2-hexyl-3-methyl-4(1H)-quinolinone

• 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: 2-hexyl-3-methyl-4(1H)-quinolinone
• 英文别名: 2-hexyl-3-methylquinolin-4(1H)-one；2-hexyl-3-methyl-1H-quinolin-4-one
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: JQICIXPIBWEGRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-hexyl-3-methyl-4(1H)-quinolinone 生成 Acetic acid 2-hexyl-3-methyl-quinolin-4-yl ester
  参考文献：
  名称：

  Minowa, Nobuto; Imamura, Kei-ichi; Shibahara, Seiji, Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 7, p. 1213 - 1215

  摘要：

  DOI：
• 作为产物：
  描述：

  o-heptanoylaminophenylacetone 在 sodium t-butanolate 作用下， 生成 2-hexyl-3-methyl-4(1H)-quinolinone
  参考文献：
  名称：

  一种肿瘤血管新生抑制剂己啉酮及其制备方法 和用途

  摘要：

  本发明提供了一种肿瘤血管新生抑制剂己啉酮及其制备方法和用途，属于医药技术领域。具体地说，其名称为2-己烷基-3-甲基-4（1H）-喹啉酮，其化学式为C16H21NO，命名为己啉酮。还提供了所述化合物的制备方法和对肿瘤血管新生的抑制作用。本发明己啉酮为全合成。本发明式Ⅰ化合物不仅对对肿瘤血管新生的抑制作用，且安全性好，从而为开发一种新的治疗肿瘤药物提供了可能。

  公开号：

  CN103319403B

文献信息

• HHQ-4, a quinoline derivate, preferentially inhibits proliferation of glucose-deprived breast cancer cells as a GRP78 down-regulator
  作者：Xiao Xiao、Shuo Li、Xiaoxun Zhang、Jinjian Lu、Weiguang Wang、Shijia Zhou、Jingyao Zhang、Rui Wang、Ao Li

  DOI：10.1016/j.taap.2019.04.017

  日期：2019.6

  As a central regulator for endoplasmic reticulum (ER) stress, glucose-regulated protein 78 (GRP78), controls the activation of ER-transmembrane signaling mechanisms by inducing unfolded protein response (UPR) in response to ER stress. Although limited glucose availability often occurs in poorly vascularized solid cancers, cancer cells often initiate the UPR to support cellular homeostasis and survival under stress conditions. Therefore, targeting GRP78 expression and UPR pathway activation may provide a new strategy for anticancer therapy. Based on this premise, we investigated the molecular mechanisms of a synthetic quinolone derivative, 2-hexyl-3-methyl-4(1H)-quinolinone (HHQ-4), in regulating the GRP78 expression and UPR transcriptional program under glucose deprivation or 2-deoxy-D-glucose (2-DG)-stressed conditions. We found that HHQ-4 suppressed the transcriptional and translational expression of GRP78 gene in glucose-deprived breast cancer cells. HHQ-4 also showed selective antiproliferative activity against glucose-deprived breast cancer cells. Constitutive expression of GRP78 completely prevented breast cancer cells from HHQ-4-mediated proliferation inhibition during glucose starvation, stressing the important role of suppression of the GRP78 in HHQ-4-mediated cell proliferation inhibition. HHQ-4 was also found to exert inhibitory activity against breast cancer cell proliferation by suppressing three survival arms of the UPR, including PERK/eIF2 alpha/ATF4, IRE1/XBP1, and ATF6, which orchestrate an intricate signaling network to modulate GRP78 gene transcription under glucose-deprived stress. Furthermore, HHQ-4 combined with 2-DG synergistically inhibited breast cancer cell proliferation. Our findings show HHQ-4 could be a promising candidate, alone or in combination with 2-DG, for selectively inhibiting breast cancer cell proliferation by down-regulating the transcription and expression of GRP78 under stressful microenvironments.
• Minowa, Nobuto; Imamura, Kei-ichi; Shibahara, Seiji, Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 7, p. 1213 - 1215
  作者：Minowa, Nobuto、Imamura, Kei-ichi、Shibahara, Seiji

  DOI：——

  日期：——
• 一种肿瘤血管新生抑制剂己啉酮及其制备方法 和用途
  申请人：重庆理工大学

  公开号：CN103319403B

  公开（公告）日：2016-03-30

  本发明提供了一种肿瘤血管新生抑制剂己啉酮及其制备方法和用途，属于医药技术领域。具体地说，其名称为2-己烷基-3-甲基-4（1H）-喹啉酮，其化学式为C16H21NO，命名为己啉酮。还提供了所述化合物的制备方法和对肿瘤血管新生的抑制作用。本发明己啉酮为全合成。本发明式Ⅰ化合物不仅对对肿瘤血管新生的抑制作用，且安全性好，从而为开发一种新的治疗肿瘤药物提供了可能。