12-(4-chloro-butyl)-6,7-dihydro-12H-5-oxa-12-azadibenzo[a,e]azulene | 1079395-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 12-(4-chloro-butyl)-6,7-dihydro-12H-5-oxa-12-azadibenzo[a,e]azulene
• CAS: 1079395-83-7
• 化学式: C₂₀H₂₀ClNO
• 分子量: 325.838
• InChiKey: UPQDRAPTTROKOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  14.16
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  亚甲基二磷酸四乙酯 、 12-(4-chloro-butyl)-6,7-dihydro-12H-5-oxa-12-azadibenzo[a,e]azulene 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 337.5h， 以5.7%的产率得到
  参考文献：
  名称：

  Synthesis and biological evaluation of indolyl bisphosphonates as anti-bone resorptive and anti-leishmanial agents

  摘要：

  A series of indole conjugated bisphosphonate derivatives have been synthesized and evaluated for their in vitro anti-bone resorptive activity using bone marrow osteoclast culture. Two bisphosphonates 23 and 24 significantly inhibited osteoclastogenesis, 23 showed inhibition at 10 and 100 pM which was lower than the concentration of standard drug alendronate, and 24 inhibited osteoclastogenesis at 100 nM which was comparable to alendronate. Two other compounds 13 and 14 also showed inhibition comparable to alendronate, but were cytotoxic in the osteoblast cells. The two active bisphosphonates 23 and 24 induced significant osteoclast apoptosis at concentrations 100 nM for compound 24 and at 10 pM for compound 23 compared to alendronate. In vivo effect of active bisphosphonates 23 and 24 resulted in osteoclastogenesis of bone marrow cells (BMCs) to almost 40-50% (23 showing 8.4% decrease and 24 showing 9.0%) compared to 16.5% of the ovariectomized group. Further, screening of anti-leishmanial activity, four compounds 24-25 and 27-28 showed more than 80% inhibition against both the promastigote and amastigote stages of the Leishmania parasite. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.024
• 作为产物：
  描述：

  1-溴-4-氯丁烷 、 7,12-dihydro-6H-benzo[2,3]oxepino[4,5-b]indole 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以81%的产率得到12-(4-chloro-butyl)-6,7-dihydro-12H-5-oxa-12-azadibenzo[a,e]azulene
  参考文献：
  名称：

  Synthesis and biological evaluation of indolyl bisphosphonates as anti-bone resorptive and anti-leishmanial agents

  摘要：

  A series of indole conjugated bisphosphonate derivatives have been synthesized and evaluated for their in vitro anti-bone resorptive activity using bone marrow osteoclast culture. Two bisphosphonates 23 and 24 significantly inhibited osteoclastogenesis, 23 showed inhibition at 10 and 100 pM which was lower than the concentration of standard drug alendronate, and 24 inhibited osteoclastogenesis at 100 nM which was comparable to alendronate. Two other compounds 13 and 14 also showed inhibition comparable to alendronate, but were cytotoxic in the osteoblast cells. The two active bisphosphonates 23 and 24 induced significant osteoclast apoptosis at concentrations 100 nM for compound 24 and at 10 pM for compound 23 compared to alendronate. In vivo effect of active bisphosphonates 23 and 24 resulted in osteoclastogenesis of bone marrow cells (BMCs) to almost 40-50% (23 showing 8.4% decrease and 24 showing 9.0%) compared to 16.5% of the ovariectomized group. Further, screening of anti-leishmanial activity, four compounds 24-25 and 27-28 showed more than 80% inhibition against both the promastigote and amastigote stages of the Leishmania parasite. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.024