4-amino-3-carbethoxy-1,2-dihydrospiro(naphthalene-2,1'-cyclohexane)

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-amino-3-carbethoxy-1,2-dihydrospiro(naphthalene-2,1'-cyclohexane)
• 英文别名: 4-amino-3-ethoxycarbonyl-1,2-dihydrospiro[naphthalene-2,1'-cyclohexane]；ethyl 4'-amino-1'H-spiro[cyclohexane-1,2-naphthalene]-3'-carboxylate；ethyl 1-aminospiro[4H-naphthalene-3,1'-cyclohexane]-2-carboxylate
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: QJTPPVJCWRKSQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-3-carbethoxy-1,2-dihydrospiro(naphthalene-2,1'-cyclohexane) 在 乙酸酐 、 一水合肼 作用下， 以 乙醇 、 苯 为溶剂， 反应 12.0h， 生成 3-amino-4-oxo-3,4,5,6-tetrahydrospiro(benzo[h]quinazoline-5,1'-cyclohexane)
  参考文献：
  名称：

  Synthesis of spiro(benzo[h]quinazoline-5,1?-cyclohexane) derivatives

  摘要：

  DOI：

  10.1007/bf01165913
• 作为产物：
  描述：

  环己酮 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 77.0h， 生成 4-amino-3-carbethoxy-1,2-dihydrospiro(naphthalene-2,1'-cyclohexane)
  参考文献：
  名称：

  Novel inhibitors of bacterial virulence: Development of 5,6-dihydrobenzo[h]quinazolin-4(3H)-ones for the inhibition of group A streptococcal streptokinase expression

  摘要：

  Resistance to antibiotics is an increasingly dire threat to human health that warrants the development of new modes of treating infection. We recently identified 1 (CCG-2979) as an inhibitor of the expression of streptokinase, a critical virulence factor in Group A Streptococcus that endows blood-borne bacteria with fibrinolytic capabilities. In this report, we describe the synthesis and biological evaluation of a series of novel 5,6-dihydrobenzo[h]quinazolin-4(3H)-one analogs of 1 undertaken with the goal of improving the modest potency of the lead. In addition to achieving an over 35-fold increase in potency, we identified structural modifications that improve the solubility and metabolic stability of the scaffold. The efficacy of two new compounds 12c (CCG-203592) and 12k (CCG-205363) against biofilm formation in Staphylococcus aureus represents a promising additional mode of action for this novel class of compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.046

文献信息

• Methods and compositions for treating bacterial infection
  申请人：Ginsburg David

  公开号：US08501722B2

  公开（公告）日：2013-08-06

  The present invention relates to chemical compounds, methods for their discovery, and their therapeutic and research use. In particular, the present invention provides compounds as therapeutic agents against bacterial infections.

  本发明涉及化合物、其发现方法以及它们的治疗和研究用途。特别地，本发明提供了化合物作为治疗细菌感染的治疗剂。
• METHODS AND COMPOSITIONS FOR TREATING BACTERIAL INFECTION
  申请人：Ginsburg David

  公开号：US20100331351A1

  公开（公告）日：2010-12-30

  The present invention relates to chemical compounds, methods for their discovery, and their therapeutic and research use. In particular, the present invention provides compounds as therapeutic agents against bacterial infections.

  本发明涉及化合物、其发现方法及其治疗和研究用途。具体而言，本发明提供化合物作为治疗细菌感染的治疗剂。
• Synthesis of 2-alkyl thio-substituted 4-oxo-3-p-tolyl-3,4,5,6-tetrahydrospiros-(Benzo[h]quinazoline-5,1′-cycloalkanes)
  作者：A. I. Markosyan、R. A. Kuroyan、K. V. Karapetyan

  DOI：10.1007/bf02251821

  日期：1999.12
• KUROYAN, R. A.;MARKOSYAN, A. I.;OGANISYAN, A. SH.;OGANISYAN, M. G., ARM. XIM. ZH., 42,(1989) N, S. 527-529
  作者：KUROYAN, R. A.、MARKOSYAN, A. I.、OGANISYAN, A. SH.、OGANISYAN, M. G.

  DOI：——

  日期：——
• Synthesis of 4-oxo-2-thioxo-1,2,3,4,5,6-hexahydrospiro(benzo[h]quinazoline-5,1′-cyclohexane and its reaction with dibromoalkanes
  作者：A. I. Markosyan、R. A. Kuroyan、S. V. Dilanyan、A. Sh. Oganesyan、M. S. Aleksanyan、A. A. Karapetyan、Yu. T. Struchkov

  DOI：10.1007/bf02251672

  日期：1999.1