ethyl 4-hydroxy-6,8-dimethylquinoline-3-carboxylate | 31601-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 4-hydroxy-6,8-dimethylquinoline-3-carboxylate
• 英文别名: ethyl 6,8-dimethyl-4-oxo-1H-quinoline-3-carboxylate
• CAS: 31601-85-1
• 化学式: C₁₄H₁₅NO₃
• mdl: MFCD00173389
• 分子量: 245.278
• InChiKey: AKBJMLWAUZEZSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-6,8-dimethylquinoline-3-carboxylate 、 N,N-二甲基乙二胺 以 二苯醚 为溶剂， 生成 4-Hydroxy-6,8-dimethyl-quinoline-3-carboxylic acid (2-dimethylamino-ethyl)-amide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator

  摘要：

  A series of novel quinoline-3-carboxamide derivatives were synthesized and evaluated for their immunomodulatory activity. The compounds were tested in vitro for effects on spleen lymphocyte proliferation and TNF-alpha production by macrophage. Three compounds showed immunomodulatory profiles similar to and more potent than those of linomide and FR137316 and were selected for further pharmacological studies in vivo. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.040
• 作为产物：
  描述：

  ethyl 4-hydroxy-6,8-dimethylquinoline-3-carboxylate 以 二苯醚 为溶剂， 生成 ethyl 4-hydroxy-6,8-dimethylquinoline-3-carboxylate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator

  摘要：

  A series of novel quinoline-3-carboxamide derivatives were synthesized and evaluated for their immunomodulatory activity. The compounds were tested in vitro for effects on spleen lymphocyte proliferation and TNF-alpha production by macrophage. Three compounds showed immunomodulatory profiles similar to and more potent than those of linomide and FR137316 and were selected for further pharmacological studies in vivo. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.040

文献信息

• US4343804A
  申请人：——

  公开号：US4343804A

  公开（公告）日：1982-08-10
• Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator
  作者：Jun-Feng He、Liu-Hong Yun、Ri-Fang Yang、Zhi-Yong Xiao、Jun-Ping Cheng、Wen-Xia Zhou、Yong-Xiang Zhang

  DOI：10.1016/j.bmcl.2005.04.040

  日期：2005.6

  A series of novel quinoline-3-carboxamide derivatives were synthesized and evaluated for their immunomodulatory activity. The compounds were tested in vitro for effects on spleen lymphocyte proliferation and TNF-alpha production by macrophage. Three compounds showed immunomodulatory profiles similar to and more potent than those of linomide and FR137316 and were selected for further pharmacological studies in vivo. (c) 2005 Elsevier Ltd. All rights reserved.
• How to Convert a Walk-in Hood into a Manufacturing Facility: Demonstration of a Continuous, High-Temperature Cyclization to Process Solids in Flow
  作者：Timothy D. White、Charles A. Alt、Kevin P. Cole、Jennifer McClary Groh、Martin D. Johnson、Richard D. Miller

  DOI：10.1021/op500239f

  日期：2014.11.21

  An intramolecular thermal cyclization protocol was developed in a flow reactor to take advantage of the high pressures and temperatures that are easily obtained in small scale autoclave reactors that have been modified to handle slurries. This reactor was equipped with a fill/empty pumping system to enable easy and nearly complete transfer of slurries. The reaction conditions were designed to take advantage of the insolubility of the product in order to separate it from residual starting material by filtration after short reaction times. Recycling of the filtrate maximized the yield and throughput while minimizing decomposition. Recycles were accomplished using a strip to dryness protocol that was easily performed in a rotary evaporator. This new equipment set was designed with lab-hood manufacturing in mind, a minimized footprint, and the system was completely automated for charging, emptying, rinsing, and reacting. Additional efforts for quick screening and alternate modes of addition were also investigated.