2'-Hydroxy-3'-(morpholin-4-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone | 875769-70-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-Hydroxy-3'-(morpholin-4-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone
• 英文别名: (E)-3-(2-chlorophenyl)-1-[2-hydroxy-4,6-dimethoxy-3-(morpholin-4-ylmethyl)phenyl]prop-2-en-1-one
• CAS: 875769-70-3
• 化学式: C₂₂H₂₄ClNO₅
• 分子量: 417.889
• InChiKey: ZZPAWPMJLULMCV-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-Hydroxy-3'-(morpholin-4-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone 在 硫酸 、 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(2-Chlorophenyl)-5,7-dimethoxy-8-(morpholin-4-ylmethyl)chromen-4-one
  参考文献：
  名称：

  Nitrogen-containing flavonoids as CDK1/Cyclin B inhibitors: Design, synthesis, and biological evaluation

  摘要：

  A novel series of nitrogen-containing flavonoids 5a-1, 6a,b, and 7a,b were designed and synthesized as cyclin-dependent kinases (CDKs) inhibitors. The representative compounds 5a, 5b, 5e, and 5g showed potent CDK1/Cyclin B inhibitory activities. All compounds displayed a significant growth inhibitory action in vitro against Bel-7402, PC-3, ECA-109, A-549, HL-60, and MCF-7 cancer cell lines. Flow cytometry analysis showed that 5b induced apoptosis in PC-3 cells. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.07.088
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 盐酸 、 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 水 、 异丙醇 、 丙酮 为溶剂， 生成 2'-Hydroxy-3'-(morpholin-4-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone
  参考文献：
  名称：

  Nitrogen-containing flavonoids as CDK1/Cyclin B inhibitors: Design, synthesis, and biological evaluation

  摘要：

  A novel series of nitrogen-containing flavonoids 5a-1, 6a,b, and 7a,b were designed and synthesized as cyclin-dependent kinases (CDKs) inhibitors. The representative compounds 5a, 5b, 5e, and 5g showed potent CDK1/Cyclin B inhibitory activities. All compounds displayed a significant growth inhibitory action in vitro against Bel-7402, PC-3, ECA-109, A-549, HL-60, and MCF-7 cancer cell lines. Flow cytometry analysis showed that 5b induced apoptosis in PC-3 cells. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.07.088

文献信息

• Synthesis and biological evaluation of nitrogen-containing chalcones as possible anti-inflammatory and antioxidant agents
  作者：Babasaheb P. Bandgar、Sachin A. Patil、Rajesh N. Gacche、Balaji L. Korbad、Balwant S. Hote、Santosh N. Kinkar、Shivkumar S. Jalde

  DOI：10.1016/j.bmcl.2009.11.068

  日期：2010.1

  A novel series of nitrogen-containing chalcones were synthesized by Mannich reaction and were screened for anti-inflammatory related activities such as inhibition of cyclooxygenase-2 (COX-2), trypsin and beta-glucuronidase. The antioxidant potential was demonstrated using 1,1-diphenyl-2-picryl hydrazine (DPPH) radical scavenging activity. The results of the above studies shows that the compounds synthesized were found to be effective inhibitors of above pro-inflammatory enzymes, and were found to be possess moderate radical scavenging potential. Overall, the results of the studies reveal that the chalcones with N-methyl piperazine methyl and piperidine methyl substitution (4c, 3b, 4d, 6b) seems to be important for inhibition of beta-glucuronidase. Whereas the chalcones with piperidine methyl substitution (8b, 7b, 7c, 6c, 4b, 3c, 3b) were observed as effective inhibitors of COX-2, while the same compounds were found to be less reactive against COX-1 as compared to COX-2. (C) 2009 Elsevier Ltd. All rights reserved.
• Nitrogen-containing flavonoids as CDK1/Cyclin B inhibitors: Design, synthesis, and biological evaluation
  作者：Tao Liu、Zhongmiao Xu、Qiaojun He、Yanhong Chen、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.bmcl.2006.07.088

  日期：2007.1

  A novel series of nitrogen-containing flavonoids 5a-1, 6a,b, and 7a,b were designed and synthesized as cyclin-dependent kinases (CDKs) inhibitors. The representative compounds 5a, 5b, 5e, and 5g showed potent CDK1/Cyclin B inhibitory activities. All compounds displayed a significant growth inhibitory action in vitro against Bel-7402, PC-3, ECA-109, A-549, HL-60, and MCF-7 cancer cell lines. Flow cytometry analysis showed that 5b induced apoptosis in PC-3 cells. (c) 2006 Published by Elsevier Ltd.