3-甲基-巴豆酸-(3-氯-苯胺) | 91089-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲基-巴豆酸-(3-氯-苯胺)
• 英文名称: 3-methyl-crotonic acid-(3-chloro-anilide)
• 英文别名: 3-Methyl-crotonsaeure-(3-chlor-anilid)；2-Butenamide, N-(3-chlorophenyl)-3-methyl-；N-(3-chlorophenyl)-3-methylbut-2-enamide
• CAS: 91089-55-3
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: DYNVGFUQFOJQAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-甲基-巴豆酸-(3-氯-苯胺) 在 劳森试剂 、 aluminum (III) chloride 作用下， 以 邻二氯苯 、 甲苯 为溶剂， 反应 5.0h， 生成 7-chloro-4, 4-dimethyl-3,4-dihydro-1H-quinoline-2-thione
  参考文献：
  名称：

  Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents

  摘要：

  A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 mu M when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.038
• 作为产物：
  描述：

  3-甲基巴豆酰氯 、 3-氯苯胺 生成 3-甲基-巴豆酸-(3-氯-苯胺)
  参考文献：
  名称：

  2-Pyrones. XXII. β-Methylglutaconic Acid, β-Methylglutaconanilic Acids and Related Dianilides, Pyridones and Pyridazones

  摘要：

  DOI：

  10.1021/ja01599a042

文献信息

• Design, Synthesis, and Biological Evaluation of β-Trifluoroethoxydimethyl Selenides as Potent Antiosteoporosis Agents
  作者：Yao Wu、Bin Li、Linkun Ying、Yao Chen、Yuxin Zhang、Chaoming Hu、Yichi Zhang、Lele Yi、Weiwei Xue、Shengbin Huang、Zengqiang Song

  DOI：10.1021/acs.jmedchem.4c00438

  日期：——

  An efficient protocol for the synthesis of β-trifluoroethoxydimethyl selenides was achieved under mild reaction conditions, and 39 compounds were prepared. All compounds were evaluated for their abilities to inhibit RANKL-induced osteoclastogenesis, compound 4aa exhibited the most potent activity. Further investigations revealed that 4aa could inhibit F-actin ring generation, bone resorption, and osteoclast-specific

  在温和的反应条件下实现了β-三氟乙氧基二甲基硒化物的有效合成方案，并制备了39种化合物。评估了所有化合物抑制 RANKL 诱导的破骨细胞生成的能力，化合物4aa表现出最有效的活性。进一步的研究表明， 4aa可以在体外抑制 F-肌动蛋白环的生成、骨吸收和破骨细胞特异性基因表达。蛋白质印迹分析表明，化合物4aa消除了 RANKL 诱导的丝裂原激活蛋白激酶和 NF-kB 信号通路。此外， 4aa还对MC3T3-E1前成骨细胞的成骨细胞产生显着影响。体内实验表明，化合物4aa可显着改善卵巢切除 (OVX) 小鼠模型中的骨质流失。此外，表面等离子体共振实验结果表明4aa可能与RANKL结合。总的来说，上述研究结果表明，化合物4aa作为潜在的RANKL抑制剂，通过调节破骨细胞分化的抑制和成骨细胞分化的刺激来避免OVX引发的骨质疏松症。
• 2-Pyrones. XXII. β-Methylglutaconic Acid, β-Methylglutaconanilic Acids and Related Dianilides, Pyridones and Pyridazones
  作者：Richard H. Wiley、C. L. deSilva

  DOI：10.1021/ja01599a042

  日期：1956.9
• Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents
  作者：Eun Lee、SeulAa Han、Guo Hua Jin、Hwa Jin Lee、Woo-Young Kim、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2013.04.038

  日期：2013.7

  A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 mu M when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism. (c) 2013 Elsevier Ltd. All rights reserved.