3-(4-chlorophenyl)-2H-naphtho[2,3-e][1,3]oxazine-2,4-(3H)-dione | 58523-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(4-chlorophenyl)-2H-naphtho[2,3-e][1,3]oxazine-2,4-(3H)-dione
• 英文别名: 3-(4-chloro-phenyl)-naphtho[2,3-e][1,3]oxazine-2,4-dione；3-(4-Chlorophenyl)benzo[g][1,3]benzoxazine-2,4-dione
• CAS: 58523-68-5
• 化学式: C₁₈H₁₀ClNO₃
• 分子量: 323.735
• InChiKey: VJZDFGDJEYAKJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  草酰氯 、 色酚 AS-E 以 对二甲苯 为溶剂， 以52%的产率得到3-(4-chlorophenyl)-2H-naphtho[2,3-e][1,3]oxazine-2,4-(3H)-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Conformationally Constrained Analogues of Naphthol AS-E as Inhibitors of CREB-Mediated Gene Transcription

  摘要：

  Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.

  DOI：

  10.1021/jm300043c

文献信息

• Kekre,J.S.; Sunthankar,S.V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1976, vol. 14, p. 212 - 213
  作者：Kekre,J.S.、Sunthankar,S.V.

  DOI：——

  日期：——
• BINDRA R.; SINGH H.; SHARMA S.; IYER R. N., INDIAN J. PHARM. <IJPA-AO>, 1975, 37, NO 6, 133-136
  作者：BINDRA R.、 SINGH H.、 SHARMA S.、 IYER R. N.

  DOI：——

  日期：——
• Design, Synthesis, and Biological Evaluation of Conformationally Constrained Analogues of Naphthol AS-E as Inhibitors of CREB-Mediated Gene Transcription
  作者：Min Jiang、Bingbing X. Li、Fuchun Xie、Frances Delaney、Xiangshu Xiao

  DOI：10.1021/jm300043c

  日期：2012.4.26

  Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.