3-(吡啶-3-基氨基)环己-2-烯-1-酮 | 154152-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-(吡啶-3-基氨基)环己-2-烯-1-酮
• 英文名称: 3-(pyridin-3-ylamino)cyclohex-2-enone
• 英文别名: 3-(pyridin-3-ylamino)cyclohex-2-en-1-one
• CAS: 154152-62-2
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD24389884
• 分子量: 188.229
• InChiKey: LRWCFGPBSCFMJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  351.1±42.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(吡啶-3-基氨基)环己-2-烯-1-酮 在 碳酸氢钠 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 3-[(2-methoxypyridin-3-yl)amino]cyclohex-2-en-1-one
  参考文献：
  名称：

  多卤化杂环烯胺酮的光化学：环化和脱卤之间的竞争

  摘要：

  描述了在各种条件下多卤化烯胺酮的光化学，以得到官能化的四氢氮杂咔唑酮 (9, 15)。起始烯胺酮 (2, 7, 14) 也经历了竞争性脱卤，产生了一系列次级产物。考虑了反应的机械方面。

  DOI：

  10.1515/hc.2003.9.2.189
• 作为产物：
  描述：

  3-氨基吡啶 、 1,3-环己二酮 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-(吡啶-3-基氨基)环己-2-烯-1-酮
  参考文献：
  名称：

  一锅三组分反应合成一类新型联喹啉吡啶杂化物及其抗菌活性

  摘要：

  在存在条件下，通过一锅式2-氯-3-甲酰基喹啉，活性亚甲基化合物和3-（吡啶-3-基氨基）环己-2-烯酮的环缩合反应，合成了一个新的含吡啶基类小分子文库。催化量的氢氧化钠 该协议可以快速合成一些联喹啉吡啶杂化物的结构多样的新型化合物，以进行抗菌筛选。筛选了这些化合物对革兰氏阳性菌（枯草芽孢杆菌，破伤风梭菌，肺炎链球菌），革兰氏阴性菌（大肠杆菌，鼠伤寒沙门氏菌，霍乱弧菌）的抗菌活性和抗真菌活性烟曲霉，白色念珠菌。发现一些联喹啉化合物比一线标准药物更有效或等效。使用Lowenstein-Jensen培养基评估了这些化合物对结核分枝杆菌H37Rv菌株的体外抗结核活性。化合物4g在6.25μg/ mL处表现出令人信服的活性，并具有96％的抑制作用，非常适合进一步修饰以在对抗结核病中获得更有效的化合物。 在存在条件下，通过一锅式2-氯-3-甲酰基喹啉，活性亚甲基化合物和3-（吡啶-3-基氨基）环己-

  DOI：

  10.1007/s12039-012-0254-0

文献信息

• Design, synthesis and molecular modeling of biquinoline–pyridine hybrids as a new class of potential EGFR and HER-2 kinase inhibitors
  作者：Chetan B. Sangani、Jigar A. Makawana、Yong-Tao Duan、Yong Yin、Shashikant B. Teraiya、Nilesh J. Thumar、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2014.07.094

  日期：2014.9

  A new series of biquinoline-pyridine hybrids were designed and synthesized by a base-catalyzed cyclocondensation through one-pot multicomponent reaction. All compounds were tested for in vitro anticancer activities against two cancer cell lines A549 (adenocarcinomic human alveolar basal epithelial) and Hep G2 (liver cancer). Enzyme inhibitory activities of all compounds were carried out against EGFR and HER-2 kinase. Of the compounds studied, majority of the compounds showed effective anticancer activity against used cancer cell lines. Compound 9i (IC50 = 0.09 mu M) against EGFR and (IC50 = 0.2 mu M) against HER-2 kinase displayed the most potent inhibitory activity as compared to other member of the series. In the molecular modelling study, compound 9i was bound in to the active pocket of EGFR with four hydrogen bonds and two pi-cation interactions having minimum binding energy Delta G(b) = -54.4 kcal/mol. (C) 2014 Elsevier Ltd. All rights reserved.
• Design, synthesis and molecular modeling of pyrazole–quinoline–pyridine hybrids as a new class of antimicrobial and anticancer agents
  作者：Chetan B. Sangani、Jigar A. Makawana、Xin Zhang、Shashikant B. Teraiya、Lin Lin、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2014.01.018

  日期：2014.4

  A new series of pyrazole-quinoline-pyridine hybrids were designed based on molecular hybridization technique and synthesized by a base-catalyzed cyclocondensation reaction through one-pot multicomponent reaction. All compounds were tested for in vitro antibacterial and anticancer activities. Enzyme inhibitory activities of all compounds were carried out against FabH and EGFR. Of the compounds studied, majority of the compounds showed effective antibacterial as well as anticancer activity against used strains and cancer cell lines respectively. Compound 7k (IC50 = 0.51 +/- 0.05 mu M) against EGFR and 7b displayed the most potent inhibitory activity with IC50 of 3.1 mu M against FabH as compared to other member of the series. In the molecular modeling study, compound 7k was bound in to the active pocket of EGFR with three hydrogen bond and one pi-cation interaction with minimum binding energy Delta G(b) = -54.6913 kcal/mol, as well as compound 7b was bound in to the active site of FabH with hydrogen bond and pi-sigma interactions with minimum binding energy Delta G(b) = -45.9125 kcal/mol. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Blache, Yves; Chavignon, Olivier; Sinibaldi-Troin, Marie E., Heterocycles, 1994, vol. 38, # 6, p. 1241 - 1246
  作者：Blache, Yves、Chavignon, Olivier、Sinibaldi-Troin, Marie E.、Gueiffier, Alain、Teulade, Jean C.、et al.

  DOI：——

  日期：——
• JPH05331144A
  申请人：——

  公开号：JPH05331144A

  公开（公告）日：1993-12-14
• Synthesis of a novel class of some biquinoline pyridine hybrids via one-pot, three-component reaction and their antimicrobial activity
  作者：NIMESH M SHAH、MANISH P PATEL、RANJAN G PATEL

  DOI：10.1007/s12039-012-0254-0

  日期：2012.5

  one-pot cyclocondensation of 2-chloro-3-formyl quinoline, active methylene compounds and 3-(pyridine-3-ylamino)cyclohex-2-enone in the presence of catalytic amount of sodium hydroxide. The protocol offers rapid synthesis of structurally diverse novel class of some biquinoline pyridine hybrids for antimicrobial screening. These compounds were screened for their antibacterial activity against Gram-positive

  在存在条件下，通过一锅式2-氯-3-甲酰基喹啉，活性亚甲基化合物和3-（吡啶-3-基氨基）环己-2-烯酮的环缩合反应，合成了一个新的含吡啶基类小分子文库。催化量的氢氧化钠 该协议可以快速合成一些联喹啉吡啶杂化物的结构多样的新型化合物，以进行抗菌筛选。筛选了这些化合物对革兰氏阳性菌（枯草芽孢杆菌，破伤风梭菌，肺炎链球菌），革兰氏阴性菌（大肠杆菌，鼠伤寒沙门氏菌，霍乱弧菌）的抗菌活性和抗真菌活性烟曲霉，白色念珠菌。发现一些联喹啉化合物比一线标准药物更有效或等效。使用Lowenstein-Jensen培养基评估了这些化合物对结核分枝杆菌H37Rv菌株的体外抗结核活性。化合物4g在6.25μg/ mL处表现出令人信服的活性，并具有96％的抑制作用，非常适合进一步修饰以在对抗结核病中获得更有效的化合物。 在存在条件下，通过一锅式2-氯-3-甲酰基喹啉，活性亚甲基化合物和3-（吡啶-3-基氨基）环己-