4-(3-(4-hexyl-1H-1,2,3-triazol-1-yl)propyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

• 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: 4-(3-(4-hexyl-1H-1,2,3-triazol-1-yl)propyl)-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: 4-[3-(4-Hexyltriazol-1-yl)propyl]-1,4-benzoxazin-3-one；4-[3-(4-hexyltriazol-1-yl)propyl]-1,4-benzoxazin-3-one
• 化学式: C₁₉H₂₆N₄O₂
• 分子量: 342.441
• InChiKey: GZLDUZCOYCLHFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(3-bromopropyl)-2H-benzo[b][1,4]oxazin-3(4H)-one 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 四丁基溴化铵 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 4-(3-(4-hexyl-1H-1,2,3-triazol-1-yl)propyl)-2H-benzo[b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  Rational design, synthesis and anti-proliferative evaluation of novel 1,4-benzoxazine-[1,2,3]triazole hybrids

  摘要：

  A series of novel 1,2,3-triazole-1,4-benzoxazine hybrids 5a-n were efficiently synthesized employing click chemistry approach and evaluated for anti-proliferative activity against four cancer cell lines such as HeLa (cervical), MIAPACA (pancreatic), MDA-MB-231 (breast) and IMR32 (neuroblastoma). Compounds 5n and 5g exhibited promising anti-proliferative activity with GI(50) values ranging from 1.2 to 2.5 mu M and 0.1-1.1 mu M respectively against all cell lines, like HeLa, MDA-MB-231, MIAPACA and IMR32, while compound 51 showed significant activity against MDA-MB-231 and IMR32 with GI(50) values ranging from 1.1 and 1.4 mu M. This is the first report on the synthesis and in vitro anti-proliferative evaluation of 1,2,3-triazole-1,4-benzoxazine hybrids. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.051

文献信息

• Rational design, synthesis and anti-proliferative evaluation of novel 1,4-benzoxazine-[1,2,3]triazole hybrids
  作者：Rajitha Bollu、Jyothsna Devi Palem、Rajashaker Bantu、Vijayacharan Guguloth、Lingaiah Nagarapu、Sowjanya Polepalli、Nishant Jain

  DOI：10.1016/j.ejmech.2014.10.051

  日期：2015.1

  A series of novel 1,2,3-triazole-1,4-benzoxazine hybrids 5a-n were efficiently synthesized employing click chemistry approach and evaluated for anti-proliferative activity against four cancer cell lines such as HeLa (cervical), MIAPACA (pancreatic), MDA-MB-231 (breast) and IMR32 (neuroblastoma). Compounds 5n and 5g exhibited promising anti-proliferative activity with GI(50) values ranging from 1.2 to 2.5 mu M and 0.1-1.1 mu M respectively against all cell lines, like HeLa, MDA-MB-231, MIAPACA and IMR32, while compound 51 showed significant activity against MDA-MB-231 and IMR32 with GI(50) values ranging from 1.1 and 1.4 mu M. This is the first report on the synthesis and in vitro anti-proliferative evaluation of 1,2,3-triazole-1,4-benzoxazine hybrids. (C) 2014 Elsevier Masson SAS. All rights reserved.