6-chloro-2-(thiophen-2-yl)-4H-benzo[d][1,3]oxazin-4-one | 73314-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-chloro-2-(thiophen-2-yl)-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 6-chloro-2-thiophen-2-yl-benzo[d][1,3]oxazin-4-one；6-chloro-2-(thiophen-2-yl)-4H-3,1-benzoxazin-4-one；6-chloro-2-thiophen-2-yl-3,1-benzoxazin-4-one
• CAS: 73314-31-5
• 化学式: C₁₂H₆ClNO₂S
• 分子量: 263.704
• InChiKey: SUOQHPFHBWXBSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-2-(thiophen-2-yl)-4H-benzo[d][1,3]oxazin-4-one 在 ammonium acetate 、 三氯氧磷 作用下， 反应 10.0h， 生成 4,6-dichloro-2-(2-thienyl)quinazoline
  参考文献：
  名称：

  The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of In vitro and In vivo studies

  摘要：

  We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3-pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.047
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸 在 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 6-chloro-2-(thiophen-2-yl)-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of In vitro and In vivo studies

  摘要：

  We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3-pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.047

文献信息

• Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
  作者：Subir Panja、Srabani Maity、Biju Majhi、Brindaban C. Ranu

  DOI：10.1002/ejoc.201900935

  日期：2019.9.8

  An efficient procedure for the Pd‐catalyzed olefination of 4H‐benzo[d][1,3]oxazin‐4‐ones with activated alkenes has been achieved via C‐H activation. The site selectivity of the reaction was explained by a DFT study.

  通过C-H活化，实现了有效的Pd催化4H-苯并[d] [1,3]恶嗪-4-烯与活化烯烃的烯化反应。DFT研究解释了反应的位点选择性。
• Eid; Aboul-Enein; El-Difrawy, European Journal of Medicinal Chemistry, 1979, vol. 14, # 5, p. 463 - 466
  作者：Eid、Aboul-Enein、El-Difrawy、et al.

  DOI：——

  日期：——
• EID A. I.; ABUOL-ENEIN M. N.; EL-DIFRAWY S.; BIBERS M.; EL-HAWARY S., EUR. J. MED. CHEM.-CHIM. THER., 1979, 14, NO 5, 463-466
  作者：EID A. I.、 ABUOL-ENEIN M. N.、 EL-DIFRAWY S.、 BIBERS M.、 EL-HAWARY S.

  DOI：——

  日期：——
• The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of In vitro and In vivo studies
  作者：Moorthy S.S. Palanki、Paul E. Erdman、Minghuan Ren、Mark Suto、Brydon L. Bennett、Anthony Manning、Lynn Ransone、Cheryl Spooner、Sonal Desai、Arnie Ow、Ryuichi Totsuka、Peter Tsao、Wataru Toriumi

  DOI：10.1016/j.bmcl.2003.08.047

  日期：2003.11

  We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3-pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described. (C) 2003 Elsevier Ltd. All rights reserved.