

  日期：——

  Starting from 4-substituted-phthalazin-1(2H)-one (1), A series of new 2-(5,6-dihydro-4H-1,2,4-triazolo[4,3-a]benz[f]azepin-1-yl)methyl)-4-substituted phthalazin-1(2H)-ones derivatives (5) have been synthesized. The structure of synthesized new compounds was established by spectral data and screened for their antimicrobial activities against various bacteria and fungi strains.

  从 4-取代酞嗪-1(2H)-酮 (1) 开始，合成了一系列新的 2-(5,6-二氢-4H-1,2,4-三唑并[4,3-a]苯并[f]氮杂卓-1-基)甲基)-4-取代酞嗪-1(2H)-酮衍生物 (5)。通过光谱数据确定了合成的新化合物的结构，并筛选了它们对各种细菌和真菌菌株的抗菌活性。
• Targeting the Polyamine Transport System with Benzazepine- and Azepine-Polyamine Conjugates
  作者：Sophie Tomasi、Jacques Renault、Bénédicte Martin、Stephane Duhieu、Virginie Cerec、Myriam Le Roch、Philippe Uriac、Jean-Guy Delcros

  DOI：10.1021/jm1007648

  日期：2010.11.11

  The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.
• ——
  作者：T. V. Golovko

  DOI：10.1023/a:1023918911369

  日期：——